TEST BANK for Organic Chemistry: 4th Edition by David R Klein. INTEGRATED WITH SOLUTIONS MANUAL. by ACADEMIAMILL

Klein, Organic Chemistry 4e Chapter 1 1.

Chemical reactions occur as a result of___________

A. B. C. D. E.

the attraction between opposite charges. the nucleus–nucleus interactions. the motion of electrons. like atoms interacting. combining two chemicals.

Answer: C Learning Objective: 1.1 Compare and contrast organic and inorganic compounds Difficulty: Easy 2.

From the following, identify the item which does not contain organic compounds.

A. B. C. D. E.

medicine socks a plant a coin a plastic cup

Answer: D Learning Objective: 1.1 Compare and contrast organic and inorganic compounds Difficulty: Easy 3.

What is the difference between inorganic and organic compounds?

A. B. C. D. E.

organic compounds do not contain carbon organic compounds contain carbon organic compounds are without pesticides inorganic compounds contain carbon inorganic compounds are composed exclusively of transition metal elements

Answer: B Learning Objective: 1.1 Compare and contrast organic and inorganic compounds Difficulty: Easy 4.

Constitutional isomers do not differ in___________.

A. B. C. D. E.

physical properties atomic connectivity molecular formula name constitution

Answer: C Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 5.

What is the relationship between the following compounds?

A. B. C. D. E.

isotopes constitutional isomers the same structure composed of different elements no relationship

Answer: B Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 6.

What is the relationship between the following compounds?

A. B. C. D. E.

resonance isomers constitutional isomers empirical isomers There is no relationship isotopes

Answer: B Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula

Difficulty: Easy 7.

Carbon is considered to be___________.

A. B. C. D. E.

tetravalent divalent trivalent monovalent pentavalent

Answer: A Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 8.

Which of the following compounds are constitutional isomers of each other?

A. B. C. D. E.

I and II III and IV I, II and IV II, III and IV I, II, and III

Answer: E Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 9.

Which of the following compounds are constitutional isomers of each other?

A. B. C. D. E.

I and II II and III III and IV I and IV II and III

Answer: D Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 10.

Identify three constitutional isomers having the molecular formula C4H8BrCl

A. B. C. D. E.

I, II, and III II, III, and IV III, IV, and V I, III, and IV II, III, and V

Answer: D Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 11.

Identify three constitutional isomers having the molecular formula C4H8O.

A. B. C. D. E.

I, II, and III II, III, and IV III, IV, and V I, II, and IV II, III, and V

Answer:

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 12.

What force is NOT considered in the formation of a covalent bond?

A. B.

repulsion between two positively charged nuclei force of attraction between positively charged nuclei and negatively charged electrons repulsion between negatively charged electrons repulsion between positively charged nuclei and negatively charged electrons the distance between the atoms’ nuclei

C. D. E.

Answer: D Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Easy 13.

What is the correct Lewis dot structure for the sulfur atom, S?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Easy 14.

What is the correct Lewis dot structure for the carbon atom, C?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Easy 15.

What is the correct Lewis structure for the molecule shown in the box below?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Easy 16.

What is the correct Lewis structure for the molecule shown in the box below?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Medium 17.

What is the correct Lewis structure for the molecule shown in the box below?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Medium 18.

Which of the following compounds has two lone pairs on the central atom?

A. B. C. D. E.

CO2 SCl2 NF3 CS2 SO3

Answer: B Learning Objective: 1.3 Define covalent bond, valence electrons, octet rule, and lone pair Difficulty: Medium 19.

What is the formal charge on oxygen in the following structure?

A. B. C. D. E.

212+ 1+ 0

Answer: D Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Easy 20.

What is the formal charge on nitrogen in the following structure?

A. B. C. D. E.

212+ 1+ 0

Answer: D Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Easy 21.

What is the formal charge on oxygen in the following structure?

A. B. C. D. E.

0 1+ 2+ 12-

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

Difficulty: Easy 22.

What is the formal charge on oxygen in the following structure?

A. B. C. D. E.

2+ 21+ 10

Answer: E Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Easy 23.

Which of the following structures have a formal charge of zero on the carbon atom?

A. B. C. D. E.

I and III II and III III and IV I and IV II and IV

Answer: C Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 24.

Which of the following structures have a 1- formal charge on the sulfur atom?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Easy 25.

Which of the following structures have a 1+ formal charge on the sulfur atom?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Easy 26.

What are the formal charges on boron and nitrogen in the following structure?

A. B. C. D. E.

B = 1+, N = 1+ B = 1+, N = 1B = 1-, N = 1B = 1-, N = 1+ B = 1-, N = 0

Answer: D

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 27.

What are the formal charges on boron and oxygen in the following structure?

A. B. C. D. E.

B = 1-, O = 1B = 1-, O = 1+ B = 1+, O = 1+ B = 1+, O = 1B = 1-, O = 0

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 28.

Which of the following structures have 1+ formal charge on the central atom?

A. B. C. D. E.

I II III III and V IV and V

Answer: E Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 29.

Which of the following structures have a formal charge on at least one atom?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 30.

Which of the following structures have a 1– formal charge on the nitrogen atom?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 31.

The bonding pattern of oxygen with a formal charge of 1– could be described as___________.

A. B. C. D. E.

one lone pair of electrons and three single bonds two lone pairs of electrons and two single bonds three lone pairs of electrons, and one single bond one lone pair of electrons, one single, and one double bond zero lone pairs, and two single and one double bond

Answer: C

Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 32.

In an ammonium ion, nitrogen has a valence of 4, and zero nonbonding electrons. What is the correct formal charge of nitrogen with 4 covalent bonds?

A. B. C. D. E.

22+ 11+ 0

Answer: D Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 33.

What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 34.

What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Hard 35.

What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Hard 36.

What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Hard 37.

What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Hard 38.

Which of the following bond-line structures are of the same compound?

I and II

B. C. D. E.

II and III III and IV I and III II and IV

Answer: E Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 39.

Which of the following bond-line structures represent the same compound?

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

What is the correct Lewis structure for the molecule in the box, including the formal charge(s), if any?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Hard 41.

The electronegativity increase___________.

A. B. C. D. E.

from left to right, top to bottom from right to left, bottom to top from left to right, bottom to top from right to left, top to bottom from upper right to lower left

elements

the

periodic

table

tends

Answer: C Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 42.

Which of the following is the least electronegative element?

A. B. C. D. E.

B C N O F

Answer: A Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 43.

Which of the following is the most electronegative element?

A. B. C. D. E.

B C N O H

Answer: D

Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 44.

Which of the following is the least electronegative element?

A. B. C. D. E.

P N Mg Si K

Answer: E Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 45.

Which of the following is the most electronegative element?

A. B. C. D. E.

P N S O F

Answer: E Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 46.

What is the correct order of increasing electronegativity for Rb, F and O?

A. B. C. D. E.

Rb < F < O Rb < O < F O < F < Rb F < Rb < O O < Rb < F

Answer: B Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy

47.

Which of the following series has the correct order of elements in increasing electronegativity?

A. B. C. D. E.

C < N < B < Br P < N < As < F Li < B < N < F Cl < Cs < C < Co Be < B < Ba < Br

Answer: C Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 48.

The Cl—Cl bond is best described as___________.

A. B. C. D. E.

nonpolar covalent polar covalent ionic coordinate covalent None of these.

Answer: A Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 49.

The C—Cl bond is best described as___________.

A. B. C. D. E.

nonpolar covalent polar covalent ionic coordinate covalent None of these.

Answer: B Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 50.

The bond between potassium and oxygen is best described as___________.

A. B. C. D. E.

nonpolar covalent polar covalent ionic coordinate covalent None of these.

Answer: C Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 51.

The bond between carbon and hydrogen is best described as___________.

A. B. C. D. E.

nonpolar covalent polar covalent ionic coordinate covalent None of these.

Answer: A Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 52.

Which of the following is the correct depiction of the dipole moment for a C—F bond?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy

53.

Which of the following illustrates the correct placement of partial charges for a P— Cl bond?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Easy 54.

Which of the following is the correct representation of partial charges at the indicated atoms?

A. B. C. D. E.

I = d+; II = d+; III = d+ I = d–; II = d–; III = d– I = d+; II = d+; III = d– I = d–; II = d–; III = d+ I = d+; II = d–; III = d+

Answer: D Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Medium 55.

Which atom has the largest d+ in the following compound?

A. B. C. D. E.

N O Br H C

Answer: E Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Medium 56.

Which of the following statements best describes the C—Cl bond in the following compound?

A. B. C. D. E.

nonpolar; no dipole polar; d+ at carbon and d– at chlorine polar; d– at carbon and d+ at chlorine polar; d– at carbon and d– at chlorine ionic

Answer: B Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Medium 57.

Which of the following compounds have both polar covalent and ionic bonds?

A. B. C. D. E.

NH4Br H2O2 HCN H2 S CH4

Answer: A Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Medium

A. B. C. D. E.

I II III IV V

Answer: B 58.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through

converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy

60.

For NaOCH3, identify each bond as polar covalent, nonpolar covalent or ionic.

A. B. C. D. E.

NaO = polar covalent; NaO = ionic; NaO = ionic; NaO = polar covalent; NaO = polar covalent;

OC = polar covalent; OC = polar covalent; OC = ionic; OC = nonpolar covalent; OC = nonpolar covalent;

CH = nonpolar covalent CH = nonpolar covalent CH = nonpolar covalent CH = polar covalent CH = nonpolar covalent

Answer: B Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Medium 61.

For the following compound, identify the polar covalent bond(s) from the options provided.

A. B. C. D. E.

I and II II and III I and III I only II only

Answer: C Learning Objective: 1.5 Describe the relationship between electronegativity and covalent, polar covalent, and ionic bonds Difficulty: Medium 62.

Orbitals with the same energy are called___________.

A. B. C.

quantum orbitals atomic orbitals antibonding orbitals

D. E.

bonding orbitals degenerate orbitals

Answer: E Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 63.

What is the letter designation for the following atomic orbital?

A. B. C. D. E.

s p d f g

Answer: B Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy

64.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy

65.

In quantum mechanics a node (nodal surface or plane) is the___________.

A. B. C. D. E.

location where y is negative location where y is positive location where y2 is positive location where y2 is negative location where y is zero

Answer: E Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 66.

Which of the following principle states that “Each orbital can accommodate a maximum of two electrons with opposite spin”?

A. B. C. D. E.

Aufbau principle Pauli exclusion principle Hund’s Rule Heizenberg Uncertainty principle Le Chatelier’s principle

Answer: B Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 67.

Which of the following principle states “When orbitals of equal energy are available, every orbital gets one electron before any gets two electrons”?

A. B. C. D. E.

Aufbau principle Pauli exclusion principle Hund’s Rule Heizenberg Uncertainty principle Le Chatelier’s principle

Answer: C Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 68.

Which of the following represents the ground state electron configuration for a phosphorous atom?

A. B. C. D. E.

1s22s22p63s13p4 1s22s22p63s23p4 1s22s22p63s23p3 1s22s22p63s23p2 1s22s22p63s23p5

Answer: C Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 69.

The atomic number for nitrogen is 7. Which of the following represents the ground state electron configuration for a nitrogen atom?

A. B. C. D. E.

1s22s12p4 1s22p5 2s22p5 1s22s2 2p3 1s22s23s3

Answer: D Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 70.

Which element has the ground state electron configuration of 1s22s22p63s23p5?

A. B. C. D. E.

oxygen fluorine sulfur chlorine bromine

Answer: D Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 71.

Which element has the ground state electron configuration of 1s22s22p63s23p4?

A. B.

Cl S

C. D. E.

P Al N

Answer: B Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 72.

What is the electronic configuration for the nitride ion?

A. B. C. D. E.

1s22s22p0 1s22s22p2 1s22s22p3 1s22s22p4 1s22s22p6

Answer: E Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Hard 73.

What is the electronic configuration for the magnesium ion?

A. B. C. D. E.

1s22s22p63s2 1s22s22p6 1s22s22p4 1s22s22p63s1 1s22s22p63s22p2

Answer: B Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 74.

What is the electronic configuration for the oxide ion?

A. B. C. D. E.

1s22s22p6 1s22s22p2 1s22s22p4 1s22s02p6 1s22s22p63s22p2

Answer: A Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 75.

Which element has the following electronic configuration?

1s A. B. C. D. E.

boron carbon silicon nitrogen fluorine

Answer: D Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 76.

Which element has the following electronic configuration?

1s A. B. C. D. E.

boron carbon silicon nitrogen fluorine

Answer: E Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 77.

The following ground state electron configuration violates___________.

1s A. B. C. D. E.

the Aufbau principle the Pauli Exclusion principle Hund’s Rule Heisenberg’s Uncertainty principle None of these.

Answer: C Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 78.

The following ground state electron configuration violates___________.

1s A. B. C. D. E.

the Aufbau principle the Pauli Exclusion principle Hund’s Rule Heisenberg’s Uncertainty principle None of these.

Answer: A Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 79.

The following ground state electron configuration violates___________.

1s A. B. C. D. E.

the Aufbau principle the Pauli Exclusion principle Hund’s Rule Heisenberg’s Uncertainty principle None of these.

Answer: B Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 80.

Ar, K+, and Cl– have equal numbers of electrons, and are considered isoelectronic. Select the correct ground state electron configuration for them.

A. B. C. D. E.

1s22s22p63s23p6 1s22s22p63s6 1s22s22p23s23p5 1s22s22p63s13p64s1 1s22s22p63s23p2

Answer: A Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Medium 81.

Constructive interference of waves results in___________.

A. B. C. D. E.

a wave with smaller amplitude a wave with larger amplitude cancellation of both waves formation of a node Both C and D

Answer: B Learning Objective: 1.8 Define a bond in terms of valence bond theory Difficulty: Easy 82.

Destructive interference of waves results in___________.

A. B. C. D. E.

a wave with smaller amplitude a wave with larger amplitude cancellation of both waves formation of a node Both C and D

Answer: E Learning Objective: 1.8 Define a bond in terms of valence bond theory Difficulty: Easy

83.

All single bonds can be classified as___________.

A. B. C. D. E.

nonpolar covalent polar covalent ionic sigma bonds pi bonds

Answer: D Learning Objective: 1.8 Define a bond in terms of valence bond theory Difficulty: Easy 84.

Which bonding type has circular symmetry with respect to the bond axis?

A. B. C. D. E.

sigma bond pi bond delta bond covalent bond ionic bond

Answer: A Learning Objective: 1.8 Define a bond in terms of valence bond theory Difficulty: Medium 85.

Which best describes the difference between valence bond theory and molecular orbital (MO) theory? ___________.

A. B. C. D. E.

valence bond theory requires the linear combination of atomic orbitals MO theory requires the linear combination of atomic orbitals valence bond theory considers only individual atomic orbitals Both A and B Both B and C

Answer: E Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs Difficulty: Medium 86.

How many molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?

A. B. C. D. E.

1 2 3 4 5

Answer: B Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs Difficulty: Medium 87.

Which molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?

A. B. C. D. E.

two bonding molecular orbitals only one bonding molecular orbital one bonding molecular orbital and one antibonding molecular orbital two antibonding molecular orbitals only one antibonding orbital

Answer: C Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs Difficulty: Medium 88.

How are electrons distributed in the molecular orbitals when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?

A. B.

two electrons in the bonding molecular orbital one electron in the bonding molecular orbital, one electron in the non–bonding molecular orbital one electron in the bonding molecular orbital, one electron in the antibonding molecular orbital two electrons in the antibonding molecular orbital two electrons in the non–bonding molecular orbital

C. D. E.

Answer: A Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs Difficulty: Medium

89.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

According to molecular orbital theory the highest energy molecular orbital that is occupied with an electron is referred to as___________.

A. B. C. D. E.

degenerate antibonding the LCAO the LUMO the HOMO

Answer: E

Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs Difficulty: Easy 92.

According to molecular orbital theory the lowest energy molecular orbital that is unoccupied with an electron is referred to as___________.

A. B. C. D. E.

degenerate antibonding the LCAO the LUMO the HOMO

Answer: D Learning Objective: 1.9 Compare and contrast molecular orbital theory and valence bond theory, molecular orbitals and atomic orbitals, and bonding MOs and antibonding MOs Difficulty: Easy 93.

Identify the incorrect statement in regards to the overlap of 1s atomic orbitals of two hydrogen atoms resulting in constructive interference?

A. B. C. D. E.

a sigma bonding molecular orbital is formed the bonding molecular orbital formed is lower in energy than the 1s atomic orbital the bonding molecular orbital formed has a node between the atoms the bonding molecular orbital formed has circular symmetry a maximum of two electrons may occupy the bonding molecular orbital

For the following chemical reaction, how many hydrogen atoms are added or lost?

A. B. C. D. E.

one hydrogen atom added two hydrogen atoms added one hydrogen atom lost two hydrogen atoms lost no change in the number of hydrogen atoms

Answer: D

Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 95.

For the following chemical reaction, how many hydrogen atoms are added or lost?

A. B. C. D. E.

one hydrogen atom added two hydrogen atoms added one hydrogen atom lost two hydrogen atoms lost no change in the number of hydrogen atoms

Interaction of the following two atomic orbitals in the orientation shown results in what kind of molecular orbital?

A. B. C. D. E.

a sigma bonding molecular orbital is formed a pi bonding molecular orbital is formed a sigma antibonding molecular orbital is formed a pi antibonding molecular orbital is formed destructive interference occurs so no molecular orbital is formed

Answer: B Learning Objective: 1.9 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 97.

Interaction of the following two atomic orbitals results in what kind of molecular orbital, in the orientation shown?

A. B. C. D. E.

a sigma bonding molecular orbital is formed a pi bonding molecular orbital is formed a sigma antibonding molecular orbital is formed a pi antibonding molecular orbital is formed constructive interference occurs so no molecular orbital is formed

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 98.

What is the hybridization state of the oxygen atom in the following compound?

A. B. C. D. E.

sp sp2 sp3 sp3d s2 p

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 99.

What is the hybridization state of the carbon in CO2?

A. B. C. D. E.

sp sp2 sp3 sp3d s2 p

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

Difficulty: Medium 100.

What is the hybridization state of the nitrogen atom in the following compound?

A. B. C. D. E.

sp sp2 sp3 sp3d s2 p

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 101.

What is the hybridization state of the boron atom in the following compound?

A. B. C. D. E.

sp sp2 sp3 sp3d s2 p

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 102.

What is the hybridization state of the carbon (I) atom in the following compound?

B. C. D. E.

sp2 sp3 sp3d sp3d2

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 103.

What is the hybridization state of the nitrogen atom in the following compound?

A. B. C. D. E.

sp sp2 sp3 sp4 s2 p

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 104.

The lone pairs of electrons on the nitrogen atom in the following compound are located in which orbital?

A. B. C. D. E.

sp2 sp3 sp s p

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium

105.

Which of the following structures have carbon with sp2 hybridization state?

A. B. C. D. E.

I and II III and IV I and III II and IV I and IV

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 106.

Which of the indicated carbon atoms have sp2 hybridization state in the following compound?

A. B. C. D. E.

I and II III and IV II and III I and III II and IV

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 107.

What is the correct order of hybridization state for the numbered carbon atoms in the following compound?

A. B. C. D. E.

I = sp3, II = sp2, III = sp I = sp2, II = sp, III = sp2 I = sp, II = sp2, III = sp3 I = sp, II = sp2, III = sp I = sp2, II = sp3, III = sp2

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 108.

How many s—sp2 sigma bonds are in the following compound?

A. B. C. D. E.

2 3 4 5 6

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 109.

The C2—C3 bond in the following compound results from the overlap of which orbitals?

A. B. C.

sp–sp2 sp–sp3 sp2–sp2

D. E.

sp2–sp3 sp3–sp2

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 110.

The sigma bond that is part of C=C in the following compound results from the overlap of which orbitals?

A. B. C. D. E.

sp–sp2 sp–sp3 sp2–sp2 sp2–sp3 sp3–sp2

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 111.

The C—C sigma bond in ethyne (H—CºC—H) results from the overlap of which orbitals?

A. B. C. D. E.

sp–sp sp–sp3 sp2–sp2 sp–s p–p

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 112.

How many pi bonds are present in the following compound?

A. B. C. D. E.

one two three four five

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 113.

How many pi bonds are present in the following compound?

A. B. C. D. E.

two three four five six

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 114.

How many sigma bonds are present in the following compound?

A. B. C.

20 22 24

D. E.

25 27

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 115.

The sigma bond that is part of C=N in the following compound results from the overlap of which orbitals?

A. B. C. D. E.

sp2–sp2 sp–sp sp2–sp3 sp3–sp3 sp3–sp2

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 116.

The bonds indicated by the arrow in the following compound results from the overlap of which orbitals?

A. B. C. D. E.

sp2–sp2 sp3–sp3 p–p Both A and B Both A and C

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium

117.

Which orbitals are involved in the C—O sigma bond in acetone, shown below?

A. B. C. D. E.

Csp2—Osp2 Csp3—Osp3 Csp—Osp Cp—Op Csp—Op

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 118.

Which of the following best describes the orbitals involved in the formation of the C=O bond in acetone, shown below?

A. B. C. D. E.

s = C sp 2 œO sp 2 and p = C sp 2 - O sp 2

s = C sp 2 œO sp 2 and p = C p - O p s = C sp 3 œO sp 2 and p = C p - O p s = C p œO p

and p = C sp 2 - O sp 2

s = C sp œO sp

and p = C p - O p

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 119.

The C—H bond in the methyl cation, CH3+, results from the overlap of which orbitals?

A. B.

sp3–sp2 sp3–sp3

C. D. E.

sp2–s sp3–p p–s

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 120.

The lone pair of electrons in the methyl anion, :CH3—, resides in which orbital?

A. B. C. D. E.

s2 p sp sp3 sp2

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 121.

What is the hybridization state of the indicated atoms in the following compound?

A. B. C. D. E.

I = sp ; I = sp2 ; I = sp3 ; I = sp2 ; I = sp2 ;

II = sp2 ; II = sp ; II = sp2 ; II = sp3 ; II = sp2 ;

III = sp3 ; III = sp2 ; III = sp ; III = sp2 ; III = sp2 ;

IV = sp2 IV = sp3 IV = sp2 IV = sp IV = sp3

Answer: B Learning Objective: 1.10 Explain how pi bonds an sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 122.

The carbon and oxygen atoms in carbon monoxide are connected by which type of bond(s)?

A. B. C. D. E.

a sigma (s) bond two sigma (s) bonds a pi (p) bond two pi (p) bonds both A and D

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 123.

The N—H bond in the following compound is a ___________ and is formed from the___________.

A. B. C. D. E.

σ bond; sp2 – s orbital overlap σ bond; sp3 – s orbital overlap π bond; sp3 – s orbital overlap π bond; sp2 – p orbital overlap π bond; p – p orbital overlap

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 124.

Identify the shortest bond in the following compound.

A. B. C. D. E.

I II III IV I and III have the same length

Answer: C

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 125.

Identify from the following options the compound having the shortest carbon– carbon bond?

A. B. C. D. E.

I II III IV All the carbon bonds are equal in length

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 126. Which of the statements best describes the carbon-carbon bond length and strength for the following compounds.

A. B. C. D. E.

the shortest and strongest bond is found in compound I the shortest and strongest bond is found in compound II the shortest and weakest bond is found in compound I the shortest and weakest bond is found in compound II the shortest bond is found in compound I and the weakest bond in compound II

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 127.

Identify the longest C—C bond(s) in the following compound?

A. B. C. D. E.

I II III I and III I and II

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 128.

Rank the indicated C—C bonds in increasing order of bond length.

A. B. C. D. E.

I < II < III II < III < I III < I< II II < I< III I < III< II

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 129.

Identify the compound with the strongest carbon – nitrogen bond.

A. B. C. D. E.

CH3CH2CH=NH CH3CH2NH2 CH3CH2C≡N (CH3)3N The strength of the carbon-nitrogen bonds are the same

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 130.

Identify the compound with the longest carbon – nitrogen bond.

A. B. C. D. E.

CH3CH2CH=NH CH3CH2NH2 CH3CH2C≡N CH3CH=NCH3 The length of all the carbon-nitrogen bonds are the same

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 131.

What is the molecular geometry at the central atom in in the molecule shown in the box?

A. B. C. D. E.

tetrahedral trigonal planar trigonal pyramidal square planar linear

Answer: A Learning Objective: 1.11 Describe VSEPR theory Difficulty: Easy 132.

Identify the following compound(s) having trigonal planar molecular geometry?

B. C. D. E.

II III IV I and IV

Answer: A Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Easy 133.

Identify the following compound(s) having trigonal pyramidal molecular geometry?

A. B. C. D. E.

I II III IV I and IV

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Easy 134.

Identify the following compound(s) having bent molecular geometry?

A. B. C. D. E.

I II III IV I and IV

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium

135.

Identify the following compound(s) having trigonal planar molecular geometry?

A. B. C. D. E.

I, II and III II and III III and V V only All of these

Answer: C Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 136.

Identify the following compound(s) having tetrahedral arrangement of electron pairs?

A. B. C. D. E.

I, II and III I, II, IV and V III and IV and V IV and V All of these

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 137.

Which of the following compounds have trigonal planar arrangement of electron pairs?

A. B. C.

I, II and III I, II, IV and V III and IV and V

D. E.

II and III All of these

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 138.

What is the molecular geometry at the central atom in in the molecule shown in the box?

A. B. C. D. E.

trigonal planar trigonal pyramidal square planar tetrahedral None of these

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 139.

What is the molecular geometry at the central atom in the molecule shown in the box?

A. B. C. D. E.

trigonal planar trigonal pyramidal square planar tetrahedral bent

Answer: A Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 140.

What is the molecular geometry at the nitrogen atom in the following compound?

A. B. C. D. E.

trigonal planar trigonal pyramidal linear tetrahedral bent

Answer: E Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 141.

Which compound does NOT have a linear molecular geometry?

A. B. C. D. E.

CO2 H2 O BeCl2 HCN C2 H2

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 142.

What is the approximate bond angle around the indicated carbon atom?

A. B. C. D. E.

60° 90° 109.5° 120° 180°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Easy

143.

What is the approximate bond angle around the indicated carbon atom?

A. B. C. D. E.

60° 90° 109.5° 120° 180°

Answer: E Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Easy 144.

What is the approximate bond angle around the nitrogen atom?

A. B. C. D. E.

90° 109.5° 120° 180° 100°

Answer: C Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 145.

What is the hybridization state and molecular geometry around the carbon atom in the molecule shown in the box?

A. B. C. D.

90° 109.5° 105° 120°

180°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 146.

What is the hybridization state and molecular geometry around the carbon atom in the molecule shown in the box?

A. B. C. D. E.

sp2, 120° sp, 180° sp3, 109.5° sp3, 120° sp, 120°

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 147.

What is the hybridization state and approximate bond angle around nitrogen in the following compound?

A. B. C. D. E.

sp2, 109.5° sp2, 107° sp3, 109.5° sp3, 107° sp2, 120°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 148.

What is the hybridization state and approximate bond angle around oxygen in the following compound?

A. B. C. D. E.

sp, 109.5° sp2, 109.5° sp3, 109.5° sp2, 120° sp, 180°

Answer: C Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Hard 149.

What is the hybridization state and molecular geometry around the sulfur atom in the molecule shown in the box?

A. B. C. D. E.

sp2, tetrahedral sp2, trigonal planar sp3, tetrahedral sp3, trigonal pyramidal sp2, trigonal pyramidal

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Hard 150.

What is the hybridization state and molecular geometry around the carbon atom in the molecule shown in the box?

A. B. C. D. E.

sp, linear sp2, trigonal planar sp3, tetrahedral sp3, trigonal pyramidal sp2, trigonal pyramidal

Answer: A Learning Objective: 1.11 Describe VSEPR Theory

Difficulty: Medium 151.

Identify the hybridization state, molecular geometry and approximate bond angle for the species shown in box below.

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, 120° sp2, trigonal pyramidal, 180°

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 152.

Identify the hybridization state, molecular geometry and approximate bond angle for the species shown in box below.

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, <109.5° sp2, trigonal pyramidal, 180°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 153.

Identify the hybridization state, molecular geometry and approximate bond angle around the central atom for the molecule shown in box below.

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, <109.5° sp2, trigonal pyramidal, 180°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Hard 154.

Identify the hybridization state, molecular geometry and approximate bond angle around the carbon atom for the molecule shown in box below.

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, <109.5° sp2, trigonal pyramidal, 180°

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Hard 155.

Following is the structure for Propranolol, an antihypertensive drug. Identify the hybridization state, molecular geometry and approximate bond angle at the nitrogen atom in Propranolol.

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, ~109.5° sp2, trigonal pyramidal, 180°

Answer: B

Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 156.

Identify the hybridization state, molecular geometry and approximate bond angle at the indicated nitrogen atom in the following compound.

A. B. C. D. E.

sp2, bent, 109° sp2, bent, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, ~109.5° sp2, trigonal pyramidal, 120°

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Hard 157.

Tryptophan is an essential amino acid that is important in the synthesis of the neurotransmitter serotonin. Identify the hybridization state, molecular geometry and approximate bond angle at the indicated carbon atom.

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, ~109.5° sp2, trigonal pyramidal, 180°

Answer: B Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Hard 158.

Which of the following covalent bonds has the largest dipole moment?

A. B. C. D. E.

C—C C—H C—O N—H H—F

Answer: E Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Easy 159.

Which of the following compounds has no dipole moment?

A. B. C. D. E.

CH4 NH3 HF HCl HBr

Answer: A Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Easy 160.

Which of the following compounds has polar covalent bonds?

A. B. C. D. E.

NH3 Na2O H2 KF CH4

Answer: A Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Easy 161.

Which of the following compounds have a net dipole moment?

A. B. C. D.

CBr4 CO2 CH4 H2 O

C2 H4

Answer: D Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Medium 162.

Which of the following compounds does not have a dipole moment?

A. B. C. D. E.

HCl NCl3 CO BF3 H2 O

Answer: D Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Medium 163.

Which of the following compounds has a net dipole moment of zero?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Medium 164.

Identify the following compound(s) having a dipole moment?

A. B. C. D. E.

II III II and III I, II and III II, III and IV

Answer: E Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Medium 165.

Rank the following compounds in order of decreasing dipole moment.

A. B. C. D. E.

I > II > III II > III > I I > III > II III > II > I II > I > III

Answer: D Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Hard 166.

Rank the following compounds in order of decreasing dipole moment.

A. B. C. D. E.

I > II > III II >III > I I > III > II III > I > II II > I > III

Answer: D

Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Medium

167.

For the following transformation, how many hydrogen atoms are added or lost?

A. B. C. D. E.

one hydrogen atom added two hydrogen atoms added one hydrogen atom lost two hydrogen atoms lost no change in the number of hydrogen atoms

For the following equation, how many hydrogen atoms are added or lost?

A. B. C. D. E.

one hydrogen atom added two hydrogen atoms added one hydrogen atom lost two hydrogen atoms lost no change in the number of hydrogen atoms

For the following equation, how many hydrogen atoms are added or lost?

one hydrogen atom added

B. C. D. E.

two hydrogen atoms added one hydrogen atom lost two hydrogen atoms lost no change in the number of hydrogen atoms

170.

Which of the intermolecular forces listed below is generally considered the strongest?

A. B. C. D. E.

London dispersion forces fleeting dipole-dipole interactions dipole-dipole interactions hydrogen bonding the vital force

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 171.

Which intermolecular force is generally considered the weakest?

A. B. C. D. E.

ion-dipole interactions London dispersion forces dipole-dipole interactions hydrogen bonding covalent bonding

Answer: B Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 172.

Which intermolecular force is primarily responsible for base pairing within the double helix of DNA?

A. B. C.

ion-dipole interactions London dispersion forces dipole-dipole interactions

D. E.

hydrogen bonding covalent bonding

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 173.

What is the strongest intermolecular force possible between molecules of the following structure?

A. B. C. D. E.

ion-dipole interactions London dispersion forces dipole-dipole interactions hydrogen bonding covalent bonding

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 174.

What is the strongest intermolecular force possible between molecules of the following structure?

A. B. C. D. E.

ion-dipole interactions London dispersion forces dipole-dipole interactions hydrogen bonding covalent bonding

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 175.

Which of the following statements best explains the observation that hydrogen fluoride has the highest boiling point of all the hydrogen halides?

A. B. C. D. E.

The fluorine in HF is the smallest atom for all of the halogens. Fluorine is the most electronegative of the atoms. Hydrogen fluoride can participate in hydrogen bonding. HF is very reactive and can react and dissolve glass. HF is a weak acid, and doesn’t completely dissociate.

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 176.

Identify the following compound(s) having the greatest London dispersion forces between like molecules?

A. B. C. D. E.

I II III IV II and IV

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 177.

Identify the following compound(s) having the highest boiling point?

A. B. C. D. E.

I II III IV II and III

Answer: B

Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 178.

Identify the following compound(s) having the lowest boiling point?

A. B. C. D. E.

I II III IV II and IV

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 179.

Which of the following compounds have the lowest boiling point?

A. B. C. D. E.

CH3Cl CH2Cl2 CH4 CHCl3 CCl4

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 180.

Identify the following compound(s) having the lowest boiling point?

B. C. D. E.

II III IV I and III

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 181.

Rank the following compounds in decreasing order of boiling point.

A. B. C. D. E.

III > I > IV > II II > I > IV > III III > I > II > IV IV > II > I > III I > III > II > IV

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 182.

Rank the following compounds in decreasing order of boiling point.

A. B. C. D. E.

III > I > IV > II II > IV > I > III III > I > II > IV IV > II > I > III I > III > II > IV

Answer: B Learning Objective: 1.13 Describe the basic nature of all intermolecular forces

Difficulty: Hard 183.

Rank the following compounds in decreasing order of boiling point.

A. B. C. D. E.

III > I > IV > II II > IV > III > I III > I > II > IV IV > II > I > III I > III > II > IV

Answer: A Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 184.

For the following equation, how many hydrogen atoms are added or lost?

A. B. C. D. E.

one hydrogen atom added two hydrogen atoms added one hydrogen atom lost two hydrogen atoms lost no change in the number of hydrogen atoms

What is the correct Lewis structure for the molecule shown in the box below?

A. B. C. D. E.

I II III IV none of these

186.

Identify the following compound(s) expected to be the most soluble in water?

A. B. C. D. E.

I II III IV II and III

Answer: B Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility Difficulty: Easy 187.

Identify the following compound(s) expected to be the most soluble in butane, CH3CH2CH2CH3?

A. B. C. D. E.

I II III IV II and III

For soap to remove and dissolve oil in water, what molecular features are needed?

A. B. C. D. E.

one end of the molecule must be polar the compound must contain oxygen atoms one end of the molecule must be nonpolar Both A and C All A, B and C

Answer: D Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility Difficulty: Medium 189.

Amino acids are the building blocks of proteins. Which statement best describes the physical properties of the following amino acid?

A. B. C. D. E.

high melting point and low solubility in water large dipole moment and no hydrogen bonding high melting point and large dipole moment low solubility in water and small dipole moment small dipole moment and hydrophobic

Answer: C Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil

or grease from clothing, including a statement of the basic principle involved in solubility Difficulty: Medium 190.

Which statement best describes the physical properties of the following sugar?

A. B. C. D. E.

high melting point and high solubility in water large dipole moment and no hydrogen bonding low melting point and large dipole moment low solubility in water and large dipole moment small dipole moment and hydrophobic

Answer: A Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility Difficulty: Medium 191. Naproxen, sold under the trade name Aleve, has the following structure. What is the molecular formula for naproxen?

A. B. C. D. E.

C13H15O3 C14H14O3 C12H16O3 C14H16O3 C14H18O3

192. AZT, used in the treatment of AIDS, has the following structure. What is the molecular formula for AZT?

A. B. C. D. E.

C9H14N5O4 C9H9N5O4 C9H12N5O4 C10H13N5O4 C11H12N5O4

Answer: D Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 193. Capsaicin, found in peppers, has the following structure. What is the molecular formula for capsaicin?

A. B. C. D. E.

C18H27NO3 C18H27NO3 C18H27NO3 C18H27NO3 C18H27NO3

Answer: A Learning Objective: 1.6 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium

194.

Of the following examples, which would be considered organic compounds?

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: E Learning Objective: 1.1 Compare and contrast organic and inorganic compounds Difficulty: Easy 195.

Constitutional isomers differ in ____________.

A. B. C. D. E.

physical properties atomic connectivity molecular formula A and B B and C

Answer: D

Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 196.

What is the relationship between the following compounds?

A. B. C. D. E.

isotopes constitutional isomers the same structure composed of different elements no relationship

Answer: B Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 197.

What is the relationship between the following compounds?

A. B. C. D. E.

resonance isomers constitutional isomers empirical isomers There is no relationship isotopes

Answer: B Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 198.

Which of the following compounds are constitutional isomers?

A. B. C. D. E.

I and II I and III I, II and IV II, III and IV I, II, and III

Answer: E Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 199.

Which of the following compounds are constitutional isomers of each other?

A. B. C. D. E.

I and II II and III III and IV I and IV II and III

Answer: D Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 200.

Identify three constitutional isomers having the molecular formula C4H8BrCl

A. B. C. D. E.

I, II, and III II, III, and IV III, IV, and IV I, III, and V II, III, and V

Answer: D Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Easy 201.

Identify three constitutional isomers having the molecular formula C4H8O.

A. B. C. D. E.

I, II, and III II, III, and IV III, IV, and IV I, II, and IV II, III, and V

Answer: B Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 202.

Which of the following represent identical molecules?

A. B. C. D. E.

I and II II and III III and IV IV and V II and IV

Answer: E Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium

203. Identify the two compounds that are NOT constitutional isomers having the molecular formula C4H8O.

A. B. C. D. E.

I and V II and IV I and III II and IV III and V

Answer: A Learning Objective: 1.2 Describe structural theory of matter, molecular formula and structural formula Difficulty: Medium 204.

What are the formal charges on the atoms indicated for the following structure?

A. B. C. D. E.

I = 0; I = 1-; I = 1+; I = 1-; I = 0;

II = 1+; II = 0; II = 1-; II = 1+; II = 1-;

III = 2+ III = 1+ III = 2+ III = 1III = 2+

Answer: E Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 205.

What are the formal charges on fluorine and nitrogen in the following structure?

A. B. C. D. E.

F = 1+, N = 1+ F = 0, N = 1F = 1-, N = 1F = 0, N = 1+ F = 1+, N = 1-

Answer: D Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 206.

What are the formal charges on boron and oxygen in the following structure?

A. B. C. D. E.

B = 1-, O = 1B = 1-, O = 1+ B = 1+, O = 1+ B = 1+, O = 1B = 1-, O = 0

Answer: B Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated Difficulty: Medium 207.

Which of the following have a 1+ formal charge on the central atom?

A. B. C. D. E.

I II III III and V IV and V

Answer: E Learning Objective: 1.4 Define formal charge and describe how formal charge is calculated

Difficulty: Medium 208.

Which of the following principle states “The lowest energy orbital is filled first”?

A. B. C. D. E.

Aufbau principle Pauli exclusion principle Hund’s Rule Heizenberg Uncertainty principle Le Chatelier’s principle

Answer: A Learning Objective: 1.7 Describe the shape and phase of s and p atomic orbitals and the process of filling orbitals with electrons Difficulty: Easy 209.

Which of the indicated carbon atoms in the following compound have an sp2 hybridization state?

A. B. C. D. E.

I and II III and IV II and III I and III II and IV

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 210.

What is the correct order of hybridization state for the numbered carbon atoms in the following compound?

A. B.

I = sp3, II = sp2, III = sp I = sp2, II = sp, III = sp2

C. D. E.

I = sp, II = sp2, III = sp3 I = sp, II = sp2, III = sp I = sp2, II = sp3, III = sp2

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 211.

How many s—sp2 sigma bonds are in the following compound?

A. B. C. D. E.

2 3 4 5 6

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 212.

The C2—C3 bond in the following compound results from the overlap of which orbitals?

A. B. C. D. E.

sp–sp2 sp–sp3 sp2–sp2 sp2–sp3 sp3–sp2

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 213.

The sigma bond that is part of C=C in the following compound results from the overlap of which orbitals?

A. B. C. D. E.

sp–sp2 sp–sp3 sp2–sp2 sp2–sp3 sp3–sp2

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 214.

How many pi bonds are present in the following compound?

A. B. C. D. E.

one two three four five

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 215.

How many pi bonds are present in the following compound?

A. B. C. D. E.

two three four five six

Answer: E

Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 216.

How many sigma bonds are present in the following compound?

A. B. C. D. E.

20 22 24 25 27

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 217.

The sigma bond that is part of C=N in the following compound results from the overlap of which orbitals?

A. B. C. D. E.

sp2–sp2 sp–sp sp2–sp3 sp3–sp3 sp3–sp2

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 218.

The bonds indicated by the arrow in the following compound results from the overlap of which orbitals?

sp2–sp2

B. C. D. E.

sp3–sp3 p–p Both A and B Both A and C

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 219.

Which orbitals are involved in the C—O sigma bond in acetone, shown below?

A. B. C. D. E.

Csp2—Osp2 Csp3—Osp3 Csp—Osp Cp—Op Csp—Op

Answer: A Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 220.

Which of the following best describes the orbitals involved in the formation of the C=O bond in acetone, shown below?

A. B. C. D. E.

s = C sp 2 œO sp 2 and p = C sp 2 - O sp 2

s = C sp 2 œO sp 2 and p = C p - O p s = C sp 3 œO sp 2 and p = C p - O p s = C p œO p

and p = C sp 2 - O sp 2

s = C sp œO sp

and p = C p - O p

Answer: B Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium

221.

Identify the shortest bond in the following compound.

A. B. C. D. E.

I II III IV I and III are of equal length

Answer: C Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Easy 222.

Identify the longest C—C bond(s) in the following compound?

A. B. C. D. E.

I II III IV II and IV are of equal length

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 223.

Identify the longest C—C bond(s) in the following compound?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Medium 224.

Identify the longest C—C bond(s) in the following compound?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed Difficulty: Hard 225.

Rank the indicated C—C bonds in increasing order of bond length.

A. B. C. D. E.

I < II < III < IV II < IV < III < I III < I < IV < II III < I < II < IV IV < II < I < III

Answer: D Learning Objective: 1.10 Explain how pi bonds and sp3, sp2, and sp hybrid orbital sets are formed

Difficulty: Hard 226.

Following is the structure for Propranolol, an antihypertensive drug. Identify the hybridization state, molecular geometry and approximate bond angle at the indicated oxygen atom in Propranolol?

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, bent, 120° sp3, tetrahedral, 109.5° sp3, bent, ~109.5° sp2, bent, 180°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 227.

Following is the structure for Propranolol, an antihypertensive drug. Identify the hybridization state, molecular geometry and approximate bond angle at the nitrogen atom in Propranolol?

A. B. C. D. E.

sp2, tetrahedral, 109° sp2, trigonal planar, 120° sp3, tetrahedral, 109.5° sp3, trigonal pyramidal, ~109.5° sp2, trigonal pyramidal, 180°

Answer: D Learning Objective: 1.11 Describe VSEPR Theory Difficulty: Medium 228.

Rank the following compounds in order of decreasing dipole moment.

A. B. C. D. E.

I > II > III II >III > I I > III > II III > I > II II > I > III

Answer: D Learning Objective: 1.12 Describe how dipole moment is used in calculating the ionic character of a bond Difficulty: Medium 229.

What is the strongest intermolecular force possible between molecules of the following structure?

A. B. C. D. E.

ion-dipole interactions London dispersion forces dipole-dipole interactions hydrogen bonding covalent bonding

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 230.

What is the strongest intermolecular force possible between molecules of the following structure?

A. B. C. D. E.

ion-dipole interactions London dispersion forces dipole-dipole interactions hydrogen bonding covalent bonding

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 231.

Which of the following compounds have the greatest London dispersion forces between like molecules?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 232.

Identify the following compound expected to have the highest boiling point?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 233.

Identify the following compound expected to have the lowest boiling point?

B. C. D. E.

II III IV V

Answer: A Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Easy 234.

Identify the following compound expected to have the lowest boiling point?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 235.

Rank the following compounds in decreasing order of boiling point.

A. B. C. D. E.

III > I > IV > II II > I > IV > III III > I > II > IV IV > II > I > III I > III > II > IV

Answer: D Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 236.

Rank the following compounds in decreasing order of boiling point.

A. B. C. D. E.

III > I > IV > II II > IV > I > III III > I > II > IV IV > II > I > III I > III > II > IV

Answer: B Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 237.

Rank the following compounds in decreasing order of boiling point.

A. B. C. D. E.

III > I > IV > II II > IV > III > I III > IV > I > II IV > II > I > III I > III > II > IV

Answer: A Learning Objective: 1.13 Describe the basic nature of all intermolecular forces Difficulty: Medium 238.

Identify the following compound expected to be the most soluble in water?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil

or grease from clothing, including a statement of the basic principle involved in solubility Difficulty: Easy 239.

Identify the following compound expected to be the most soluble in butane, CH3CH2CH2CH3?

A. B. C. D. E.

I II III IV V

Amino acids are the building blocks of proteins. Which statement best describes the physical properties of the following amino acid?

A. B. C. D. E.

Answer: C Learning Objective: 1.14 Compare the actions of soap and dry cleaning in removing oil or grease from clothing, including a statement of the basic principle involved in solubility Difficulty: Medium 241.

Which statement best describes the physical properties of the following sugar?

A. B. C. D. E.

Klein, Organic Chemistry 4e Chapter 2 1.

What is the molecular formula for the following compound? H H H H H C C O C C H H H

A. B. C. D. E.

H H

C2 H6 O C4 H6 O C4H10O C2 H4 O None of these

Answer: C Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 2.

Which of the following compounds have a molecular formula of C2H6O?

A. B. C. D. E.

I II III IV Both I and III

Answer: E Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 3.

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3CHCH3CH2OH CH3CH2CH2OH (CH3)2CHCH2OH CH3CH2CH2OCH3 CH3CH3CHCH2OH

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3CHOHCH2CHClCH3 CH3CHOH(CH2)2CHClCH3 (CH3)2CHOHCH2CH2Cl HOCH3CHCH2CH2CH3CHCl CH3C2H4CH3OHCl

Answer: B Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 5.

Which of the following is the correct condensed structure for the following compound?

A. B. C.

CH2=CH(CH2)3C(CH3)3 CH2=(CH2)4C(CH3)3 (CH3)2CH(CH2)4CH3

D. E.

CH2=C(CH2)3(CCH3)3 (CH)3(CH2)3C(CH3)3

Answer: A Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 6.

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

HC≡C(CH2)3C(CH3)3 HC≡C(CH2)3C(CH3CH3CH3) (CH3)3C2(CH2)3CH3 CH3C≡C(CH2)3C(CH3)3 CH3C≡C((CH2)C(CH3))3

Answer: D Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 7.

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3C(CH3)2(CH2)2(CH)BrC(CH3)2 CH3CH3CH3C(CH2)2C(CH3)2CHBr (CH3)3C(CH2)3BrCHCH3CH3 CH3CH3CH3C(CH2)2CHBrCHCH3CH3 (CH3)3C(CH2)2CHBrCH(CH3)2

What is the molecular formula for the following compound?

A. B. C. D. E.

C2H6O C4H6O C4H10O C2H4O C2H5O

Which of the following compounds have a molecular formula of C2H6O?

A. B. C. D. E.

I II III IV V

10.

Which of the following is the correct molecular formula for (CH3CH2)4C?

A. B. C. D. E.

C8H20 C5H20 C9H20 C6 H5 C3H20

Which of the following is the correct Lewis structure for CH3(CH2)2NH2?

A. B. C. D. E.

I II III IV V

Which of the following is the correct Lewis structure for CH3(CH2)2OH?

A. B.

I II

C. D. E.

III IV V

Which of the following is the correct Lewis structure for (CH3)2CHCH2OH?

A. B. C. D. E.

I II III IV V

Which of the following is the correct Lewis structure for (CH3)3C(CH2)2NHCH3?

A. B. C. D. E.

I II III IV V

Which of the following is the correct Lewis structure for CH3C≡C(CH2)3C(CH3)3?

A. B.

I II

C. D. E.

III IV V

Which of the following (CH3)3C(CH2)2OCH(CH2CH3)2?

A. B. C. D. E.

I II III IV V

the

correct

Lewis

structure

for

Identify the partially condensed structure for the molecule shown in the box below.

A. B. C. D. E.

I II III IV V

Identify the partially condensed structure for the molecule shown in the box below.

19.

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3CHCH3CH2OH CH3CH2CH2OH (CH3)2CHCH2OH CH3CH2CH2OCH3 CH3CH3CHCH2OH

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3CHOHCH2CHClCH3 CH3CHOH(CH2)2CHClCH3 (CH3)2CHOHCH2CH2Cl HOCH3CHCH2CH2CH3CHCl CH3C2H4CH3OHCl

Which of the following is the correct condensed structure for the following compound?

A. B. C. D.

CH2=CH(CH2)3C(CH3)3 CH=(CH2)4C(CH3)3 (CH3)2CH(CH2)4CH3 CH2=C(CH2)3(CCH3)3

(CH)3(CH2)3C(CH3)3

A. B. C. D. E.

HC≡C(CH2)3C(CH3)3 HCC(CH2)3C(CH3CH3CH3) (CH3)3C2(CH2)3CH3 CH3C≡C(CH2)3C(CH3)3 CH3CC((CH2)C(CH3))3

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3C(CH3)2(CH2)2(CH)BrC(CH3)2 CH3CH3CH3C(CH2)2C(CH3)2CHBr (CH3)3C(CH2)3BrCHCH3CH3 CH3CH3CH3C(CH2)2CHBrCHCH3CH3 (CH3)3C(CH2)2CHBrCH(CH3)2

24. Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3CH3CH3CCH2CH2OCHCH2CH3CH2CH3 (CH3)3(CH2)2OC(CH2CH3)2 (CH3)3CCH2OCHCH2CH3 (CH3)3C(CH2)2OCH(CH2CH3)2 (CH3)3(CCH2)2O(CHCH2CH3)2

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

(CH3)2N(CH2)3CH(CH3)2 CH3CH2NCH2CH(CH3)2 N(CH3)2CH(CH2)3(CH3)2 CH3CH3NCH23CHCH3CH3 (CH3)2(NCH2)3(CHCH3)2

26.

Tamiflu®, the most effective antiviral drug used to treat avian influenza, has the following structure. Identify the functional groups in Tamiflu®.

A. B. C. D. E.

I = ester; I = ether; I = ester; I = alcohol; I = ether;

II = aromatic; II = aromatic; II = alkene; II = alkyne; II = alkene;

III = carboxylic acid III = anhydride III = ether III = carboxylic acid III = ester

Answer: E Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 27.

Aspartame, an artificial sweetener used in Equal® and diet beverages, has the following structure. Identify the functional groups in Aspartame.

A. B. C. D. E.

I = aromatic; I = alkene; I = aromatic; I = alkene; I = aromatic;

II = amine; II = amide; II = amine; II = amine; II = amide;

III = carboxylic acid III = alcohol III = ester III = anhydride III = carboxylic acid

Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 28.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 29.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 30.

Which of the following structures have -1 as a formal charge on an oxygen atom?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium

Which of the following structures have -1 as a formal charge on the nitrogen atom?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 32.

How many lone pairs of electrons are found on the indicated atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy

33.

Which of the following is the correct bond-line structure for (CH3)4C?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 34.

Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 35.

Which of the following (CH3)2CHCH2C(CH3)3?

the

correct

bond-line

structure

for

B. C. D. E.

II III IV V

Answer: D Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 36.

Which of the following CH3C≡C(CH2)2CH(CH3)2?

A. B. C. D. E.

I II III IV V

the

correct

bond-line

structure

for

Answer: E Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 37.

Which of the following is CH3CHOH(CH2)2CH(CH2CH3)2?

A. B. C. D.

I II III IV

the

correct

bond-line

structure

for

Which of the following CH3CH2O(CH2)2CH(CH3)2.

A. B. C. D. E.

I II III IV V

the

correct

bond-line

structure

for

Answer: A Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 39.

Which of the following (CH3)2N(CH2)3CH(CH3)2.

A. B. C. D. E.

I II III IV V

Answer: B

the

correct

bond-line

structure

for

Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 40.

Which of the following is CH3C≡C(CH2)3C(CH3)2CH2OCH3.

A. B. C. D. E.

I II III IV V

the

correct

bond-line

structure

for

Identify bond-line structures for constitutional isomer with a molecular formula of C2H4O.

A. B. C. D. E.

I and V II and IV I, III, and V II, III, and IV IV and V

Identify bond-line structures for constitutional isomers with a molecular formula of C3H8O.

A. B. C. D. E.

I and II I and III II, IV, and V II and IV I and IV

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

(CH3)3C(CH2)2(CH2CH3)(CH2)2CH(CH3)CH2CH3 (CH3)3CCH2CH(CH2CH3)2(CH2)2CHCH3 CH3CH3CH3CCH2CH(CH2CH3)CH2CH(CH3)CH2CH3 (CH3)3CCH2CHCH2CH3CH2CHCH3CH2CH3 (CH3)3CCH2CH(CH2CH3)(CH2)2CH(CH3)CH2CH3

44.

Which of the following is the correct condensed structure for the following compound?

A. B. C. D. E.

CH3CH3CH3C(CH2)2CH(NH2)CH=CHCH3 (CH3)3C(CH2)2CH(NH2)CH=CHCH3 (CH3)3CCH2CH(NH2)CH=CHCH3 (CH3)3CCH2CHN(H)2(CH)2CH3 (CH3C)3(CH2)2CHNH2(CH)2CH3

Identify bond-line structures for constitutional isomers with a molecular formula of C4H10O.

A. B. C. D. E.

I and II II and III III and IV IV and V II and IV

Identify bond-line structures for constitutional isomers with a molecular formula of C4H11N.

A. B. C. D. E.

I and II II and III III and IV IV and V II and IV

For the following compound identify the indicated lone pairs as localized or delocalized.

A. B. C. D. E.

I = both localized; I = both localized; I = one localized and one delocalized; I = one localized and one delocalized; I = both delocalized;

II = both localized II = one localized and one delocalized II = both localized II = one localized and one delocalized II = both delocalized

Answer: D Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Medium 48.

For the following compound identify the indicated lone pairs as localized or delocalized.

A. B. C. D. E.

I = both delocalized; I = both localized; I = both delocalized; I = one localized and one delocalized; I = one localized and one delocalized;

II = localized II = localized II = delocalized II = localized II = delocalized

Answer: E Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Medium 49.

For the following compound what is the hybridization state and molecular geometry at the indicated atoms.

A. B. C. D. E.

I = sp2, bent; I = sp2, bent; I = sp2, linear; I = sp, linear; I = sp2, trigonal planar;

II = sp2, trigonal pyramidal II = sp2, trigonal planar II = sp2, trigonal pyramidal II = sp2, trigonal planar II = sp2, trigonal planar

Answer: B Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Hard 50.

Which of the following compounds contain an alcohol functional group?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 51.

Which of the following compounds contain an alkene functional group?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 52.

Which of the following compounds contain an amine functional group?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 53.

Which of the following compounds contain a ketone functional group?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 54.

Which of the following compounds contain an aromatic ring?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 55.

Which of the following compounds contain an ester functional group?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 56.

Which of the following compounds contain an amide functional group?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 57.

Which of the following compounds contain an anhydride functional group?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 58.

Which of the following compounds contain an alkyne functional group?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 59.

Which of the following compounds contain a thiol functional group?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 60.

Which of the following compounds contain an alkyl halide functional group?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 61.

What functional groups are present in the following compound? O

A. B. C. D. E.

ketone and alkene ketone and alkyne aldehyde and alkene aldehyde and alkyne ester and alkene

Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 62.

Which of the following compounds have both a ketone and an ester functional group?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium

63.

Norethynodrel, a component of the first combined oral contraceptive, has the following structure. Identify the functional groups indicated in Norethynodrel.

A. B. C. D. E.

I = aldehyde; I = ketone; I = ketone; I = anhydride; I = ester;

II = alkyne; II = alkene; II = aromatic; II = alkene; II = alkene;

III = alcohol; III = alcohol; III = alcohol; III = carboxylic acid; III = alcohol;

IV = alkene IV = alkyne IV = alkyne IV = alkene IV = alkyne

Answer: B Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 64.

Identify the functional groups indicated in the following compound.

A. B. C. D. E.

I = alcohol; I = ester; I = alcohol; I = ether; I = alcohol;

II = amine; II = ketone; II = amide; II = amide; II = aldehyde;

III = thiol III = thiol III = sulfide III = thiol III = sulfide

Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 65.

Tamiflu®, the most effective antiviral drug used to treat avian influenza, has the following structure. Identify the indicated functional groups in Tamiflu®.

A. B. C. D. E.

I = ketone; I = ester; I = amine; I = amide; I = amine;

II = amine; II = amide; II = amide; II = amine; II = amine;

III = alkene III = alkyne III = alkene III = alkene III = aromatic

Answer: D Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 66.

Aspartame, an artificial sweetener used in Equal® and diet beverages, has the following structure. Identify the functional groups in Aspartame.

A. B. C. D. E.

I = ester; I = ester; I = ether; I = ether; I = anhydride;

II = amide; II = amine; II = amide; II = amine; II = ketone;

III = amine III = amide III = amine III = amide III = amine

Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 67

For the following compound what is the hybridization state and molecular geometry at the indicated atoms.

A. B. C. D. E.

I = sp2, bent; I = sp2, linear; I = sp2, bent; I = sp, trigonal planar; I = sp, linear;

II = sp2, trigonal pyramidal II = sp2, bent II = sp2, bent II = sp, trigonal planar II = sp, linear

Answer: C Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Hard 68

Caffeine has the following structure. Identify the hybridization state and molecular geometry at the indicated atoms.

A. B. C. D. E.

I = sp3, trigonal pyramidal; I = sp3, trigonal planar; I = sp2, trigonal pyramidal; I = sp2, trigonal planar; I = sp3, trigonal pyramidal;

II = sp2, trigonal planar II = sp2, bent II = sp, linear II = sp2, bent II = sp2, bent

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 70.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: E Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 71.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 72.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 73.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: E Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 74.

How many hydrogen atoms are connected to the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy

75.

How many lone pairs of electrons are found on the indicated atom?

A. B. C. D. E.

one two three four none

Answer: E Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 76.

What is the formal charge on a carbon atom bound to three other carbon atoms and no lone pairs?

A. B. C. D. E.

-2 -1 0 +1 +2

Answer: D Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 77.

What is the formal charge on a carbon atom bound to three other carbon atoms and one lone pair?

A. B. C. D. E.

-2 -1 0 +1 +2

Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 78.

How many lone pairs of electrons are found on the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 79.

How many lone pairs of electrons are found on the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 80.

How many lone pairs of electrons are found on the indicated carbon atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy

81.

What is the formal charge on the oxygen atom in the following compound?

A. B. C. D. E.

+1 +2 -1 -2 0

Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 82.

What is the formal charge on the nitrogen atom in the following compound?

A. B. C. D. E.

-1 -2 +1 +2 0

Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 83.

What is the formal charge on the nitrogen atom in the following compound?

A. B. C. D. E.

+1 +2 -1 -2 0

Answer: A

Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 84.

What is the formal charge on the indicated oxygen atom in the following compound?

A. B. C. D. E.

+1 +2 -1 -2 0

Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 85.

What is the formal charge on the nitrogen atom in the following compound?

A. B. C. D. E.

+1 +2 -1 -2 0

Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 86.

Which of the following structures have +1 as a formal charge on an oxygen atom?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 87.

Which of the following structures have +1 as a formal charge on the nitrogen atom?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 88.

Determine the formal charge on each atom as indicated for the structure below.

I = +1;

II = 0;

III = -1

B. C. D. E.

I = -1; I = 0; I = -1; I = +1;

II = +1; II = -1; II = 0; II = 0;

III = 0 III = +1 III = +1 III = +1

Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 89.

Diazomethane has the molecular formula CH2N2. Determine the formal charge on each atom as indicated for the structure below.

A. B. C. D. E.

I = -1; I = +1; I = 0; I = 0; I = 0;

II = +1; II = 0; II = -1; II = +1; II = +1;

III = 0 III = -1 III = +1 III = -1 III = 0

Answer: D Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 90.

Consider the structure in the box, and then identify the bond-line representation, with appropriate formal charges if needed, from the options provided.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 91.

How many lone pairs of electrons are on the oxygen atom?

A. B. C. D. E.

one two three four none

Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 92.

How many lone pairs of electrons are on the nitrogen atom?

A. B. C. D. E.

one two three four none

Answer: B

Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 93.

How many lone pairs of electrons are on the oxygen atom?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 94.

How many lone pairs of electrons are on the nitrogen atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 95.

How many lone pairs of electrons are on the nitrogen atom?

A. B. C. D. E.

one two three four none

Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 96.

How many lone pairs of electrons are on the indicated oxygen atom?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 97.

How many lone pairs of electrons are on the indicated oxygen atom?

A. B. C. D. E.

one two three four none

Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy

98.

How many total lone pairs of electrons are in the following compound?

A. B. C. D. E.

one two three four none

Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 99.

Identify the structure that shows the correct placement of all lone pairs for the compound illustrated in the box below.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium

100.

Identify the structure that shows the correct placement of all lone pairs for the compound illustrated in the box below.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 101.

The representation of the indicated bond in the following compound is _____ of the paper.

A. B. C. D.

in the plane out of the plane behind the plane None of these

Answer: B Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure

Difficulty: Easy 102.

The representation of the indicated bond in the following compound is _____ of the paper.

A. B. C. D.

in the plane out of the plane behind the plane None of these

Answer: C Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 103.

The representation of the indicated bond in the following compound is _____ of the paper.

A. B. C. D.

in the plane out of the plane behind the plane None of these

Answer: C Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 104.

Which of the following is a Fischer projection?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 105.

Which of the following is a Haworth projection?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 106.

Which of the following pairs are resonance structures of each other?

A. B. C. D. E.

I II III IV II and IV

Answer: D Learning Objective: 2.7 Define "resonance”, describing the relationship between resonance and molecular orbital theory Difficulty: Easy 107.

Which of the following pairs are resonance structures of each other?

A. B. C. D. E.

I II III IV II and IV

Answer: C Learning Objective: 2.7 Define "resonance”, describing the relationship between resonance and molecular orbital theory Difficulty: Easy 108.

The spreading of electrons over two or more atoms in a compound is called_______.

A. B. C.

isomerism delocalization stereoisomerism

D. E.

localization None of these

Answer: B Learning Objective: 2.7 Define "resonance”, describing the relationship between resonance and molecular orbital theory Difficulty: Easy 109.

Delocalization of electrons over two or more atoms _______ a molecule.

A. B. C. D. E.

destabilizes delocalizes localizes stabilizes None of these

Answer: D Learning Objective: 2.7 Define "resonance”, describing the relationship between resonance and molecular orbital theory Difficulty: Easy 110.

Resonance structures have _______ connectivity of atoms and _______ distribution of electrons.

A. B. C. D. E.

different, same same, same different, different same, different None of these

Answer: D Learning Objective: 2.7 Define "resonance”, describing the relationship between resonance and molecular orbital theory Difficulty: Medium 111.

Which statement best describes a resonance hybrid?

A. The process of dealing with the inadequacy of bond-line structures. B. A structure showing an allyl carbocation C. A representation of a molecule showing all the bonds and lone pairs D. Molecules with the same molecular formula, but different atom connectivity. E. A representation of a molecule that can alternatively be represented by drawing two or more resonance structures.

Answer: E Learning Objective: 2.7 Define "resonance”, describing the relationship between resonance and molecular orbital theory Difficulty: Medium 112.

Which of the following examples violates the rules for curved arrows?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Easy 113.

Which of the following examples violates the rules for curved arrows?

A. B. C. D. E.

I I and II I and III II and III III and IV

Answer: C Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows

Difficulty: Easy 114.

Which of the following examples violates the rules for curved arrows?

A. B. C. D. E.

I and II II and III III, and IV I and III II and IV

Answer: D Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Medium 115.

Why is the single curved arrow shown insufficient to draw a resonance structure?

A. B. C. D. E.

The resulting structure would have a positive on the most electronegative atom The resulting structure would have an octet rule violation The resulting structure would have a negative on the most electronegative atom The resulting structure would have a negative on the least electronegative atom The resulting structure would have an atom with less than an octet

Answer: B Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Medium 116.

Identify the resonance structure(s) indicated by the curved arrow.

A. B. C. D. E.

I II III IV I and III

Answer: A Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 117.

Identify the resonance structure indicated by the curved arrows.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 118.

Identify the resonance structure indicated by the curved arrows.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 119.

Identify the resonance structure indicated by the curved arrows.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 120.

Identify from the options given the proper curved arrow to convert the first resonance structure into the second resonance structure.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 121.

Identify from the options given the proper curved arrow to convert the first resonance structure into the second resonance structure.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium

122.

Identify from the options given the proper curved arrows to convert the first resonance structure into the second resonance structure.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 123.

For the structure shown in the box below identify a corresponding correct resonance structure.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 124.

For the structure shown in the box below identify a corresponding correct resonance structure.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 125.

For the structure shown in the box below identify corresponding correct resonance structures.

A. B. C.

I and II II and III III and IV

D. E.

I and III II and IV

Answer: B Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 126.

For the structure shown in the box below identify corresponding correct resonance structures.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: C Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 127.

For the structure shown in the box below identify a corresponding correct resonance structure.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 128.

For the structure shown in the box below identify corresponding correct resonance structures.

A. B. C. D. E.

I and II II and III III and IV I, II and III II, III and IV

Answer: D Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard 129.

For the structure shown in the box below identify a corresponding correct resonance structure.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 130.

For the structure shown in the box below identify a corresponding correct resonance structure.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy

131.

For the structure shown in the box below identify a corresponding correct resonance structure.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy

132.

For the structure shown in the box below identify two corresponding correct resonance structures.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: D Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard

133.

For the structure shown in the box below identify two corresponding correct resonance structures.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: C Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard 134.

For the structure shown in the box below identify two corresponding correct resonance structures.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: B Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard 135.

Identify the most significant resonance structure(s).

A. B. C. D. E.

I II III I and III II and III

Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 136.

Identify the most significant resonance structure(s).

A. B. C. D. E.

I II III I and II II and III

Answer: A Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 137.

Identify the most significant resonance structure(s).

A. B. C. D.

I II III I and II

II and III

Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 138.

Identify the most significant resonance structure(s).

A. B. C. D. E.

I II III I and II III and IV

Answer: A Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Hard 139.

Identify the most significant resonance structure(s).

A. B. C. D. E.

I II III IV All structures are of equal significance

Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 140.

Identify the most significant resonance structure(s).

A. B. C. D. E.

I II III IV All structures are of equal significance

Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 141.

Identify the most significant resonance structure(s).

A. B. C. D. E.

I II III IV II and IV

Answer: D Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Hard 142.

Identify the most significant resonance structure.

A. B. C. D.

I II III IV

Answer: E Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 143.

What is the relationship between the following compounds?

A. B. C. D. E.

constitutional isomers resonance structures conformers identical compounds conjugate acid and conjugate base

Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 144.

What is the relationship between the following compounds?

A. B. C. D. E.

constitutional isomers resonance structures conformers identical compounds stereoisomers

Answer: A Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 145.

What is the relationship between the following compounds?

A. B. C. D. E.

constitutional isomers resonance structures conformers identical compounds different compounds

Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 146.

What is the relationship between the following compounds?

A. B. C. D. E.

constitutional isomers resonance structures conformers identical compounds different compounds

Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 147.

Identify the resonance hybrid for the following structure.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial charges, reflecting the combination of individual resonance structures Difficulty: Medium 148.

Identify the resonance hybrid for CH2=CHCH=CHCH2+.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial charges, reflecting the combination of individual resonance structures Difficulty: Medium 149.

Identify the resonance hybrid for the following structure.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial charges, reflecting the combination of individual resonance structures Difficulty: Medium

150.

The lone pair on nitrogen in the following compound is _______.

A. B. C. D. E.

localized delocalized conjugated resonance stabilized unhybridized

Answer: A Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 151.

The lone pairs on oxygen in the following compound are best described as _______.

A. B. C. D. E.

both localized both delocalized one localized and one delocalized unhybridized allylic to each other

The lone pair on nitrogen in the following compound is _______.

A. B. C. D.

localized delocalized conjugated resonance stabilized

unhybridized

Answer: A Learning Objective: 2.12 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 153.

The lone pairs on oxygen in the following compound are best described as _______.

A. B. C. D. E.

both localized both delocalized one localized and one delocalized unhybridized allylic to each other

The lone pairs on nitrogen in the following compound are best described as _______.

A. B. C. D. E.

all three pairs localized all three pairs delocalized two localized pairs and one delocalized pair one localized pair and two delocalized pairs unhybridized

155.For the following compound identify the indicated lone pairs as localized or delocalized.

A. B. C. D. E.

I = localized; I = delocalized; I = localized; I = delocalized; I = delocalized;

II = delocalized II = localized II = delocalized II = localized II = delocalized

III = one localized and one delocalized III = one localized and one delocalized III = both delocalized III = both localized III = one localized and one delocalized

A. B. C. D. E.

I = both delocalized; I = both localized; I = both localized; I = one localized and one delocalized; I = one localized and one delocalized;

II = two localized and one delocalized II = two localized and one delocalized II = one localized and two delocalized II = one localized and two delocalized II = two localized and one delocalized

157.

For the following compound identify the indicated lone pairs as localized or delocalized.

A. B. C. D. E.

I = both delocalized; I = both localized; I = both delocalized; I = one localized and one delocalized; I = one localized and one delocalized;

II = localized II = localized II = delocalized II = localized II = delocalized

For the following compound what is the hybridization state and molecular geometry at the indicated atoms.

A. B. C. D. E.

I = sp3, tetrahedral; I = sp3, bent; I = sp3, bent; I = sp3, tetrahedral; I = sp2, trigonal pyramidal;

II = sp2, trigonal pyramidal II = sp2, trigonal planar II = sp2, trigonal pyramidal II = sp2, trigonal planar II = sp, trigonal planar

159.

Caffeine has the following structure. Identify the hybridization state and molecular geometry at the indicated atoms.

A. B. C. D. E.

I = sp3, trigonal pyramidal; I = sp3, trigonal planar; I = sp2, trigonal pyramidal; I = sp2, trigonal planar; I = sp3, trigonal pyramidal;

II = sp3, trigonal pyramidal II = sp3, trigonal planar II = sp2, trigonal pyramidal II = sp2, trigonal planar II = sp2, trigonal planar

Enalapril, is a drug used in the treatment of heart disease. What is the hybridization state at the indicated atoms in Enalapril?

A. B. C. D. E.

I = sp2, trigonal planar; I = sp3, trigonal pyramidal; I = sp2, trigonal pyramidal; I = sp2, trigonal planar; I = sp3, trigonal pyramidal;

II = sp3, trigonal pyramidal II = sp3, trigonal pyramidal II = sp2, trigonal pyramidal II = sp2, trigonal planar II = sp2, trigonal planar

Klein, Organic Chemistry 4e Chapter 3 1.

A Brønsted-Lowry acid is defined as a

A. B. C. D. E.

proton acceptor. proton donor. species remaining after acid is deprotonated. species remaining after base is protonated. species that can react with water.

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 2.

A Brønsted-Lowry base is defined as a

A. B. C. D. E.

proton acceptor. proton donor. species remaining after acid is deprotonated. species remaining after base is protonated. species that can react with water.

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 3.

A conjugate acid is defined as a

A. B. C. D. E.

proton acceptor. proton donor. species remaining after acid is deprotonated. species remaining after base is protonated. species that can react with water.

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy

A conjugate base is defined as a

A. B. C. D. E.

proton acceptor. proton donor. species remaining after acid is deprotonated. species remaining after base is protonated. species that can react with water.

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 5.

For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate acid.?

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 6.

For the following reaction, respectively identify the Brønsted-Lowry acid and the conjugate acid.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 7.

For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate base.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: E Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 8.

For the following reaction, respectively identify the Brønsted-Lowry acid and the conjugate base.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy

For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate base.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: E Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 10.

Which of the following is not a Brønsted-Lowry acid?

A. B. C. D. E.

CH3OH CH3CH3 HCl CH3SH H2 O

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 11.

Which of the following is not a Brønsted-Lowry base?

A. B. C. D. E.

CH3OH CH3OCH3 CH3NH2 CH3CH3 CH3SH

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium

12.

In a Brønsted-Lowry acid-base reaction, the acid is defined as

A. B. C. D. E.

a proton acceptor. a proton donor. the product resulting from loss of a proton. the product resulting from gaining a proton. the most reactive species.

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 13.

In a Brønsted-Lowry acid-base reaction, the base is defined as

A. B. C. D. E.

a proton acceptor. a proton donor. the product resulting from loss of a proton. the product resulting from gaining a proton. the most reactive species.

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 14.

Which of the following is always formed from the loss of proton from a BrønstedLowry acid?

A. B. C. D. E.

a Lewis acid a conjugate acid a conjugate base a species with a negative charge a neutral solution

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy

15.

Which of the following is always formed from the gain of proton by a BrønstedLowry base?

A. B. C. D. E.

a Lewis base a conjugate acid a conjugate base a species with a positive charge a neutral solution

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 16.

Identify the conjugate base of nitric acid.

A. B. C. D. E.

NO3– NO2– HNO3 HNO2 H2NO3+

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 17.

Identify the conjugate base of phosphoric acid.

A. B. C. D. E.

HPO42– H2PO4– HPO32– PO43– H2PO3–

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 18.

Identify the conjugate base of CH3CH2SH.

CH3CH2S–

B. C. D. E.

CH3CH2– CH3CH2SH2+ CH3CH2S2– CH3CH2+

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 19.

Identify the conjugate acid of CH3CH2OH.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 20.

Identify the conjugate acid of CH3-O-CH3.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy

21.

Identify the conjugate acid of the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 22.

Identify the conjugate base of CH3C≡CH.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 23.

Identify the conjugate base of CH3CH2NH2.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 24.

Identify the conjugate base of the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 25.

Identify the conjugate base of the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 26.

For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate base.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 27.

For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate acid.

A. B. C. D.

I and II I and III I and IV II and IIII

II and IV

Answer: E Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 28.

For the following reaction, respectively identify the Brønsted-Lowry acid and the conjugate base.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 29.

For the following reaction, respectively identify the Brønsted-Lowry acid and the conjugate acid.

A. B. C. D. E.

I and II I and III I and IV II and IIII II and IV

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium

30.

For the following reaction identify the acid, base, conjugate acid and conjugate base.

A. B. C. D. E.

I = base; I = acid; I = base; I = acid; I = base;

II = acid; II = base; II = acid; II = base; II = base;

III = conjugate base; III = conjugate base; III = conjugate acid; III = conjugate acid; III = conjugate acid;

IV = conjugate acid IV = conjugate acid IV = conjugate base IV = conjugate base IV = conjugate acid

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 31.

For the following reaction identify the acid, base, conjugate acid and conjugate base.

A. B. C. D. E.

I = base; I = acid; I = base; I = acid; I = base;

II = acid; II = base; II = acid; II = base; II = base;

III = conjugate base; III = conjugate base; III = conjugate acid; III = conjugate acid; III = conjugate acid;

IV = conjugate acid IV = conjugate acid IV = conjugate base IV = conjugate base IV = conjugate acid

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 32.

For the following reaction identify the acid, base, conjugate acid and conjugate base.

A. B. C.

I = base; I = acid; I = base;

II = acid; II = base; II = acid;

III = conjugate base; III = conjugate base; III = conjugate acid;

IV = conjugate acid IV = conjugate acid IV = conjugate base

D. E.

I = acid; I = base;

II = base; II = base;

III = conjugate acid; III = conjugate acid;

IV = conjugate base IV = conjugate acid

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium 33.

The tail of the curved arrow must start at ________electron density and the head must end at ________electron density.

A. B. C. D. E.

low, high high, high low, low high, low none of the above

Answer: D Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Easy 34.

For the following acid-base reaction identify the correct curved arrow mechanism.

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 35.

For the following acid-base reaction identify the correct curved arrow mechanism.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 36.

For the following acid-base reaction identify the correct curved arrow mechanism.

A. B. C. D. E.

I II III IV V

Answer: B to show flow of electrons in acid-base reactions Difficulty: Medium 37.

For the following acid-base reaction identify the correct curved arrow mechanism.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 38.

For the following acid-base reaction identify the correct curved arrow mechanism.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 39.

Identify the acid and the base and provide a curved arrow mechanism for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 40.

The following reaction mechanism contains mistakes. Which of the following statements correctly describes how the curved arrows should be drawn?

A. B.

The curved arrow should start at the oxygen atom labeled (I) The curved arrow should start at the hydride (IV), go to hydrogen atom (II) with a second arrow starting from the O—H bond and going to the oxygen atom (I) The curved arrow should start at the O—H bond and go to hydride (IV) There should be and additional arrow from the oxygen atom (I) to the sodium ion (III) There should be an arrow from the oxygen atom (I) to the hydrogen atom (II)

C. D. E.

Answer: B Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium

41.

The following reaction mechanism contains mistakes. Which of the following statements correctly describes how the first curved arrows should be drawn?

A. B. C.

The curved arrow should start at sodium ion labeled (III) The curved arrow should start at the hydrogen atom labeled (II) The curved arrow should start at bond between the oxygen atom (I) and the hydrogen atom (II) The curved arrow should start at the nitrogen atom labeled (IV) There should be an arrow from the oxygen atom (I) to the hydrogen atom (II)

D. E.

Answer: D Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 42.

A. B. C. D. E.

The following reaction mechanism contains mistakes. Which of the following statements correctly describes how the first curved arrows should be drawn?

\ The first arrow (I) should start at the sodium ion The second arrow (II) should go in the opposite direction The second arrow (II) should start at the bond between the H and Br The arrow labeled II should go in the opposite direction The arrow labeled II is unnecessary

Answer: C Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 43.

Identify the structure produced by the following acid-base reaction mechanism.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Medium 44.

Identify the structure produced by the following acid-base reaction mechanism.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions Difficulty: Hard 45.

What is the Keq for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Easy 46.

Which of the following compounds is most acidic?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Easy 47.

Which of the following compounds is most basic?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Medium 48.

Which of the following compounds is most acidic?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Medium 49.

Which of the following compounds is most basic?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Medium 50.

Which of the following compounds is most basic?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Medium 51.

Tryptophan, shown below, is an essential amino acid that is important in the synthesis of the neurotransmitter serotonin.. Rank the indicated protons in order of increasing acidity.

A. B. C. D. E.

Least acidic: Least acidic: Least acidic: Least acidic: Least acidic:

I < II < III II < III < I III < I < II I < III < II II < I < III

Most acidic Most acidic Most acidic Most acidic Most acidic

Answer: A Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Hard 52.

Histidine an amino acid has the following structure. Rank the indicated protons in order of increasing acidity.

A. B. C. D. E.

Least acidic: Least acidic: Least acidic: Least acidic: Least acidic:

I < II < III II < III < I III < I < II I < III < II II < I < III

Most acidic Most acidic Most acidic Most acidic Most acidic

Answer: E Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Hard 53.

For the following acid-base reaction, predict the position of the equilibrium and identify the most stable basic compound.

favor the right side with compound I being the most stable base

B. C. D. E.

favor the right side with compound II being the most stable base favor the right side with compound III being the most stable base favor the left side with compound I being the most stable base favor the left side with compound II being the most stable base

Answer: C Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Medium 54.

For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

A. B. C. D. E.

favor the right side with compound I being the most acidic compound favor the right side with compound II being the most acidic compound favor the left side with compound I being the most acidic compound favor the left side with compound II being the most acidic compound favor the left side with compound III being the most acidic compound

Answer: E Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Medium 55.

For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

A. B. C. D. E.

Answer: D

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Hard 56.

For the following acid-base reaction, predict the position of the equilibrium and identify the most stable basic compound.

A. B. C. D. E.

favor the right side with compound I being the most basic compound favor the right side with compound II being the most basic compound favor the right side with compound III being the most basic compound favor the left side with compound I being the most basic compound favor the left side with compound II being the most basic compound

Answer: A Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium Difficulty: Hard 57.

Which of the following compounds is most acidic?

A. B. C. D. E.

HF HCl HBr HI H2 O

Answer: D Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO) Difficulty: Easy 58.

Which of the following compounds is most acidic?

A. B. C. D. E.

CH3OH HCl HF CH3SH CH3NH2

Answer: B Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO) Difficulty: Easy 59.

Which of the following best explains which compound is more acidic? HF or HBr

A. B. C. D. E.

HF is more acidic due to the F atom being more electronegative than Br HBr is more acidic due to the Br atom being less electronegative than F HF is more acidic due to the F– anion being smaller in size HBr is more acidic due to the Br– anion being larger in size HF is capable of participating in hydrogen bonding and therefore is a strong acid

Which of the following best explains which compound is more acidic? CH3OH and CH3NH2

A. B. C. D. E.

CH3OH is more acidic due to oxygen being more electronegative than nitrogen CH3NH2 is more acidic due to nitrogen being less electronegative than oxygen CH3OH is more acidic as it results in a stronger conjugate base CH3NH2 is more acidic as it results in a stronger conjugate base Both compounds are capable of hydrogen bonding and are of equal acidity

Answer: A Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO) Difficulty: Medium 61.

Which of the following best explains which proton is more acidic?

A. B. C. D. E.

The H (I) attached to S is more acidic due to oxygen being more electronegative The H (II) attached to O is more acidic due to sulfur being more electronegative The H (I) attached to S is more acidic due to sulfur being more electronegative The H (II) attached to O is more acidic due to oxygen being more electronegative The H (I) attached to S is more acidic due to the sulfur having a larger volume resulting in a more stable anion and a weak conjugate base.

Answer: E Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO) Difficulty: Medium 62.

Rank the indicated protons in order of increasing acidity.

A. B. C. D. E.

Least acidic: Least acidic: Least acidic: Least acidic: Least acidic:

I < II < III II < III < I III < I < II I < III < II II < I < III

Most acidic Most acidic Most acidic Most acidic Most acidic

Which of the following compounds is most acidic?

A. B. C.

I II III

D. E.

IV V

Consider the shown proton on each compound and identify which is most acidic.

A. B. C. D. E.

I II III IV V

Rank the indicated protons in decreasing order of acidity.

A. B. C. D. E.

Most acidic: Most acidic: Most acidic: Most acidic: Most acidic:

Answer: D

II > I > III II > III > I I > III > II I > II > III III > II > I

Least acidic Least acidic Least acidic Least acidic Least acidic

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO) Difficulty: Medium 66.

Which compound has the most acidic proton?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO) Difficulty: Medium 67.

Which of the indicated protons is most acidic?

A. B. C. D. E.

I II III IV V

68.

Which of the following compounds is most acidic?

A. B. C. D. E.

I II III IV V

Which of the following compounds is most acidic?

A. B. C. D. E.

I II III IV V

Which of the following compounds is most acidic?

A. B. C. D. E.

I II III IV V

Which of the following compounds is most acidic?

A. B. C. D. E.

I II III IV V

Rank the following compounds in decreasing order of acidity.

A. B. C. D.

III > II > IV > I II > IV > III > II IV > III > II > I IV > II > III > I

III > IV > II > I

Which of the indicated protons is most acidic?

A. B. C. D. E.

I II III IV V

Which of the following best explains which proton is more acidic?

A. B. C. D. E.

The H (I) is more acidic due to having less carbons attached to the nitrogen The H (II) is more acidic due to having less carbons attached to the nitrogen The H (I) is more acidic due to inductive effects by the closer fluorine atoms The H (II) is more acidic due to inductive effects by the closer fluorine atoms The H (II) is more acidic as the fluorine atoms are further away

Answer: C

Which of the following best explains why phenol is more acidic than ethanol.

The conjugate base of phenol is resonance stabilized, resulting in a weaker conjugate base. The conjugate base of phenol is resonance stabilized, resulting in a stronger conjugate base. The conjugate base of phenol has a localized charge, resulting in a stronger conjugate base. The conjugate base of ethanol has a localized charge. The conjugate base of ethanol has a delocalized charge.

B. C. D. E.

Consider the shown proton on each molecule below, and select the statement that best explains which compound is more acidic.

Compound II is more acidic; the conjugate base of compound I has the negative charge on the more electronegative oxygen atom. Compound I is more acidic; the conjugate base of compound I has the negative charge on the more electronegative oxygen atom. Compound II is more acidic; the conjugate base of compound II has the negative charge on the more electronegative oxygen atom. Compound I is more acidic; the conjugate base of compound II has the negative charge on the more electronegative oxygen atom.

B. C. D.

Both compounds are equally stable as both protons are adjacent to a double bond.

Aspartic acid, an amino acid, has the structure shown below. Which of the following best explains which proton is most acidic?

Proton I is most acidic due to conjugate base stabilization by resonance and being further from the inductive effect of the positive nitrogen atom. Proton II is most acidic due being attached to the carbon closest to the positive nitrogen atom. Proton III is most acidic due to being attached to a positive nitrogen atom. Proton IV is most acidic due to conjugate base stabilization by resonance and being closer to the inductive effect of the positive nitrogen atom. Proton V is most acidic due to the possibility of conjugate base stabilization by resonance with the adjacent C=O bond.

B. C. D. E.

For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

A. B. C.

D. E.

favor the left side with compound III being the most acidic compound The reaction is at equilibrium so all the compounds are in equal concentration

Answer: A Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Easy 79.

For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

A. B. C. D. E.

favor the right side with compound I being the most acidic compound favor the right side with compound III being the most acidic compound favor the left side with compound I being the most acidic compound favor the left side with compound III being the most acidic compound The reaction is at equilibrium so all the compounds are in equal concentration

Answer: D Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Easy 80.

For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

A. B. C. D. E.

favor the right side with compound I being the most acidic compound favor the right side with compound II being the most acidic compound favor the right side with compound III being the most acidic compound favor the left side with compound III being the most acidic compound favor the left side with compound II being the most acidic compound

Answer: B Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Easy

81.

For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

A. B. C. D. E.

favor the right side with compound I being the most acidic compound favor the right side with compound III being the most acidic compound favor the left side with compound I being the most acidic compound favor the left side with compound III being the most acidic compound the reaction is at equilibrium so all the compounds are in equal concentration

Answer: A Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Easy 82.

For the following acid-base reaction, predict the position of the equilibrium and identify the most stable basic compound.

A. B. C. D. E.

favor the right side with compound I being the most stable base favor the right side with compound IV being the most stable base favor the left side with compound I being the most stable base favor the left side with compound II being the most stable base the reaction is at equilibrium so all the compounds are in equal concentration

Answer: B Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 83.

For the following acid-base reaction, predict the position of the equilibrium and identify the most stable basic compound.

A. B. C. D. E.

favor the right side with compound I being the most stable base favor the right side with compound II being the most stable base favor the left side with compound I being the most stable base favor the left side with compound II being the most stable base favor the left side with compound III being the most stable base

Answer: D Learning Objective: 3.5 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 84.

Determine if H2O is a suitable reagent to protonate each of the two compounds shown below.

A. B. C. D. E.

I = yes; II = no I = no; II = no I = no; II = yes I = yes; II = yes Not possible to determine with the information provided

Answer: B Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 85.

Determine if H2O is a suitable reagent to protonate each of the two compounds shown below.

A. B. C. D. E.

I = yes; II = no I = no; II = no I = no; II = yes I = yes; II = yes Not possible to determine with the information provided

Answer: C Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 86.

Which of the following best explains if H2O is a suitable reagent to protonate the compound shown below.

no, water would not protonate the compound as the resulting conjugate base would not be stabilized by resonance no, water would not protonate the compound as the negative charge is more stable on the nitrogen atom no, water would not protonate the compound as both water and the nitrogen in the compound have two bonds yes, water would protonate the compound as the resulting conjugate base would be stabilized by resonance yes, water would protonate the compound as the resulting conjugate base would have a negative on the more electronegative oxygen atom

B. C. D. E.

Answer: E Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 87.

Which of the following best explains if H2O is a suitable reagent to protonate the compound shown below.

A. B.

no, water would not protonate the compound as water is a base no, water would not protonate the compound as the negative charge is resonance stabilized on the compound yes, water would protonate the compound as the resulting conjugate base would have a negative on an oxygen atom yes, water would protonate the compound as the resulting conjugate base would be stabilized by resonance yes, water would protonate the compound as it has two hydrogen atoms attached to an oxygen atom, where the compound has none

C. D. E.

Answer: B

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 88.

Determine if NaOH is a suitable reagent to deprotonate each of the two compounds shown below.

A. B. C. D. E.

I = yes; II = no I = no; II = no I = yes; II = yes I = no; II = yes Not possible to determine with the information provided

Answer: D Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 89.

Determine if NaNH2 is a suitable reagent to deprotonate each of the two compounds shown below.

A. B. C. D. E.

I = yes; II = yes I = no; II = no I = no; II = yes I = yes; II = no Not possible to determine with the information provided

Answer: A Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Medium 90.

Which of the following best explains if NaOH is a suitable reagent to deprotonate the compound shown below.

A. B. C. D. E.

no, there are no protons attached to the sp2 carbons no, the compound would not be soluble in NaOH no, the base has a negative charge on an oxygen atom, whereas the compound’s conjugate base would have a negative charge on the carbon atom yes, NaOH is considered a strong base yes, protons attached to sp2 carbons are more acidic than those attached to sp3 carbons

Answer: C Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Hard 91.

Which of the following best explains if NaNH2 is a suitable reagent to deprotonate the compound shown below.

no, the resulting conjugate base would have a localized negative on a carbon atom where NaNH2 has a negative on the more electronegative nitrogen atom no, there are no acidic protons attached to the oxygen atoms no, NaNH2 produces NH3 when protonated which then will leave the reaction mixture yes, the resulting conjugate base would have delocalization of charge over two oxygen atoms, whereas NaNH2 has a localized negative charge. yes, as NaNH2 has only two hydrogen atoms attached to the nitrogen atom, and the compound has eight total hydrogen atoms

B. C. D. E.

Answer: D Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Hard 92.

Which of the following best explains if CH3CH2ONa is a suitable reagent to deprotonate the compound shown below.

A. B. C. D. E.

no, CH3CH2ONa would not deprotonate the compound since nitrogen has a lone pair and will not act as an acid no, CH3CH2ONa has a negative charge on an oxygen atom, whereas the compound’s conjugate base would have a negative charge on a nitrogen atom yes, if deprotonated the negative charge would be more stable on the nitrogen atom yes, CH3CH2ONa is considered a strong base yes, the nitrogen atom has a proton that can be donated to an appropriate base

Answer: B Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Hard 93.

Which of the following best explains if H2O is a suitable reagent to protonate the compound shown below.

no, water would not protonate the compound as the negative charge is more stable on the larger sulfur atom no, water would not protonate the compound as the resulting conjugate base would not be stabilized by resonance yes, water would protonate the compound the sodium ion rather be a counter ion to oxygen than sulfur yes, water would protonate the compound as the resulting conjugate base would be stabilized by resonance yes, water would protonate the compound as the resulting conjugate base would have a negative on the more electronegative oxygen atom

B. C. D. E.

Answer: A Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases Difficulty: Hard 94.

Which of the following best describes the leveling effect?

A. B.

The ability of a compound to dissolve in a given amount of solvent The limiting of a compound’s acidity or basicity by respective deprotonation or protonation by the solvent The cause of weak acids or weak bases to incompletely dissociate in water

D. E.

The reason that explains why moving down the periodic table results in compounds that are more acidic The reduction of inductive effects as electronegative atoms are moved further from the acidic proton.

Answer: B Learning Objective: 3.7 Describe the significance in understanding leveling effects Difficulty: Medium 95.

Which of the following solvents can be used with NaNH2?

A. B. C. D. E.

CH3CH2OH CH3OH H2 O Liquid NH3 CH3CO2H

Answer: D Learning Objective: 3.7 Describe the significance in understanding leveling effects Difficulty: Medium 96.

Which of the following solvents cannot be used with (CH3)3COK?

A. B. C. D. E.

(CH3CH2)2O (CH3)3COH H2 O Liquid NH3 Tetrahydrofuran (THF)

Answer: C Learning Objective: 3.7 Describe the significance in understanding leveling effects Difficulty: Medium 97.

Which of the following solvents can be used with (CH3)3CLi?

A. B. C. D. E.

CH3CH2OH CH3OH H2 O Liquid NH3 CH3(CH2)4CH3

Answer: E Learning Objective: 3.7 Describe the significance in understanding leveling effects

Difficulty: Medium 98.

As a result of the "leveling effect," the strongest acid that can exist in appreciable concentration in aqueous solution is ________.

A. B. C. D. E.

H2SO4 HCl H3O+ HNO3 H2 O

Answer: C Learning Objective: 3.7 Describe the significance in understanding leveling effects Difficulty: Easy 99.

As a result of the "leveling effect," the strongest base that can exist in appreciable concentration in aqueous solution is ________.

A. B. C. D. E.

(CH3)3CLi NaNH2 H3O+ HO– H2 O

Answer: D Learning Objective: 3.7 Describe the significance in understanding leveling effects Difficulty: Easy 100.

Why is ethanol a better solvating solvent than tert-butyl alcohol?

A. B.

ethanol is less sterically hindered and more capable of interacting with the solute tert-butyl alcohol is less sterically hindered and more capable of interacting with the solvent ethanol is less sterically hindered and less capable of interacting with the solvent tert-butyl alcohol is less sterically hindered and less capable of interacting with the solvent tert-butyl alcohol has more carbons than ethanol making it more soluble in aqueous solutions

C. D. E.

Answer: A Learning Objective: 3.8 Describe the significance in understanding solvating and steric effects Difficulty: Easy

101.

Identify the most sterically hindered alcohol.

A. B. C. D. E.

CH3OH CH3CH2OH (CH3)2CHOH (CH3)3COH CH3CH2CH2CH2OH

Answer: D Learning Objective: 3.8 Describe the significance in understanding solvating and steric effects Difficulty: Easy 102.

What is a cation?

A. B. C. D. E.

a negatively charged ion a positively charged ion a sodium atom a hydrogen molecule an atom that has gained electrons

Answer: B Learning Objective: 3.9 Explain what is meant by a counterion Difficulty: Easy 103.

What is the counterion in NaOCH2CH3?

A. B. C. D. E.

Na+ NaO– CH3CH2– CH3CH2O– Na–

Answer: A Learning Objective: 3.9 Explain what is meant by a counterion Difficulty: Easy 104.

What is the counterion in (CH3)3CLi?

A. B.

CH3+ CH3–

C. D. E.

(CH3)3C– Li+ (CH3)3C+

Answer: D Learning Objective: 3.9 Explain what is meant by a counterion Difficulty: Easy 105.

What is a counterion in (CH3)3COK?

A. B. C. D. E.

K– (CH3)3CO+ KO– (CH3)3CO– K+

Answer: E Learning Objective: 3.9 Explain what is meant by a counterion Difficulty: Easy 106.

A Lewis acid is defined as ________.

A. B. C. D. E.

a proton donor an electron pair donor a proton acceptor an electron pair acceptor a species that generates OH– in water

Answer: D Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 107.

A Lewis base is defined as ________.

A. B. C. D. E.

a proton donor an electron pair donor a proton acceptor an electron pair acceptor a species that generates H+ in water

Answer: B

Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 108.

CH3CH2OCH2CH3, is best classified as a ________.

A. B. C. D. E.

Brønsted-Lowry acid Lewis acid Brønsted-Lowry base Lewis base Both C and D

Answer: E Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 109.

BF3, is best classified as a ________.

A. B. C. D. E.

Brønsted-Lowry acid Lewis acid Brønsted-Lowry base Lewis base Both A and D

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 110.

The following compound is best classified as a ________.

A. B. C. D. E.

Brønsted-Lowry acid Lewis acid Brønsted-Lowry base Lewis base Both C and D

Answer: E

Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 111.

The following compound is best classified as a ________.

A. B. C. D. E.

Brønsted-Lowry acid Lewis acid Brønsted-Lowry base Lewis base Both C and D

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 112.

Which of the following compounds is not a Lewis acid?

A. B. C. D. E.

BH3 AlCl3 CH3CH3 CH3CH2+ FeBr3

Answer: C Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 113.

Which of the following compounds is not a Lewis acid?

A. B. C. D. E.

BF3 FeCl3 CH3CH2+ Ph3P AlBr3

Answer: D

Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 114.

For the following reaction, identify the Lewis acid.

A. B. C. D. E.

I II III Both I and III Both II and III

Answer: A Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 115.

For the following reaction, identify the Lewis acid.

A. B. C. D. E.

I II III Both I and III Both II and III

Answer: A Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 116.

For the following reaction, identify the Lewis acid.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 117.

For the following reaction, identify the Lewis acid.

A. B. C. D. E.

I II III Both I and III Both II and III

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 118.

For the following reaction, identify the Lewis base.

A. B. C.

I II III

D. E.

Both I and III Both II and III

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 119.

For the following reaction, identify the Lewis base.

A. B. C. D. E.

I II III Both I and III Both II and III

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Easy 120.

For the following reaction, identify the Lewis acid and the Lewis base.

A. B. C. D. E.

I = Lewis base; I = Lewis acid I = Lewis base I = Lewis acid II = Lewis base

III = Lewis acid II = Lewis base II = Lewis acid III = Lewis base III = Lewis acid

Answer: C Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium

121. In a Brønsted-Lowry acid-base reaction, the conjugate acid is defined as A. B. C. D. E.

a proton acceptor a proton donor the product resulting from loss of a proton the product resulting from gaining a proton the most reactive species

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 122.

For the following reaction, identify the Lewis acid and the Lewis base.

A. B. C. D. E.

I = Lewis base; I = Lewis acid I = Lewis base I = Lewis acid II = Lewis base

III = Lewis acid II = Lewis base II = Lewis acid III = Lewis base III = Lewis acid

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 123.

Identify the expected product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 124.

Identify the expected product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 125.

For the following reaction identify the acid and the base and predict the products.

A. B. C. D. E.

I = acid; I = base; I = acid; I = base; I = acid;

II = base; II = acid; II = base; II = acid; II = base;

products = III, V, and VI products = III and IV products = IV and VII products = III, V, and VI products = IV, V, and VI

Answer: A Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Hard 126.

For the following reaction identify the acid and the base and predict the position of the equilibrium.

A. B. C. D. E.

I = acid; I = base; I = acid; I = base; I = acid;

II = base; II = acid; II = base; II = acid; II = base;

favor the right side favor the right side favor the left side favor the left side at equilibrium so equally favors both sides

Answer: B Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Hard

127.

In a Brønsted-Lowry acid-base reaction, the conjugate acid is defined as

A. B. C. D. E.

a proton acceptor a proton donor the product resulting from loss of a proton the product resulting from gaining a proton the most reactive species

Answer: D Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 128.

In a Brønsted-Lowry acid-base reaction, the conjugate base is defined as

A. B. C. D. E.

a proton acceptor a proton donor the product resulting from loss of a proton the product resulting from gaining a proton the most reactive species

Answer: C Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 129.

Identify the conjugate base of CH3CH2OH.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Easy 130.

Identify the conjugate acid of CH3CH2NH2.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base Difficulty: Medium

131.

Which of the following compounds is most acidic?

A. B. C. D. E.

CH3OH CH3Br CH3Cl CH3SH CH3NH2

Which of the following compounds is least acidic?

A. B. C. D. E.

I II III IV V

Which of the following compounds is most acidic?

A. B. C.

I II III

D. E.

IV V

Which of the indicated protons is least acidic?

A. B. C. D. E.

I II III IV V

What is an anion?

A. B. C. D. E.

a negatively charged ion a positively charged ion a sodium atom a hydrogen molecule an atom that has lost electrons

Answer: A Learning Objective: 3.9 Explain what is meant by a counterion Difficulty: Easy 136.

Which of the following compounds is not a Lewis base?

H2 O

B. C. D. E.

NH3 NH2– CH3CH3 CH3OCH3

Answer: D Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium 137.

Which of the following compounds is not a Lewis Base?

A. B. C. D. E.

NaOH (CH3)3COK CH3CH2CH2CH2Li Ph3P (CH3)3C+

Answer: E Learning Objective: 3.10 Describe how Lewis acids and bases differ from BrønstedLowry acids and bases Difficulty: Medium

138.

Identify the conjugate acid of CH3-NH-CH3.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Easy 139.

Which of the following best explains which compound is more basic?

CH3OH and CH3NH2 A. B. C. D. E.

CH3OH is more basic due to oxygen being more electronegative than nitrogen CH3NH2 is more basic due to nitrogen being less electronegative than oxygen CH3OH is more basic as it results in a weaker conjugate acid CH3NH2 is more basic as it results in a stronger conjugate acid Both compounds are capable of hydrogen bonding and are of equal basicity

Answer: B Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Easy 140.

From the two compounds below identify which is more basic along with the best explanation.

A. B. C. D. E.

I is more basic since it is only bound to one hydrogen atom II is more basic due to the delocalized electrons on the nitrogen atom I is more basic due to the localized electrons on the nitrogen atom II is more basic due to inductive effects from the aromatic ring Both compounds are capable of hydrogen bonding and are of equal basicity

Answer: B Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Easy 141.

From the two compounds below identify which would produce the more acidic conjugate acid along with the best explanation.

The conjugate acid of II is more acidic as it would have three hydrogen atoms attached The conjugate acid of I is more acidic due to protonation of the localized electrons on the nitrogen atom

C. D. E.

The conjugate acid of II is more acidic as the compound would no longer have delocalized electrons The conjugate acid of I is more acidic as compound II has resonance in the aromatic ring Once both compounds are protonated they can no longer hydrogen bond and thus are of equal acidity

Answer: B Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Easy 142.

Which of the indicated protons is most acidic?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Medium 143.

Which of the indicated atoms would be most basic?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Medium 144.

Which of the indicated protons would be most acidic?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Hard 145. For the following reaction identify the acid and the base and predict the position of the equilibrium.

A. B. C. D. E.

I = acid; I = base; I = acid; I = base; I = acid;

II = base; II = acid; II = base; II = acid; II = base;

favor the right side favor the right side favor the left side favor the left side at equilibrium so equally favors both sides

Answer: D Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO) Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 4 1.

What is the parent chain of the following compound?

A. B. C. D. E.

octane hexane heptane decane nonane

Answer: A Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 2.

What is the parent chain of the following compound?

A. B. C. D. E.

hexane heptane octane nonane decane

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 3.

What is the parent chain of the following compound?

A. B. C. D. E.

pentane hexane heptane octane nonane

Answer: C Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 4.

What is the name of the parent chain of the following compound?

A. B. C. D. E.

pentane hexane heptane octane nonane

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 5.

What is the IUPAC name of the following compound?

A. B. C. D. E.

3-isopropyl-5-ethylheptane 2-methyl-3-ethyl-5-ethylheptane 3-ethyl-5-isopropylheptane 2-methyl-3,5-diethylheptane 3,5-diethyl-2-methylheptane

Answer: E Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium

What is the IUPAC name of the following compound?

A. B. C. D. E.

2,5-diethylhexane 3,6-dimethyloctane 2-ethyl-5-methylheptane 2,5-dimethylheptane 1,2-di-sec-butylethane

Answer: B Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 7.

What is the IUPAC name of the following compound?

A. B. C. D. E.

2,3,5-triethylhexane 2,4,5-triethylhexane 2,4-diethyl-5-methylheptane 4-ethyl-3,6-dimethyloctane 3,6-dimethyl-5-ethyloctane

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 8.

What is the IUPAC name of the following compound?

1-ethyl-2-methylcyclohexane

B. C. D. E.

2-ethyl-1-methylcyclohexane 1-ethyl-2-methylhexane cyclononane ethylmethylcyclohexane

Answer: A Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 9.

What is the IUPAC name of the following compound?

A. B. C. D. E.

2,3-dimethyl-1-ethyl-cyclopropane 1-ethyl-2,3-dimethylcyclopentane 3-ethyl-1,2-dimethyl-cyclopentane 1-ethyl-2,3-methylcyclohexane 1,2,3-ethyl-dimethylcyclopentane

Answer: B Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 10.

What is the IUPAC name of the following compound?

A. B. C. D. E.

3,6-dimethylbicyclo[3.3.1]octane 2,5-dimethylbicyclo[3.3.0]octane 2,7-dimethylbicyclo[3.3.0]octane 1,4-dimethylbicyclo[3.3.1]octane 3,8-dimethylbicyclo[3.3.0]octane

Answer: C Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Hard

11.

What is the IUPAC name of the following compound?

A. B. C. D. E.

3-isopropylpentane 3-ethyl-4-methylpentane 1,1-diethyl-2-methylpropane 3-(1,1-dimethylmethyl)pentane 3-ethyl-2-methylpentane

Answer: E Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 12.

What is the IUPAC name of the following compound?

A. B. C. D. E.

4-butyl-5-ethyl-3,6-dimethylheptane 3-sec-butyl-4-butyl-5-methylheptane 3-butyl-2,4,5-triethyl-hexane 5-sec-butyl-4-ethyl-3-methylnonane 3,4-di-sec-butyl-octane

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 13.

What is the IUPAC name of the following compound?

A. B. C. D. E.

1,1,3-trimethylcyclopentane 1,3,3-trimethylcyclopentane 1,1,3-trimethylcyclopropane 1,3,3-trimethylcyclopropane 1-methyl-3-isopropylcyclopentane

Answer: A Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 14.

What is the IUPAC name of the following compound?

A. B. C. D. E.

1-methyl-3-tert-butylcyclooctane 1-tert-butyl-3-methylcyclooctane 1-methyl-7-tert-butylcyclooctane 1-tert-butyl-7-methylcyclooctane 3-methyl-1-(dimethylethyl)cyclooctane

Answer: B Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 15.

Which of the following have an isopropyl group as a substituent on the parent chain?

A. B. C. D. E.

I II III I and II II and III

Answer: E Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 16.

What is the common name of the following substituent?

A. B. C. D. E.

isopropyl tert-butyl isobutyl sec-butyl neopentyl

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 17.

Which of the following is [2.2.2]bicyclooctane?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 18.

Which of the following is a tert-butyl group?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 19.

Which of the following is 3-ethyl-2,4,6-trimethyloctane?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 20.

Which of the following is 3-ethyl-3-methylpentane?

A. B. C.

I II III

D. E.

IV V

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 21.

Which of the following is 1-cyclopropyl-3-methylcyclopentane?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 22.

What is the IUPAC name of the following compound?

A. B. C. D. E.

bicyclo[6.5.4]undecane bicyclo[4.3.2]nonane [4.3.2]bicyclononane [2.3.4]bicycloundecane bicyclo[4.3.2]undecane

Answer: E Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Hard

23.

Which of the following IUPAC names represent structures that are constitutional isomers of C6H14.

A. B. C. D. E.

I and II III and V I, III and V II, III and IV I, III and IV

Answer: C Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Hard 24. Which pair of the following compounds are constitutional isomers?

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: B Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Medium 25.

Which of the following compounds are constitutional isomers?

A. B. C. D. E.

I and II II and III III and IV I and IV II and IV

Answer: D Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Medium 26.

Which pair of the following compounds are constitutional isomers?

A. B. C. D. E.

I and III II and IV I and IV II and III I, II, and III

Answer: A Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Medium 27.

What is the relationship between the following two compounds?

A. B. C. D. E.

constitutional isomers different representations of the same molecule completely different/not constitutional isomers isotopes resonance hybrids

Answer: A Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Easy 28.

What is the relationship between the following two compounds?

A. B C. D. E.

constitutional isomers different representations of the same molecule completely different/not constitutional isomers isotopes resonance hybrids

Answer: C Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Easy 29.

What is the relationship between the following two compounds?

A. B C. D. E.

constitutional isomers different representations of the same molecule completely different/not constitutional isomers isotopes resonance hybrids

Answer: C Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Easy 30.

What is the relationship between the following two compounds?

constitutional isomers

B C. D. E.

different representations of the same molecule completely different/not constitutional isomers isotopes resonance hybrids

Answer: B Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Easy 31.

What is the relationship between the following two compounds?

A. B C. D. E.

constitutional isomers different representations of the same molecule completely different/not constitutional isomers isotopes resonance hybrids

Answer: A Learning Objective: 4.3 Describe the procedures to follow to avoid duplication In drawing constitutional isomers Difficulty: Easy 32.

What is the correct coefficient for oxygen that would balance the following combustion reaction?

A. B. C. D. E.

2 4 6 8 10

Answer: D Learning Objective: 4.4 Define heat of combustion, describing how it can be measured Difficulty: Medium 33.

What is the correct coefficient for oxygen that would balance the following combustion reaction?

A. B. C. D. E.

11 13 15 17 19

Answer: E Learning Objective: 4.4 Define heat of combustion, describing how it can be measured Difficulty: Medium 34.

Identify the correct coefficients required to balance the following combustion reaction?

A. B. C. D. E.

I = 5; I = 15; I = 15; I = 10; I = 3;

II = 10; II = 10; II = 10; II = 15; II = 2;

III = 15 III = 10 III = 15 III = 10 III = 3

Answer: B Learning Objective: 4.4 Define heat of combustion, describing how it can be measured Difficulty: Hard 35.

Identify the correct coefficients required to balance the following combustion reaction?

A. B. C. D. E.

I = 4; I = 16; I = 8; I = 2; I = 9;

II = 5; II = 10; II = 5; II = 4; II = 15;

III = 12 III = 11 III = 6 III = 6 III = 5

Answer: C Learning Objective: 4.4 Define heat of combustion, describing how it can be measured Difficulty: Hard

36.

Identify the isomer of C9H20 that is the most stable?

A. B. C. D. E.

nonane 3-methyloctane 2,2-dimethylheptane 2,2,3,4-tetramethylpentane 2,6-dimethylheptane

Answer: D Learning Objective: 4.4 Define heat of combustion, describing how it can be measured Difficulty: Medium 37.

The reaction shown below is an example of

A. B. C. D. E.

catalytic cracking thermal cracking catalytic reforming thermal reforming combustion

Answer: B Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons Difficulty: Medium 38.

The process that converts straight-chain alkanes into branched hydrocarbons is called _____________.

A. B. C. D. E.

hydrogenation cracking reforming hydrolysis combustion

Answer: C Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons Difficulty: Easy

39.

Identify the size of the hydrocarbon that is used in gasoline.

A. B. C. E.

C1 – C4 C5 – C12 C12 – C18D. C20 and higher nonvolatile liquids C20 and higher nonvolatile solids

Answer: B Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons Difficulty: Easy 40.

Identify the size of the hydrocarbon that is used in natural gas.

A. B. C. D. E.

C1 – C4 C5 – C12 C12 – C18 C20 and higher nonvolatile liquids C20 and higher nonvolatile solids

Answer: A Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons Difficulty: Easy 41.

Identify the size of the hydrocarbon that is used in jet fuel.

A. B. C. D. E.

C1 – C4 C5 – C12 C12 – C18 C20 and higher nonvolatile liquids C20 and higher nonvolatile solids

Answer: C Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons Difficulty: Easy 42.

Identify the size of the hydrocarbon that is used in asphalt.

A. B.

C1 – C4 C5 – C12

C. D. E.

C12 – C18 C20 and higher nonvolatile liquids C20 and higher nonvolatile solids

Answer: E Learning Objective: 4.5 Describe the sources of alkanes, including the processes for converting crude oil to useful hydrocarbons Difficulty: Easy 43.

Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

Answer: A Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 44.

Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

Answer: B Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium

45.

Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

Answer: D Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 46.

Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium

47.

Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 48.

Which of the following is the correct Newman projection for the following compound as viewed down the indicated bond in the conformation shown?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 49.

Which of the following is the correct wedge and dash structure for the following Newman projection?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 50.

Which of the following is the correct wedge and dash structure for the following Newman projection?

A. B. C.

I II III

D. E.

IV V

Answer: C Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 51.

Which of the following is the correct wedge and dash structure for the following Newman projection?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Medium 52.

Which of the following is the correct wedge and dash structure for the following Newman projection?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Hard 53.

Which of the following is the correct wedge and dash structure for the following Newman projection?

Answer: A Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Hard 54.

Which of the following is the correct wedge and dash structure for the following Newman projection?

Answer: B

Learning Objective: 4.6 Discuss the various types of drawings used to illustrate the conformations of alkanes Difficulty: Hard 55.

Which of the following is a Newman projection of an eclipsed conformation for ethane?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Easy 56.

Which of the following is a Newman projection of a staggered conformation for ethane?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Easy

57.

Which of the following is a Newman projection of an eclipsed conformation for propane?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Easy 58.

Which of the following is a Newman projection of a staggered conformation for propane?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Easy 59.

Consider the energy diagram showing the conformational analysis of propane and match the indicated position with the correct confirmation below.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Medium 60.

What is the eclipsing cost of Br and H if the energy difference between the staggered and eclipsed conformations of bromoethane, shown in the box below, is 13 kJ/mol?

A. B. C. D. E.

4 kJ/mol 5 kJ/mol 8 kJ/mol 13 kJ/mol 3.8 kJ/mol

Answer: B Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them

Difficulty: Hard 61.

What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane?

A. B. C. D. E.

3.8 kJ/mol 4 kJ/mol 6 kJ/mol 11 kJ/mol 18 kJ/mol

Answer: E Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Hard 62.

Which of the following is a gauche conformation for butane?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 63.

Which of the following is an anti conformation for butane?

B. C. D. E.

II III IV E

Answer: A Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 64.

Which of the following is a CH3–CH3 eclipsed conformation for butane?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 65.

Which of the following is a CH3-H eclipsed conformation for butane?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane

Difficulty: Easy 66.

Which of the following is the correct Newman projection for the following compound showing the two methyl groups are anti?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Medium 67.

Which of the following is the correct Newman projection for the following compound showing the gauche conformation?

Answer: D Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Medium

68.

How many substituents does the following compound have?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 69.

How many substituents does the following compound have?

A. B. C. D. E.

one two three four none

Answer: C Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 70.

Consider the energy diagram showing the conformational analysis of propane and match the indicated position with the correct confirmation below.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Medium 71.

Which of the following is the lowest energy conformation of the following compound looking down the indicated bond?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 72.

Which of the following is the highest energy conformation of the following compound looking down the indicated bond?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 73.

Which of the following is the highest energy conformation of the following compound looking down the indicated bond?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 74.

Which of the following is the highest energy conformation of the following compound looking down the indicated bond?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Easy 75.

Which of the following cycloalkanes has the most angle strain?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 4.9 Discuss strain in cycloalkanes Difficulty: Easy 76.

Which of the following cycloalkanes has the least angle strain?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.9 Discuss strain in cycloalkanes Difficulty: Easy 77.

Which of the following is a boat conformation of cyclohexane?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains Difficulty: Easy 78.

Which of the following is a chair conformation of cyclohexane?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains Difficulty: Easy

79.

How many substituents does the following compound have?

A. B. C. D. E.

none one two three four

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 80.

Which of the following is a chair conformation of the following substituted cyclohexane?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy 81.

For the following cyclohexene identify each substituent as axial or equatorial.

A. B. C. D. E.

Br = axial; Br = axial; Br = equitorial; Br = equitorial; Br = neither;

Cl = axial Cl = equitorial Cl = equitorial Cl = axial Cl = neither

Answer: B Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy 82.

Identify the cyclohexane chair conformation with an axial ethyl substituent and equatorial methyl group.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Medium 83.

Identify the correct chair conformation of cyclohexane showing all of the equatorial hydrogen atoms.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Medium 84.

Which of the following illustrates an axial OH?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy 85.

Which of the following illustrates a correctly positioned equatorial OH?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy 86.

Identify the correct chair conformation of cyclohexane showing all of the axial hydrogen atoms.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy

How many substituents does the following compound have?

A. B. C. D. E.

none one two three four

Answer: D Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium

88.

Identify the correct chair confirmations of the following compound and then indicate which one is more stable.

A. B. C. D. E.

I and II are correct chair stuctures and I is most stable I and II are correct chair stuctures and II is most stable I and III are correct chair stuctures and III is most stable II and III are correct chair stuctures and II is most stable II and III are correct chair stuctures and III is most stable

Answer: C Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored Difficulty: Medium 89. Identify the correct chair confirmations of the following compound and then indicate which one is more stable.

A. B. C. D. E.

Answer: D

Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored Difficulty: Medium 90.

Which is the most stable chair conformation of the following compound?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored Difficulty: Easy 91.

Which is the most stable chair conformation of the following compound?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored Difficulty: Easy 92.

Which is the most stable chair conformation of the following compound?

A. B. C. D. E.

I II III IV V

Which is the most stable chair conformation of the following compound?

A. B. C.

I II III

D. E.

IV V

Answer: A Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored Difficulty: Hard 94.

Identify the other chair conformation of the following compound.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.12 Describe the possible positions of the substituent in monosubstituted cyclohexanes, what happens in a ring flip, and which conformation is favored Difficulty: Easy 95.

Identify the correct chair confirmations of the following compound and then indicate which one is more stable.

I and II are correct chair stuctures and I is most stable

B. C. D. E.

I and II are correct chair stuctures and II is most stable I and III are correct chair stuctures and III is most stable II and III are correct chair stuctures and II is most stable II and III are correct chair stuctures and III is most stable

Identify the correct chair confirmations of the following compound and then indicate which one is least stable.

A. B. C. D. E.

I and II are correct chair stuctures and I is least stable I and II are correct chair stuctures and II is least stable I and III are correct chair stuctures and I is least stable II and III are correct chair stuctures and II is least stable II and III are correct chair stuctures and III is least stable

Identify the most stable chair conformation of the most stable isomer of 1,3,5trimethylcyclohexane.

A. B.

I II

C. D. E.

III IV V

Answer: D Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 98.

Identify the most stable chair conformation of the most stable isomer of 1-ethyl-3isopropylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 99.

Identify the most stable chair conformation of the most stable isomer of 1,4diethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 100.

Identify the least stable chair conformation of the most stable isomer of 1,4diethylcyclohexane

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 101.

Identify the most stable chair conformation of the most stable isomer of 1,2,4trimethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium

102. Identify the least stable chair conformation of the most stable isomer of 1,2,4trimethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 103. Which of the following is the lowest energy chair conformation of the following cyclohexane?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 104.

Which of the following is the lowest energy chair conformation of the following cyclohexane?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 105.

Identify the most stable chair conformation of the most stable isomer of 1-ethyl2,4-dimethylcyclohexane.

A. B. C. D. E.

I II III IV E

Answer: C Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 106.

Identify the least stable chair conformation of the most stable isomer of 1-ethyl2,4-dimethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 107.

On each chair structure identify the relationship of the substituents as cis or trans?

A. B. C. D. E.

I = trans; II = trans I = cis; II = cis I = trans; II = cis I = cis; II = trans not possible to tell while in a chair structure

Answer: C Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Easy 108.

On each chair structure identify the relationship of the substituents as cis or trans?

A. B. C.

I = trans; I = cis; I = trans;

II = trans II = cis II = cis

D. E.

I = cis; II = trans not possible to tell while in a chair structure

Answer: D Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Easy 109.

On each chair structure identify the relationship of the substituents as cis or trans?

A. B. C. D. E.

I = trans; II = trans I = cis; II = cis I = trans; II = cis I = cis; II = trans not possible to tell while in a chair structure

Answer: A Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Easy 110.

On each chair structure identify the relationship of the substituents as cis or trans?

A. B. C. D. E.

I = trans; II = trans I = cis; II = cis I = trans; II = cis I = cis; II = trans not possible to tell while in a chair structure

Answer: B Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Easy 111.

Identify the most stable conformation of trans-1,4-diethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Medium 112.

Identify the most stable chair conformation of cis-1,4-diethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Medium 113.

Which of the following substituted cyclohexanes is most stable?

A. B. C.

I II III

D. E.

IV V

Answer: B Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Hard 114.

Which of the following substituted cyclohexanes is most stable?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Hard 115.

Which of the following substituted cyclohexanes is most stable?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Hard

116.

Identify the lowest energy chair conformation of the most stable isomer of 4isopropyl-1,2-dimethylcyclohexane.

Answer: C Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Medium

117.

How many substituents does the following compound have?

A. B. C. D. E.

one two three four none

Answer: B Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Easy 118.. How many substituents does the following compound have?

A. B. C. D. E.

one two three four five

Answer: E

Learning Objective: 4.2 List the four steps involved in assigning IUPAC (systematic) names to chemical compounds, including bicyclic Difficulty: Medium 119.

What is the total energy cost associated with the compound below adopting the shown conformation?

A. B. C. D. E.

3.8 kJ/mol 4 kJ/mol 6 kJ/mol 11 kJ/mol 18 kJ/mol

Answer: A Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Easy 120.

What is the total energy cost associated with the compound below adopting the shown conformation?

A. B. C. D. E.

3.8 kJ/mol 4 kJ/mol 6 kJ/mol 11 kJ/mol 19 kJ/mol

Answer: E Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Medium 121.

What is the total energy cost associated with the compound below adopting the shown conformation?

A. B. C. D. E.

3.8 kJ/mol 11 kJ/mol 14 kJ/mol 16 kJ/mol 18 kJ/mol

Answer: E Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Hard 122.

What is the total energy cost associated with the compound below adopting the shown conformation?

A. B. C. D. E.

6 kJ/mol 11 kJ/mol 19 kJ/mol 23 kJ/mol 25 kJ/mol

Answer: D Learning Objective: 4.7 Describe the staggered and eclipsed conformations of ethane and the difference in energy between them Difficulty: Hard 123.

Identify the lowest energy conformation of butane as a Newman projection looking down the C2-C3 bond.

A. B. C.

I II III

D. E.

IV V

Answer: A Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Medium 124.

Which of the following is a the most stable conformation of cyclohexane?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains Difficulty: Easy 125.

Which of the following is a the least stable conformation of cyclohexane?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 4.10 Describe the chair and boat conformations of cyclohexane including a comparison of their torsional strains Difficulty: Medium 126.

Identify the highest energy conformation of butane as a Newman projection looking down the C2-C3 bond.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.8 Discuss the potential energies of the different staggered and eclipsed conformations of butane Difficulty: Medium 127.

For the following cyclohexene identify each substituent as axial or equatorial.

A. B. C. D. E.

F = axial; F = axial; F = equitorial; F = equitorial; F = neither;

Cl = axial Cl = equitorial Cl = equitorial Cl = axial Cl = neither

Answer: C Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy 128.

For the following cyclohexene identify each substituent as axial or equatorial.

A. B. C. D. E.

F = axial; F = axial; F = equitorial; F = equitorial; F = neither;

Cl = axial Cl = equitorial Cl = equitorial Cl = axial Cl = neither

Answer: D Learning Objective: 4.11 Illustrate the chair forms of a cyclohexane conformation Difficulty: Easy 129.

Which is the least stable chair conformation of the following compound?

A. B. C. D. E.

I II III IV V

Which of the following is the highest energy chair conformation of the following cyclohexane?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 4.13 Discuss the three-dimensional orientation and relative energy levels of the substituents in disubstituted cyclohexanes Difficulty: Medium 131.

Identify the least stable conformation of trans-1,4-diethylcyclohexane.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 4.14 Discuss the nature of cis and trans stereoisomers Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 5 1.

What is the relationship between the following two compounds?

A. B. C. D.

constitutional isomers stereoisomers identical not isomers; different compounds entirely

Answer: A Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes Difficulty: Easy 2.

What is the relationship between the following two compounds?

A. B. C. D.

constitutional isomers stereoisomers identical not isomers; different compounds entirely

Answer: C Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes Difficulty: Easy 3.

What is the relationship between the following two compounds?

OH A. B. C.

constitutional isomers stereoisomers identical

not isomers; different compounds entirely

Answer: B Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes Difficulty: Easy 4.

What is the relationship between the following two compounds?

A. B. C. D.

constitutional isomers stereoisomers identical not isomers; different compounds entirely

What is the relationship between the following two compounds?

A. B. C. D.

constitutional isomers stereoisomers identical not isomers; different compounds entirely

What is the relationship between the following two compounds?

O OH A. B. C. D.

constitutional isomers stereoisomers identical not isomers; different compounds entirely

Which term best describes the alkene below?

OMe

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Which term best describes the alkene below?

F F A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Answer: D

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes Difficulty: Easy 9.

Which term best describes the alkene below?

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Which term best describes the alkene below?

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Which term best describes the alkene below? O O

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Answer: D Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes Difficulty: Medium 12.

Which term best describes the left-hand double bond in the alkene below?

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Shown below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Which term describes the double bond indicated by the arrow?

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

Shown below is the structure of Singulair® (montelukast), a medication used to manage asthma. Is the double bond of montelukast cis, trans, or neither?

A. B. C. D.

cis only trans only both terms may be used neither cis nor trans

What is the total number of isomers with the molecular formula C4H8?

A. B. C. D. E.

2 3 6 8 9

Answer: C

Learning Objective: 5.1 Compare constitutional isomers and stereoisomers, including an explanation of how the terms cis and trans are applied to stereoisomeric alkenes and disubstituted cycloalkanes

Difficulty: Hard 16.

What is the total number of isomers with the molecular formula C4H6?

A. B. C. D. E.

2 3 6 8 9

Answer: E

Which arrow(s) indicates chiral center(s) in the compound shown?

O OH O

A. B. C. D. E.

a and b b and c c and d a, c, and d b. c, and e

Answer: D

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium

18.

Which arrow(s) indicates chiral center(s) in nicotine, the molecule shown below?

N N A. B. C. D. E.

a b c and d d and e a, b, and d

Answer: B

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 19.

Which arrow indicates the chiral center in the compound shown?

O O OH HO

A. B. C. D. E.

a b c d e

Answer: D

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 20.

Which arrow(s) indicates the chiral center(s) in the compound shown?

OH OH

OH A. B. C. D. E.

a a and b a and d c, d, and e a, b, c, d, and e

Answer: E

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 21.

Which arrow(s) indicates the chiral center(s) in the compound shown?

OH NH2

A. B. C. D. E.

a b a and b b and c d and e

Answer: D

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 22.

Identify the relationship between the following two structures. OH

A. B. C.

enantiomers identical neither

Answer: B Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 23.

Identify the relationship between the following two structures.

A. B. C.

enantiomers identical neither

Answer: A Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 24.

Identify the relationship between the following two structures.

OH A. B. C.

enantiomers identical neither

Answer: B Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 25.

Identify the relationship between the following two structures.

OH A. B. C.

enantiomers identical neither

Answer: A Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Easy 26.

Identify the relationship between the following two structures.

A. B. C.

enantiomers identical neither

Answer: B Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium 27.

Which of the choices is an enantiomer of the compound shown?

A. B. C. D.

I II III IV

Answer: E

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium 28.

Which of the choices is an enantiomer of the compound shown?

A. B. C. D.

I II III IV

Answer: A

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium 29.

Which of the choices is an enantiomer of the compound shown?

A. B. C. D.

I. II III IV

Answer: D

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium 30. HO

Which of the choices is an enantiomer of the compound shown? O

OH OH

A. B. C. D.

I. II III IV

Answer: B

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium 31.

Which of the choices is an enantiomer of the compound shown?

A. B. C. D.

I. II III IV

Answer: C

Learning Objective: 5.2 Describe the most common cause of chirality in a molecule, and draw a pair of enantiomers Difficulty: Medium 32.

Assign the absolute configuration of the chiral center as R or S.

N N

A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 33.

Assign the absolute configuration of the chiral center as R or S. O O OH

A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 34.

Assign the absolute configuration of the chiral center as R or S.

OH A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: A Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 35.

Assign the absolute configuration of the chiral center as R or S.

OH A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 36.

Assign the absolute configuration of the chiral center as R or S. OH

A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: A Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system

Difficulty: Easy 37.

Assign the absolute configuration of the chiral center as R or S.

OH A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: A Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 38.

The structure shown is Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chiral centers as R or S.

A. B. C. D.

The left-hand center is S; the right-hand center is R The left-hand center is R; the right-hand center is S Both centers are S Both centers are R

Answer: A Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 39.

The structure shown is Singulair® (montelukast), a medication used to manage asthma. Assign the absolute configuration of the chiral center as R or S.

A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: A Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 40.

The structure shown is Plavix® (clopidogrel), a medication used to manage blood clots. Assign the absolute configuration of the chirality center as R or S.

A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 41.

The structure shown is Cymbalta® (duloxetine), a medication used to manage depression. Assign the absolute configuration of the chiral center as R or S.

A. B. C. D.

R S R and S are both possible The chiral center is neither R or S

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 42.

What is the appropriate IUPAC name for compound shown?

A. B. C. D.

(R)-4-methyl-2-pentanol (S)-4-methyl-2-pentanol (R)-2-methyl-4-pentanol (S)-2-methyl-4-pentanol

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 43.

What is the appropriate IUPAC for the compound shown?

OH A. B. C. D.

(R)-6-octanol (S)-6-octanol (R)-3-octanol (S)-3-octanol

Answer: D

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 44.

Which of the following is the correct structure for the compound (R)-2-pentanol?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 45.

Which of the following is the correct structure for the compound (S)-3methylheptane?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium

46.

Which of the following structures is (S)-3-methylheptane?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 47.

Which of the following structures is (S)-3-methylheptane?

B. C. D. E.

II III IV V

Answer: E

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 48.

Which of the following is the correct IUPAC name of the following structure?

A. B. C. D.

(S)-3-ethyl-2-methylhexane (R)-3-ethyl-2-methylhexane (S)-3-ethyl-2-methylpentane (R)-3-ethyl-2-methylpentane

Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium 49.

Which of the following is the correct IUPAC name of the following structure?

A. B. C. D.

(S)-2-ethylhexane (S)-3-methylheptane (R)-2-ethylhexane (R)-3-methylheptane

Answer: D Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Medium

50.

Which choice correctly represents the structure below as a wedge-dash structure with any/all stereocenters correctly labeled with their absolute configuration?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Hard 51.

Which choice correctly represents the structure below as a wedge-dash structure with any/all stereocenters correctly labeled with their absolute configuration? Br

A. B. C. D. E.

I II III IV V

Answer: A OH R Br S

Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Hard 52.

Identify the relationship between these two structures.

A. B. C.

diastereomers enantiomers the same compound

different compounds

Answer: A Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Hard 53.

Rank the following from highest to lowest priority according to the Cahn-IngoldPrelog system.

-F

II.

-H

III.

-OH

IV.

-SH

A. I > II > III > VI B. IV > I > III > I C. III > IV > II > I D. II > I > III > IV E. IV > III > II > I Answer: B Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 54.

Rank the following from highest to lowest priority according to the Cahn-IngoldPrelog system.

-CH3

II.

-CN

III.

-CH2OH

IV.

-Br

A. I > II > III > VI B. IV > I > III > I C. III > IV > II > I D. II > I > III > IV E. IV > III > II > I Answer: E Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 55.

Rank the following from highest to lowest priority according to the Cahn-IngoldPrelog system.

-CH2CH3

II.

-CHCH2

III.

-CCH

IV.

-CH3

A. III > IV > II > I B. I > II > III > VI C. IV > I > III > I D. III > II > I > IV E. IV > III > II > I Answer: D Learning Objective: 5.3 Describe how the configuration of a chirality center is assigned using the Cahn-Ingold-Prelog system Difficulty: Easy 56.

What is the % ee of a sample of carvone that exhibits a specific rotation of −20, given that the specific rotation of (R)-carvone is −61?

A. 20% B. 33% C. 50% D. 61% E. 66% Answer: B Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium 57.

What is the % ee of a sample of carvone that exhibits a specific rotation of −40, given that the specific rotation of (R)-carvone is −61?

A. 20% B. 33% C. 50% D. 61% E. 66% Answer: E Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium

58.

If a sample of carvone gives a specific rotation of −60 and the specific rotation of (R)-carvone is −61, does the unknown sample primarily have the R or S absolute configuration?

A. R B. S C. It is a racemic mixture. D. This cannot be determined from the information given Answer: A Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium 59.

If a sample of carvone gives a specific rotation of 0 and the specific rotation of pure (R)-carvone is −61, what is the configuration of the unknown sample?

A. R B. S C. It is a racemic mixture. D. This cannot be determined from the information given Answer: C Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium 60.

What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of −52?

A. B. C. D.

−61 64 0 61

Answer: D Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium

61.

What is the specific rotation of a sample of carvone that is an equal mixture of the R and S enantiomers? (R)- carvone has a specific rotation of −61.

A. B. C. D.

−61 64 0 61

Answer: C Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium 62.

What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 10, given that the specific rotation of (R)-carvone is −61?

A. B. C. D.

42 84 16 58

What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is −61?

A. B. C. D.

26% 51% 49% 75%

Answer: A Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium

64.

What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 10, given that the specific rotation of (R)-carvone is −61?

A. B. C. D.

42 84 16 58

What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is −61?

A. B. C. D.

25.5% 51% 49% 74.5%

What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of −20, given that the specific rotation of (R)-carvone is −61?

A. B. C. D.

20% 66.5% 33.5% 61%

Answer: B Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium

67.

What is the percentage of the R enantiomer in a sample of limonene that has a specific rotation of −38, given that the specific rotation of (S)-limonene is −116?

A. B. C. D. E.

20% 66% 33.3% 61% 32.7%

The structure of Crestor (rosuvastatin), a medication used to reduce cholesterol, is shown. If the specific rotation for this compound is known to be +100, what would be the specific rotation for the stereoisomer shown at the right?

A. +100 B. -100 C. 0 D. Impossible to predict Answer: D Learning Objective: 5.4 Compare the effects of a pair of enantiomers on planepolarized light, discussing how the relative amounts of the two enantiomers affect the observed rotation of plane-polarized light Difficulty: Medium 69.

What is the relationship of the following two structures?

OH NH

A. B. C. D.

enantiomers diastereomers constitutional isomers identical

Answer: B Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 70.

What is the relationship of the following two structures? OH

OH NH

A. B. C. D.

enantiomers diastereomers constitutional isomers identical

Answer: A Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 71.

What is the relationship of the following two structures? HO

HO O HO

A. B. C. D.

O OH

enantiomers diastereomers constitutional isomers identical

O OH

Answer: A Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 72.

What is the relationship of the following two structures? OH

HO O

O HO

A. B. C. D.

O OH

enantiomers diastereomers constitutional isomers identical

Answer: D Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 73.

What is the relationship of the following two structures? HO

HO O HO

A. B. C. D.

O OH

enantiomers diastereomers constitutional isomers identical

Answer: B Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 74.

Which structure is an enantiomer of following shown?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 75.

Which structure is an enantiomer of the compound shown?

OH HO

A. B. C. D. E.

I II III IV None is possible

Answer: none. There is no stereocenter, so the compound is not chiral and thus does not have an enantiomer.

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 76.

Which structure is an enantiomer of following shown? O

A. B. C. D. E.

O OH

I II III IV No enantiomers are possible.

Answer: A

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 77.

Which structure is a diastereomer of the compound shown? O

O OH

A. B. C. D. E.

I only II only III only I and II III and IV

Answer:

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Hard 78.

Which compound is a diastereomer of the structure shown?

A. B. C. D. E.

I II III IV There are no diastereomers.

Answer: E. There is only one stereocenter, so the compound does not have a diastereomer.

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Hard 79.

Which compound is a diastereomer of the structure shown? OH OH

A. B. C. D. E.

I only II only III only I and II I and III

Answer: E OH

OH OH

OH or

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Hard 80.

How many stereoisomers are there for the compound shown? O

HO A. B.

1 2

C. D. E.

3 4 5

Answer: D

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Hard 81.

How many stereoisomers are there for the compound shown? OH NH

A. B. C. D. E.

1 2 3 4 5

Answer: D

Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Hard 82.

Which of the following choices is a diastereomer of the first structure shown?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 83.

Which of the following choices is a diastereomer of the first structure shown.

A. B. C. D.

I II III IV

Answer: D Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium

84.

Which of the following choices is a diastereomer of the first structure shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 5.5 Compare stereoisomers with diastereomers, explaining how many stereoisomers a compound can have Difficulty: Medium 85.

Is the following a meso compound? Cl

A. Yes, because it cannot be superimposed with mirror image compounds. B. Yes, because it cannot be superimposed with similar compounds that are not mirror images. C. Yes, because it has reflectional symmetry. D. No, because it has a mirror image. E. No, because it has two chiral centers. Answer: C Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral Difficulty: Medium

86.

Which of the following can exist as a meso isomer?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral Difficulty: Medium 87.

Does the following contain a plane of symmetry?

A. Yes, because it can be divided into two halves that would look identical if reflected in a mirror. B. Yes, because it has at least one chiral center and that is required for a plane of symmetry to exist. C. Yes, because it contains a ring. D. No, because it is achiral. E. No, because it has a mirror image. Answer: A Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral Difficulty: Easy 88.

Which of the choices correctly illustrates a plane of symmetry in the compound shown?

A. I B. II C. III D. IV E. There are no planes of symmetry present. Answer: C

Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral Difficulty: Easy 89.

Draw in the plane of symmetry in the following compound.

A. B. C. D.

I II III IV

E. There are no planes of symmetry present. Answer: E Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral Difficulty: Hard 90.

What is the total number of stereoisomers of this compound?

A. B. C. D. E.

1 2 4 7 None

Answer: D

How many stereoisomers are possible for 2,3-dimethylbutane?

A. B. C. D. E.

1 2 4 7 None

Answer: E. None. It has no stereocenters. Learning Objective: 5.6 Compare rotational and reflectional symmetry, discussing if and how an axis of symmetry and plane of symmetry affects chirality and whether a meso compound is chiral or achiral Difficulty: Hard

92.

How many stereoisomers are possible for 1,3,5-trimethylcyclohexane.

A. B. C. D. E.

1 2 4 7 None

Answer: B

A. B. C. D. E.

Draw the meso isomer of the following compound.

I II III IV No meso isomer exists.

Answer: A

Draw the meso isomer of the following compound. OH

MeO2C

CO2Me OH

A. B. C. D. E.

I II III IV No meso isomer exists.

Answer: A

Draw the meso isomer of the following compound. OH

A. B. C. D. E.

I II III IV No meso isomer exists.

Answer: B

How many possible stereoisomers are there for Crestor ® (rosuvastatin), a medication used to reduce cholesterol?

A. 2 B. 4 C. 6 D. 8 Answer: D

Which of the following choices represents the Fischer projection of the compound shown? Br

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 98.

Which of the following choices represents the Fischer projection of the compound shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 99.

Which of the following choices represents the Fischer projection of the compound shown? OH OH

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 100. Which of the following choices represents the Fischer projection of the compound shown? OH

OH OH

A. B. C. D. E.

I II III IV V

Answer: V

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 101. Which of the following choices represents the wedge/dash drawing of the Fischer projection shown? H HO

A. B. C. D. E.

OH H

I II III IV V

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 102. Which of the following choices represents the wedge/dash drawing of the Fischer projection shown? HO HO H

H H OH

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 103. Which of the following choices represents the wedge/dash drawing of the Fischer projection shown? HO HO HO H

H H H OH

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard

104. Which of the following choices represents the wedge/dash drawing of the Fischer projection shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 105.

Which of the following is a correct Fischer projection of the following compound?

A. B.

I II

C. D.

III IV

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 106.

Which of the following is a correct Fischer projection of the following compound?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 107.

Which of the following is a correct Fischer projection of the following compound?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 108.

Which of the following structures is the correct wedge/dash drawing of the following Fischer projection?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard

109.

Which of the following structures is a correct wedge/dash drawing of the following Fischer projection?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 110.

What is the relationship between the following two molecules?

H H

Br Br

A. B. C. D.

enantiomers diastereomers identical constitutional Isomers

Br Br

H H

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Easy

111.

What is the relationship between the following two molecules?

HO H HO H

H OH H OH

A. B. C. D.

enantiomers diastereomers identical constitutional Isomers

H H H HO

OH OH OH H

Answer: B Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Easy 112.

What is the relationship between the following two molecules? Br H Br

A. B. C. D.

Br H

enantiomers diastereomers identical constitutional Isomers

Answer: C Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Medium 113.

Assign the following stereocenter as having the R or S absolute configuration.

OH H Et

A. B. C. D.

S R S and R Neither S nor R

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Medium 114. H HO

Assign the following stereocenter as having the R or S absolute configuration.

A. B. C. D.

S R S and R Neither S nor R

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 115.

Assign the following stereocenter as having the R or S absolute configuration.

Et H H

Br H

A. B. C. D.

S R S and R Neither S nor R

Answer: D Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Medium 116.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

(R)-2-butanol (R)-2-propanol (S)-3-butanol (R)-3-butanol (S)-2-butanol

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Medium 117.

Which of the following is the IUPAC name for the following compound?

A. B. C. D.

(S)-2-pentanol (S)-2-butanol (R)-2-pentanol (R)-2-butanol

Answer: A Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 118.

Identify the relationship between these two structures.

A. B.

diastereomers enantiomers

C. D.

identical unrelated compounds

Answer: C. Learning Objective: 5.7 Draw a Fischer projection of glucose or another sugar Difficulty: Hard 119.

What is the relationship between the two structures shown?

A. B. C. D.

identical enantiomers diastereomers none of these

Answer: A Learning Objective: 5.8 Describe conformationally mobile systems Difficulty: Hard 120.

What is the relationship between the two structures shown?

A. B. C. D.

same compound enantiomers diastereomers none of these

Answer: B Learning Objective: 5.8 Describe conformationally mobile systems Difficulty: Hard 121.

What is the relationship between the two structures shown?

A. B. C. D.

same compound enantiomers diastereomers none of these

Answer: C Learning Objective: 5.8 Describe conformationally mobile systems Difficulty: Hard 122.

What is the relationship between the two structures shown?

A. B. C. D.

same compound enantiomers diastereomers none of these

Answer: D Learning Objective: 5.8 Describe conformationally mobile systems Difficulty: Hard 123.

What is the relationship between the two structures shown?

A. B. C. D.

same compound enantiomers diastereomers none of these

Answer: C Learning Objective: 5.8 Describe conformationally mobile systems Difficulty: Hard

124.

Stereoisomers that result from the hindered rotation of a single bond are most specifically called ___________.

A. B. C. D. E.

constrained diastereomers atropisomers enantiomers diastereomers constitutional isomers

Answer: B Learning Objective: 5.9 Discuss ways in which a compound can be chiral without containing a chiral center Difficulty: Medium 125.

What is the relationship between the two structures shown?

A. B. C. D.

same compound enantiomers diastereomers none of these

Answer: B Learning Objective: 5.9 Discuss ways in which a compound can be chiral without containing a chiral center Difficulty: Medium 126.

Identify the hybridization of the middle carbon of an allene.

A. B. C. D.

sp sp2 sp3 sp4

Answer: A Learning Objective: 5.9 Discuss ways in which a compound can be chiral without containing a chiral center Difficulty: Medium

127.

Which of the following strategies will NOT be an effective way to separate enantiomers?

A. B. C. D.

chiral chromatography distillation crystallization chiral resolving agents

Answer: B Learning Objective: 5.10 Describe resolution and methods to separate enantiomers Difficulty: Medium 128.

When a racemic mixture is reacted with a single enantiomer of another compound, then a pair of _________ is formed.

A. B. C. D.

identical compounds enantiomers diastereomers none of the above

Answer: B Learning Objective: 5.10 Describe resolution and methods to separate enantiomers Difficulty: Medium 129.

In chiral column chromatography, __________ adsorbent is used to separate a pair of enantiomers.

A. B. C. D.

an achiral a polar a nonpolar a chiral

Answer: D Learning Objective: 5.10 Describe resolution and methods to separate enantiomers Difficulty: Medium 130.

Is the following alkene E, Z, or neither?

OMe

B. Z C. Neither D. It is one or the other, but which is impossible to determine from the information given. Answer: E Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 131.

Is the following alkene E, Z, or neither?

F F A. E B. Z C. Neither D. It is one or the other, but which is impossible to determine from the information given. Answer: C Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 132.

Is the following alkene E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: A Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 133.

Is the following alkene E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: B Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 134.

Is the following alkene E, Z, or neither? O O

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: C Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 135.

Is the alkene on the left in the molecule below E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: A Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes

Difficulty: Medium 136.

Is the following alkene E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: B Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 137.

Is the following alkene E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: A Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 138.

Is the following alkene E, Z, or neither?

A. B.

E Z

C. D.

Neither It is impossible to determine from the information given.

Answer: A Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 139.

Is the following alkene E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Answer: B Learning Objective: 5.11 Describe how stereodiscriptors are assigned for certain trisubstituted and tetrasubstituted alkenes Difficulty: Medium 140.

Is the double bond indicated by an arrow in Crestor® (rosuvastatin), a medication used to reduce cholesterol, classified as E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Difficulty: Medium 141.

Is the double bond of Singulair® (montelukast), a medication used to manage asthma, classified as E, Z, or neither?

A. B. C. D.

E Z Neither It is impossible to determine from the information given.

Klein, Organic Chemistry 4e Chapter 6 1.

Using Table 6.1, estimate the enthalpy change of the following reaction under standard conditions. I

A. B. C. D. E.

HBr

-8 kJ/mol -6 kJ/mol 0 kJ/mol +6 kJ/mol +8 kJ/mol

Answer: E Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Medium 2.

Using Table 6.1, estimate the enthalpy change of the following reaction under standard conditions. +

A. B. C. D. E.

-45 kJ/mol -29 kJ/mol 0 kJ/mol +29 kJ/mol +45 kJ/mol

Answer: +29 kJ/mol Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Medium 3.

Using Table 6.1, estimate the enthalpy change of the following reaction under standard conditions. + F

H2O

+ OH

-16 kJ/mol

B. C. D. E.

-8 kJ/mol +4 kJ/mol +8 kJ/mol +16 kJ/mol

Answer: B Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Medium 4.

Using Table 6.1, which of the following is the enthalpy change of the following reaction under standard conditions?

A. B. C. D.

-21 kJ/mol +21 kJ/mol -171 kJ/mol +171 kJ/mol

Answer: A Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Easy 5.

Using Table 6.1, which of the following is the enthalpy change of the following reaction under standard conditions? +

H2O

A. B. C. D.

-8 kJ/mol +8 kJ/mol -506 kJ/mol +63 kJ/mol

Answer: A Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Medium

Later in the course, we will compare the halogenation of differently substituted carbons, comparing reactions like the ones below. Which of the following statements is true about reactions I and II?

A. B. C. D.

Both reactions have a positive heat of reaction (∆Ho) Neither reaction has a positive heat of reaction (∆Ho) Only reaction I has a positive heat of reaction (∆Ho) Only reaction II has a positive heat of reaction (∆Ho)

Later in the course, we will compare the halogenation of differently substituted carbons, comparing reactions like the ones below. Which of the following reactions has a more exothermic heat of reaction (∆Ho)?

A. Reaction I has a more exothermic heat of reaction (∆Ho) B. Reaction II has a more exothermic heat of reaction (∆Ho) C. Reaction I has a more exothernic heat of reactions ((∆Ho) at low temperatures and the opposite is true at high temperatures D. Both reactions consistently have the same heat of reaction (∆Ho) E. It is impossible to determine from the information given. Answer: B Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Medium Answer: B Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Medium 8.

You are working in a research laboratory and have developed a new reagent that cleaves C-H bonds homolytically. Unfortunately, this reagent can achieve only one of the transformations shown below. In light of the known bond dissociation energies, which transformation is most likely to be achieved?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Hard

9. What type of bond cleavage does the following reaction involve? HOOH

A. B. C. D.

2 HO

homolytic heterolytic covalent ionic

What type of bond cleavage does the following reaction involve? Br

A. B. C. D.

homolytic heterolytic covalent ionic

In a homolytic bond cleavage, ____ are formed.

A. B. C. D.

ions radicals only cations only anions

Answer: B Learning Objective: 6.1 Define enthalpy, homolytic and heterolytic bond cleavage, discussing heat of reaction and the relation of its sign to direction of energy transfer Difficulty: Easy

12.

In a heterolytic bond cleavage, ____ are formed.

A. B. C. D.

ions radicals only cations only anions

Predict the sign of ∆S for the following reaction.

A. B. C.

N N

positive negative no change

Answer: B Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Easy 14.

Predict the sign of ∆S for the following reaction. Br

A. B. C.

HBr

positive negative no change

Answer: A Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Easy

15.

Predict the sign of ∆S for the following reaction. OH

A. B. C.

positive negative no change

Answer: B Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Easy 16.

Predict the sign of ∆S for the following reaction. O OH

A. B. C.

positive negative no change

Answer: A Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Medium 17.

Predict the sign of ∆S for the following reaction.

A. B. C.

positive negative no change

Answer: B Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Medium 18.

Why is the entropy change negative for ring closures?

A. B. C. D.

Closing a ring results in fewer molecules. Closing a ring results in more molecules. Closing a ring releases energy. Closing a ring restricts the rotation around individual carbon-carbon bonds.

Answer: D Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Hard 19.

Which of the following would you expect to have the most negative ∆S?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Hard 20.

Of following reactions, which one(s) would you expect to have a negative ∆S?

A. B. C. D. E.

I II III IV I and II

Answer: E Learning Objective: 6.2 Define entropy, discussing the role of entropy in spontaneous processes Difficulty: Hard 21.

Predict the sign of ∆G for an exothermic reaction with an increase in entropy.

A. positive B. negative C. no change D. cannot predict without additional information Answer: B Learning Objective: reactions Difficulty: Easy

6.3 Discuss Gibbs free energy and endergonic and exergonic

22.

Predict the sign of ∆G for an endothermic reaction with an increase in entropy.

A. B. C. D.

positive negative no change cannot predict without additional information

Answer: D Learning Objective: reactions Difficulty: Easy

6.3 Discuss Gibbs free energy and endergonic and exergonic

23.

Predict the sign of ∆G for an exothermic reaction with a decrease in entropy.

A. B. C. D.

positive negative no change cannot predict without additional information

Answer: D Learning Objective: reactions Difficulty: Easy

6.3 Discuss Gibbs free energy and endergonic and exergonic

24.

Predict the sign of ∆G for an endothermic reaction with a decrease in entropy.

A. B. C. D.

positive negative no change cannot predict without additional information

Answer: A Learning Objective: reactions Difficulty: Easy

6.3 Discuss Gibbs free energy and endergonic and exergonic

25.

Which of the following indicates a reaction with a negative ∆G?

A. B. C. D.

endergonic, spontaneous endergonic, not spontaneous exergonic, spontaneous exergonic, not spontaneous

Answer: C Learning Objective: reactions Difficulty: Easy

6.3 Discuss Gibbs free energy and endergonic and exergonic

26.

Which of the following indicates a reaction with a positive ∆G?

A. B. C. D.

endergonic, spontaneous endergonic, not spontaneous exergonic, spontaneous exergonic, not spontaneous

Answer: B Learning Objective: reactions Difficulty: Easy

6.3 Discuss Gibbs free energy and endergonic and exergonic

27.

Does a reaction with a positive ∆G favor reactants or products?

A. B. C. D. E.

Reactants Products Neither It is impossible to tell without knowing the enthalpy It is impossible to tell without know the entropy

Answer: A Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Easy 28.

Does a reaction with a value of 0 for ∆G favor reactants or products?

A. B. C. D. E.

Reactants Products Neither It is impossible to tell without knowing the enthalpy It is impossible to tell without know the entropy

Answer: C Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Easy

29.

Does a reaction with a positive ∆S and a positive ∆H favor reactants or products?

A. B. C. D.

Reactants Products Neither It is impossible to determine without knowing the temperature

Answer: D Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Hard 30.

Does a reaction with a positive ∆S and a negative ∆H favor reactants or products?

A. B. C. D.

Reactants Products Neither It is impossible to determine without knowing the temperature

Answer: B Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Hard 31.

Does a reaction with a Keq = 10 favor reactants or products?

A. B. C. D.

Reactants Products Neither It is impossible to determine without knowing the temperature

Answer: A Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Easy 32.

Does a reaction with a ∆H of 14 kJ/mol and a ∆S of 150 J/mol·K at 298 K favor reactants or products?

Reactants

B. C. D.

Products Neither It is impossible to determine without more information

Answer: B Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Hard 33.

Does a reaction with a ∆H of 20 kJ/mol and a ∆S of 10 J/mol·K at 298 K favor reactants or products?

A. B. C. D.

Reactants Products Neither It is impossible to determine without more information

Answer: A Learning Objective: 6.4 Describe the factors that affect equilibrium and that determine whether the reaction favors the reactants or products Difficulty: Hard 34.

Given the following rate law, what is the order of the reaction with respect to MeI?

Rate = k[MeI][NaCN]

A. B. C. D. E.

Zero First Second Third Fourth

Answer: B Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 35.

Given the following rate law, what is the order of the reaction with respect to tertbutyl iodide? I Rate = k [ ]

A. B. C. D. E.

Zero First Second Third Fourth

Answer: B Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 36.

Given the following rate law, what is the order of the reaction with respect to sodium cyanide?

Rate = k[MeI][NaCN]2 A. B. C. D. E.

Zero First Second Third Fourth

Answer: C Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 37.

What is the energy of activation for the following reaction?

A. B. C. D. E.

10 kJ/mol 15 kJ/mol 20 kJ/mol 30 kJ/mol 35 kJ/mol

Answer: A10 kJ/mol Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 38.

What is the energy of activation for the following reaction?

A. B. C. D. E.

10 kJ/mol 15 kJ/mol 20 kJ/mol 30 kJ/mol 35 kJ/mol

Answer: A kJ/mol Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 39.

Based on the following energy diagram, is the reaction exothermic or endothermic?

endothermic

B. C. D.

exothermic isothermic it is impossible to tell from the information given

Answer: B Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Hard 40.

Based on the following energy diagram, is the reaction exothermic or endothermic?

A. B. C. D.

endothermic exothermic isothermic it is impossible to tell from the information given

Answer: A Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Hard 41.

What is the effect of a catalyst on a reaction?

A. B. C. D.

It increases the rate. It decreases the entropy. It changes the equilibrium. It makes the products more stable.

Answer: A Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 42.

Which of the following describes the effect of a catalyst on a reaction?

A. B. C. D.

It lowers the free energy of the products. It makes the reactants less stable. It changes the equilibrium constant. It lowers the energy of activation.

Answer: D Learning Objective: 6.5 Compare kinetics and thermodynamics Difficulty: Easy 43.

Which of the following is an energy diagram for a three-step reaction?

Answer: B Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 44.

Which of the following is an energy diagram for a two-step reaction?

Answer: B Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 45. Which illustration shows an energy diagram for an endothermic reaction with two steps?

Answer: D Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 46. Which illustration shows an energy diagram for an exothermic reaction with three steps?

Answer: B Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 47.

Which energy diagram below represents a concerted exothermic reaction?

Answer: C Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 48.

Which of the following energy diagrams shows a concerted endothermic reaction?

Answer: D Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 49.

Which of the following energy diagrams shows the reaction with the smallest energy of activation?

Answer: A Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 50.

What is a transition state?

A. B. C. D.

An isolable intermediate in a reaction. The starting materials of the reaction. A local maximum on the energy diagram. A low-energy point between the starting materials and the product.

Answer: C Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Easy 51.

What is an intermediate?

A. B. C. D.

A local maximum on the energy diagram. A point on the reaction pathway that has a discrete minima. A point half-way between the starting materials and products. The highest energy compound on an energy diagram.

Answer: B Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Easy 52.

Which of the following energy diagrams is of a reaction with one transition state?

Answer: A Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 53.

Which of the following energy diagrams is of a reaction with one intermediate?

Answer: B Learning Objective: 6.6 Describe an energy diagram, including what is represented by the peaks and valleys, and the Hammond postulate Difficulty: Medium 54.

Which arrow identifies the nucleophilic site in the molecule shown?

A. B. C. D. E.

a b c d e

Answer: A

Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 55.

Which arrow identifies the nucleophilic site in the molecule shown?

A. B. C. D. E.

a b c d e

Answer: E

Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 56.

Which arrow(s) identifies the nucleophilic site(s) in the molecule shown?

A. B. C. D. E.

a and b b and c d e a and e

Answer: B Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Medium 57. Which arrow(s) identifies the nucleophilic center(s) in the molecule shown? Identify the nucleophilic centers in the following molecule.

A. B. C. D. E.

a b c a and b b and c

Answer: E

Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 58.

Identify the nucleophilic atom in the Me3P.

A. B. C. D.

P C H Me

Answer: A Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 59.

Identify the electrophilic site in the molecule shown.

A. B. C. D. E.

a b c d e

Answer: B O

Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy

60.

Identify the electrophilic site in the molecule, CH3CH2NHCH2CH3.

A. B. C. D. E.

H N CH2 CH3 there is no electrophilic site

Answer: E Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 61.

Identify the electrophilic site in the molecule shown.

A. B. C. D. E.

a b c d e

Answer: B

Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 62.

Identify the electrophilic site in the molecule shown.

A. B. C. D. E.

a b c d e

Answer: A Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 63.

A. B. C. D.

Identify the electrophilic site in the molecule shown. B

C O B no electrophilic site

Answer: C Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Medium 64.

Which of the structures shown cannot be a nucleophile?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 65.

Which of the structures shown cannot be an electrophile?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 6.7 Compare nucleophiles, electrophiles, and carbocations Difficulty: Easy 66.

Which of the choices shown is hydride?

A. B. C. D.

H+ H H− H2

Answer: C Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Easy 67.

Which of the structures shown is the most stable cation?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Easy 68.

Which pattern of arrow pushing is involved in the reaction step shown.

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: A Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Easy 69.

Indicate which pattern of arrow pushing is involved in the reaction step shown.

OH2

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: B Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Easy 70.

Indicate which pattern of arrow pushing it is involved in the reaction step shown.

OH2 H

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: A Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Easy 71.

Indicate which pattern of arrow pushing it is involved in the reaction step shown.

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: D Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement

Difficulty: Easy 72.

Indicate which pattern of arrow pushing it is involved in the reaction step shown.

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: C Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Easy 73.

Melphalan, a drug used in chemotherapy, reacts with itself in the body before binding with its target, as illustrated in the mechanism below. Which two patterns of arrow pushing are seen in is reaction?

Answer: Nucleophilic attack and loss of leaving group Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Medium 74.

The reaction shown has three mechanistic steps. Which choice shows the curved arrows necessary to complete the mechanism?

A. B. C. D.

I II III The reaction will not occur

Answer: C .

Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Medium 75.

H 2O

A. B. C. D.

What is wrong with the mechanism shown?

There is no leaving group, so there should be no arrows. The arrow should be removing a proton from the H2O group. An arrow is also needed to indicate the loss of the leaving group. The arrow is backwards.

Answer: C Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Medium 76.

H2O

A. B. C. D.

What is wrong with the mechanism shown?

Answer: D Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Medium 77.

Which of the mechanistic steps shown represents a nucleophilic attack?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Medium 78.

Which of the mechanistic steps shown represents the loss of a leaving group?

A. B. C. D.

I II III IV

Learning Objective: 6.8 List the four characteristic arrow pushing patterns and discuss the events of carbocation rearrangement Difficulty: Medium

79.

Identify the sequence of curved arrows (electron movement) in the steps of the reaction shown.

A. B. C. D.

proton transfer, proton transfer proton transfer, loss of leaving group nucleophilic attack, proton transfer proton transfer, nucleophilic attack

Answer: A Learning Objective: 6.9 Describe what happens in a concerted process, including the kinds of arrow-pushing patterns that can be found Difficulty: Medium 80.

Identify the sequence of curved arrows (electron movement) in the steps of the reaction shown.

A. B. C. D.

proton transfer, proton transfer, nucleophilic Attack proton transfer, loss of leaving group nucleophilic attack, proton transfer, loss of leaving group proton transfer, nucleophilic attack, proton transfer

Answer: D Learning Objective: 6.9 Describe what happens in a concerted process, including the kinds of arrow-pushing patterns that can be found Difficulty: Hard 81.

Identify the sequence of curved arrows (electron movement) in the steps of the reaction shown.

H Cl

A. proton transfer, proton transfer B. proton transfer, loss of leaving group C. nucleophilic attack, proton transfer D. proton transfer, nucleophilic attack Answer: D Learning Objective: 6.9 Describe what happens in a concerted process, including the kinds of arrow-pushing patterns that can be found Difficulty: Hard 82.

What pattern of curved arrow pushing is the second step of this reaction?

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: B Learning Objective: 6.9 Describe what happens in a concerted process, including the kinds of arrow-pushing patterns that can be found Difficulty: Hard 83.

What pattern of curved arrow pushing is the fourth step of this reaction?

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: A Learning Objective: 6.9 Describe what happens in a concerted process, including the kinds of arrow-pushing patterns that can be found Difficulty: Hard 84.

What pattern of curved arrow pushing is the second step of this reaction?

H Cl

A. B. C. D.

proton transfer loss of leaving group nucleophilic attack rearrangement

Answer: C Learning Objective: 6.9 Describe what happens in a concerted process, including the kinds of arrow-pushing patterns that can be found Difficulty: Medium 85. Which choice shows the likely correctly uses arrows to show the movement of electrons in the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: curved arrow Difficulty: Hard

6.10 Describe the proper placement of the head and tail of a

86. Which choice shows the likely correctly uses arrows to show the movement of electrons in the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B 6.10 Describe the proper placement of the head and tail of a curved arrow Difficulty: Hard 87. What is the proper placement for an arrow to show the movement of electrons in the resonance structure shown?

A. I B. II C. III D. IV E. V Answer: B 6.10 Describe the proper placement of the head and tail of a curved arrow Difficulty: Hard 88.

Which letters indicate the nucleophilic and electrophilic sites in the reactants of the reaction shown?

A. B. C.

The nucleophile is c and the electrophile is e. The nucleophile is b and the electrophile is d. The nucleophile is e and the electrophile is c.

D. E.

The nucleophile is a and the electrophile is c. The nucleophile is b and the electrophile is e.

Answer: C

6.10 Describe the proper placement of the head and tail of a curved arrow Difficulty: Easy 89.

Identify the nucleophilic and electrophilic sites in the substrate and reagent of the following reaction.

A. B. C. D. E.

The nucleophile is c and the electrophile is e. The nucleophile is b and the electrophile is d. The nucleophile is c and the electrophile is b. The nucleophile is b and the electrophile is c. The nucleophile is d and the electrophile is b.

Answer: E

6.10 Describe the proper placement of the head and tail of a curved arrow Difficulty: Medium 90.

Will cation shown undergo rearrangement?

A. B.

Yes No

Answer: A

Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Easy 91.

Will cation shown undergo rearrangement?

A. B.

Yes No

Answer: B Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Easy 92.

Will cation shown undergo rearrangement?

A. B.

Yes No

Answer: A Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Easy 93.

Will cation shown undergo rearrangement?

A. B.

Yes No

Answer: A Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Easy

94.

Which of the structures shown is the most likely structure of the given cation after rearrangement?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Easy 95. What is the most likely structure of the cation shown after it has undergone rearrangement?

A. B.

I II

C. D. E.

III IV V

Answer: D

Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Hard 96.

What is the most likely product for the following cation rearrangement.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 6.11 Discuss when a carbocation rearrangement will occur Difficulty: Hard 97.

Identify the appropriate arrow in the equation shown.

A. B. C. D. Answer: C Learning Objective: 6.12 Describe reversible and irreversible reactions and how they are represented using arrows Difficulty: Medium 98.

Identify the appropriate arrow in the equation shown.

A. B. C. D. Answer: C Learning Objective: 6.12 Describe reversible and irreversible reactions and how they are represented using arrows Difficulty: Medium 99.

Identify the appropriate arrow in the equation shown.

A. B. C. D. Answer: A Learning Objective: 6.12 Describe reversible and irreversible reactions and how they are represented using arrows Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 7 1.

Which of the choices is a substitution reaction?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy 2. Which of the choices is a substitution reaction?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy 3. Which of the choices is a substitution reaction?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Medium 4. Which of the choices is an elimination reaction?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy 5. Which of the choices is an elimination reaction?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy

What is the nucleophile in the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy 7.

What is the electrophile in the reaction shown?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy 8.

What is the nucleophile in the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy 9.

What is the electrophile in the reaction shown?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Easy

10.

What are the nucleophile, electrophile, and leaving group in the reaction shown below?

A. B. C. D. E.

Nucleophile 2-chlorobutane; electrophile NaOH; leaving group Cl Nucleophile 2-chlorobutane; electrophile Cl; leaving group NaOH Nucleophile Cl; electrophile NaOH, leaving group 2-chlorobutane Nucleophile NaOH; electrophile 2-chlorobutane; leaving group Cl Nucleophile 2-chlorobutane; electrophile NaOH, leaving group Cl

Answer: D

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Medium 11.

What are the nucleophile, electrophile, and leaving group in the reaction shown below?

A. B. C. D. E. Answer: B

+ Br

Nucleophile bromo-2-propene; electrophile cyclohexoxide; leaving group Br Nucleophile cyclohexoxide; electrophile bromo-2-propene; leaving group Br Nucleophile Br; electrophile bromo-2-propene, leaving group cyclohexoxide Nucleophile cyclohexoxide; electrophile Br; leaving group bromo-2-propene Nucleophile Br; electrophile cyclohexoxide; leaving group bromo-2-propene

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions Difficulty: Medium 12.

Which of the choices is a primary alkyl halide?

A. B. C. D.

(CH3)2CHCH2Cl (CH3)2CClCH2CH3 (CH3)2CHCHClCH3 (CH3)2CHCH2CCl(CH3)2

Answer: A Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Easy 13.

Which of the choices is a secondary alkyl halide?

A. B. C. D.

(CH3)2CHCH2Cl (CH3)2CClCH2CH3 (CH3)2CHCHClCH3 (CH3)2CHCH2CCl(CH3)2

Answer: C Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Easy 14.

Which of the choices is a tertiary alkyl halide?

A. B. C. D.

(CH3)2CHCH2Cl (CH3)2CClCH2CH3 (CH3)2CHCHClCH3 (CH3)2CHCH2CHClCH2CH3

Answer: B Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Easy

15.

Which of the choices is a secondary alkyl halide?

A. B. C. D.

1-Bromo-2-methylpropane 2-Bromopropane 1-Bromobutane 2-Bromo-2-methylpropane

Answer: B Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 16.

Which of the choices is a tertiary alkyl halide?

A. B. C. D.

1-Bromo-2-methylpropane 2-Bromopropane 1-Bromobutane 2-Bromo-2-methylpropane

Answer: D Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 17.

What is the classification for the halide shown?

A. B. C. D.

primary halide secondary halide tertiary halide quaternary halide

Answer: C Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium

18.

What is the IUPAC name for the compound shown?

A. B. C. D.

3-Fluorobutane 2-Fluorobutane (S)-2-Fluorobutane (R)-2-Fluorobutane

Answer: D Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 19.

What is the IUPAC name for the compound shown?

A. B. C. D.

Chlorocyclopentane 2-Chloro-1-methylcyclopentane 1-Methyl-2-chlorocyclopentane 1-Chloro-2-methylcyclopentane

Answer: D Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Easy 20.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

2-Bromo-4-pentylhexane (2S,4S)-2-Bromo-4,5-diethylheptane 3,4-Diethyl-6-bromoheptane 2-Bromo-4-methylhexane (2R,4R)-2-Bromo-4,5-diethylheptane

Answer: B Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 21.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

1,2-bromocyclopentane (1R, 2S)-1,2-dibromocyclopentane (1S, 2S)-1,2-dibromocyclopentane (1S, 2R)-1,2-dibromocyclopentane (1R, 2R)-1,2-dibromocyclopentane

Answer: C Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 22.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

1-bromocyclobutane 1,1-bromocyclobutane 1,1,-dibromobutane 1,1-dibromocyclobutane dibromobutane

Answer: D Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 23.

A. B. C. D. E.

What is the IUPAC name for the compound shown?

5-bromo-1-fluorohexane 2-fluoro-5-bromohexane 5-fluoro-2-bromohexane bromofluorhexane 2-bromo-5-fluorohexane

Answer: E Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 24.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

(1S, 3R)-1-chloro-3-ethyl-3-methylcyclohexane (1S, 3R)-3-chloro-1-methyl-1-ethylcyclohexane (1R, 3S)-1-ethyl-1-methyl-3-chlorocyclohexane (1R, 3S)-3-chloro-1-ethyl-1-methylcyclohexane (1S, 3R)-3-chlorocyclohexyl-1-methylethane

Answer: D Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Hard 25.

What is the correct structure for 2-bromo-3-methylbutane?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Easy 26.

What is the correct structure for 3-ethyl-1-iodocyclohexane?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Easy 27.

What is the correct structure for (2S,5R)-2-fluoro-5-methylnonane?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 28.

Which choice shows the structure of 1-chloro-4-isopropylheptane?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Medium 29.

Which choice(s) shows the structure of cis-1,2-dibromocyclopentane?

A. B. C. D. E.

I II III I and II I, II, and III

Answer: D

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°,

2°, or 3°) to an alkyl halide Difficulty: Medium 30.

Which choice shows the structure of (4R,8S)-4-iodo-2,2,8-trimethyldecane.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide Difficulty: Hard 31.

Which of the following is a reasonable definition of a concerted reaction?

A. B. C. D.

a reaction in which bond breaking occurs first a reaction in which all bond-breaking and bond-forming occurs at the same time a reaction in which bond forming occurs first a substitution reaction

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 32.

When drawing a curved arrow mechanism, the tail of the arrow starts at______.

the bond that is being formed

B. C. D.

the atom with the positive charge the source of electrons that is being moved the location to which the electrons are being moved

Answer: C Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 33.

When drawing a curved arrow mechanism, the head of the arrow goes to__________.

A. B. C. D.

the bond that is being formed the bond that is being broken the source of electrons that is being moved the location to which the electrons are being moved

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 34.

Which of the following is the rate equation for the SN2 reaction shown?

A. B. C. D. E.

Rate = k[1-bromopropane] Rate = k[NaCN] Rate = k[1-bromopropane] [NaCN] Rate = k[1-bromopropane]2 Rate = k[1-bromopropane]2 [NaCN]2

Answer: C Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 35.

Which of the following is the rate equation for the reaction shown?

Rate = k[CH3CH2CH2CHBrCH3]

B. C. D. E.

Rate = k[NaN3] Rate = k[CH3CH2CH2CHBrCH3] [NaBr] Rate = k[CH3CH2CH2CHBrCH3] [NaN3] Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3]

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 36. Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentration of 1-chloro-3-methylbutane was doubled? Consider the following SN2 reaction,

A. B. C. D. E.

The rate would double. The rate would triple. The rate would quadruple. The rate would be halved. There would be no effect

Answer: A Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 37. Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentration of NaN3 was doubled?

A. B. C. D. E.

The rate would double. The rate would triple. The rate would quadruple. The rate would increase by a factor of 6. There would be no effect

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 38. Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentrations of both 1-chloro-3-methylbutane and NaN3 were doubled?

A. B. C. D. E.

The rate would double. The rate would triple. The rate would quadruple. The rate would be halved. There would be no effect

Answer: C Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentrations of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved? 39.

A. B. C. D. E.

The rate would double. The rate would triple. The rate would quadruple. The rate would be halved. There would be no effect

Answer: E Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 40. Which choice shows the correct curved arrow mechanism for the given SN2 reaction?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 41.

What is the predicted product of the SN2 reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 42.

What is predicted to be produced by the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 43.

Which of the choices is a mechanism for an SN2 reaction?

A. B. C. D. E.

I II III IV Both I & II

Answer: C Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 44.

Predict the product for the SN2 reaction shown.

A. B. C. D. E.

I II III IV I and II

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 45.

Predict the product for the SN2 reaction shown.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 46.

Predict the product for the reaction shown.

A. B. C. D. E.

I II III IV None of these

Answer: C Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 47.

Predict the product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 48.

Predict the product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 49.

Predict the product for the following reaction.

(1R, 3S)-1-bromo-3-sec-butylcyclopentane + NaN3

A. B. C.

I II III

D. E.

IV V

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 50.

Which of the alkyl halides shown will undergo the fastest SN2 reaction?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 51.

Which of the alkyl halides shown is essentially unreactive in an SN2 reaction? Br

Br II

III

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 52.

Rank the compounds shown from most to least reactive in an SN2 reaction.

A. B. C. D. E.

I > IV > II > III II > I > IV > III III > IV > I > II IV > I > II > III IV > III > I > II

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 53.

Rank the compounds shown from most to least reactive in an SN2 reaction.

I > IV > II > III

B. C. D. E.

II > I > IV > III III > IV > I > II I > III > II > IV IV > III > I > II

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 54.

Which of the alkyl halides shown will undergo the slowest SN2 reaction?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 55.

Which potential energy diagram describes the SN2 reaction shown?

A. B. C. D. E.

I II III IV None of the above

Answer: A Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 56.

Which choice shows the transition state for the given SN2 reaction?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 57.

Which choice shows the transition state for the given SN2 reaction?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 58.

Which illustration shows the transition state for the addition of

(S)-1-iodo-3-

methylpentane to NaSCH3?

A. B. C. D. E. Answer: D

I II III IV No reaction will occur.

δLearning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 59. What is the likely product of the SN2 reaction shown?

A. B. C. D. E.

I II III IV None of these

Answer: A Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 60. What is the likely product of the SN2 reaction shown?

A. B. C. D. E.

I II III IV None of these

Answer: A Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Easy 61. What is the likely product of the SN2 reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Medium 62.

What is the curved arrow mechanism for the first step of the SN2 reaction shown?

A. B. C. D. E.

I II III IV V

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 64.

Predict the product for the SN2 reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including

the transition state, the effects of substitution, and stereochemical outcome Difficulty: Hard 65.

Describe a strong nucleophile.

A. B. C. D.

an anion a cation a radical a neutral compound

Answer: A Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Medium 66.

Which of the choices is NOT a nucleophile?

A. B. C. D. E.

OHNH3 CH3OH NH4+ All of these

Answer: D Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Easy 67.

Which of the choices is a strong nucleophile?

A. B. C. D. E.

OHH2 O CH3OH NH4+ All of these

Answer: A Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Easy 68.

Which of the choices is a weak nucleophile?

A. B. C. D. E.

OHH2 O CH3ONH4+ All of these

Answer: B Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Easy 69.

Which of the structures shown is an aprotic solvent?

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Easy 70.

Which of the structures shown is a protic solvent?

A. B. C. D.

I II III IV

none of these

Answer: B Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Easy 71.

What is an important difference between protic and aprotic solvents?

A. B. C. D. E.

protic solvents stabilize anions only aprotic solvents stabilize anions only protic solvents stabilize cations only aprotic solvents stabilize both cations and anions protic solvents stabilize both cations and anions

Answer: E Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Medium 72.

What set of reaction conditions would favor an SN2 reaction involving 2-bromo-3methylbutane?

A. B. C. D.

a weak nucleophile in a protic solvent a weak nucleophile in an aprotic solvent a strong nucleophile in a protic solvent a strong nucleophile in an aprotic solvent

Answer: D Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions Difficulty: Easy

73.

Which solvent(s) would favor an SN2 reaction by a secondary alcohol?

A. B. C. D. E.

acetone ethanol water propanol ammonia

Answer: A

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Medium 74.

Which choice is a good example of an aprotic solvent?

A. B. C. D. E.

NH3 H2O OHDMSO EtOH

Answer: D Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Easy 75.

Which of the examples shows a mechanism of a concerted elimination?

H Br

OMe

H Br

OMe

H OMe

III

H IV

A. B. C. D.

H OMe

OMe

I II III IV

Answer: A Learning Objective: 7.5 Describe the characteristics of E2 reactions, including rate and substrate effects, and the differences between elimination and substitution reactions Difficulty: Easy 76.

Identify the type of elimination involved in an E2 mechanism.

A. B. C. D. E.

alpha elimination beta elimination gamma elimination delta elimination omega elimination

Answer: B

Learning Objective: 7.5 Describe the characteristics of E2 reactions, including rate and substrate effects, and the differences between elimination and substitution reactions Difficulty: Easy 77.

What can you predict about the stability of the structures shown?

A. B. C. D.

I is predicted to be more stable than II. II is predicted to be more stable than I. I and II are predicted to be equally stable. It is impossible to predict without more information.

Answer: A Learning Objective7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Easy 78.

What can you predict about the stability of the structures shown?

I is predicted to be more stable than II.

B. C. D.

II is predicted to be more stable than I. I and II are predicted to be equally stable. It is impossible to predict without more information.

Answer: B Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Easy 79.

What can you predict about the stability of the structures shown?

A. B. C. D.

I is predicted to be more stable than II. II is predicted to be more stable than I. I and II are predicted to be equally stable. It is impossible to predict without more information.

Answer: A Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium 80.

What can you predict about the stability of the structures shown?

A. B. C. D.

1-methyl-2-cyclohexene 2-methylcyclohexene 3-methylcyclohexene 1-methyl-5-cyclohexene

A. B. C. D. E.

I is predicted to be more stable than II. II is predicted to be more stable than I. III is predicted to be more stable than I. II is predicted to be more stable than II. I, II, and III are predicted to be equally stable.

Answer: C Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Easy 81.

Which statement is true about the stability of cycloalkenes?

A. Highly substituted alkenes are less stable than unsubstituted alkenes. B. Cis alkenes are more stable than trans alkenes. C. It is stable for a bridgehead of a bicyclic system can include a trans bond in a small ring. D. Bicyclic rings with 10 carbons in one of the rings can have a trans double bond at the bridgehead position. Answer: D Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium 82.

Is the structure shown stable?

A. B. C. D. E.

Yes, because it is consistent with Bredt’s rule. Yes, because it consists of two joined rings. Yes, because it has a trans double bond. No, because the ring is too small. No, because it has a cis double bond.

Answer: D Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium 83.

Which type of alkene would be predicted to be the most stable?

A. B. C. D. E.

A highly substituted cis alkene. An unsubstituted cis alkene. A highly substituted trans alkene. An unsubstituted trans alkene. An alkene bonded only to hydrogens.

Answer: C

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Easy 84.

Which alkene is predicted to be the most stable?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium

85.

Why is it unnecessary to specify whether the double bond in a four-carbon ring is cis or trans?

A. B. C. D.

Cis double bonds are unstable in such small rings. Trans double bonds are unstable in such small rings. Double bonds in rings are not classified as cis or trans. Double bonds do not form in such small rings.

Answer: B Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Easy 86.

Does the molecule below violate Bredt’s rule?

A. B. C. D. E.

Yes, because there is a trans double bond in a ring. Yes, because the bond angles are too small. Yes, because the molecule is not aromatic. No, because the ring is sufficiently large. No, because the double bond includes the bridgehead carbon.

Answer: D Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium

87.

What characteristic would let you recognize that something might be a good protic solvent?

A. B. C. D. E.

It has a bright color. It has a low boiling point. It has a low melting point. It is hydrophobic. It forms hydrogen bonds.

Answer B Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Medium 88

When you run the same reaction using fluoride and then iodide as nucleophiles, you find that fluoride reacts more rapidly. What can you do to cause the reaction involving iodide to become faster than the reaction using fluoride?

A. B. C. D. E.

Change the solvent from methanol to DMSO. Change the solvent from DMSO to methanol. Increase the concentration of both nucleophiles. Use a stronger base. Increase the concentration of the solvent.

Answer: B Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Hard 89

Which of the following statements is true of polar aprotic solvents?

A B. C. D.

They are capable of hydrogen bonding. They can increase the rate of SN2 reactions by orders of magnitude. They are relatively uncommon. They favor SN1 reactions.

Answer: B Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2

reactions. Difficulty: Easy 90

Why do polar aprotic solvents favor SN2 reactions?

A Hydrogen bonding stabilizes the reaction intermediates. B. Hydrogen bonding stabilizes the leaving group. C. Polar aprotic solvents can’t stabilize anions and therefore nucleophiles have higher energy when they are used. D. Protic solvents destabilize nucleophiles and that reduces the likelihood of reaction. Answer: C Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Easy 91

Which of the following choices can be stabilized by polar protic solvents?

A B. C. D.

Cations Anions Neutral species Both cations and anions

Answer: D Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Easy 92.

You discover that the energy of activation for an SN2 reaction decreases when you change the solvent. What is the most likely reason for this finding?

A B. C. D.

You have substituted a polar aprotic solvent for a polar protic solvent. You have substituted a polar protic solvent for a polar aprotic solvent. You have substituted an impure solvent for a pure solvent. You have substituted a pure solvent for an impure solvent.

Answer: B Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions.

Difficulty: Hard 93

Which of the reactions below is expected to proceed the most rapidly?

A B. C. D. E.

CH3CH2CH2Br + NaOH in DMSO CH3CH2CH2Br + NaOH in acetone CH3CH2CH2Br + NaOH in ethanol A and B B and C

Answer: D Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Easy 94

Why are SN1 reactions favored by polar protic solvents?

A. Polar protic solvents contribute leaving groups. B. Polar protic solvents stabilize the nucleophile. C. Polar protic solvents cannot form hydrogen bonds. D. Polar protic solvents stabilize intermediates. Answer: D Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Easy 95

If you dissolve NaCl in a polar protic solvent, what will happen?

A. B. C. D.

Both Na+ and Cl- will be stabilized by interactions with the solvent Only Na+ will be stabilized by interactions with the solvent Only Cl- will be stabilized by interactions with the solvent Neither Na+ nor Cl- will be stabilized by interactions with the solvent

Answer: A Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Medium 96.

An energy diagram shows the potential energy during a specific SN1 reaction.

Two curves are present, both of which rise to a peak and then decrease in a pattern expected for an exergonic reaction. However, one curve is consistently substantially higher than the second curve. What is a reasonable explanation for this difference? A.

The top curve represents the reaction in water and the bottom curve represents the reaction in DMSO. The top curve represents the reaction in a DMF and the bottom curve represents the reaction in ethanol. The top curve represents the reaction in ammonia and the bottom curve represents the reaction in water. The top curve represents the reaction in DMSO and the bottom curve represents the reaction in acetone.

B. C. D.

Answer: B Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions. Difficulty: Hard

97.

Rank the structures shown from most to least stable.

A. B. C. D. E.

III

I > II > III > IV II > III > IV > I III > IV > 1 > II IV > I > III > II I > IV > III > II

Answer: D Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium 98.

Rank the structures shown from most to least stable.

A. B. C. D. E.

I > II > III III > II > I II > III > I II > I > III I > III > II

Answer: E Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Medium 99.

Which of the alkenes shown is more stable?

A. B. C. D.

I II They are equally stable. It is impossible to tell without more information.

Answer: B Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Hard 100.

Rank the structures shown from most to least stable.

A. B. C. D. E.

I > II > III II > I > III III > I > II III > II > I II > III > I

Answer: D Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes. Difficulty: Hard 101.

Which choices shows the mechanism for the elimination reaction shown, assuming that it is a concerted reaction?

A. I B. II C. III D. IV E. V Answer: B

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 102.

Show the mechanism for the elimination reaction shown, assuming that it is a concerted reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy

103.

Which of the structure(s) shown is the most reactive in an E2 reaction?

A. B. C. D. E.

I II III I and II are equally most reactive II and III are equally most reactive

Answer: C Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 104.

Which of the structures shown is the major product of the given elimination?

A. B. C. D.

I II III None of the above

Answer: A Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 105.

Which of the structures shown is the major product of the given elimination?

A. B. C. D.

I II III None of the above

Answer: B Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 106.

What would be the best base for performing the elimination reaction shown?

A. B. C. D.

KOCH3 KOCH(CH3)2 KOC(CH3)3 this reaction is not an elimination reaction

Answer: C Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 107.

Which of the following would be the best base for performing the elimination reaction shown?

A. B. C. D.

KOCH3 KOCH(CH3)2 KOC(CH3)3 this reaction is not an elimination reaction

Answer: A Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 108.

What major product(s) will be yielded by the elimination reaction shown?

A. B. C. D. E.

I II III IV I and IV

Answer: A Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 109.

What is the product of the following elimination?

OMe Cl

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 110.

What is the product of the elimination reaction shown?

OMe

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 111.

Which of the alkyl halides shown would yield the indicated product upon reaction with sodium ethoxide?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 112.

Which of the alkyl halides shown would yield the indicated product upon reaction with sodium ethoxide?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 113.

Which isomer(s) of 2-bromo-1,1,3-trimethylcyclohexane would be most reactive in an E2 elimination?

A. B. C. D. E.

I II III I and II III and IV

Answer: D

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 114.

Draw the major product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 115.

Draw the major product of the reaction shown.

A. B. C. D.

I II III IV

Answer: C

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 116.

Draw the major product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 7.8 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 117.

Draw the major product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 118.

What is the predicted major product of elimination reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 119.

What is the predicted major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 120.

What is the predicted major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Hard 121.

What is the predicted major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction,

including regiochemistry and stereochemistry Difficulty: Medium 122.

What is the predicted major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 123.

What is the predicted major product for the reaction shown?

B. C. D. E.

II III IV V

Answer: E

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 124.

What is the mechanism for the following elimination?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 125.

What is the mechanism for the elimination reaction shown?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 126.

Which of the choices shows the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium 127.

What is the mechanism for the E2 reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Medium

128.

What is the predicted product for the E2 reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry Difficulty: Easy 129.

What set of reaction conditions would favor an SN1 reaction on 2-bromo-3methylbutane?

A. B. C. D.

weak nucleophile in a protic solvent weak nucleophile in an aprotic solvent strong nucleophile in a protic solvent strong nucleophile in an aprotic solvent

Answer: A Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Easy 130.

Which of the steps shown would not occur in a substitution reaction?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Easy 131.

What describes the mechanism of the reaction shown below?

A. B. C. D. E.

Bromine leaves, forming a carbocation Na+ is added to Br CN- is added, forming a carbocation Na+ and CN- are added simultaneously Br- leaves and CN- is added simultaneously

Answer: A

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Easy 132.

What is the curved arrow mechanism for the first step of the reaction shown?

NaCl Cl

III

A. B. C. D.

I II III IV

Cl-

Answer: E Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Medium 133121.

Which description best explains the mechanism for the reaction shown?

A. Br- leaves, producing a carbocation. A rearrangement occurs, allowing SH- to add to the bottom vertex of the ring. B. Br- leaves and SH- is added simultaneously, then a rearrangement occurs. C. SH- is added, which forces Br- to leave. This allows rearrangement to take place. D. Br- leaves, producing a carbocation. A rearrangement occurs, allowing SH- to add to the bottom vertex. E. Rearrangement occurs, forcing Br- to leave. This allows SH- to add to the bottom vertex. Answer: A Br

+ Br

Which of the choices gives the rate equation for the following SN1 reaction?

A. B. C. D.

Rate = k[H2O] Rate = k[1-chloro-1-methylcyclohexane] [H2O] Rate = k[chloride ion] Rate = k[1-chloro-1-methylcyclohexane]

Which of the choices gives the rate equation for the following SN1 reaction?

2-chloro-2-methylpentane + NaI A. B. C. D.

Rate = k[NaI] Rate = k[2-chloro-2-methylpentane] [NaI] Rate = k[chloride ion] Rate = k[2-chloro-2-methylpentane]

Which choices is a potential energy diagram for an exothermic SN1 reaction?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Medium 137.

Which of the alkyl halides shown undergoes the fastest SN1 reaction?

A. B. C. D. E.

I II III IV V

Which of the alkyl halides shown undergoes the slowest SN1 reaction?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Medium

139.

Rank the compounds shown from most to least reactive in an SN1 reaction.

A. B. C. D. E.

I > IV > II > III II > I > IV > III III > IV > I > II IV > I > II > III IV > III > I > II

Rank the compounds shown from most to least reactive in an SN1 reaction.

A. B. C. D. E.

I > IV > II > III II > III > I > IV III > II > I > IV I > III > II > IV IV > III > I > II

141.

Which of the compounds shown will undergo the fastest SN1 reaction?

A. B. C. D. E.

I II III IV I and IV

Which of the compounds shown undergo the fastest SN1 reaction?

A. B. C. D. E.

I II III IV V

Which of the statements given is true about the stereochemistry of SN1 reaction?

A. B. C.

retention of configuration at the electrophilic center inversion of configuration at the electrophilic center 50:50 mixture of retention and inversion of configuration at the electrophilic center slightly more inversion than retention at the electrophilic center slightly more retention than inversion at the electrophilic center

D. E.

What is the predicted product of the SN1 reaction shown?

B. C. D.

II III IV

What is the predicted product for the SN1 reaction shown?

A. B. C. D.

I II III IV

What is the predicted product for the SN1 reaction shown?

A. B. C. D.

I II III IV

What are the predicted products for the SN1 reaction shown?

A. B. C. D. E.

I II III IV V

III

A. B. C. D. E.

I II III IV V

148.

What are the predicted products for the reaction shown?

+ Cl

III

A. B. C. D. E.

I II III IV V

Predict the product(s) for the SN1 reaction shown.

A. B. C. D. E.

II III IV I and IV II and III

Provide a curved arrow mechanism for the first step of the following reaction.

III

A. B. C. D. E.

I II III IV V

What is the predicted major product for the reaction shown?

A. B. C. D. E.

I II III I and III II and IV

What is the predicted major product for the SN1 reaction shown?

A. B. C. D. E.

I II I and IV II and III V

Answer: D

What is the predicted major product for the SN1 reaction shown?

A. B. C. D. E.

I II I and III II and IV None of these

What is the predicted curved arrow mechanism for the reaction shown?

Mechanism:

A. B. C. D. E.

I II III I and II are equally possible II and III are equally possible

Which reaction mechanism accurately describes this reaction?

A. B. C. D. E.

I only II only I is more common, but II is also a likely mechanism. II is more common, but I is also a likely mechanism. It is impossible to tell from the information given.

A. B. C. D. E.

I II III IV V

Answer: B

Predict the major product(s) of the reaction shown.

A. B. C. D. E.

I I and II III IV III and IV

Answer: D

Which of the compounds shown will undergo rearrangement in an SN1 reaction?

A. B. C. D. E.

I II III IV V

Predict the major product for the SN1 reaction shown.

A. B. C. D. E.

I II III IV V

Which of the compounds given will undergo rearrangement during a solvolysis reaction?

A. B. C. D. E.

3-iodo-5-methylheptane 3-iodo-2-methylheptane 3-iodo-3-methylheptane 3-iodoheptane cis-1-iodo-3-methylcyclohexane

What is the predicted major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Which of the structures shown is the most reactive in an E1 reaction?

A. B. C. D. E.

I II III II and III are equally reactive in an E1 reaction. I, II, and III are equally reactive in an E1 reaction

163.

Which of the structures shown is most reactive in an E1 reaction?

A. B. C. D. E.

I II III II and III are equally reactive in an E1 reaction. I, II, and III are equally reactive in an E1 reaction.

For the following dehydration, draw the structure of the intermediate carbocation.

B. C. D. E.

II III IV V

For the following dehydration, draw the structure of the intermediate carbocation.

A. B. C. D. E.

I II III IV V

What is the predicted product for the following rearrangement?

elimination with no

A. B. C. D. E.

I II III IV II and III

What is the structure of the intermediate carbocation formed during the dehydration reaction shown?

A. B. C. D. E.

I II III IV V

What is the major organic product of the dehydration reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C

What is the product of the dehydration reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C

What error is in the dehydration reaction mechanism shown?

A. There is an arrow missing that should show the movement of electrons from the bond between H and SO3H and SO3H. B. There is an arrow missing that should show the movement of a pair of electrons from O to the bond connecting it to C. C. OH does not initiate the reaction in the first step. D. O should not have a positive charge in the second structure. E. This type of reaction does not produce a carbocation. Answer: A Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Hard 171.

What error is in the dehydration reaction mechanism shown?

A. The reaction should begin with an arrow pointing from SO3H2 to OH, not from O H to SO3H2. B. OH2 should not have a positive charge as oxygen is too electronegative to be stable in this form. C. Water needs to be added to H bonded to the third structure so that the electrons of the bond can move to form a double bond at the upper right side. D. The arrow pointing from O H to SO3H2 should point to S and not to H. E. The arrow shown on the third structure should point to the positively charged carbon, not to the bond at the upper right side. Answer: C Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Easy 172.

Which of the energy diagrams shown describes the given reaction?

Answer: A

Assuming that the reaction below is exothermic, which of the energy diagrams shown could describe it?

A. B. C. D. E.

I II III IV V

Answer: A

Which pattern of arrow pushing is associated with the first step in any dehydration reaction?

A. B. C. D. E.

proton transfer loss of leaving group rearrangement it is impossible to know without more information none of these patterns of arrow pushing are used in the first step of dehydration

reactions Answer: A Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes Difficulty: Hard 175.

What are the steps of arrow pushing involved in the following mechanism?

A. B. C. D. E.

proton transfer loss of leaving group followed by proton transfer and then rearrangement proton transfer and loss of leaving group rearrangement and loss of leaving group proton transfer, loss of leaving group, rearrangement, and then proton transfer

Will the following alcohol undergo rearrangement during a dehydration reaction?

A. B. C. D. E.

Yes, it will definitely undergo rearrangement. Rearrangement is possible, but will not always occur. Rearrangement will occur about half of the time. Rearrangement will not occur. It is impossible to determine without more information.

Answer: D

Will the following alcohol be likely to undergo rearrangement during a dehydration reaction?

A. B. C. D. E.

Yes, it will undergo rearrangement. Rearrangement is possible, but usually will not occur. Rearrangement will occur about half of the time. Rearrangement will not occur. It is impossible to determine without more information.

What is the structure of a rearranged carbocation that does not have a fourmembered ring in the following acid-catalyzed dehydration of the following compound?

A. B. C. D. E.

I II III IV V

Answer: C

What is the predicted product of the elimination reaction shown?

A. B. C. D. E.

I II III IV V

Answer: E

Based upon the energy diagram shown, is this reaction an E1 or an E2 elimination?

A. B. C. D.

E1 elimination E2 elimination It is impossible to determine from the diagram alone. The diagram suggests that it is not an elimination reaction.

Answer: B Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 181.

Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

A. B. C. D.

E1 elimination E2 elimination It is impossible to determine from the diagram alone. The diagram suggests that it is not an elimination reaction.

Answer: A Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 170.

What substitution reaction mechanism is the compound shown most likely to undergo?

A. B. C. D.

SN 1 SN 2 Either SN1 or SN2 None of these

Answer: C Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 183.

What substitution reaction mechanism is the compound shown most likely to undergo?

A. B. C. D.

SN 1 SN 2 Either SN1 or SN2 None of these

Answer: C Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 184.

What substitution reaction mechanism is the compound shown most likely to undergo?

A. B. C. D.

SN 1 SN 2 Either SN1 or SN2 None of these

Answer: A Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 185.

What substitution reaction mechanism is most likely for the conversion shown?

A. B. C. D.

SN 1 SN 2 Either SN1 or SN2 None of these

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 186.

What substitution reaction mechanism is most likely for the conversion shown?

A. B. C. D.

SN 1 SN 2 Either SN1 or SN2 None of these

Answer: A Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 187.

What substitution reaction mechanism is most likely for the conversion shown?

A. B. C. D.

SN 1 SN 2 Either SN1 or SN2 None of these

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 188.

Which of the choices is a strongest nucleophile in a polar protic solvent?

A. B. C. D. E.

FClBrIAll of these

Answer: D Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 189.

Which of the choices is a weakest nucleophile in a polar protic solvent?

A. B. C. D. E.

FClBrIAll of these

Answer: A Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 190.

Which of the choices is a strongest nucleophile in a polar protic solvent?

F-

B. C. D. E.

ClOHSHAll of these

Answer: D Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 191.

Which of the compounds shown has the best leaving group?

A. B. C. D. E.

I II III IV All of these

Answer: D Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 192.

What is the predicted product for the reaction shown?

A. B. C. D. E.

I II III IV I and III

Answer: C Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 193.

What is the predicted product for the reaction shown?

A. B.

I II

C. D. E.

III IV I and II

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 194.

What is the predicted product for the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Hard

195.

What is (are) the predicted product(s) for the following reaction?

A. B. C. D. E.

I II III I and II I and III

Answer: E

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 196.

By what mechanism is the reaction shown likely to occur?

A. B. C.

SN1 SN2 E1

D. E.

E2 It is impossible to tell from the information given.

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 197.

By what mechanism is the reaction shown likely to occur?

A. B. C. D. E.

SN1 SN2 E1 E2 It is impossible to tell from the information given.

Answer: D Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 198.

By what mechanism is the reaction shown likely to occur?

A. B. C. D. E.

SN1 (major) and/or E1 (minor) SN2 (major) and/or E2 (minor) E1 only E2 only It is impossible to tell from the information given.

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy

199.

By what mechanism is the reaction shown likely to occur?

A. B. C. D. E.

SN1 SN2 E1 or E2 SN1 or E1 SN2 or E2

Answer: E1 or SN1 Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 188.

By what mechanism is the following reaction likely to occur?

A. B. C. D. E.

SN1 SN2 E1 E2 It is impossible to tell from the information given.

Answer: D Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 189.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 190.

What is (are) the most likely product(s) for the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Hard 203.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Hard 204.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II I and III II and III I, II, and III

Answer: C

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 205.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 206.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Hard 207.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II III V V

Answer: D

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Hard 208.

What is (are) the most likely product(s) for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Medium 209. Which term best describes the most likely role of the given species in a substitution or elimination reaction? CN

A. B. C. D. E.

nucleophile base it is equally likely to act as a nucleophile or as a base it will not act as either a nucleophile or a base it is impossible to tell from the information given

Answer: A Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy

210. Which term best describes the most likely role of the given species in a substitution or elimination reaction? Is the following more likely a nucleophile or a base?

A. B. C. D. E.

nucleophile base it is equally likely to act as a nucleophile or as a base it will not act as either a nucleophile or a base it is impossible to tell from the information given

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 211.

Which of the choices is the strongest nucleophile?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 212.

Which of the choices is the strongest nucleophile?

I A. B. C. D.

MeOH

MeO

III

I II III IV

Answer: B Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 213.

Which of the choices is most likely to act as a base rather than a nucleophile?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 214.

Which of the choices is most likely to act as a base rather than a nucleophile?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 7.09 Predict the products of reactions that may result in either substitution or elimination Difficulty: Easy 215.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D.

NaCl in water NaCl in ether HCl in water TsCl/pyridine followed by NaCl

Answer: C Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions Difficulty: Medium 216.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D. E.

HBr followed by NaI NaH followed by CH3CH2 HCl followed by CH3CH2MgBr TsCl/pyridine followed by NaCl NaOH followed by NaSH

Answer: B Learning Objective:

7.10 Determine how alcohols and alkyl sulfonates behave in

substitution and elimination reactions Difficulty: Hard 217.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D. E.

conc. H2SO4 followed by CH3NH2 NaH followed by CH3CH2 NaOH followed by CH3NH2 TsCl/pyridine followed by NaCl NaBr followed by CH3NH2

Answer: E Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions Difficulty: Hard 218.

Which reagents are appropriate to carry out the conversion shown?

1. conc. H2SO4, 2.

O Na

1. HBr; 2.

C. D.

O Na 1. NaOH; 2. 1. TsCl/pyridine; 2.CH3CH2COH

O Na O

1. TsCl/pyridine

O Na

Answer: E Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions Difficulty: Hard 219.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D.

H2S in water H2S in DMSO NaSH in water NaSH in DMSO

Answer: D Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product Difficulty: Easy 220.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D.

HN3 in water HN3 in acetonitrile NaN3 in water NaN3 in acetonitrile

Answer: D Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product Difficulty: Easy

221.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D.

NaOH in water NaOH in ether H2 O CH3OH

Answer: C Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product Difficulty: Medium 222.

Which reagents are appropriate to carry out the conversion shown?

A. B. C. D. E.

CH3CH2OH CH3CH2COOH NaOH followed by CH3CH2OH t-BuOK NaOH followed by CH3CH2MgBr

Answer: A Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product Difficulty: Medium 223.

How could you change the reaction conditions given to most strongly favor an E2 mechanism?

A. B. C. D. E.

Use a higher concentration of water Use a stronger base Add a stronger nucleophile Use a tertiary alkyl halide Increase the concentration of the reactant

Answer: B Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product Difficulty: Easy 224.

How could you change the reaction conditions given to most strongly favor an E1 mechanism?

A. B. C. D. E.

Use a higher concentration of water Use a weaker base Use a stronger nucleophile Use a primary alkyl halide Increase the concentration of the reactant

Answer: B Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 8 1.

In an addition reaction to an alkene, the π bond is _________.

A. B. C. D. E.

a nucleophile an electrophile a leaving group A and B B and C

Answer: A Learning Objective: 8.1 Define an addition reaction, name five kinds of addition reactions, and list the groups added in each kind of reaction Difficulty: Easy 2.

Addition reactions of alkenes are characterized by _________.

A. B. C. D. E.

formation of a π bond addition of two groups across a double bond breaking of a π bond A and B B and C

Answer: E Learning Objective: 8.1 Define an addition reaction, name five kinds of addition reactions, and list the groups added in each kind of reaction Difficulty: Moderate 3.

Alkenes are found in _________, which are used by living organisms to trigger specific behavioral responses in other members of the same species.

A. B. C. D. E.

polymers olefins hormones pheromones monomers

Answer: D Learning Objective: 8.2 Provide examples of alkenes in both nature and industry Difficulty: Easy 4.

What is a compound that does not have a double bond?

A. B. C. D. E.

allicin (garlic) geraniol (roses) cholesterol limonene (oranges) ammonia

Answer: E Learning Objective: 8.2 Provide examples of alkenes in both nature and industry Difficulty: Easy 5.

Identify the compound that is NOT produced industrially from an alkene.

A. B. C. D. E.

acetic acid methanol isopropyl alcohol acetone ethylene glycol

Answer: B Learning Objective: 8.2 Provide examples of alkenes in both nature and industry Difficulty: Easy 6.

The alkene precursor to the industrial production of ethanol is _________.

A. B. C. D. E.

ethane ethene ozonolysis propylene acetic acid

Answer: B Learning Objective: 8.2 Provide examples of alkenes in both nature and industry Difficulty: Easy 7.

The alkene precursor to the industrial production of acetone is _________.

A. B. C. D. E.

isopropyl alcohol propane dihydroxylation ethylene propene

Answer: E Learning Objective: 8.2 Provide examples of alkenes in both nature and industry Difficulty: Easy 8.

Most π bonds are quite prone to reaction with a(n) _________, also referred to as electron-seeking reagents.

A. B. C. D. E.

alcohol nucleophile solvent electrophile leaving group

Answer: D Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored Difficulty: Easy 9.

The decrease in entropy (the DS value is negative) observed for alkene addition reactions results from _________.

A. B. C. D. E.

the breaking of a π and s bond. the formation of two s bonds. the reaction being exothermic. two molecules reacting to form a single molecule. the temperature dependence of the DS term.

Which statement best describes the temperature dependence of an addition reaction?

A. B. C. D. E.

Addition reactions are thermodynamically favored at all temperatures. Addition reactions are thermodynamically disfavored at all temperatures. Addition reactions are thermodynamically favored at low temperatures. Addition reactions are thermodynamically favored at high temperatures. Addition reactions are thermodynamically impossible.

Answer: C Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored Difficulty: Easy 11.

For an addition reaction, why does free energy, DG, become more positive with increasing temperature?

A. B. C. D. E.

The positive entropy dominates at high temperature. The negative entropy dominates at high temperature. The positive enthalpy dominates at high temperature. The negative enthalpy dominates at high temperature. The enthalpy and entropy cancel at high temperature.

Answer: B Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored Difficulty: Moderate 12.

For this question, the “entropy term” refers to “-TΔS”. Addition reactions are generally favorable at low temperatures because _________.

A. B. C. D. E.

the positive enthalpy term is larger than the negative entropy term the negative enthalpy term is larger than the positive entropy term the positive enthalpy term is smaller than the negative entropy term the negative enthalpy term is smaller than the positive entropy term the enthalpy and entropy terms are equal

The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is named after which chemist?

A. B. C. D.

Vladimir Markovnikov Friedrich Wöhler Emil Fischer Paul Walden

Alexander M. Zaitsev

Answer: A Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 14.

The regioselectivity and stereospecificity in the hydrohalogenation of an alkene is best described as

A. B. C. D. E.

Markovnikov orientation with syn-addition. Markovnikov orientation with anti-addition. anti-Markovnikov orientation with syn-addition. anti-Markovnikov orientation with anti-addition. Markovnikov orientation with both syn- and anti-addition.

Answer: E Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 15.

In the addition reaction of HI to 2-methyl-2-butene, what is the first step?

A. B. C. D. E.

attack of 2-methyl-2-butene initiated by an iodide ion attack of 2-methyl-2-butene initiated by an iodine atom isomerization of 2-iodo-2-methylbutene formation of a carbocation at carbon two (C-2) formation of carbocation at carbon three (C-3)

Answer: D Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 16.

Which of the structures shown depicts the most likely carbocation intermediate formed in the hydrohalogenation reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 17.

What is the expected product for the hydrohalogenation of the following alkene with HBr?

Br Br

A. B. C. D. E.

III

I II III IV V

Answer: E Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 18.

What is the expected Markovnikov addition product from the addition of HI to 2methyl-2-butene?

2-iodopentane

B. C. D. E.

2-iodo-2-methylbutane 1-iodo-2-methylbutane 1-iodo-3-methylbutane 2-iodo-3-methylbutane

Answer: B Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 19.

What is the expected product when the given alkene undergoes Markovnikov hydrohalogenation with HBr?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 20.

What is the expected major product of the following reaction?

B. C. D. E.

II III IV V

Answer: C Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 21.

What is the expected major product of the following reaction?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 22.

What is the expected major product for the following reaction?

B. C. D. E.

II III IV V

Answer: D Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 23.

Which of the molecules below arises when the given alkene undergoes antiMarkovnikov hydrohalogenation with HBr?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 24.

Which of the alkenes shown below would produce a chiral center upon Markovnikov hydrohalogenation?

A. B. C.

I II III

D. E.

IV V

Answer: B Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 25.

Predict the major product(s) for the following reaction:

A. B. C. D. E.

I II III II & III IV

Answer: A Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 26.

Which of the alkenes below would be expected to produce at least one chiral center upon hydrohalogenation in the presence of peroxide?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 27.

Which of the given reaction schemes would produce the molecule shown below as the major product?

A. B. C. D. E.

I II III Both I and II Both II and III

Answer: E Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 28.

Which of the molecules below are enantiomers formed as products upon reaction of HBr with 4-methylpent-1-ene?

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: E Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

Difficulty: Moderate 29.

Which of the following carbocations is (are) likely to undergo rearrangement through a methyl shift?

A. B. C. D. E.

I II III I and II I, II and III

Answer: D Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 30.

Which of the following carbocations is (are) likely to undergo rearrangement through a hydride shift?

A. B. C. D. E.

I II III I and II I and III

Answer: E Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate

31.

Predict the expected major product(s) of HCl addition to the alkene below?

A. B. C. D. E.

I and II II and III III and IV II and IV V

Answer: A Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 32.

Predict the expected major product(s) of HBr addition to the alkene shown below?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate

33.

Predict the expected major product of the reaction below?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 34.

What is the IUPAC name of the expected major product of the following reaction?

A. B. C. D. E.

1-chloro-2-methylbutane 1-chloro-3-methylbutane 2-chloro-2-methylbutane 2-chloro-3-methylbutane 1-chloropentane

Answer: C Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Hard 35.

Select the expected major product(s) of the following reaction.

A. B. C. D. E.

I II III I and II I and III

Answer: C Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 36.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

isohexene 2-methyl-5-hexene 5-methyl-2-hexene 5-methyl-1-hexene 2-methyl-6-hexene

Answer: D Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes. Difficulty: Easy 37.

For the following reaction sequence identify the expected major organic product(s).

B. C. D. E.

II III I and II I, II and III

Answer: C Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 38.

Identify the structure of the expected major organic product expected upon completion of the following reaction:

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Easy 39.

The product shown in the box in the scheme can be produced by treatment of each of the alkenes shown with HCl. Which reaction intermediate would explain this observation.

A. B. C. D. E.

I II III IV None of the above

Answer: B Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate 40.

When the two constitutional isomers shown below in the following scheme, are reacted with HCl the same major product is formed. Identify the structure of this major product.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Hard 41.

Addition of HI to the alkene given below, results in a significant yield of the product shown. What other product(s) might also be obtained?

A. B. C. D. E.

I II III I and II II and III

Answer: D Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Hard 42.

The regioselectivity and stereospecificity in the acid-catalyzed hydration of an alkene is best described as

A. B. C. D. E.

Answer: E Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Easy 43.

Predict the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Easy 44.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Easy 45.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Easy 46.

Identify the major product from the following reaction.

A. B. C. D. E.

I and III II II and III IV III and V

Answer: D Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 47.

What is the expected major product for the following reaction?

B. C. D. E.

II III IV V

Answer: A Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Hard 48.

Identify the compound that would react most slowly with a dilute aqueous solution of H2SO4.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 49.

The three compounds below can form a carbocation under aqueous acidic conditions. Which will form the same carbocation?

A. B. C. D. E.

II only I and II I and III II and III All three will form the same carbocation

Answer: E

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 50.

What would be the optimal conditions to achieve the following synthesis?

A. B. C. D. E.

dilute H2SO4 concentrated H2SO4 dilute HBr concentrated HBr aqueous NaOH

Answer: B Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 51.

What would be the optimal conditions to achieve the following synthesis?

A. B. C. D. E.

dilute aqueous H2SO4 concentrated H2SO4 dilute aqueous HBr concentrated HBr aqueous NaOH

Answer: A Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 52.

Which of the following is the major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Hard 53.

Describe the product(s) of the reaction below.

A. B. C. D. E.

only one stereoisomer an equal mixture of enantiomers a mixture of diastereomers and their enantiomers a mixture of constitutional isomers a mixture of constitutional isomers and their enantiomers

Answer: B Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Hard 54.

For the following reaction sequence identify the expected major organic product(s).

A. B. C. D. E.

I II III I and II I and III

Answer: D Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Easy 55.

For the following reaction provide the expected major organic product(s). Include all stereoisomers and clearly show relevant stereochemistry.

A. B. C. D. E.

I II III I and II II and III

Answer: A Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Easy 56.

Identify the expected major organic product(s) of the following reaction.

A. B. C. D. E.

I II III I and II II and III

Answer: C Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 57.

The synthesis shown below generates an achiral product from a chiral starting material. Identify the intermediate that would explain the production of an achiral product.

A. B. C. D. E.

I II III II and V V

Answer: C Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry Difficulty: Moderate 58.

The regioselectivity and stereospecificity in the reaction of an alkene with Hg(OAc)2 and water (the oxymercuration of an alkene) is best described as

A. B.

Markovnikov orientation with syn-addition. Markovnikov orientation with anti-addition.

C. D. E.

anti-Markovnikov orientation with syn-addition. anti-Markovnikov orientation with anti-addition. Markovnikov orientation with both syn- and anti-addition.

Answer: B Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Easy 59.

What molecular transformation is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?

A. B. C. D. E.

Markovnikov addition of H2O, promoting rearrangement Markovnikov addition of H2O, preventing rearrangement anti-Markovnikov addition of H2O, promoting rearrangement anti-Markovnikov addition of H2O, preventing rearrangement anti-Markovnikov addition of H2O, syn-hydroxylation

Answer: B Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Easy 60.

What is the expected major product for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Easy 61.

What is the expected major product for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Easy 62.

What is the expected major product for the following reaction?

A. B.

I II

C. D. E.

III IV V

Answer: D Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Easy 63.

Identify the expected major product(s) for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Easy 64.

When an alkene is subjected to treatment with Hg(OAc)2 in EtOH, followed by reaction with basic NaBH4, what functional group is formed?

A. B. C. D. E.

ether epoxide alkane syn diol alkyne

Answer: A Learning Objective: 8.7 Discuss hydration of an alkene by oxymercurationdemercuration, explaining why there is no carbocation rearrangement Difficulty: Moderate

65.

When a terminal alkene undergoes hydroboration-oxidation, two constitutional isomers are possible, but only one isomer is observed as the major product. Such reactions are described as _________.

A. B. C. D. E.

stereospecific regiospecific stereoselective regioselective constitutionally constrained

Answer: D Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Easy 66.

Any proper mechanism of hydroboration-oxidation must explain the observed _________ addition of the H and OH to the alkene as well as the _____________ regiochemistry.

A. B. C. D. E.

syn; Markovnikov anti; anti-Markovnikov syn; anti-Markovnikov anti; Markovnikov stepwise; mixed

Answer: C Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Easy 67.

The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as

A. B. C. D. E.

Markovnikov orientation with syn-addition. Markovnikov orientation with anti-addition. Anti-Markovnikov orientation with syn-addition. Anti-Markovnikov orientation with anti-addition. Markovnikov orientation with both syn- and anti-addition.

Answer: C Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

Difficulty: Easy 68.

What reagent(s) would accomplish the following synthesis?

A. B. C. D. E.

H2O/H+ H2O/ROOR NaOH, H2O 1. Hg(OAc)2, H2O; 2) NaBH4 1. BH3•THF; 2. NaOH, H2O2, H2O

Answer: E Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Easy 69.

Identify the expected major product(s) for the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Easy

70.

Identify the expected major product(s) for the following reaction sequence?

A. B. C. D. E.

I II III I and II I and III

Answer: E Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Moderate 71.

What is the expected major product for the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Moderate 72.

What is the expected major product for the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Moderate 73.

What is the expected major product for the following reaction sequence?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Moderate 74.

Identify the expected major organic product(s) generated upon completion of the following reaction sequence.

A. B. C. D. E.

I II III I and II II and III

Answer: A Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation Difficulty: Easy 75.

Identify the product from the hydrogenation of an alkene.

A. B. C. D. E.

dihaloalkane alkane haloalkane alcohol ether

Answer: B Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 76.

Identify the major organic product for the reaction shown below.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 77.

Provide the name of the product formed from the following reaction:

A. B. C. D. E.

1-chloro-2-methylcyclohexane 1-chloro-3-methylcyclohexane 1-chloro-4-methylcyclohexane 1-chloro-5-methylcyclohexane 5-chloro-1-methylcyclohexane

Answer: B Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Moderate 78.

Provide the name of the product formed from the following reaction:

A. B. C. D. E.

No reaction cis-1,2-dimethylcyclohexane trans-3,4-dimethylhexane trans-1,2-dimethylhexane cis-3,4-dimethylhexane

Answer: A Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 79.

Which of the following sets of reagents accomplishes the transformation shown below?

A. B. C. D. E.

H2/HCl H2/H2SO4 H2/Pd H2O/Pd H2O/H2SO4

Answer: C Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Moderate 80.

Which of the reagents below would convert cyclopentene into cyclopentane?

A. B. C. D. E.

H2 and Pt dilute H2SO4 Heat conc. H2SO4 Br2

Answer: A Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 81.

Which alkene would yield 3-methylpentane when subjected to catalytic hydrogenation?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Moderate 82.

How many moles of hydrogen gas (H2) are consumed in the catalytic reduction of 1 mole of the following compound?

A. B. C. D. E.

0.5 1 2 3 4

Answer: C Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 83.

How many moles of hydrogen gas (H2) are required to completely reduce 1 mole of the following compound?

A. B. C. D. E.

0.5 1 2 3 4

Answer: C Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 84.

Which of the catalysts listed are used in the homogenous catalytic hydrogenation of alkenes?

I. Ni A. B. C. D. E.

II. Pt

III. Wilkinson’s catalyst

IV. Pd

I II III IV II and IV

Answer: C Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 85.

In conducting the catalytic hydrogenation of an alkene, which catalyst listed is most likely to be soluble in the organic solvent?

A. B. C. D. E.

Ni Pt Pd Wilkinson’s catalyst All of the above are soluble

Answer: D Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 86.

Wilkinson’s catalyst accomplishes which of the listed molecular transformations?

A. B. C. D. E.

syn addition of H2 to an alkene anti addition of H2 to an alkene syn dihydroxylation of an alkene anti dihydroxylation of an alkene oxidative cleavage of an alkene

Answer: A Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 87.

Identify Wilkinson’s catalyst.

A. B. C. D.

(Ph3P)3RhCl (Ph3P)3RhBr (Ph3P)3PbCl (Ph3P)3PbBr

(Ph3P)3RuCl

Answer: A Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Easy 88.

Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

A. B. C. D. E.

2-methyl-1-pentene 2-methyl-2-pentene 4-methyl-2-pentene 4-methyl-1-pentene All of the above

Answer: E Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Moderate 89.

For the complete reduction of 1 mole of the following molecule with H2 using a Pd catalyst, how many moles of H2 are consumed?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Moderate 90.

Identify the major organic product(s) generated from the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition Difficulty: Moderate 91.

Which reaction intermediate is formed when 4-methylcyclohexene reacts with Br2 dissolved in CCl4?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Easy 92.

What is the expected major product upon completion of the following?

A. B. C. D.

1-chloropentane 2-chloropentane 1,1-dichloropentane 2,2-dichloropentane

1,2-dichloropentane

Answer: E Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Easy 93.

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

A. B. C. D. E.

2,3-dibromo-2-methylpentane 2,2-dibromo-3-methylpentane 3,3-dibromo-2-methylpentane 2-bromo-2-methylpentane 3-bromo-2-methylpentane

Answer: A Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Easy 94.

Which of the statements describes the products expected from the halogenation reaction shown below?

A. B. C. D. E.

Equal amounts of I and II are produced. Equal amounts of III and IV are produced. Equal amounts of I and III are produced. Equal amounts of II and III are produced. A mixture of I, II and III are produced.

Answer: A Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Hard

95.

Identify the expected first intermediate formed during the reaction of an alkene with Br2 and H2O.

A. B. C. D. E.

a bromonium ion. the most stable carbocation with OH on the adjacent carbon. the most stable carbocation with Br on the adjacent carbon. a cyclic oxonium ion. the most stable carbanion.

Answer: A Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Easy 96.

What major product is expected from the following reaction?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Easy 97.

What is the expected major product for the following reaction?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Moderate 98.

Identify the major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Moderate 99.

The reaction following reaction is expected to produce which of the following as the major product?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Moderate 100. Identify the expected major organic product from the reaction shown below.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Easy

101. Identify the intermediate that would give rise to the product shown in the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Moderate 102. Predict the product(s) for the following reaction.

A. B. C. D. E.

I and II II and III III and IV I and III V only

Answer: A Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Moderate

103. Identify the Fischer projection(s) of the major product(s) of the reaction shown below.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: C Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry Difficulty: Hard 104.

For the reaction sequence below, identify the expected major products.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 8.11 Describe the process for anti dihydroxylation Difficulty: Moderate 105. For the reaction sequence below, identify the expected major product(s).

A. B. C. D. E.

I II III I and III I, II and III

Answer: D Learning Objective: 8.11 Describe the process for anti dihydroxylation Difficulty: Moderate 106. What are the major products for the following reaction sequence?

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: E Learning Objective: 8.11 Describe the process for anti dihydroxylation Difficulty: Moderate

107.

Which of the following is the IUPAC name for the following compound?

A. B. C. D. E.

2-ethyl-1,1,3-trimethylbutene 3-ethyl-2,4-dimethyl-2-pentene 2,4-dimethylhexene 4-ethyl-1,3-dimethyl-3-pentene 3-isopropyl-2-methyl-2-pentene

Answer: B Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Easy 108. Identify the expected products for the following dihydroxylation reaction.

A. B. C. D. E.

Equal amounts of I and II Equal amounts of III and IV Equal amounts of I and IV Equal amounts of II and III Equal amounts of I and III

Answer: E Learning Objective: 8.11 Describe the process for anti dihydroxylation Difficulty: Hard 109. An unknown alkene was reacted with MCPBA in dichloromethane, followed by reaction with H2O/H+. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?

A. B. C. D. E.

(Z)-3-methylpent-2-ene (E)-3-methylpent-2-ene 2-methylpent-2-ene 2,3-dimethylbut-2-ene 1,2-diemthylbut-2-ene

Answer: A Learning Objective: 8.11 Describe the process for anti dihydroxylation Difficulty: Hard 110. Identify the Fischer projection(s) of the major product(s) of the following reaction sequence.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: E Learning Objective: 8.11 Describe the process for anti dihydroxylation Difficulty: Hard 111. Identify the expected major organic product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.12 Describe a syn dihydroxylation reaction 112. Treatment of 1,2-dimethylcyclopentene with OsO4 with NMO produces which of the following?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.12 Describe a syn dihydroxylation reaction Difficulty: Easy 113. Identify the expected major organic product generated from the reaction sequence shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.12 Describe a syn dihydroxylation reaction Difficulty: Easy 114. Which of the following alkene addition reactions occur specifically in syn fashion? A. B. C. D. E.

dihydroxylation using catalytic OsO4, NMO halohydrin formation with Br2 halogenation with Cl2 hydrohalogenation with HCl oxymercuration-demercuration

Answer: A Learning Objective: 8.12 Describe a syn dihydroxylation reaction Difficulty: Easy 115. What is the expected major product for the following reaction sequence?

A. B.

I II

C. D. E.

III IV V

Answer: A Learning Objective: 8.12 Describe a syn dihydroxylation reaction Difficulty: Easy 116. Provide the expected major organic product(s) of the reaction sequence shown.

A. B. C. D. E.

I only II only III only III and V IV and V

Answer: C Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Easy 117. Which of the following reagents effectively cleaves both the sigma and pi bonds of an alkene? A. B. C. D. E.

Cl2 RCO3H H2SO4 cold KMnO4, NaOH 1. O3; 2. DMS

Answer: E Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Easy 118. How many carbonyl groups (C=O) are generated upon treatment of the molecule

below with ozone, followed by zinc metal and water?

A. B. C. D. E.

0 2 3 4 8

Answer: E Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Moderate 119. Of the alkenes shown, which would produce the product shown below, upon treatment with ozone, followed by zinc metal and water?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Moderate 120. What is the expected major product of the reaction sequence shown below?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Moderate 121. What are the expected major products from the reaction sequence shown below?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Moderate 122. Identify the expected major organic products generated in the reaction sequence shown below.

A. B. C. D. E.

I and II II and III III and IV IV and V III and V

Answer: C Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis Difficulty: Moderate 123. Which of the following alkene addition reactions occur specifically with an anti orientation? A. B. C. D. E.

hydroboration-oxidation addition of Br2 addition of H2 addition of H2O in dilute acid oxymercuration-demercuration

Answer: B Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Easy 124. The Markovnikov product resulting from an addition reaction to a trisubstituted alkene is formed because _________. A. B. C. D. E.

the product is statistically favored steric hindrance favors its formation the reaction proceeds via the more stable carbocation the reaction forms the more stable product All of the above are valid reasons

Answer: C

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Easy 125.

What is the expected major product for the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Easy 126. Which reagents are most likely to accomplish the reaction shown below?

A. B. C. D. E.

1. BH3∙THF; 2. H2O2, NaOH H+ , H 2 O 1. Hg(OAc)2, H2O; 2. NaBH4 H2O, ROOR NaOH, H2O

Answer: A Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Easy 127. Which reaction is not stereospecific?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Moderate 128. Identify the expected product(s) of the following reaction.

A. B. C. D. E.

a meso dibromide a mixture of optically active enantiomeric dibromides a mixture of diasteromeric isomers (Z)-3,4-dibromo-3-hexene (E)-3,4-dibromo-3-hexene

Answer: A Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Hard 129. Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?

A. B. C. D. E.

I II III IV Both II and IV

Answer: B Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Hard 130. What is the expected major product resulting from the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Moderate 131. What is the expected major product resulting from the following reaction.

A. B. C. D. E.

I II III IV All of the above are produced in equal amounts

Answer: B Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Moderate 132. Identify the Fischer projection(s) of the major product(s) for the following reaction

A. B. C. D. E.

I and II II and II III and IV I and III II and IV

Answer: A Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Moderate 133. Identify the Fischer projection(s) of the major product(s) for the following reaction

A. B. C. D. E.

I and II II and II III and IV I and III II and IV

Answer: D Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Moderate 134. Identify the product of the following reaction that illustrates the correct regiochemical and stereochemical transformation.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Moderate 135.

Identify the best reagents to accomplish a Markovnikov addition of water to an unsymmetrical alkene with minimal skeletal rearrangement.

A. B. C. D. E.

water and dilute acid water and concentrated acid 1. Hg(OAc)2, H2O; 2. NaBH4, NaOH 1. BH3•THF; 2. H2O2, NaOH 1. OsO4 2. NaHSO3, H2O

Answer: C Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 136. For the reaction sequence shown, what is the expected major product?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 137. What is the expected major product of the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 138. What is the expected major product of the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard 139. Which is the correct sequence of steps necessary to complete the following transformation?

I then II then III

B. C. D. E.

II then I then III II then IV III then I I then IV then II then III

Answer: B Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard 140. What is the expected major product of the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard

141. Predict the expected major product of the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 142. Predict the expected major products of the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 143. Predict the expected major product(s) of the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 144. What is the expected major product of the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard

145. Identify the major product(s) for the following reaction sequence.

A. B. C. D. E.

I I & II III III & IV V

Answer: B Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard 146. What is the expected major product of the following reaction sequence?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard 147. For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship.

A. B. C. D. E.

I and II; III and IV; I and II; II and III; I and IV;

enantiomers enantiomers diastereomers diastereomers enantiomers

Answer: D Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard 148.

A. B.

Identify the structure of (E)-4,5-dimethylhept-3-ene.

E. Answer: E Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Moderate 149.

Identify the IUPAC name for the following compound.

A. B. C. D. E.

1-methyl-2-cyclohexene 2-methylcyclohexene 3-methylcyclohexene 1-methyl-5-cyclohexene 6-methyl-cyclohexene

Answer: C Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Easy 150.

Which of the following is the correct structure of 4-methylcyclopentene?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Easy 151. Consider the information given below and identify the structure of the unknown compound A, with a molecular formula of C8H14. Compound A reacts with Br2/CCl4. Upon reaction of A with excess H2/Ni, 1-ethyl-2-methylcyclopentane is produced.

Subjecting A to ozonolysis, the product shown below is produced as the major organic product. Identify the correct structure of compound A, and provide a brief and clear explanation relating the data provided with the structure selected.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Hard

152.

Which of the following is the correct structure of 2-methyl-1-butene?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Moderate

153.

Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A. B. C. D. E.

I is neither; II is E I is neither; II is Z I is Z; II is neither I is Z; II is E I is E; II is Z

Answer: A Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Easy 154.

Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A. B. C. D. E.

I is neither; II is Z I is E; II is E I is Z; II is Z I is Z; II is E I is E; II is Z

Answer: B Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Easy 155.

Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A. B. C.

I is neither; II is E I is E; II is E I is Z; II is Z

D. E.

I is Z; II is E I is E; II is Z

Answer: B Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Moderate 156.

Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A. B. C. D. E.

I is neither; II is E I is E; II is E I is Z; II is Z I is Z; II is E I is E; II is Z

Answer: E Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Moderate 157.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

(Z)-4-cyclopentyl-2-pentene (E)-4-cyclopentyl-4-methyl-2-butene (Z)-4-cyclopentyl-4-methyl-2-butene (E)-4-cyclopentyl-2-pentene (Z)-2-cyclopentyl-3-pentene

Answer: D Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Easy 158.

Identify the E isomer of 2-methyl-3-heptene.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Moderate 159.

Identify the E isomer of 3,4-dimethyl-3-heptene.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes Difficulty: Moderate

160. Which of the following alkene addition reactions occur stereospecifically in anti fashion? A. B. C. D. E.

dihydroxylation using catalytic OsO4, NMO catalytic hydrogenation of H2 hydroboration-oxidation halohydrin formation with Br2 and H2O oxymercuration-demercuration

Answer: D

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Easy 161. Which of the following alkene addition reactions occur stereospecifically in syn fashion? A. B.

C. D. E.

dihalogenation with Br2 halohydrin formation with Br2 and H2O acid catalyzed hydration catalytic hydrogenation of H2 oxymercuration-demurcuration

Answer: D Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction Difficulty: Easy 162. Which is the correct sequence of steps necessary to complete the following reaction?

A. B. C. D. E.

I then II then III II then I then III II then IV III then I III then IV

Answer: C Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond Difficulty: Moderate 163. Which of the following starting molecules would NOT give rise to the major product shown in the following reaction?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides Difficulty: Moderate

Klein, Organic Chemistry 4e Chapter 9 1.

Which of the following describes the orbital overlap of the C2—C3 sigma bond in the molecule shown?

CH3 C C CH2CH3 A. B. C. D. E.

sp–sp sp2–sp2 sp3–sp3 p–p sp3–sp

Answer: A Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 2.

Which of the following describes the orbital overlap of the C3—C4 sigma bond in the molecule shown?

H3C C C C C CH3

A. B. C. D. E.

sp–sp sp2–sp2 sp3–sp3 p–p sp3–sp

Answer: A Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 3.

Which two orbitals overlap to form the sigma bond between the atoms shown?

A. B. C. D. E.

sp3–sp3 p–p sp2–sp2 s–s sp–sp

Answer: E Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 4.

What is the hybridization of the carbon atoms numbered 1 and 2, respectively, in this structure? H H 2 C C 1 C C H

A. B. C. D. E.

sp3, sp2 sp2, sp2 sp, sp sp2, sp sp, sp2

Answer: D Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 5.

Which bond types are involved in forming the bond between these two carbon atoms?

A. B. C. D. E.

three anti-bonds three σ bonds two σ bonds and one π bond one σ bond and two π bonds three π bonds

Answer: D Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 6.

Which of the following statements best describes how alkynes react?

The triple bond of an alkyne is electron-rich and therefore reacts as nucleophiles.B. The triple bond of an alkyne is electron-poor and therefore alkynes react as nucleophiles.

C. D. E.

Alkynes have low general reactivity and therefore do not easily act as nucleophiles or as electrophiles. The triple bond of an alkyne is electron-rich and therefore alkynes react as electrophiles. The triple bond of an alkyne is electron-poor and therefore alkynes react as electrophiles.

Answer: A Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 7. Which of the following statements is true about the molecule shown? H–C≡C–CH3 A. B. C. D. E.

It contains a total of three sigma bonds. It contains a total of three pi bonds. The H–C≡C bond angle is about 109.5°. The C≡C–C bond angle is 180°. All carbon-carbon bonds are of equal length.

Answer: D Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 8. What is the shape of the molecule shown? H–C≡C–H A. B. C. D. E.

tetrahedral linear trigonal pyramidal bent trigonal bipyramidal

Answer: B Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named Difficulty: Easy 9.

What is the IUPAC name for the molecule shown?

Br CH3 H3C C CH3 H2C C C CH2

A. B. C. D. E.

6-bromo-3-octyne 6-bromo-6-methyl-3-heptyne 2-bromo-2-methyl-4-heptyne 6-bromo-6,6-dimethyl-3-hexyne 2-bromo-4-octyne

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 10.

What is the IUPAC name for the molecule shown?

CH2CH3 CH3CH2 C C CH CH2CH3

A. B. C. D. E.

1,1-diethyl-2-pentyne 3-(1-butynyl)pentane 5-ethyl-3-octyne 3-ethyl-4-heptyne 5-ethyl-3-heptyne

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 11.

What is the IUPAC name for the molecule shown?

H 3C HC C C CHCH2CH3 H 3C CH2CH2CH3

A. B. C. D. E.

2-methyl-5-propyl-3-heptyne 5-ethyl-2-methyl-3-octyne 1-isopropyl-3-ethyl-1-hexyne 6-methyl-3-propyl-4-heptyne 4-ethyl-7-methyl-5-octyne

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 12.

What is the IUPAC name for the molecule shown?

H3C CH3 C CH3 H3C C C C CH3 H

A. B. C. D. E.

2,2,3-trimethyl-4-hexyne 4-tert-butyl-2-pentyne 4,5,5-trimethyl-2-hexyne 4,5,5,5-tetramethyl-2-pentyne 2,2-dimethyl-3-(1-propynyl)butane

Answer: C Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 13.

What is the IUPAC name for the molecule shown?

A. B. C. D. E.

5,6,6-trimethyl-1-heptyne 5-tert-butyl-1-hexyne 2,2,3-trimethyl-6-heptyne 2,2,3-(3-butynyl)butane sec-butyl-tert-butylacetylene

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 14.

What is the IUPAC name for the molecule shown?

A. B. C. D. E.

Cl Cl

1,1,1-trichloro-4-hexyne 4,4,4-trichloro-1-butyne 1,1,1-trichloro-2-butyne 5,5,5-trichloro-2-pentyne 6,6,6-trichloro-2-hexyne

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 15.

What is the IUPAC name for the molecule shown?

A. B. C. D. E.

4,4-dimethyl-2-pentyne 2,2-dimethyl-4-heptyne 1-tert-butyl-3-heptyne 6,6-dimethyl-3-heptyne 6,6,6-trimethyl-3-hexyne

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 16.

What is the IUPAC name for the molecule shown?

A. B. C. D. E.

4-ethyl-2-pentyne 2-ethyl-3-pentyne 3-methyl-4-hexyne 4-methyl-2-hexyne sec-Butylpropyne

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 17.

Which of the following is a structure for hepta-3,6-dien-1-yne?

A. B. C. D. E.

I II III Iv V

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 18.

Which of the following is the structure for 2-hexyne?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy

19.

Which of the following is the structure for 3-sec-butyl-1-heptyne?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 20.

Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.

A. B. C. D. E.

1-bromo-3-hexyne 6-bromo-3-hexyne 1-bromo-2-hexyne 6-bromo-4-hexyne 1-bromo-4-hexyne

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 21.

Provide the IUPAC name for HC≡CCH2CH2CH3.

pentyne

B. C. D. E.

1-pentyne butyne 1-butyne 2-butyne

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 22. Provide the IUPAC name for the molecule shown. Cl3CCH2CH2CH2C≡CH. A. B. C. D. E.

6,6,6-trichloro-1-hexyne 1,1,1-trichloro-5-hexyne 5,5,5-trichloro-1-pentyne 1-heptyne trichlorobutylacetylene

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 23. Provide the IUPAC name for the molecule shown. Cl3C(CH2)4C≡CH. A. B. C. D. E.

4,4,4-trichloro-1-butyne 1,1,1-trichloro-6-heptyne 1,1,1-trichloro-5-heptyne 6,6,6-trichloro-1-hexyne 7,7,7-trichloro-1-heptyne

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 24. Provide the IUPAC name for the molecule shown. (CH3)2CHC≡CCH2C(CH3)3. A. B.

1,1,5,5,5-pentamethyl-2-pentyne 1,1,1,5,5-pentamethyl-3-pentyne

C. D. E.

2,2,6-trimethyl-4-heptyne 2,6,6-trimethyl-3-heptyne tert-butylisopropylacetylene

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 25.

Provide the systematic IUPAC name for the molecule shown.

(CH3)3CCH2C≡CCH2CH(CH3)CH2CH3 A. B. C. D. E.

2,7,7-trimethyl-5-nonyne 2-ethyl-7,7-dimethyl-4-octyne 2,2,7-trimethyl-4-nonyne 7-ethyl-2,2-trimethyl-4-octyne 6-undecyne

Answer: C Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 26.

What is the IUPAC name for the molecule shown?

A. B. C. D. E.

3-bromo-4-acetylenylheptane 3-(1-bromopropyl)-1-hexyne 3-bromo-4-propyl-5-hexyne 4-bromo-3-propyl-1-hexyne 4-ethynyl-5-bromo-heptane

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 27.

Which of the following is the acceptable structure for (R)-5-bromohept-2-yne?

A. B. C. D. E.

Br III

I II III IV V

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 28.

What is the IUPAC name for the molecule shown?

A. B. C. D. E.

(E)-5-methyl-5-hepten-1-yne (Z)-5-methyl-5-hepten-1-yne (E)-3-methyl-2-hepten-6-yne (Z)-3-methyl-2-hepten-6-yne (E)-2-butynyl-2-butene

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 29.

What is the IUPAC name for the molecule shown?

A. B. C. D.

(E)-4-isopropyloct-3-en-5-yne (Z)-4-isopropyloct-3-en-5-yne (E)-5-isopropyloct-5-en-3-yne (Z)-5-isopropyloct-5-en-3-yne

(E)-4-(2-methylethyl)oct-3-en-5-yne

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 30.

Which structure shown below represents (Z)-3,5-dichloro-3-hexen-1-yne? Cl

Cl Cl

Cl I

A. B. C. D. E.

Cl II

Cl III

Cl IV

I II III IV I and II

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 31.

Which of the following molecules has two chiral centers with E isomeres and a triple bond between carbons 6 and 7?

A. B.

I II

C. D. E.

III IV V

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 32.

Which of the following is a structure for octa-3,6-dien-1-yne?

A. B. C. D. E.

HC≡CCH=CHCH=CHCH2CH3 CH3CH=CHCH2C≡CC≡CH CH3CH=CHCH2CH=CHC≡CH CH3C≡CCH=CHCH=CHCH3 H2C=CHC≡CCH2CH=CHCH3

Answer: C Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 33.

Which of the following is the structure for 2,5,5-trimethylhept-3-yne?

A. B. C. D. E.

CH3CH2CH(CH3)C≡CCH2CH(CH3)2 CH3CH2C(CH3)2C≡CCH(CH3)2 (CH3CH2)2C(CH3)C≡CCH2CH3 CH3CH2C(CH3)2C≡CC(CH3)3 CH3CH2CH2CH(CH3)C≡CC(CH3)3

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 34.

What is the IUPAC name for the molecule shown below? Cl

A. B.

(4R,5Z)-4-chlorohept-5-en-2-yne (4S,5E)-4-chlorohept-5-en-2-yne

C. D.

(2E,4S)-4-chlorohept-2-en-5-yne (2E,4R)-4-chlorohept-2-en-5-yne

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Hard 35.

What is the IUPAC name for diisobutylacetylene?

A. B. C. D. E.

diisopropylbutyne 2,7-dimethyl-4-octyne 3,6-dimethyl-4-octyne 2,5-diethyl-3-hexyne sec-butylacetylene

Answer: B Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Hard 36.

What is the IUPAC name for di-sec-butylacetylene?

A. B. C. D. E.

2-ethyl-5-methyl-3-heptyne 2,7-dimethyl-4-octyne 3,6-dimethyl-4-octyne 2,5-diethyl-3-hexyne 2,2,5,5-tetramethyl-3-hexyne

Answer: C Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Hard 37. Which of the following are constitutionally isomeric alkynes with the molecular formula C5H8?

Answer:

A. B. C. D. E.

I only II only I and II I and III only I, II, and III

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 38.

What name or names are CH3CH(CH3)C(CH3)2C≡CCH(CH3)2?

appropriate

IUPAC

A. B. C. D. E.

2,5,5,6-tetramethyl-3-heptyne 2,5,5,6-tetramethylhept-3-yne 2,5,5,6-tetramethyl-3-heptyne or 2,5,5,6-tetramethylhept-3-yne 2,3,3,7-tetramethyl-4-heptyne 2,3,3,7-tetramethyl-4-heptyne or 2,3,3,7-tetramethylhept-4-yne

names

for

Answer: C Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 39.

What name or names CH3C≡CC(CH3)2CH(CH2CH3)2?

A. B. C. D. E.

2-ethyl-3,3-dimethylhept-2-yne 5-ethyl-4,4-methylhept-2-yne 2-ethyl-3,3-dimethyl-3-heptyne 5-ethyl-4,4-dimethyl-2-heptyne 5-ethyl-4,4-methylhept-2-yne

are

appropriate

IUPAC

names

for

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 40. A.

What is an appropriate IUPAC name for CH3CHBrC≡C(CH2)3CH3? 3-bromo-2-heptyne

B. C. D. E.

2-bromo-3-heptyne 3-bromo-2-octyne 2-bromooct-2-yne 2-bromo-3-octyne

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 41.

Provide a name for the following compound.

A. B. C. D. E.

4-sec-butyl-2-octyne 5-sec-butyl-6-(2-propyne)-octyne 4-butyl-3-methyl-5-heptyne 4-tert-butyl-oct-2-yne 2-yne-3-(1-methylpropyl)-octane

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 42.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

4,4-dimethylcyclododecyne 9,9-dimethylcyclodecyne 9,9-methylcyclodecyne 4,4-dimethylcyclodecyne 4,4-methylcyclodecyne

Answer: D Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Medium 43.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

2,3-(S)-6,6-tetramethyl-oct-4-yne (S)-2,3,6,6-tetramethyloct-4-yne (R,S)-2,3,6,6-tetramethyl-4-octyne (S,R)-2,3,6,6-tetramethyloct-4-yne (R)-2,3,6,6-tetramethyloct-4-yne

Answer: B (S)-2,3,6,6-tetramethyloct-4-yne or (S)-2,3,6,6-tetramethyl-4-octyne Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Hard 44.

Provide an IUPAC name for the following compound:

A. B. C. D. E.

(3Z,5E)-5-fluoro-2-methylnon-3-en-6-yne (3Z,5R)-5-fluoro-2-methyl-3-nonen-6-yne (3Z,5S)-5-fluoro-2-methyl-3-nonen-6-yne (3E,5R)-5-fluoro-2-methylnon-3-en-6-yne (3E,5S)-5-fluoro-2-methylnon-3-en-6-yne

Answer: E Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Hard 45.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

(4R,5S)-4-bromo-5-chloro-3-ethylhex-1-yne (4R,5S)-5-bromo-4-chloro-3-ethyl-1-hexyne (4R,5S)-3-ethyl-4-bromo-5-chloro-1-hexyne (4S,5S)-4-bromo-5-chloro-3-ethylhex-1-yne (4R,5R)-4-bromo-5-chloro-3-ethylhex-1-yne

Answer: A Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 46.

Which line-bond structure represents 2,5,9-trimethyl-2-decen-7-yne?

A. I B. II C. III D. IV E. V Answer: V

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal Difficulty: Easy 47.

Rank the following carbanions in order of increasing base strength.

HC C

H2C CH

CH3CH2

III

A. B. C. D. E.

I < II < III II < III < I III < II < I III < I < II II < I < III

Answer: A Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 48.

Rank the following conjugate acids in order of increasing pKa.

A. B. C. D. E.

I < II < III II < III < I III < II < I III < I < II II < I < III

Answer: A Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 49.

What is the hybridization for the carbanion of the ion shown below?

A. B. C. D. E.

sp sp2 sp3 s2 p s2 p 2

Answer: A Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 50.

Rank the following bases in order of decreasing basicity.

HC C

CH3CH2O

CH3CH2

H2N

H2C CH

III

A. B. C. D. E.

III > I > V > II > IV III > V > IV > I> II V > I > III > II > IV III > IV > II > V > I IV > II > I > III > V

Answer: B Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 51.

Rank the following acids in order of decreasing acidity.

H 2O

H2C CH2

CH3CH3

HC CH

NH3

III

A. B. C. D. E.

V > I > IV > II > III III > IV > II > I > V V > I > III > II > IV I > IV > V > II > III IV > I > V > II > III

Answer: D Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

Difficulty: Easy 52.

Which of the circled hydrogen atoms is the most acidic?

H H C H H

H H3C C H CH3

A. B. C. D. E.

CH3 H3C C H CH3 III

H H 2C C H IV

H 3C C C H V

I II III IV V

Answer: E Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 53. The molecule shown reacts with terminal alkynes as a ____. NaNH2 A. B. C. D. E.

Brønsted acid Brønsted base reducing agent catalyst electrophile

Answer: B Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 54.

Which of the bases below would quantitatively deprotonate a terminal alkyne?

A. B. C. D. E.

BuLi NH3 NaOH NaOCH2CH3 t-BuOK

Answer: A

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 55.

Which of the bases below would result in the most complete deprotonation of the alkyne, shown in the reaction below?

H3C C C H

A. B. C. D. E.

H3C C C

NaOCH2CH3 (sodium ethoxide) t-BuONa (sodium tert-butoxide) NaH (sodium hydride) NaHCO3 (sodium bicarbonate) NaOH (sodium hydroxide)

Answer: C Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy 56.

Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

A. B. C. D. E.

Acetylide anions are resonance stabilized. The 4 p electrons of the acetylide anion better stabilize a negative charge. The electronegativity of sp carbons is greater than that of sp2 carbons. The electronegativity of sp carbons is less than that of sp2 carbons. Acetylene has only two hydrogen atoms whereas ethylene has four.

Answer: C Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Medium 57.

Select the best explanation for why methanol, CH3OH, cannot be used as a solvent for the deprotonation of a terminal alkyne by sodium amide, NaNH2.

A. B. C. D.

Sodium amide is not a strong enough base to deprotonate the alkyne. Sodium amide in methanol reduces alkynes to alkenes. Methanol is a poor solvent for dissolving alkynes. Methanol is more acidic than the alkyne and will be deprotonated before N a N H 2.

Methanol is toxic and should be avoided when possible.

Answer: D Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Medium 58.

What are the products of the reaction shown below?

CH3OH + CH3C≡C–Na+ → ? CH3C≡CCH3 + Na+OH– CH3C≡CH + CH3O–Na+ CH3C≡COCH3 + Na+OH– CH3OC≡CH + Na+CH3– no reaction

A. B. C. D. E.

Answer: B Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Medium 59.

The major result of treating 1-butyne with 6M aqueous NaOH would be:

A. B. C. D. E.

the production of sodium alkynide. the production of an alkene. the production of an alkane. the production of an enol. no reaction,

Answer: E Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Medium 60.

Which of the circled hydrogen atoms is the least acidic?

H H C H H

H H3C C H CH3

CH3 H3C C H CH3 III

H H 2C C H IV

H 3C C C H V

B. C. D. E.

II III IV V

Answer: C Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Hard 61.

Of the species listed below, select those less basic than acetylide.

A. B. C. D. E.

BuLi NaNH2 NaOCH3 A and C B and C

Answer: C Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Hard 62.

Rank the following hydrocarbons in order of decreasing acidity (most acidic to least acidic).

A. B. C. D. E. F.

III

I > II > III I > III > II II > III > I II > I > III III > I > II III > II > I

Answer: F Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons Difficulty: Easy

63.

For the reaction shown below, select the expected major product.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Medium 64.

Identify the major product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Medium

65.

Identify the major product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Medium 66.

Select the expected major product of the reaction sequence shown. 1) Br2

2) 3 eq. NaNH2/NH3 3) H2O

A. B. C. D. E.

3-methylhexyne 1-bromo-3-methylhexybe 2-bromo-3-methylhexyne 3-methyl-1-hexyne 3-methyl-2-hexyne

Answer: D Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Medium 67.

The most frequent method for preparing terminal alkynes using an elimination reaction involves dissolving sodium amide (NaNH2) in liquid ammonia (NH3). Which of the following statements offers the best explanation for the above statement?

A. B. C. D. E.

Sodium amide deprotonates internal alkynes, which begins the series of reactions necessary reactions to generate a terminal alkyne. Sodium amide deprotonates the terminal alkyne, driving formation of the alkynide ion. Sodium amide is required because it increases the stability of the terminal alkyne, stabilizing the intermediate. This provides an environment in which terminal alkynes are more stable than the internal alkynes and therefore the favored product. Steric hindrance favors preparation of the less substituted terminal alkyne.

Answer: B Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Medium 68.

Describe a sequence of reactions by which 2-hexyne can be prepared from acetylene while minimizing the number of steps required.

A. B. C. D. E.

1. NaNH2; 2. CH3CH2CH2Br; 3. NaNH2; 4. CH3Br 1. NaNH2; 2. CH3Br; 3. CH3CH2CH2Br; 1. NaNH2; CH3Br; 3. NaNH2; 4. CH3CH2CH2Br A or B A or C

Answer: E Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Easy 69.

A dihalide in which the halogens are attached on adjacent carbons is called a _______________ dihalide.

A. B. C. D. E.

vicinal geminal vinylic allylic cis

Answer: A Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Easy

70.

A dihalide in which the halogens are attached on the same carbon is called a _______________ dihalide.

A. B. C. D. E.

vicinal geminal vinylic allylic cis

Answer: B Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides Difficulty: Easy 71.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 72.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 73.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 74. What will be produced through the reaction of an alkyne with sodium and ammonia?

A. B. C. D. E.

a cis alkene a trans alkene a diene an alkyne an alkane

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy

75.

What will be produced through the reaction of an alkyne with hydrogen and Lindlar’s catalyst?

A. B. C. D. E.

a cis alkene a trans alkene a diene an alkyne an alkane

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 76.

What will be produced through the reaction of an alkyne with hydrogen and a metal catalyst?

A. B. C. D. E.

a cis alkene a trans alkene a diene an alkyne an alkane

Answer: E Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 77.

Select the expected major organic product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 78.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 79.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 80.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy

81.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 82.

Select the expected major organic product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 83.

How many moles of hydrogen are required for the complete reduction of 1 mole of (3E,5Z)-3-methylhepta-3,5-dien-1-yne?

A. B. C. D. E.

1 2 3 4 5

Answer: D Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 84.

Select the reagent(s) needed to accomplish the reaction shown.

A. B. C. D. E.

H2, Ni H2, Ni2B Na, NH3(l) A or B B or C

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 85.

Select the best reagent(s) to convert 3-heptyne to cis-3-heptene.

A. B. C. D. E.

NaNH2, NH3 Na, NH3 H2, Lindlar’s catalyst A and C B and C

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy

86.

Which of the reagents shown would convert 2-pentyne to trans-2-pentene?

A. B. C. D. E.

NaNH2, NH3 Na, NH3 H2, Lindlar’s catalyst H2, Pd/C H2O, HgSO4/H2SO4

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 87.

Select the best reagent(s) to convert 3-heptyne to trans-3-heptene.

A. B. C. D. E.

Na/NH3 1 eq. NaNH2, NH3 excess NaNH2, NH3 H2/Pt H2/Lindlar's catalyst

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 88.

Select the reagent(s) needed to accomplish the reaction shown.

CH3CH2 C C CH2CH3

A. B. C. D. E.

CH2CH3 C C H3CH2C H

H2, Pd H2, Lindlar’s catalyst Na, NH3(l) A or B B or C

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy

89.

Which of the compounds shown will be produced by the reaction of 3,4,5-trimethyl4-hexen-1-yne with H2 and Pd/C?

A. B. C. D. E.

2,3,4-trimethylhexane 3,4,5-trimethylhexane 2,3,4-trimethyl-1-hexene 3,4,5-trimethyl-1-hexyne 2,3,4-trimethyl-5-hexyne 2

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 90. A. B. C. D. E.

Which of the compounds below will be produced by the reaction of (3E,5Z)-3methylhepta-3,5-dien-1-yne with H2 and Pd/C? 1-sec-butylbutane 2-butylbutane 3-methylheptane 3-methyl-1-heptyne (3E,5Z)-3-methyl-1,3,5-heptatriene 2

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 91.

To convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane, the best option would be to add _________.

A. B. C. D. E.

H2, Lindlar’s catalyst Na, NH3(l) 2 moles of HCl 2 moles H2, Pt 1 mole H2, Pt

Answer: D Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 92.

Which of the reagents shown would be expected to convert 2-pentyne to (Z)-2pentene?

A. B.

H2, Pt Na, NH3

C. D. E.

H2, Lindlar's catalyst excess HCl HgSO4, H2O

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 93.

What is the IUPAC name of the expected product of the reaction shown? Na

NH3(l)

A. B. C. D. E.

2-methylhexane (Z)-2-methyl-4-hexene (E)-2-methyl-4-hexene (Z)-5-methyl-2-hexene (E)-5-methyl-2-hexene

Answer: E Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 94.

Select the reagent(s) needed to accomplish the reaction shown below.

CH3CH2 C C CH2CH3

A. B. C. D. E.

H C C H3CH2C CH2CH3

H2, Ni H2, Ni2B H2, Lindlar’s catalyst A and B B and C

Answer: E Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 95.

What is the expected major organic product from the treatment of 4-methyl-2pentyne with excess hydrogen in the presence of a platinum catalyst?

A. B. C. D. E.

4-methylpentane 2-methylpentane 4-methyl-2-pentene 2-methyl-2-pentene 4-methyl-4-pentene

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 96.

What is the expected major organic product from the treatment of 4-methyl-2pentyne with hydrogen in the presence of Lindlar's catalyst?

A. B. C. D. E.

(E)-4-methyl-2-pentene (E)-4-methyl-2-pentene and (Z)-4-methyl-2-pentene (Z)-4-methyl-2-pentene 2-methylpentane 4-methylpentane

Answer: C(Z)-4-methyl-2-pentene Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 97.

What is the expected major organic product from the treatment of 4-methyl-2pentyne with sodium metal in liquid ammonia?

A. B. C. D. E.

(Z)-4-methyl-2-pentene (E)-2-methyl-4-pentene (Z)-4-methyl-4-pentene (Z)-2methyl-2-pentane (E)-4-methyl-2-pentene

Answer: E Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 98.

In the reaction between an alkyne and Na metal in liquid ammonia, Na acts as an a(n) ___________.

A. B. C.

Brønsted acid Brønsted base reducing agent

D. E.

catalyst electrophile

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 99.

In a dissolving metal reduction of an alkyne, a postulated intermediate is the trans alkenyl radical (shown below). In which orbital type would the unpaired electron be located? H

A. B. C. D. E.

sp sp2 sp3 p s

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 100. For the reaction shown below, the expected product will have a stereochemistry of ______. H2 Pt

A. B. C. D. E.

only (S) only (R) racemic meso achiral

Answer: E Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium

101. How many distinct eight-carbon hydrocarbon products would be formed in the complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne in the presence of a palladium catalyst? A. B. C. D. E.

1 2 3 6 8

Answer: A Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Medium 102. For the reaction shown below, the resulting stereochemistry of the expected product is best described as: H2 Ni2B (P-2)

A. B. C. D. E.

(R,E) (S,E) (R,Z) (S,Z) only (S)

Answer: D Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Hard 103. What reagent(s) are required to prepare trans-2-heptene from 2-heptyne? A. B. C. D. E.

H2, Lindlar’s catalyst Na, NH3(l) H2, Pt Cl2, CCl4 O3, H2O

Answer: B Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy

104. What reagent(s) are needed to accomplish the synthesis shown?

A. B. C. D. E.

H2, Lindlar’s catalyst Na, NH3(l) H2, Pt Cl2, CCl4 O3, H2O

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 105. Determine which compound will react with sodium in liquid ammonia to form trans3-hexene. A. B. C. D. E.

cis-3-hexene trans-2-hexene 3-hexyne 2-hexyne cis-2-hexene

Answer: C Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes Difficulty: Easy 106. Which of the compounds shown below would be the most likely product expected from the reaction shown?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Easy 107. Identify the expected major product from the treatment of 1-pentyne with 1 equivalent of HBr. A. B. C. D. E.

1-bromo-1-pentene 2-bromo-1-pentene 1,1-dibromopentane 2,2-dibromopentane 1,2-dibromopentane

Answer: B Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Easy 108. Identify the expected major product from the treatment of 1-pentyne with 2 equivalents of HBr. A. B. C. D. E.

1-bromo-1-pentene 2-bromo-1-pentene 1,1-dibromopentane 2,2-dibromopentane 1,2-dibromopentane

Answer: D Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Easy 109. Select the structure of the expected major organic product of the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Easy 110.

What is the major expected product(s) of the reaction shown?

A. B. C. D. E.

2,2-dichloropentane 3,3-dichloropentane 2,3-dichloropentane A and B B and C

Answer: D Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Medium 111. What is the expected major organic product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Medium 112. Which of the compounds shown would be the most likely product expected from the given reaction?

A. B. C. D. E.

I and II III and IV II and III II and IV I and IV

Answer: E Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Medium 113. Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of HBr in the presence of peroxides.

A. B. C. D. E.

2-bromo-1-pentene (E)-1-bromo-1-pentene (Z)-1-bromo-1-pentene A and B B and C

Answer: E Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Medium 114.

What mechanistic intermediate is used to explain the preference for addition of the Br atom, of HBr, to the internal carbon of a terminal alkyne?

A. B. C. D. E.

Formation of an intermediate with partial positive charge on a primary carbon Formation of an intermediate with partial positive charge on a secondary carbon Addition of the H atom to the carbon already with an H. Addition of H, from HBr, to the least hindered carbon. Steric hindrance for the approach of the Br atom to the primary carbon.

Answer: B Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Medium 115. How would the expected major organic product(s) from the reaction shown be affected if ROOR were not added? (CH3)2CHCH2C CH

A. B. C. D. E.

HBr ROOR

Markovnikov addition would occur. The location of addition of Br would be unpredictable. Heat would need to be added for the reaction to proceed. The reaction would not proceed. The reaction would yield an alkane with two Br substituents.

Answer: A Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products Difficulty: Medium

Deleted: ¶

116.

Identify the best reagent(s) to accomplish the reaction shown.

(CH3)2CHCH2C CH A. B. C. D. E.

O (CH3)2CHCH2CCH3

H2SO4, HgSO4, H2O 1. Disiamylborane; 2. HO–, H2O2 K2Cr2O7, H+ NaOCl NaOH

Answer: A Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 117. Identify the best reagent(s) to accomplish the reaction shown. (CH3)2CHCH2C CH

A. B. C. D. E.

O (CH3)2CHCH2CH2CH

H2SO4, HgSO4, H2O 1. Disiamylborane; 2. HO–, H2O2 K2Cr2O7, H+ NaOCl NaOH

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 118.

What is the final product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 119.

What is the final product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 120. What is the final product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 121. What is the expected final product of the following reaction?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 122. What is the expected final product of the following reaction?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 123. What is the expected final product of the following reaction?

A. B.

I II

C. D. E.

III IV V

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 124. For the reaction shown, which of the compounds listed would be the expected enol intermediate?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 125. For the reaction shown, which of the compounds below would be the expected enol intermediate?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 126. Which of the ketones below could not be prepared by an acid-catalyzed hydration of an alkyne? O

A. B. C. D. E.

III

I II III IV V

Answer: D Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 127. Of the alkyne addition reactions shown, which involve an enol intermediate? A. B. C.

Hydroboration/oxidation HgSO4 catalyzed hydration in dilute H2SO4 Hydrohalogenation

D. E.

A and B A and C

Answer: D Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 128. Which of the following alkynes is expected to produce a single ketone in an acidcatalyzed hydration? A. B. C. D. E.

2-decyne 3-decyne 4-decyne 5-decyne All of the above will give a single product

Answer: D Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 129. Which of the following alkynes gives a single ketone in an acid-catalyzed hydration? A. B. C. D. E.

2-pentyne 2-hexyne 2-heptyne 3-hexyne 3-heptyne

Answer: D Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 130. How many different organic products would be expected from the reaction below?

A. B.

one two

C. D. E.

three four five

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 131. Which of the following alkynes would give a single product under hydroborationoxidation conditions? A. B. C. D. E.

1-hexyne 2-hexyne 3-hexyne A and B would each give a single product A and C would each give a single product

Answer: E Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 132.

Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields?

A. B. C. D. E.

1-hexyne 2-hexyne 3-hexyne 3-methyl-1-pentyne 4-methyl-1-pentyne

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 133. For the reaction shown, which of the compounds listed below would be the expected major, and final, organic product?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 134. For the reaction below, which of the alkynes listed would be expected to produce the product shown under the given conditions?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium

135. What functional group would be expected to be present in the final product of the reaction between 1-hexyne and a mixture of mercuric sulfate and aqueous sulfuric acid? A. B. C. D. E.

aldehyde ketone diol ether carboxylic acid

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 136. What functional group would be expected to be present in the final product of the reaction shown?

A. B. C. D. E.

aldehyde ketone diol enol alkene

Answer: A Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 137.

Which functional group is expected to be produced when cyclodecyne is reacted with disiamylborane, followed by treatment of basic hydrogen peroxide?

A. B. C. D. E.

aldehyde ketone diol ether carboxylic acid

Answer: B

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 138. Which of the reagents below, when reacting with a terminal alkyne, would be expected to produce a ketone as the final major organic product? H2O, H2SO4

1) Disiamylborane

1) 9-BBN

2) H2O2, NaOH

HgSO4

2) H2O2, NaOH

1) BH3•THF

A. B. C. D. E.

III

I and II II III and IV I, II and IV I, III and IV

Answer: B Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Medium 139. Provide the structure(s) of the expected major organic product of the reaction shown. CH3CH2C(CH3)2C

A. B. C. D. E.

I II III IV V

Answer: V

1) Disiamylborane 2) H2O2, NaOH

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroborationoxidation of alkynes Difficulty: Easy 140. What is the major product of the reaction shown? CH3CH2CH2 C C CH3

excess Cl2

CCl4

A. B. C. D. E.

(E)-2,3-dichloro-2-hexene (Z)-2,3-dichloro-2-hexene 2,2-dichlorohexane 3,3-dichlorohexane 2,2,3,3-tetrachlorohexane

Answer: E Learning Objective: 9.8 Describe the halogenation of alkynes, including its products Difficulty: Easy 141. What is the most likely product expected from the reaction scheme shown?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 9.8 Describe the halogenation of alkynes, including its products Difficulty: Easy

142.

Give the major product of the careful addition of 1 equivalent of Br2 to the alkyne shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.8 Describe the halogenation of alkynes, including its products Difficulty: Easy 143.

What is the most likely product expected from the reaction scheme shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products Difficulty: Easy 144. What is the structure of the major organic product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 9.8 Describe the halogenation of alkynes, including its products Difficulty: Medium 145.

What is the expected major product(s) of the treatment of 1-pentyne with 1 equivalent of Br2?

A. B. C. D. E.

1,1-dibromo-1-pentene (E)-1,2-dibromo-1-pentene (Z)-1-bromo-1-pentene A and B B and C

Answer: B Learning Objective: 9.8 Describe the halogenation of alkynes, including its products Difficulty: Easy 146.

Which of the following conditions effectively cleaves all three bonds of a carboncarbon triple bond?

A. B. C. D. E.

HgSO4 and aqueous H2SO4 1. Disiamylborane; 2. H2O2, NaOH H2, Lindlar’s catalyst 1. O3; 2. H2O Na, NH3(l)

Answer: D Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Easy 147.

Predict the major organic products of the reaction shown.

A. B. C. D. E.

I and II II and III I and IV II and III I and III

Answer: C Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Easy 148. What are the expected major products of the reaction sequence shown?

A. B. C. D. E.

I and II I, III, and V II, III, and IV I and IV II, III, IV

Answer: D Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Easy 149. What is the expected major product of the reaction sequence shown?

A. B.

I II

C. D. E.

III IV V

Answer: B Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Easy 150. How many moles of CO2 are expected to be produced by ozonolysis of one mole of the compound shown?

A. B. C. D. E.

1 2 3 4 8

Answer: C Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Easy 151.

Which of the alkynes shown would not produce carbon dioxide and a carboxylic acid as the final products upon treatment with ozone followed by water?

A. B. C. D. E.

ethyne propyne 1-butyne 1-pentyne 1-hexyne

Answer: A Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Medium 152.

Which of the following alkynes would be expected to produce only one major organic product through ozonolysis?

A. B. C. D. E.

1-hexyne 2-hexyne 3-hexyne 2-heptyne 3-heptyne

Answer: C Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Hard 153.

Provide the IUPAC name for the alkyne that would be expected to produce the two compounds listed below through ozonolysis.

CH3CH2CO2H and (CH3)3CCO2H A. B. C. D. E.

1-tert-butyl-1-butyne 2,2-dimethyl-3-hexyne 3,3-dimethyl-2-hexyne 5,5-dimethyl-3-hexyne 3-octyne

Answer: B Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Hard 154.

Which alkyne would produce the products below through ozonolysis?

A. B. C. D. E.

HC≡CC≡CCH2C≡CH HC≡CCH2CH2CH2C≡CH CH3C≡CCH2C≡CCH3 HC≡CCH2CH2C≡CCH3 CH3C≡CC≡CC≡CH

Answer: D Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Hard

155.

What are the structure(s) of the expected major organic product(s) of the following reaction? 1) O3 2) H2O

O OH

A. B. C. D. E.

I II III I and II II and III

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products Difficulty: Easy 156.

What is the IUPAC name for the expected product of the reaction shown?

H H3C A. B. C. D. E.

1) NaNH2 2) CH3CH2CH2Br

propyne 1-hexyne 2-hexyne 3-hexyne (E)-3-hexyne

Answer: C Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Easy

157.

What is the IUPAC name for the expected final product of the reaction shown?

H H A. B. C. D. E.

1) NaNH2

3) NaNH2

2) CH3CH2CH2CH2Br

4) CH3CH2Br

5-decyne 3-hexyne 1-octyne 3-octyne 5-octyne

Answer: D Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Easy 158. What is the expected major final product of the reaction sequence shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Easy

159.

What is the expected major final product of the reaction sequence shown?

A. B. C. D. E.

I II III IV None of the shown products will be produced.

Answer: D Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Medium 160. What is the expected major product of the reaction sequence shown? HC≡C:– + (CH3)2CHCH2Br ® ? A. B. C. D. E.

CH≡CH + (CH3)2CHC≡CH (CH3)2CHC≡CCH3 (CH3)2CHCH2C≡CH (CH3)2CHCHBrC≡CH CH3CHCH2C≡CCH3

Answer: C Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Medium

161.

Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne?

A. B. C. D. E.

I and III II and IV III, IV, V I, II, IV II, III, V

Answer: D Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Hard 162.

A. B. C. D. E.

Why would the following reaction sequence not produce the expected product shown?

1) NaNH2 2)

3) NaNH2 Br

4) CH3Br (NOT produced)

NaNH2 is used in the reduction of alkynes to trans alkenes. The secondary alkyl halide would undergo an elimination reaction. Br is not a good enough leaving group. The terminal alkyne is not acidic enough to be deprotonated. The reaction sequence is correct and will produce the shown product.

Answer: B Learning Objective: 9.10 Describe the alkylation of terminal alkynes Difficulty: Hard

163. What would be the final major product predicted from the reaction below? treated with 1. NaNH2, 2. (CH3)2CHCH2Br, 3. Na, NH3(l), 4. xs NaNH2, 5.H2O.

A. B. C. D. E,

I II III IV V

Answer: A

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Hard 164.

Which series of reactions would convert an internal alkene into an internal alkyne?

A. B. C. D. E.

1. Br2; 2. H2O; 3. Na, NH3 (l), 1. CH3BH; 2. H2O2, NaOH 1. xs NaNH2; 2. H2O 1. HBr; 2. ROOR; 3. H2O 1. CCl4; 2. H2O; 3. Br2

Answer: C Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Easy

165.

Which of the following methods would be expected to efficiently produce a terminal alkyne from cis-2-butene?

A. B. C. D. E.

1. H2, Pt; 2. Br2; 3. NaNH2 1. Br2, H2O; 2. 1 equivalent of NaNH2 1. Br2, CCl4; 2. xs NaNH2, H2O 1, CH3CH2MgBr; 2. NaNH2 1. HBr; 2. ROOR

Answer: C Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Easy 166.

Which sequence of reagents would be expected to accomplish the synthesis shown?

A. B. C. D. E.

1. HBr; 2. 2 NaNH2 1. Br2, CCl4; 2. 2 NaNH2 1. Br2, H2O; 2. NaNH2 1. HBr/ROOR; 2. excess NaNH2 1. Na, NH3(l)

Answer: B Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 167.

To convert an alkene into an alkyne, you can

add two bromines to form a double bond and then remove them through elimination. use Lindlar’s catalyst to convert an alkane directly into an alkyne. generally use H2O as a solvent throughout the process with no benefit to using other solvents.

B. C.

D. use peroxides and then hydrogenate the product. E. use ozonolysis followed by hydrogenation. Answer: A Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 168. To synthesize 3-octyne, you could use bromination and elimination from an intermediate created using which of the following sequences of reactions II

I 1) propyne, NaNH2 2) 1-bromopentane 3) aqueous H2SO4, cat. HgSO4

III 1) 1-butyne, NaNH2 2) 1-bromobutane 3) H2, Lindlar's cat.

IV 1) 1-butyne, NaNH2 2) 1-bromobutane 3) Na, NH3(l)

A. B. C. D. E.

1) propyne, NaNH2 2) 1-bromopentane 3) H2, Ni2B (P-2)

1) 1-butyne, NaNH2 2) 1-bromobutane 3) H2, Pd/C

I II III IV V

Answer: B Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Hard 169. Which sequence of reactions is expected to produce the product shown as the final, and major, organic product?

A. B. C. D. E.

Product I plus 1. H2, Pt; 2. Br2; 3. NaNH2 Product II plus 1. Br2, H2O; 2. 1 equivalent of NaNH2 Product I plus 1. Br2, CCl4; 2. xs NaNH2, H2O Product III plus 1, CH3CH2MgBr; 2. NaNH2 Product IV plus 1. HBr; 2. ROOR

Answer: C Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Hard 170.

Which of the following can successfully be used to synthesize an alkyne?

A. B. C. D. E.

A vicinyl or geminal dihalide that undergoes a series of two elimination reactions A terminal alkyl halide that undergoes a reaction with MCPBA and H3O+ A terminal alkyl halide that is treated with NaNH2 and H2O. A terminal alkene that is treated with HBr followed by KOH. A vicinyl or geminal dihalide that is treated with Lindlar’s catalyst followed by a strong acid.

Answer: D Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 171.

What product would you expect if you treated the reactant below with NaNH2 followed by H2O?

A. B. C.

A terminal alkyne on the side chain. An internal alkyne on the side chain An alkyne within the ringD. An alkene within the ringE. side chain with inversion of configuration

An alkene on the

Answer: B Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Hard 172.

Would the reactants below yield the same alkyne if treated with excess NH3NH2

and H2O?

A. B. D. E.

Yes, because both molecules have an internal double bond in the same position Yes, because both molecules have an internal double bond in the same position with bromines attached to the carbons at each endC. No, because the bromines are positioned cis vs trans No, because the double bond is internal and this reaction will not yield an alkyne No, because bromine is not sufficiently reactive for an alkyne to be produced.

Answer: B Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 173.

What best describes the product of the reactant shown?

A. B. C. D. E.

an internal alkene a terminal alkene an internal alkyne a terminal alkyne a mixture of internal and terminal alkybes

Answer: C Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 174.

Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

1. HC≡CH, NaNH2; 2. CH3CH2CH2Br; 3. Aqueous H2SO4, HgSO4; 4. Br2, CCl4; 5. NaNH2; 6. H2O 1. CH3C≡CH, NaNH2; 2. CH3CH2Br; 3. Disisamylborane; 4. H2O2, NaOH 1. CH3CH2Br, NaNH2; 2. CH3C≡CH; 3. O3; 4. H2O 1. CH3C≡CH, NaNH2: 2. (CH3)2CHCH2Br; 3. BH3●THF; 4. H2O2, NaOH; 5. NaNH2; 6. H2O 1. (CH3)2CHCH2Br, NaNH2; 2. HC≡CH; 3. 9-BBN; 4. H2O2, NaOH; 5. Br2, CCl4

B. C. D. D.

Answer: A Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 175.

What sequence of reactions could be used to carry out the reaction shown?

1. NaNH2; 2. H2O

1. HBr, CCl4; 2. NaNH2; 3. H2O.

1. Br2, light; 2.

D. E.

1. NaNH2; 2. ; 3. H2/Lindlar’s catalyst; 4. xs NaNH2 ; 5. H2O 1. Na, NH3; 2. H2O; 3. CCl4; 4. H2/Pt; 5. xs NaNH2

; 3. xs NaNH2, 4. H2O

Answer: D

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 176.

Why would the following synthetic route shown be an unsuccessful approach to synthesize an internal alkyne? 1) CH3CH2Br

HC C

2) NaNH2

CH3CH2C CC(CH3)3

3) (CH3)3CBr

A. An E2 reaction will be more likely than an SN2 reaction due to the presence of an alkynide ion. B. A bromide would be added the final product. C. An SN2 reaction will be favored and therefore an eliminiation produce is not expected. D. The reaction will not form the necessary alkynide anion. E. An E1 reaction will be more likely than an SN2 reaction due to the tertiary carbon in tert-butyl bromide. Answer: A Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne Difficulty: Medium 177.

Draw all constitutional isomers of the molecular formula C6H10 that are internal alkynes.

A. B. C. D. E.

I II and III I, II, and III I and III I, III, and IV

Answer: E Learning Objective: Integrated Difficulty: Medium 178.

Which of these structures are examples of constitutional isomers of the molecular formula C6H10 that are terminal alkynes?

A. B. C. D. E.

I and II I, II, and III I, III, and IV I, II, and IV I, II, III, and IV

Answer: E

Learning Objective: Integrated Difficulty: Medium 179.

Compound X is exposed to excess strong base (excess NaNH2 then H2O) to produce an alkyne (compound Y). Alkyne Y is a terminal alkyne, has a molecular formula of C5H8, and has exactly 4 distinct resonances in the (proton-decoupled) 13 C NMR spectrum. Which of the following are possible structures for compound X?

A. B. C. D.

I and II II and III III and IV I and IV

Answer: A

Learning Objective: Spectroscopy Difficulty: Hard 180.

1-Pentyne was exposed to strong base (NaNH2. then alkyl halide X, producing an internal alkyne (compound Y). Alkyne Y has exactly 4 distinct resonances in the proton-decoupled 13C NMR spectrum. What are the structures of alkyl halide X and alkyne Y?

A. B. C. D. E.

Alkyl halide X is I and alkyne Y is II Alkyl halide X is II and alkyne Y is III Alkyl halide X is I and alkyne Y is IV Alkyl halide X is II and alkyne Y is IV Alkyle halide X is I and alkyne Y is V

Answer: C

Learning Objective: Spectroscopy Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 10 1.

Which choice shows the product(s) of the homolytic cleavage of the C-C bond of ethane?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 10.1 Compare the order of stability of primary, secondary, tertiary radicals with that of carbocations, and also discuss the stability of allylic and benzylic radicals Difficulty: Easy 2.

Which of the following radicals is the most stable?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 10.1 Compare the order of stability of primary, secondary, tertiary radicals with that of carbocations, and also discuss the stability of allylic and benzylic radicals Difficulty: Easy

In the molecule shown, which of the highlighted C-H bonds (labeled from a to e) is expected to have the lowest bond dissociation energy.

A. B. C. D. E.

C-Ha C-Hb C-Hc C-Hd C-He

Answer: C Learning Objective: 10.1 Compare the order of stability of primary, secondary, tertiary radicals with that of carbocations, and also discuss the stability of allylic and benzylic radicals Difficulty: Easy 4.

Use the appropriate type of arrows to show the movement of electrons during the homolytic bond cleavage of ethane.

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 10.1 Compare the order of stability of primary, secondary, tertiary radicals with that of carbocations, and also discuss the stability of allylic and benzylic radicals Difficulty: Medium 5.

Rank the following radicals in order of decreasing stability (i.e., from most stable to least stable).

A. B. C. D. E.

IV > I > II > III III > I > II > IV III > II > I > IV III > IV > II > I II > III > I > IV

A. B. C. D. E.

Rank the following radicals in order of decreasing stability (i.e., from most stable to least stable).

IV > I > II > III III > I > II > IV III > II > I > IV III > IV > II > I II > I > III > IV

Answer: E

Which structure is an accurate depiction of a resonance structure of the radical shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 10.1 Compare the order of stability of primary, secondary, tertiary radicals with that of carbocations, and also discuss the stability of allylic and benzylic radicals Difficulty: Medium 8.

Which resonance structures below represents the most reasonable resonance structure for the radical shown?

A. B. C. D. E.

I II III IV V

Answer: A

In the structure given, which of the bonds between C and H is the weakest??

A. B. C. D. E.

C-Ha C-Hb C-Hc C-Hd C-He

Answer: D

Which term most accurately describes the process shown?

A. B. C. D. E

coupling proton transfer halogen abstraction hydrogen abstraction homolytic cleavage

Answer: D Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Medium 11.

Select the option that correctly shows the movement of electrons during the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 12.

Which term most accurately describes the process shown?

A. B. C. D. E.

hydrogen abstraction halogen abstraction homolytic cleavage coupling elimination

Answer: D Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 13.

Select the option that correctly shows the movement of electrons during the process shown.

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 14.

Which term most accurately describes the process shown?

A. B. C. D. E.

coupling hydrogen abstraction halogen abstraction homolytic cleavage addition to a π bond

Answer: E Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 15.

Select the option that correctly shows the movement of electrons during the process shown.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 16.

Which term most accurately describes the process shown below?

A. B. C. D. E.

coupling elimination halogen abstraction hydrogen abstraction homolytic cleavage

Answer: B Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 17.

Select the option that correctly shows the movement of electrons during the process shown.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy

18.

Which of the reactions shown represents an example of termination?

A. B. C. D. E.

I II III IV none of the above

Answer: C Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Easy 19.

Which of the reactions shown is an example of initiation?

A. B.

I II

C. D. E.

III IV none of the above

Answer: B Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Medium 20.

Which of the choices is an example of an initiation reaction?

A. B. C. D. E.

homolytic cleavage heterolytic cleavage hydrogen abstraction coupling hydrogen addition

Answer: A Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Medium 21.

Which of the choices is an example of a propagation step?

A. B. C. D. E.

homolytic cleavage heterolytic cleavage hydrogen abstraction coupling hydrogen addition

Answer: C Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Medium 22.

Identify an example of a termination step.

A. B. C. D. E.

homolytic cleavage heterolytic cleavage hydrogen abstraction coupling hydrogen addition

Answer: D Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Medium 23.

A. B. C. D.

Which option correctly shows the result of a feasible addition of a radical to a π bond?

I II III IV

E. V Answer: D

Learning Objective: 10.2 Name six different kinds of reactions found in radical mechanisms and the three stages of these mechanisms Difficulty: Medium 24.

Which of the following represents a propagation step in the monochlorination of methylene chloride (CH2Cl2)?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Medium 25.

Which of these choices would you expect to function as an initiator at a lower temperature than the other choices?

A. B. C.

I II III

Answer: D Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Medium 26.

A. I B. II

Select the option that correctly shows the movement of electrons during the second of a series of two propagation steps involved in the chlorination of propane.

C. III D. IV E. V Answer: B

Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Medium 27.

Which of the choices are possible termination steps in the chlorination of methane?

A. B. C. D.

I and II III and IV I and III II and IV

Answer: B Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Medium 28.

Of the choices given, which is most reactive toward chlorination?

A. B. C. D. E.

methane chloromethane dichloromethane chloroform ethane

Answer: D Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Easy

29.

What steps are needed to minimize the production of higher halogenated products during the free radical chlorination of ethane?

A. B. C. D.

use an excess of chlorine use an excess of ethane use equimolar chlorine and ethane it is not possible to minimize the production of higher halogenated products

Answer: B Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Easy 30.

Of the choices, which shows the initiation step of monochlorination of methane?

A. B. C. D. E.

I II III IV I and II

Answer: A Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Medium 31. A. B. C. D. E.

How many constitutional isomers are possible if propane is dichlorinated? 1 2 3 4 5

Answer: D

Learning Objective: 10.3 Describe the stages in the radical chlorination of methane, and explain which stage that gives the net chemical reaction Difficulty: Medium 32.

Which of the following processes causes the free radical bromination of methane to be slower than the equivalent free radical chlorination?

A. B. C. D. E.

initiation hydrogen abstraction halogen abstraction termination entropy

Answer: B Learning Objective: 10.4 Discuss which halogenation reactions are of practical use in the laboratory and explain why others are not Difficulty: Easy 33.

Which of the following is the rate-determining step in the free-radical bromination of methane?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 10.4 Discuss which halogenation reactions are of practical use in the laboratory and explain why others are not Difficulty: Easy

34.

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

A. B. C. D. E.

1-bromo-1-tert-butylcyclohexane 2-bromo-1-tert-butylcyclohexane 3-bromo-1-tert-butylcyclohexane 4-bromo-1-tert-butylcyclohexane 1-bromo-1,1-dimethylethylcyclohexane

Answer: A Learning Objective: 10.5 Describe the selectivity of halogenation reactions, and compare the positions of bromination and chlorination reactions on alkanes Difficulty: Medium 35.

A. B. C. D. E.

Cyclic compound A has molecular formula C5H10 and undergoes monochlorination to yield exactly three different constitutional isomers. Which of the following shows compound A?

I II III IV V

Answer: C

Learning Objective: 10.5 Describe the selectivity of halogenation reactions, and compare the positions of bromination and chlorination reactions on alkanes Difficulty: Hard 36.

Predict the major product of the reaction shown.

A. B. C. D.

I II III IV

Answer: D Learning Objective: 10.5 Describe the selectivity of halogenation reactions, and compare the positions of bromination and chlorination reactions on alkanes Difficulty: Easy 37.

Predict the major product(s) of the reaction shown.

A. B. C. D. E.

I II III IV I and II

Answer: E Learning Objective: 10.5 Describe the selectivity of halogenation reactions, and compare the positions of bromination and chlorination reactions on alkanes Difficulty: Easy 38.

Two compounds, A and B, each have molecular formula C6H14. Monochlorination of compound A results in the formation of two constitutional isomers.

Monochlorination of compound B results in the formation of four constitutional isomers. Which choices below correctly identifies compounds A and B?

A. B. C. D.

I II III IV

Answer: B

Learning Objective: 10.5 Describe the selectivity of halogenation reactions, and compare the positions of bromination and chlorination reactions on alkanes Difficulty: Easy

39. Which of the following statements correctly describes the nature of the transition state of the rate-determining step of the free-radical bromination of methane? A. the transition state resembles the reactants more than the products B. the transition state resembles the products more than the reactants C. the transition state equally resembles the products and reactants D. the transition state resemblance to reactants vs products is temperaturedependent Answer: B Learning Objective: 10.5 Describe the selectivity of halogenation reactions, and compare the positions of bromination and chlorination reactions on alkanes Difficulty: Hard 40.

Predict the major product(s) of the reaction shown.

A. B. C. D. E.

I II I and III II and III I, II, and III

Answer: D

Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Easy 41.

What is the correct name for the major product of the reaction shown?

A. B. C. D. E.

(R)-3-bromo-3-ethylbutane (S)-3-bromo-3-ethylbutane (R)-3-bromo-3-methylpentane (S)-3-bromo-3-methylpentane 3-bromo-3-methylpentane

Answer: E Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Easy 42.

Predict the product(s) of the reaction shown.

A. B. C. D. E.

I II III I and III III and IV

Answer: E

Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Easy 43.

Predict the major product(s) of the reaction shown.

A. B. C. D. E.

I II and IV III and V I and IV V

Answer: D Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Easy 44.

Predict the major product(s) of the following reaction.

A. B. C. D. E.

I I and II I, II, and III I, II, and IV IV

Answer: B Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Difficult 45.

Compound A has molecular formula C9H20. Compound A produces exactly three constitutional isomers upon monochlorination and produces one major constitutional isomer upon monobromination. Which of the following are possible structures of compound A?

A. B. C. D. E. F.

I II III IV V VI

Answer: E Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Easy 46.

Which of the following are possible product(s) of the reaction shown?

A. B. C. D. E.

I I, II I, II, IV, V I, III, IV, V I, II, III, IV, IV

Answer: D Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions

Difficulty: Difficult 47.

Explain whether the major product or products of the following reaction is optically active and why this is the case.

A. The product is optically acive because a chiral center is created at the right side vertex of the ring. B. The product is optically active because it has a chiral center at a terminal carbon. C. The product is not optically active because it has a chiral center that is part of the ring. D. The product is not optically active because its chiral center is not part of the ring. E. The product is not optically acive because it has no chiral centers. Answer: E

Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Medium 48.

Is the product of the reaction below optically active?

A. Yes, because the reaction produces an optically active product with a chiral center. B. Yes, because the reaction produces an optically active product with a Br on a terminal carbon. C. No, because the reaction produces a meso compound. D. No, because the reaction produces a mixture of optically active enantiomers. E. No, because it is impossible to predict where B r will be added.

Answer: D

Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Medium 49.

How many monochlorination products of 3,3-dimethylpentane are possible, including stereoisomers?

A. B. C. D. E.

1 2 4 6 8

Answer: 4

Learning Objective: 10.6 Describe the circumstances that produce racemic mixtures from radical halogenation reactions Difficulty: Medium 50.

Identify the likely major product(s) of the reaction shown.

A. B. C.

I II III

D. E.

I and III I and IV

Answer: E Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium 51.

What reagent(s) would best accomplish the following synthesis?

A. B. C. D.

Br2 PBr3 CH3Br NBS, heat

Answer: D Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Easy 52.

Which of the choices are major product(s) of the reaction shown?

A. B. C. D. E.

I I, II I, IV I, III I, II, III, IV

Answer: C Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium

53.

Compound A has molecular formula C6H12. Upon treatment with NBS and irradiation with UV light, exactly two compounds (including stereoisomers), are formed. Which of the following is a likely structure for compound A?

A. B. C. D. E.

I II III I and II I and III

Answer: E

Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Hard 54.

Upon treatment of 1-methylcyclopentene with NBS and irradiation with UV light multiple compounds (including stereoisomers) are produced, including the one shown below. How many compounds are formed in total?

A. B. C. D. E.

2 4 6 9 12

Answer: D

Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium 55.

Which of the structures shown are examples of the monobrominated compounds (including stereoisomers) produced when 2-propyl-1-pentene is treated with NBS and UV light irradiation?

A. B. C. D. E.

(R)-3-bromo-3-propyl-1-pentene and (Z)-4-(bromomethyl)-3-heptene (S)-3-bromo-2-propylpentane and (E)-4-(bromomethyl)-3-heptene (S)-3-bromo-3-propylpentane and (Z)-4-(bromomethyl)-3-heptene (R)-4-bromo-3-propyl-1-pentene and (Z)-4-(bromomethyl)-3-heptene (Z)-4-bromomethyl)-2-heptene and (E)-1-bromo-2-propyl-2-pentene

Answer: A

Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium 56.

Which of the structures shown are monobrominated compounds (including stereoisomers) produced when 1-ethyl-4-methylbenzene is treated with NBS and UV light irradiation?

A. B. C. D. E.

I II and III I, II, and V I, III, and V I, IV, and V

Answer: E

Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium 57.

Which are the two monobrominated compounds produced when 2-isopropyl-3methyl-1-butene is treated with NBS and UV light irradiation?

A. B. C. D. E.

I and II II and III I and III I and IV III and IV

Answer: A

Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium 58.

How many monobrominated compounds are produced when 2-methyl-2-butene is treated with NBS and UV light irradiation?

A. B. C. D. E.

2 4 6 8 10

Answer: C

Learning Objective: 11.7 Describe the allylic bromination of alkenes Difficulty: Medium 59.

Which of the following compounds would be expected to be least destructive to the ozone layer?

A. B.

CCl3F CCl2F2

C. D.

CCl2FCCl2F CF3CH2F

Answer: D Learning Objective: 11.8 Explain the role of ozone in the atmosphere and why it is important to life on earth’s surface Difficulty: Easy 60.

Which of the following shows the correct products initially formed when ozone absorbs ultraviolet light?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 11.8 Explain the role of ozone in the atmosphere and why it is important to life on earth’s surface Difficulty: Medium 61.

Use arrows to show the second propagation step for the reaction of a chlorine radical with ozone.

Answer:

Learning Objective: 11.8 Explain the role of ozone in the atmosphere and why it is important to life on earth’s surface Difficulty: Easy 62.

What is the structure of compound A?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 10.9 Describe the conditions necessary for an autooxidation reaction, the products of such reactions, and the utility of antioxidants Difficulty: Easy 63.

Which of the following is expected to be a major product for the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 10.9 Describe the conditions necessary for an autooxidation reaction, the products of such reactions, and the utility of antioxidants Difficulty: Easy 64.

Which of the following is expected to function as an antioxidant?

A. B. C. D. E.

I II III I and II III and V

Answer: C Learning Objective: 10.9 Describe the conditions necessary for an autooxidation reaction, the products of such reactions, and the utility of antioxidants Difficulty: Easy 65.

Which term best describes the process shown?

A. B. C. D. E.

neutralization propagation termination initiation elimination

Answer: B Learning Objective: 10.9 Describe the conditions necessary for an autooxidation reaction, the products of such reactions, and the utility of antioxidants Difficulty: Easy 66.

Which term best describes the process shown?

A. B. C. D. E.

neutralization propagation termination initiation elimination

Answer: C Learning Objective: 10.9 Describe the conditions necessary for an autooxidation reaction, the products of such reactions, and the utility of antioxidants Difficulty: Easy 67.

Predict the major product(s) of the reaction shown.

A. B. C. D. E.

I II III IV II and III

Answer: A Learning Objective: 10.9 Describe the conditions necessary for an autooxidation reaction, the products of such reactions, and the utility of antioxidants Difficulty: Easy 68.

Predict the major product(s) of the reaction shown.

A. B. C. D. E.

I II III IV II and III

Answer: E Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy

69.

Identify the intermediate that leads to the major product in the reaction of 2-methyl2-butene with hydrogen bromide and hydrogen peroxide.

A. B. C. D.

I II III IV

Answer: B Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy 70.

What chemical should be added to intermediate shown?

A. B. C. D.

hydrogen bromide and hydrogen peroxide Br2 in the presence of ultraviolet light Br2 in the presence of NBS hydrogen bromide and ultraviolet light

2-methyl-2-butene to generate the

Answer: A Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy 71.

Predict the product(s) of the reaction shown.

A. B. C. D. E.

I II II, III II, III, IV I, II, III, IV

Answer: E Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy 72.

Predict the product(s) of the reaction shown.

A. B. C. D.

I II III I, II

I, II, III, IV

Answer: C Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy 73.

Of the four choices shown, which is likely to be a major product of the reaction shown?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Hard 74.

Of the four choices shown, which is likely to be a major product of the reaction below?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Hard 75.

Compound A reacts with HBr/ROOR to give compound B. Compound C reacts with bromine and light to produce the same compound (compound B). What are likely structures for compounds A, B, and C.

A. B. C. D. E.

Compound A is I, Compound B is II, and Compound C is III Compound A is II, Compound B is I, and Compound C is IV Compound A is III, Compound B is II, and Compound C is IV Compound A is I, Compound B is III, and Compound C is II Compound A is II, Compoudn B is IV, and Compound C is III

Answer: D

Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Hard 76.

Which of the steps shown is thermodynamically unfavorable at all temperatures?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy 77.

Which choice shows the product of the reaction shown?

B. C. D. E.

I or II III II or III IV

Answer: C

Learning Objective: 10.10 Describe the mechanism and regiochemistry of the radical reaction of HBr with alkenes Difficulty: Easy 78.

Determine the repeat unit for the polymer produced in the reaction below.

A. B. C. D.

I II III IV

Answer: B Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Easy 79.

Which of the following is the repeat unit for the polymer produced in the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Easy 80.

Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate, which is shown. What is the repeat unit of PMMA?

A. B. C. D.

I II III IV

Answer: B

Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Medium 81.

Polychloroprene (Neoprene) can be prepared by the free-radical polymerization of chloroprene. Which choice shows a resonance structure that is formed during the propagation steps that lead to the isomer of polychloroprene shown below?

A. B. C. D. E.

I II III II and III III and IV

Answer: B

Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Hard

82.

Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. What is the most reasonable explanation for this result?

A. B. C. D. E.

There are C-H bonds at allylic positions in propylene. There is a double bond in propylene. The chain is not able to undergo hydrogen abstraction. There are C-C bonds at vinylic positions in propylene. Polypropylene has very few H-C bonds.

Answer: A Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Medium 83.

Which choice accurately uses arrows to show termination by coupling of two growing poly(vinyl chloride) chains?

A. B. C. D. E.

I II III II and III III and IV

Answer: C Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Easy

84.

Azobisisobutyronitrile (AIBN) is commonly used as a radical initiator. choices accurately uses arrows to show this process?

A. B. C. D. E.

I II III IV V

Answer: B

Which

Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Easy 85.

Which monomer is used for the synthesis of Teflon?

A. B. C. D.

1,1-difluoroethene 1,1,2,2-tetrafluoropropene 1,1,2,2-tetrafluoroethene tetrafluoromethane

Answer: C Learning Objective: 10.11 Describe the mechanism of the radical polymerization of ethylene, the stages of the process, and the product Difficulty: Easy 86.

Which monomer is used for the synthesis of poly(vinyl chloride)?

A. B. C. D.

1-chloroethene 1-chloroethane 1,2-dichloroethene 1-chloro-1-propene

Answer: A Learning Objective: 10.12 Define cracking, hydrocracking, and reforming Difficulty: Easy 87.

Thermal cracking of butane can produce ethyl radicals via homolytic cleavage. Does the reaction below correctly use arrows to show this process?

A. Yes, because movement of pairs of electrons is shown using fishhook arrows. B. Yes, because the cleavage is uneven. C. Yes, because fishhook arrows show movement of individual electrons to produce two equal halves that each have an unpaired electron. D. No, because fishhook arrows should not be used for reactions that show homolytic cleavage. E. No, because fishhook arrows are not appropriate to show the movement of electrons in this type of radical reaction. Answer: C

Learning Objective: 10.12 Define cracking, hydrocracking, and reforming Difficulty: Easy 88.

Does the reaction below correctly use arrows to show the movement of electrons during the thermal cracking of hexane to yield 1-butene?

A. Yes, because the presence of a radical electron means that a double bond will be formed in the product. B. Yes, because the radical electron moves lef to join a second electron to form a double bond and a right-hand electron moves left to form an unparied electron at the end of the left-hand fragment. C. Yes, because the radical in the reactant is left in place in the product. D. No, because no cracking occurs when the new double bond is formed. E. No, because the three arrows shown do not move electrons in such a way that a bond will be broken. Answer: B

Learning Objective: 10.12 Define cracking, hydrocracking, and reforming Difficulty: Easy 89.

Which choice shows the product of coupling of the following radicals?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 10.12 Define cracking, hydrocracking, and reforming Difficulty: Easy 90. What would be an appropriate series of steps to synthesize 1-iodo-2methylpropane from 2-methylpropene?

A. B. C. D. V.

NBS/hn followed by I2 HBr/ROOR follwed by KI Br2/ROOR followed by NaCl Br2/hn followed by KI KI followed by HBr/hn

Answer: B Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Easy

91. Which of the choices could be used to synthesize 2-methylpropene from 2methylpropane.

A. B. C. D. E.

KI followed by Br2/ROOR NaOH followed by NBS Br2/hn followed by NaOEt Cl2/hn NBS/hn

Answer: C

Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Easy 92.

Which of the following could be used to synthesize polyethylene from ethane?

A. B. C. D. E.

Br2/ hn, then KOtBu, then ROOR KOtBu, then Br2/hn, then ROOR HBr followed by Br2/hn NBS followed by ROOR NaCl followed by KI

Answer: A

Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Medium 93.

Which option is a reasonable synthesis of 3,4-dimethyl-2-pentanol using 2-methyl2-butene and ethanol as your sources of carbon?

A. B. C. D. E.

KOH/ HBr/ROOR followed by 1. Mg, 2. CH3CHO, 3. H3O+. NBS/hn followed by HBr/ROOR MgBrCH3 NaOH followed by Br2/hn

Answer: B

Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Medium 94.

Which sequence of reactions could be used to accomplish the given synthesis?

A. 1. Br2, light; 2. potassium t-butoxide; 3. mCPBA; 4. H3O+ B. 1. CH3MgBr; 2. NBS; 3. NaOH C. 1. HBr, light; 2. NaOH; 3. H3O+ D. 1. HBr; 2. potassium t-butoxide; 3. mCPBA; 4. H3O+ E. 1. NaOH; 2. potassium t-butoxide; 3. H3O+ Answer: A Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Medium 95.

What is a reasonable option to synthesize 4-penten-2-ol from propene?

A. B. C. D. E.

HBr/ROOR folllowed by 1. Mg, 2. CH3CHO; 3. H3O+ HBr/RPPR followed by CH3MgBr 1. Br2, light; 2. potassium t-butoxide; 3. mCPBA; 4. H3O+ Br2/NBS folllowed by 1. Mg, 2. CH3CHO; 3. H3O+ Br2/hn followed by CH3CHO and H3O+

Answer: D

Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Hard

96.

What is a reasonable option to synthesize 2-butyn-1-ol from propane?

A. B. C. D. E.

NaOH, then excess NaNH2/NH3 followed by H3O+ 2 HBr/light, folowed by CH2O and H3O+ 2 Br2/light, followed by excess NaNH2/NH3, then 1. CH2O, 2/ H3O+ CCl4/heat followed by excess NaNH2/NH3 Br2/NBS followed by CH2O and then H3O+

Answer: C

Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Medium 97.

Which sequence of reactions could be used to accomplish the given synthesis?

A. B. C. D. E.

Br2/ROOR followed by excess NaNH2/NH3 HBr/ROOR followed by HBr/ROOR 2 HBr/ROOR followed by 1. CH2O; 2/ H3O+ hn/NBS followed by HBr/ROOR 2 Br2/light, followed by excess NaNH2/NH3, then 1. CH2O; 2/ H3O+

Answer: D

Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Medium 98.

Which sequence of reactions could be used to accomplish the following synthesis?

A. 1. Br2, light; 2. KOtBu; 3. HBr, ROOR; 4. NaCN B. NaCN followed by H3O+, then treated with peroxide C. 2 Br2/light, followed by excess NaNH2/NH3, then 1. CH2O; 2/ H3O+ D. CH3MgBr followed by excess NaNH2/NH3, then Br2/light Answer: A Learning Objective: 10.13 Discuss the uses of radical halogenation in syntheses Difficulty: Medium 99.

Propose a sequence of reactions to accomplish the following synthesis.

A. B. C. D. E.

Br2, light; 2. KOtBu; 3.O3; 4 DMS 2 Br2/light, followed by excess NaNH2/NH3, then 1. CH2O; 2/ H3O+ HBr/light, followed by NaOH then H3O+ CH3COOH, then H2/Pt NBS/hn followed by O3 and then H3O+

Answer: B Learning Objective: Spectroscopy Difficulty: Hard 100.

Methylenecyclopentane can be exposed to allylic bromination conditions to give multiple regioisomeric compounds, including Compound X. Compound X can then be hydrogenated to give Compound Y, which has only 4 distinct resonances in the proton-decoupled 13C NMR spectrum. What are the structures of compounds X and Y?

A. B. C. D. E.

Compound X is I and compound Y is II Compound X is II and compound Y is I Compound X is III and compound Y is II Compound X is III an compound Y is IV Compound X is IV and compound Y is III

Answer: C

Learning Objective: Spectroscopy Difficulty: Medium 101. When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled 13C NMR spectrum are observed in the product? A. 1 B. 2 C. 4 D. 6 E. 12 Answer: C Learning Objective: Spectroscopy Difficulty: Medium

102.

When 1,1,4-trimethylcyclohexane is exposed to Br2 and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled 13C NMR spectrum are observed in the product?

A. 1 B. 2 C. 4 D. 6 E. 12 Answer: D Learning Objective: Spectroscopy Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 11 1.

Predict the major product(s) for the reaction shown.

A. B. C. D. E.

I II III IV I, III, and IV

Answer: E Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 2.

Select the best reagents for the reaction shown.

A. B. C. D. E.

HBr Br2/hn Br2/ROOR HBr/ROOR hn /NBS

Answer: D Learning Objective: 11.1 Identify the reagents for a one-step synthesis

Difficulty: Medium 3.

Select the best reagents for the reaction shown.

A. B. C. D. E.

HBr Br2/hn Br2/ROOR HBr/ROOR hn /NBS

Answer: E Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 4.

Select the best reagents for the reaction shown.

A. B. C. D. E.

HBr Br2/hn Br2, CCl4 HBr/ROOR hn /NBS

Answer: C Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 5.

Select the best reagents for the reaction shown.

A. B. C. D. E.

HBr Br2/H2O Br2, CCl4 HBr/ROOR hn /NBS

Answer: B Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 6.

Select the best reagents for the reaction shown.

A. B. C. D. E.

NaOH heat/H2SO4 CH3CO2H NaOEt B and D

Answer: E Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 7.

Provide the major product(s) for the following synthesis.

A. B. C. D. E.

I II III IV I and III

Answer: C Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 8.

Select the best reagents for the reaction shown.

A. B. C. D. E.

NaOtBu HBr H2SO4 NaOH NaSH

Answer: D Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 9.

Select the best reagents for the reaction shown.

A. B. C. D. E.

NaOtBu HBr H2SO4 NaOH NaSH

Answer: A Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 10.

Provide the major product(s) obtained from the reaction shown.

A. B. C. D. E.

I II III IV II and IV

Answer: C Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 11.

Select the best reagents for the reaction shown.

A. B.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4

C. D. E.

1. RCO3H; 2. H3O+ H2SO4, H2O 1. O3; 2. DMS

Answer: C Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 12.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4 1. RCO3H; 2. H3O+ H2SO4, H2O 1. O3; 2. DMS

Answer: A Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 13.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4 1. RCO3H; 2. H3O+ H2SO4, H2O 1. O3; 2. DMS

Answer: E Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium

14.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4 1. RCO3H; 2. H3O+ 1. BH3-THF; 2. H2O2, NaOH 1. O3; 2. DMS

Answer: B Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 15.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4 1. RCO3H; 2. H3O+ 1. BH3∙THF; 2. H2O2, NaOH 1. O3; 2. DMS

Answer: D Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 16.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4 H2, Pt 1. BH3∙THF; 2. H2O2, NaOH 1. O3;2. DMS

Answer: C Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 17.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O NaNH2 H2, Pt Na, NH3(l) H2, Lindlar’s catalyst

Answer: D Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 18.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O NaNH2 H2, Pt Na, NH3(l) H2, Lindlar’s catalyst

Answer: E Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium

19.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O 1. Hg(OAc)2, H2O; 2. NaBH4 H2, Pt 1. 9-BBN; 2. H2O2, NaOH 1. O3; 2. DMS

Answer: D Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 20.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O H2SO4, H2O, HgSO4 H2, Pt 1. 9-BBN; 2. H2O2, NaOH 1. O3; 2. DMS

Answer: B Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 21.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O H2SO4, H2O, HgSO4 NaOH excess NaNH2 1. O3; 2. DMS

Answer: D Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 22.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O H2SO4, H2O, HgSO4 NaOH excess NaNH2 1. O3; 2. H2O

Answer: E Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium 23.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O ROOR, heat NaOH excess NaNH2 1. O3; 2. H2O

Answer: B Learning Objective: 11.1 Identify the reagents for a one-step synthesis Difficulty: Medium

24.

Select the best reagents for the reaction shown.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O HBr, ROOR NaBr excess NaNH2 HBr

Answer: E Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group Difficulty: Hard 25.

Select the best reagent to convert 4,5-dimethylhex-2-yne to trans-4,5dimethylhex-2-ene.

A. B. C. D. E.

1. OsO4; 2. NaHSO3, H2O HBr, ROOR NaBr Na, NH3 HBr

Answer: D Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group Difficulty: Hard 26.

Select the best reagent to convert 1-bromo-1-methylcyclohexane to 1-bromo-2methylcyclohexane.

A. B. C. D. E.

1. KOtBu; 2. HBr 1. NaOEt; 2. HBr 1. NaOEt; 2. HBr, ROOR 1. KOtBu; 2. HBr, ROOR Br2, hn

Answer: C Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group Difficulty: Hard

27.

Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methylcyclohexanol to a secondary position?

A. B. C. D. E.

1. KOtBu; 2. Hg(OAc)2, H2O; 3. NaBH4 1. TsCl, pyr; 2. KOtBu; 3. BH3-THF; 4. H2O2, NaOH 1. H2SO4, heat; 2. BH3-THF; 3. H2O2, NaOH 1. TsCl, pyr; 2. NaOH; 3. BH3-THF; 4. H2O2, NaOH C and D

Answer: E Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group Difficulty: Hard 28.

Which sequence of reagents will accomplish the synthesis shown?

A. B. C. D. E.

1. KOtBu; 2. HBr 1. NaOEt; 2. HBr, ROOR 1. H2SO4, heat; 2. Br2, hn 1. NaOEt; 2. HBr A and D

Answer: A Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group Difficulty: Hard 29.

Which sequence of reagents will accomplish the synthesis shown?

A. B. C. D. E.

1. KOtBu; 2. 1-bromopropane 1. NaNH2; 2. 1-bromopropane 1. NaNH2; 2. 2-bromopropane 1. O3; 2. DMS 1. O3; 2. 1-bromopropane

Answer: B Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Hard 30.

Predict the major product(s) for the reaction shown.

A. B. C. D. E.

I II III IV II and III

Answer: C Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Medium 31.

Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.

A. B. C. D. E.

hept-1-en-4-yne hept-6-en-3-yne hept-3-en-6-yne hept-4-en-1-yne hept-2-en-4-yne

Answer: A Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Medium

32.

The reaction of compound A (molecular formula = C7H12) with sodium amide followed by the reaction of compound A with 1-bromobutane produces a compound with the structure (CH3)2CHCH(CH3)CC(CH2)3CH3. What is compound A?

A. B. C. D. E.

2,3-dimethylnon-4-yne 2,2-dimethylpent-1-yne 3,4-dimethylpent-1-yne 4,4-dimethylhept-1-yne 1-heptyne

Answer: C Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Medium 33.

The reaction of compound A (molecular formula = C12H24) with ozone followed by the reaction of compound A with DMS produces only (CH3)3CCH2CHO. Which of the following could be compound A?

A. B. C. D. E.

cis-2,3,7,8-tetramethyloct-4-ene trans-dodec-6-ene 4,4-dimethylpent-1-ene cis-2,2,7,7-tetramethyloct-4-ene 2,2-dimethyldec-4-ene

Answer: D Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Medium 34.

Select the best reagents for the reaction shown.

A. B. C. D.

NaNH2 1. O3; 2. H2O KMnO4 1. BH3-THF; 2. H2O2, NaOH

H2SO4, H2O

Answer: B Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Medium 35.

Compound X has the molecular formula C8H10. The reaction of compound X with excess ozone, followed by reaction of the product with dimethyl sulfide and then washing with water produces only the compounds shown. Which compound below could be for compound X that is consistent with these results.

A. B. C. D. E.

I II III I and II II and III

Answer: B

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Hard

36.

Predict the products of the reaction shown.

A. B. C. D. E.

I, III, and IV II, III, and IV I, III, and V II, IV, and VI III and IV

Answer: B Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Hard 37.

What single compound is produced when acetylene is treated with the reagents below?

butanoic aci, A. B. C.

butanoic acid propanoic acid 1,6-bromohexane

D. E.

ethylene acetaldehyde

Answer: B Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Hard 38.

Predict the sequence of reactants required to complete the following synthesis in which propanal is the only carbon-containing product.

NaNH2

CH3SCH3

H2 O

CH3CH2Br

Na/NH3(l)

H2/Pt

III

VII

A. B. C. D. E.

1. I; 2. III; 3. IV; 4. V; 5. II 1. VI; 2. IV; 3. IV; 4. VII; 5. V; 6. II 1. V; 2. II 1. I; 2. IV; 3. VI; 4. V; 5. II none of the above are correct

Answer: D Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Hard 39.

Propose a synthesis of propanoic acid from acetylene.

A. B. C. D. E.

1. Br2/CCl4; 2. xs NaNH2; 3. H2O t-BuOk followed by 1. Hg(OAc)2, H2O; 2. NaBH4 1. NaNH2; 2. CH3CH2Br followed by 1. O3; 2. H2O 1. BH3/THF; 2. H2O2, NaOH NaOEt followed by 1. BH3/THF; 2. H2O2, NaOH

Answer: C

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule Difficulty: Hard 40.

Which synthesis will yield cyclopentanone from 1-methylcyclopentane?

A. B. C. D. E.

t-BuOk followed by 1. Hg(OAc)2, H2O; 2. NaBH4 1. Br2/CCl4; 2. xs NaNH2; 3. H2O t-BuOk followed by 1. Hg(OAc)2 , H2O3 2. NaBH4 Br2/ hn, followed by KOtBu, followed by 1. O3; 2. DMS NaOEt followed by 1. Hg(OAc)2, H2O; 2. NaBH4

Answer: D

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 41.

Identify the changes that must occur to convert cis-2-butene into 2-butanol.

A. B. C. D. E.

only the identity of the functional group(s) must change only the carbon skeleton must change only the location of the functional group(s) must change only the identity and location of the functional group(s) must change both the carbon skeleton and the identity of the functional group(s) must change

Answer: A Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Medium

42.

Which choice will synthesize 1-butene from propyne?

A. B. C. D. E.

1. NaNH2; 2. CH3I followed by 1. NaNH2; 2. H2O; 3. H2/Lindlar’s catalyst 1. BH3/THF; 2. H2O2; NaOH H2/Pt, then NaOH CH3I followed by H2/Pt HBr/ROOR; 2. NaOH

Answer: A

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 43.

The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1) and then from that product into a compound in which the functional group has been changed (compound 2). Identify compounds 1 and 2.

A. Compound 1 = I; Compound 2 = III B. Compound 1 = II; Compound 2 = III

C. D. E. F.

Compound 1 = VI; Compound 2 = IV Compound 1 = II; Compound 2 = IV Compound 1 = II; Compound 2 = V Compound 1 = VII; Compound 2 = VIII

Answer: D Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 44.

Which of the following sequences converts 2-methylpropene and sodium acetylide into 3-methylbutanal?

A. B. C. D. E.

1. HBr; 2. NaCCH; 3. O3; 4. H2O 1. HBr; 2. NaCCH; 3. O3; 4. DMS 1. HBr, ROOR; 2. NaCCH; 3. O3; 4. H2O 1. HBr, ROOR; 2. NaCCH; 3. H2/Ni2B; 4. O3; 5. DMS 1. NaCCH; 2. H2/Ni2B; 3. O3; 4. DMS

Answer: D Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 45.

Which of the following sequences converts 3-methyl-1-pentene into 3-bromo-3methylpentane?

A. B. C. D. E.

1. Br2; 2. NaOH; 3. HBr 1. Br2, hn; 2. H2, Pt 1. H2, Pt; 2. Br2, hn 1. NBS, hn; 2. H2, Pt 1. HBr, ROOR; 2. NaOH; 3. HBr

Answer: C Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard

46.

Propose a synthesis to produce the following answer as one of the major products.

A. B. C. D. E.

1. CH3BH; 2. H2O2, NaOH 1. H2, Lindlar’s catalist; 2. NaCCH; 3. excess O3; 4. H2O 1. NBS, hn; 2. H2, Pt; 3. NaCCH; 4. excess O3 1. NBS, hn; 2. H2, Pt; 3. NaCCH; 4. 1 equiv. O3; 5. H2O 1. NBS, hn; 2. H2, Pt; 3. NaCCH; 4. H2O

Answer: C Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 47.

Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.

A. 1. H3O+; 2. KOtBu; 3. H2O2, NaOH B. 1. BH3-THF; 2. H2O2, NaOH C. 1. TsCl, pyr; 2. CH3-THF; 3. H2O2, NaOH D. 1. TsCl, pyr; 2. KOtBu; 3. CH3-THF; 4. H2O2, NaOH E. 1. KOtBu; 2. CH3-THF; 3. H3O+ Answer: D

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 48.

Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.

A. B. C. D. E.

1. NaOH; 2. H3O+ 1. H2SO4, heat; 2. NaBH4; 3. H3O+ 1. H2SO4, heat; 2. Hg(OAc)2, H2O; 3. NaBH4 1. Hg(OAc)2, H2O; 2. H2SO4, heat; 3. NaBH4 1. NaOMe; 2. BH3-THF; 3. H2O2, NaOH

Answer: C Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 49.

Which of the following alkenes cannot be converted into an alkyne by reacting it with bromine followed by an excess of sodium amide and then with water?

A. B. C. D. E.

I II III IV III and IV

Answer: D Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 50.

Which of the following provides a synthetic route to convert 3-bromo-2-methyl-1butene into 2-methyl-2-butene?

A. B. C. D. E.

1. NaOH; 2. H2, Pt 1. H2, Pt; 2. NaOEt 1. H2, Pt; 2. Br2 1. H2, Ni2B; 2. KOtBu 1. H2, Pt; 2. KOtBu

Answer: B Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 51.

Which order of reactions would most effectively convert trans-2-butene into 1butene?

convert to the gem-dibromoalkane, then to the terminal alkyne, then to the terminal alkene convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene convert to the terminal alkene in one step shorten the chain by two carbons, then add a two-carbon alkene to the end convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene

B. C. D. E.

Answer: A Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Medium 52.

What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

A. B. C. D. E.

1 2 3 4 5

Answer: B Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Medium 53.

What is the minimum number of steps required to convert 2-methylpropane into 1-bromo-2-methyl-2-propanol?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Medium 54.

Which synthetic route(s) would complete the reaction shown?

Synthesis I: 1. NaCCCH3; 2. Na/NH3(l) ;3. OsO4; 4. NaHSO3, H2O Synthesis II: 2. NaCCCCH3; 2. H2, Lindlar’s catalyst; 3. MCPBA; 4. aq. H2SO4 Synthesis III: 1. NaCCCCH3; 2. H2, Pt; 3. MCPBA; 4. aq. H2SO4 A. I B. II C. III D. I and II E. I and III Answer: D Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 55.

Select the appropriate synthetic route for the equation shown.

A. B. C. D. E.

1. Br2; 2. KOtBu; 3. HBr, ROOR; 4. NaSMe 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. NaSH 1. Br2, hn; 2. KOtBu; 3. NaSMe 1. Br2, hn; 2. KOtBu; 3. NaSH; 4. H3O+ 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. NaSMe

Answer: E

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 56.

Select the appropriate synthetic route for the reaction shown.

A. B. C. D. E.

1. NBS; 2. NaOEt; 3. NaSMe 1. NaOEt; 2. NBS; 3. NaSMe 1. NaOEt; 2. NBS; 3. NaSH 1. NatBu; 2. NBS, hn; 3. NaSMe 1. NaOEt; 2. NBS, hn; 3. NaSMe

Answer: E Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Hard 57.

Select the appropriate synthetic route for the reaction shown.

A. B. C. D. E.

1. O3, H3O+ 1. H2, Lindar’s; 2. O3, H3O+ 1. Br2, CCl4; 2. excess NaNH2; 3. H2O; 4. O3; 5. H2O 1. H2O, H2SO4, HgSO4; 2. excess NaNH2; 3. H2O; 4. O3; 5. H2O 1. Br2, CCl4; 2. O3; 3. H2O; 4. excess NaNH2; 5. H2O;

Answer: C Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Medium 58.

Select the appropriate synthetic route for the reaction shown.

A. B. C. D. E.

1. NaCCH; 2. 9-BBN; 3. H2O2, NaOH 1. R2BH; 2. H2O, NaOH; 3. H2O2, NaOH 1. xs NaNH2; 2. H2O; 3. O3; 4. H2O 1. NaCCH; 2. H2O2; 3. 9-BBN; 4. NaOH 1. 9-BBN; 2. NaCCH; 3. H2O2, NaOH

Answer: A Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group Difficulty: Medium 59.

Using retrosynthetic synthesis, determine which compound(s) could lead to the alkene shown in a single step.

A. B. C. D. E. F.

I II III IV I or IV I, III, or IV

Answer: E Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 60.

Using retrosynthetic synthesis, determine which compound(s) could lead to the alcohol shown in a single step.

A. B. C. D. E. F.

I II III IV I or II I, II, or IV

Answer: E Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 61.

Using retrosynthetic synthesis, determine which compound(s) could lead to the alkyne shown in a single step.

A. B. C. D. E. F.

I II III IV I or II I, II, or IV

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis

Difficulty: Medium 62.

Using retrosynthetic synthesis, determine which compound(s) could lead to the alkane shown in a single step.

A. B. C. D. E.

II or III I or IV I III IV

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 63.

Using retrosynthetic synthesis, determine which compound(s) could lead to the bromoalkene shown in a single step.

A. B. C. D. E. F.

I or III I or IV I II III IV

Answer: C Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 64.

Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that could lead to the alkyl halide (C).

A. B. C. D. E.

B = I and A = VIII B = VI and A = I B = III and A = VII B = IV and A = VII B = V and A = VIII

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 65.

Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that can lead to the alkyne (C).

A. B. C. D. E.

B = I and A = VI B = VI and A = I B = III and A = VII B = IV and A = VII B = VI and A = VIII

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 66.

Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that can lead to the alcohol (C).

A. B. C. D. E.

B = I and A = VI B = VI and A = I B = III and A = VII B = VII and A = II B = VIII and A = V

Answer: E Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 67.

Perform a retrosynthetic analysis by working backwards two steps in the given synthesis. Identify possible combinations of A and B that can lead to the compound shown (C).

A. B. C. D. E.

B = I and A = VI B = V and A = II B = IV and A = VII B = I and A = III B = VIII and A = V

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 68.

Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that can lead to the alkene (C).

A. B. C. D. E.

B = I and A = IV B = II and A = VI B = III and A = I B = I and A = VI B = III and A = II

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis

Difficulty: Medium 69.

Select the appropriate synthetic route to convert methylcyclobutane into cyclopentene.

A. B. C. D. E.

1. KOtBu; 2. BH3-THF; 3. H2O2, NaOH; 4: H2SO4, heat 1. H2, Lindlar’s catalyst; 2. BH3-THF; 3. H2O2, NaOH 1. Br2, hn; 2. KOtBu; 3. BH3-THF; 4. H2O2, NaOH; 5: H2SO4, heat 1. BH3-THF; 2. H2O2, NaOH; 3. H2, Pt 1. Br2, hn; 2. KOtBu; 3. H2O2, NaOH; 4: H2SO4, heat

Answer: C Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 70.

Select the appropriate synthetic route to convert ethylene into PVC (polyvinyl chloride).

A. B. C. D. E.

1. Br2; 2. excess NaNH2; 3. H2O; 4. 1 eq. HCl; 5. ROOR, heat 1. Br2; 2. 1 equivalent NaNH2; 3. H3O+; 4. 1 eq. HCl; 5. ROOR 1. Cl2; 2. 1 equivalent NaNH2; 3. H3O+; 4. 1 eq. HCl; 5. ROOR 1. Br2, CCl4; 2. Na, NH3(l) 1. Cl2; 2. excess NaNH2; 3. H2O; 4. ROOR, heat

Answer: A Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 71.

Select the appropriate method of converting acetylene into the polymer shown.

A. B. C. D. E.

1. NaNH2; 2. CH3Cl; 3. ROOR, heat 1. CH3Br; 2. excess HCl; 3. ROOR, heat 1. NaNH2; 2. CH3Br; 3. excess HCl; 4. ROOR 1. NaNH2; 2. CH3Br; 3. HCl (1 equiv.); 4. ROOR, heat 1. CH3Cl; 2. NaNH2; 3. CCl4; 4. ROOR, heat

Answer: D

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 72.

Select the appropriate synthetic route to convert 5-methyl-1-hexene into 5methylhexanal.

A. 1. Br2; 2. H2O; 3. Disiamylborane; 4. H2O2, NaOH B. 1. O3; 2. H2O; 3. excess NaNH2; 4. H2O C. 1. Br2; 2. H2O; 3. Disiamylborane; 4. NaOH D. 1. Br2; 2. excess NaNH2; 3. H2O; 4. Disiamylborane; 5. H2O2, NaOH E. 1. Cl2; 2. excess NaNH2; 3. H2O; 4. H2O2, NaOH Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 73.

Select the appropriate method of converting 4-methyl-1-pentene into 3methylbutanoic acid.

A. B. C. D. E.

1. CCl4; 2. excess NaNH2; 3. O3; 4. H2O 1. Br2, CCl4; 2. excess NaNH2; 3. H2O 1. Cl2, CCl4; 2. NaNH2; 3. H2O; 4. O3; 5. H2O 1. O3; 2. H2O; 3. CCl4; 4. excess NaNH2; 5. H2O 1. Br2, CCl4; 2. excess NaNH2; 3. H2O; 4. O3; 5. H2O

Answer: E

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 74.

Which of the reactions shown effectively produces 4,4-dimethyl-2-pentyne?

A. B. C. D. E.

I, II, III, and IV II, III, and IV I, II, and III I, II, and IV I, III, and IV

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 75.

Select an appropriate synthetic route to yield the given diol starting with 1,1,3,3tetramethyl-2-ethylcyclohexane.

A. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. RCO3H; 10. H3O+

B. 1. Br2, hn; 2. HBr, ROOR; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Cl; 8. H2, Pd; 9. OsO4, NMO; 10. H3O+ C. 1. Br2, hn; 2. HBr, ROOR; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. NaHSO3, H2O D. 1. Br2, hn; 2. HBr; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O E. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O Answer: E

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 76.

Select an appropriate synthetic route of the diol shown starting with 1,1,3,3tetramethyl-2-ethylcyclohexane.

A. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. RCO3H; 10. H3O+ B. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Pt; 9. OsO4, NMO; 10. NaHSO3, H2O C. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. 1 equiv. NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4; 10. H3O+ D. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O E. 1. Br2, hn; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Pd; 9. RCO3H; 10. H3O+ Answer: A

Alternatively steps 8-10 could 8. Na/NH3; 9. OsO4; 10. NaHSO3. Learning Objective: 11.5 Perform a retrosynthetic analysis

Difficulty: Hard 77.

Select an appropraite synthetic route of the compound shown starting with 4methyl-2-pentanol.

1. TsCl, pyr; 2. KOtBu; 3. HCl/ROOR; 4.

1. TsCl, pyr; 2. KOtBu; 3. HBr/ROOR; 4.

1. TsCl, pyr; 2. KOtBu; 3. HBr; 4. H3O+; 5.

1. TsCl, pyr; 2. KOtBu; 3. HBr/ROOR; 4.

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 78.

Starting with a primary alkyl bromide, which of the choices given results in an overall increase in the length of the carbon skeleton by one carbon?

A. B. C. D.

substitute bromide with acetylide, then cleave the triple bond substitute bromide with acetylide, then reduce the alkyne to an alkene substitute bromide with methoxide eliminate hydrogen bromide to produce an alkene

Answer: A Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium

79.

Starting with a primary alkyl bromide, which of the choices given results in an overall decrease in the length of the carbon skeleton by one carbon?

A. B. C. D.

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Medium 80.

Select an appropriate synthetic route for the following equation.

A. B. C. D. E.

1. NaOH; 2. BH3-THF; 3. NaOH 1. BH3-THF; 2. H3O+ 1. NaOEt; 2. H2O2, NaOH 1. NaOCH3; 2. BH3-THF; 3. H2O2, NaOH 1. NaOEt; 2. BH3-THF; 3. H2O2, NaOH

Answer: E

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 81. Select an appropriate synthetic route for the equation given.

A. B. C. D. E.

1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar’s catalyst; 6. H3O+ 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar’s catalyst; 6. RCO3H 1. NaNH2; 2. CCl4; 3. NaNH2; 4. CH3Br; 5. H2, Pd; 6. RCO3H 1. NaNH2; 2. CCl4; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar’s catalyst; 6. RCO3H 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Pt; 6. RCO3H

Answer: B

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 82.

Select an appropriate synthetic route for the equation given.

1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. OsO4; 6. H3O+

B. C. D. E.

1. MCPBA; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. Na, NH3(l); 6. RCO3H 1. MCPBA; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. OsO4; 6. H3O+ 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. Na, NH3(l); 6. RCO3H 2. CH3Br; 2. NaNH2; 3. CH3Br; 4. Na, NH3(l); 5. RCO3H

Answer: D

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 83.

Select an appropriate synthetic route for the equation given.

A. B. C. D. E.

1. NBS, hn; 2. HBr, ROOR; 3. N2 1. NBS, hn; 2. HBr, ROOR; 3. 2 NaCN 1. Br2, hn; 2. HBr, ROOR; 3. 2 NaCN 1. NBS, hn; 2. HBr; 3. 2 NaCN 1. NBS, hn; 2. HBr, ROOR; 3. 2 NaCN

Answer: D

Learning Objective: 11.5 Perform a retrosynthetic analysis

Difficulty: Hard 84.

Select an appropriate synthetic route to prepare 1,7-heptanediol from propene.

A. 1. HBr, ROOR; 2. 2 NaCCH; 3. H2, Lindlar’s catalyst; 4. BH3-THF; 5. H2O2, NaOH B. 1. NBS, light; 2. HBr; 3. 2 NaCCH; 3. H2, Lindlar’s catalyst; 5. BH3-THF; 6. H2O2, NaOH C. 1. NBS, light; 2. HBr, ROOR; 3. 2 NaCCH; 3. H2, Pt; 5. BH3-THF; 6. H2O2, NaOH D. 1. HBr; 2. 2 NaCCH; 3. H2, Lindlar’s catalyst; 4. BH3-THF; 5. H2O2, NaOH E. 1. NBS, light; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Lindlar’s catalyst; 5. BH3-THF; 6. H2O2, NaOH Answer: E

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 85.

Select an appropriate synthetic route to prepare 1,3-dibromopropan-2-ol from propene.

A. B. C. D. E.

1. NBS, light; 2. Br2, H2O 1. NBS; 2. Br2; 3. H3O+ 1. BH3-THF; 2. H2O2, NaOH; 3. Br2, H2O Br2, H3O+ Br2, H2O

Answer: A

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 86.

Select an appropriate synthetic route to prepare 3-bromo-1-propanol from propene.

1. BH3-THF; 2. H2O2, NaOH

B. C. D. 3.

1. NBS, light; 2. BH3-THF; 3. H2O2 1. NBS, light; 2. BH3-THF; 3. H2O2, ROOR 1. NBS; 2. BH3-THF; 3. H2O2, NaOH 1. NBS, light; 2. BH3-THF; 3. H2O2, NaOH

Answer: E

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 87.

Select an appropriate synthetic route for the equation given.

A. B. C. D. E.

1. NBS; 2. KCN 1. NBS, h ; 2. CH3CN 1. NBS, h ; 2. KCN 1. H2SO4; 2. KCN 1. NaCN, h

Answer: C

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 88.

Select an appropriate synthesis to lengthen the legs of “Ralph” as shown.

1. NBS, hn; 2. KCN; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Lindlar’s catalyst

B. C. D. E.

1. NBS; 2. KCN; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Lindlar’s catalyst 1. NBS, hn; 2. KCN; 2. HBr; 3. 2 NaCCH; 4. H2, Pt 1. NBS, hn; 2. NaCN; 2. HCl, ROOR; 3. 2 NaCCH; 4. H2, Pt 1. NBS, hn; 2. KCN; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Pt

Answer: E

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 89.

Select an appropriate three-step synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. Br2; 2. NaOEt; 3. HBr, ROOR 1. Br2, h ; 2. NaOEt; 3. HBr 1. Br2, h ; 2. HBr, ROOR 1. Br2, h ; 2. NaOEt; 3. HBr, ROOR 1. Br2, h ; 2. NaOEt

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 90.

Select the appropriate three-step synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. NaOEt; 2. HBr 1. NaOEt; 2. HBr; 3. tBuOK 1. HBr; 2. tBuOK 1. NaOEt; 2. Br2; 3. tBuOK 1. NaOEt; 2. Br2, hn

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 91.

Select the appropriate three-step synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. tBuOK; 2. HBr, ROOR 1. TsCl; 2. tBuOK; 3. Br2 1. TsCl; 2. tBuOK; 3. HBr 1. tBuOK; 2. TsCl; 3. HBr, ROOR 1. TsCl; 2. tBuOK; 3. HBr, ROOR

Answer: E Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 92.

Select an appropriate synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. HBr/ROOR; 2. excess NaNH2 1. Br2, hn; 2. tBuOK; 3. ROOR 1. Br2; 2. tBuOK; 3. MCPBA 1. Br2, hn; 2. tBuOK; 3. H3O+ 1. HBr; 2. tBuOK; 3. MCPBA

Answer: B

Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 93.

Propose a multi-step synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. Br2, hn; 2. NaOEt; 3. OsO4, NMO 1. HBr; 2. NaOEt; 3. OsO4, NMO 1. Br2, hn; 2. NaOCH3; 3. OsO4 1. HBr; 2. NaOCH3; 3. OsO4, NMO 1. Br2, hn; 2. NaOEt; 3. NMO

Answer: A Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 94.

Select the appropriate multi-step synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. HBr; 2. NaOEt; 3. MCPBA; 4. H3O+ 1. HBr; 2. NaOEt; 3. H3O+ 1. Br2, hn; 2. NaOEt; 3. H3O+ 1. Br2, hn; 2. NaOEt; 3. MCPBA; 4. H3O+ 1. Br2, hn; 2. NaOEt; 3. H2SO4; 4. H3O+

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard

95.

Select the appropriate synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. H2SO (1 equiv.); 2. Br2, ROOR; 3. NaSCH3 1. Conc. H2SO4; 2. Br2, ROOR; 3. NaSCH3 1. Conc. H2SO4; 2. HBr; 3. NaSCH3 1. Conc. H2SO4; 2. HBr, ROOR; 3. NaSCH3 1. Conc. H2SO4; 2. HBr, ROOR

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 96.

Select the appropriate synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. tBuOK; 2. Br2. hn; 3. CH3CH2CCNa 1. tBuOK; 2. HBr, ROOR; 3. CH3CH2CMgBr 1. tBuOK; 2. HBr; 3. CH3CH2CCNa 1. tBuOK; 2. HBr, ROOR; 3. CH3CH2CCNa 1. tBuOK; 2. HBr, ROOR; 3. H3O+

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 97.

Select the appropriate synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. HBr; 2. NaOEt; 3. BH3-THF; 4. HOOH, NaOH 1. Br2, hn; 2. NaOEt; 3. HOOH, NaOH 1. Br2, hn; 2. NaOEt; 3. BH3-THF; 4. NaOH 1. Br2, hn; 2. NaOEt; 3. BH3-THF; 4. HOOH, NaOH 1. Br2, hn; 2. NaOEt; 3. BH3-THF; 4. H2SO4; 5. HOOH, NaOH

Answer: D Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 98.

Select the synthetic sequence to accomplish the transformation shown.

A. B. C. D. E.

1. HBr; 2. tBuOK; 3. O3; 4. DMS 1. Br2, hn; 2. tBuOK; 3. O3; 4. DMS 1. Br2, hn; 2. O3; 3. DMS 1. Br2, hn; 2. tBuOK; 3. O3 1. Br2, hn; 2. O3; 3. DMS

Answer: B Learning Objective: 11.5 Perform a retrosynthetic analysis Difficulty: Hard 99.

Which statement is not associated with Green Chemistry?

A. B. C. D. E.

Maximize atom economy. Use safer solvents. Prevent waste. Run all reactions faster with high heat. Use less hazardous reagents.

Answer: D Learning Objective: 11.6 Define the goals of green chemistry Difficulty: Easy 100.

Which statement is not associated with Green Chemistry?

A. B. C. D. E.

Energy efficiency. Renewable feedstocks. Reuse solvents without purification. Prevent waste. Use catalysts, rather that stoichiometric reagents.

Answer: C Learning Objective: 11.6 Define the goals of green chemistry Difficulty: Easy 101.

Which solvent is not recommended for Green Chemistry?

A. B. C. D. E.

methylene chloride water ethanol methanol ethyl acetate

Answer: A Learning Objective: 11.6 Define the goals of green chemistry Difficulty: Easy 102.

Which solvent is best for Green Chemistry?

A. B. C. D. E.

methylene chloride water ethanol methanol ethyl acetate

Answer: B Learning Objective: 11.6 Define the goals of green chemistry Difficulty: Easy 103.

Which of the methods shown is best for multi-step reactions?

A. B. C. D. E.

two steps three steps four steps five steps six steps

Answer: A Learning Objective: 11.7 Prepare your own synthesis problems Difficulty: Easy 104.

Most synthesis problems have _________ correct answers.

A. B. C. D. E.

no one two four many

Answer: E Learning Objective: 11.7 Prepare your own synthesis problems Difficulty: Easy 105.

Taxol is a powerful _____.

A. B. C. D. E.

laxative pain-killer birth-control pill anti-cancer drug hallucinogen

Answer: D Learning Objective: 11.7 Prepare your own synthesis problems Difficulty: Easy 106.

Taxol is found in the ______ tree

A. B. C. D. E.

tea eucalyptus sausage fruit baobab Pacific yew

Answer: E

Learning Objective: 11.7 Prepare your own synthesis problems Difficulty: Easy 107.

Through a multistep synthesis, 1-bromo-2-methylcyclopentane can be converted to a compound with exactly four resonances in its proton-decoupled 13C NMR spectrum. Which synthetic pathway would prepare such a compound from 1bromo-2-methylcyclopentane?

A. B. C. D. E.

1. EtOK; 2. H2, Lindlar’s catalyst 1. EtOK; 2. HBr, Lindlar’s catalyst 1. EtOK; 2. O3 1. EtOK; 2. H3O+ 1. EtOK; 2. H2, Pt

Answer: E

Learning Objective: Spectroscopy Difficulty: Hard 108.

Through a multistep synthesis, 2-methylpentane (C6H14) can be converted to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Which synthetic pathway would prepare such a compound from 2-methylpentane?

A. B. C. D. E.

1. NBS, hn; 2. tBuOK; 3. Br2 1. NBS, hn; 2. tBuOK; 3. HBr, ROOR 1. Br2, hn; 2. tBuOK; 3. HBr, H3O+ 1. NBS, hn; 3. HBr, ROOR 1. NBS, hn; 2. tBuOK; 3. ROOR

Answer: B

Learning Objective: Spectroscopy Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 12 1.

What is the IUPAC name for the compound shown?

CH3

CH3CHCHCHCHCH 3 OH A. B. C. D. E.

CH3

4-isopropyl-3,4-dimethyl-2-butanol 2,3,4-trimethyl-4-pentanol 1,1,2,3-tetramethyl-4-pentanol 3,4,5-trimethyl-2-hexanol 3,4,5,5-tetramethyl-2-pentanol

Answer: D Learning Objective: alcohols Difficulty: Medium

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for isobutyl alcohol?

A. B. C. D. E.

2-methyl-1-propanol 2-methyl-1-butanol 1-methyl-1-propanol 1,1-dimethyl-1-ethanol 3-methyl-1-propanol

Answer: A Learning Objective: alcohols Difficulty: Medium 3.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

CH2CH3 CH3CH 2CCH 2CH3 OH A.

1,1,1-triethylmethanol

B. C. D. E.

1,1-diethyl-1-propanol 2-ethyl-3-pentanol 3-ethyl-3-pentanol t-heptanol

Answer: D Learning Objective: alcohols Difficulty: Medium

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for t-butyl alcohol?

A. B. C. D. E.

1-butanol 2-methyl-1-propanol 2-methyl-2-propanol 2-butanol 1,1-dimethyl-1-ethanol

Answer: C Learning Objective: alcohols Difficulty: Medium 5.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

A. B. C. D. E.

1-isopropyl-4-cyclopentanol 3-isopropylcyclopentanol 1-isopropyl-3-cyclopentanol 1-isopropyl-4-hydroxycyclopentane None of these

Answer: B Learning Objective: alcohols Difficulty: Medium 6.

12.1 Describe the structure, properties, and nomenclature of

What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

CH2CH3 CH3CH 2CCH 2CH2Cl OH I

A. B. C. D. E.

CH3CHCHCH2CH 2Cl OH II

I II III IV None of these

Answer: D Learning Objective: alcohols Difficulty: Medium 7.

CH2CH3

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

A. B. C. D. E.

2-methyl-5-bromocyclohexanol 3-bromo-2-methylcyclohexanol 1-bromo-4-methylcyclohexanol 4-bromo-6-methylcyclohexanol 4-bromo-2-methylcyclohexanol

Answer: E Learning Objective: alcohols

12.1 Describe the structure, properties, and nomenclature of

Difficulty: Hard 8.

What is the IUPAC name for the compound shown?

CH2CH2OH CH3CH 2C=CCH2CH3 CH3 A. B. C. D. E.

3-methyl-4-ethyl-3-hexen-6-ol 4-ethyl-3-methyl-3,6-hexenol 3-ethyl-4-methyl-3-hexen-1-ol 3-methyl-4-(2-hydroxyethyl)-3-hexene 3-(2-hydroxyethyl)-3-methyl-3-hexene

Answer: C Learning Objective: alcohols Difficulty: Hard

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

A. B. C. D. E.

4-penten-2-methyl-2-ol 4-methyl-1-penten-2-ol 2-methyl-4-penten-2-ol 4-methyl-1-penten-4-ol 4-hydroxy-4-methyl-1-pentene

Answer: C Learning Objective: alcohols Difficulty: Hard 10.

H3C

H HO

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

CCH2CH3

A. B. C. D. E.

(R)-3-hexyn-2-ol (S)-3-hexyn-2-ol (R)-2-hexyn-4-ol (S)-2-hexyn-4-ol (S)-2-hydroxy-3-hexyne

Answer: B Learning Objective: alcohols Difficulty: Hard 11.

12.1 Describe the structure, properties, and nomenclature of

What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

CH 3CH2CH 2CH 2CCH(CH3)OH Br II

I Br

CH3

CH3CCH2CH 2CH 2CHOH

Br III A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: alcohols Difficulty: Hard 12.

12.1 Describe the structure, properties, and nomenclature of

What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

OH HO

III

II OH

OH A. B. C. D. E.

HO V

I II III IV V

Answer: E Learning Objective: alcohols Difficulty: Hard 13.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

OH A. B. C. D. E.

3-isopropyl-6-hydroxynonane 4-hydroxy-6-ethyl-8-methyl-nonane 7-isopropyl-4-nonanol 7-ethyl-8-methyl-4-nonanol 3-ethyl-6-hydroxy-nonane

Answer: D Learning Objective: nomenclature of alcohols Difficulty: Hard 14.

12.1 Describe the structure, properties, and

What is the IUPAC name for the compound shown?

HO A. B. C. D. E.

5-hydroxy-5-ethyl-6-methylheptanol 5-ethyl-5-hydroxy-6-methylheptanol meso-3-ethyl-2-methyl-3-heptanol (S)-3-ethyl-2-methyl-3-heptanol (R)-3-ethyl-2-methyl-3-heptanol

Answer: E Learning Objective: alcohols Difficulty: Hard 15.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

OH A. B. C. D. E.

meso-2-bromo-1-methylcyclopentanol (1R,2S)-2-bromo-1-methylcyclopentanol (1S,2R)-2-bromo-1-methylcyclopentanol (1R,1S)-2-bromo-1-methylcyclopentanol (2R,2S)-2-bromo-1-methylcyclopentanol

Answer: B Learning Objective: alcohols Difficulty: Hard 16.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the following compound?

A. B. C. D. E.

7-cyclohexyl-2,8-dimethyl-3-decanol 1-(2-methylpropyl)-5-hydroxy-6-methyl-cyclohexane 1-methyl-2-hydoxy-7-(1-methylpropyl)-7-cyclohexyl-heptane 2,8-dimethyl-7-cyclohexyl-3-decanol 7-cyclohexyl-2,8-methyl-3-decanol

Answer: A Learning Objective: alcohols Difficulty: Hard

12.1 Describe the structure, properties, and nomenclature of

17.

What is the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: alcohols Difficulty: Hard

12.1 Describe the structure, properties, and nomenclature of

18.

What is the structure for 5-chloro-2-propyl-1-heptanol?

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: alcohols Difficulty: Hard 19.

12.1 Describe the structure, properties, and nomenclature of

What is the structure for 6-sec-butyl-7,7-dimethyl-4-decanol?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: alcohols Difficulty: Hard 20.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

A. B. C. D. E.

2-methyl-4-(1-hydroxy-2-methylpropyl)-octane 4-isobutyl-2-methyl-3-octanol 2-methyl-4-isobutyl-octane 4-isobutyl-3-hydroxymethanol 4-butyl-1,6-dimethyl-5-octanol

Answer: B Learning Objective: alcohols Difficulty: Hard 21.

What is the IUPAC name for the following compound?

HO CH 3(CH 2)4

A. B. C. D. E.

H C

(R)-1-octyn-3-ol (S)-1-octyn-3-ol (R)-3-hydroxyalkyne (S)-3-hydroxyalkyne (R,S)-1-octyn-3-ol

Answer: B Learning Objective: alcohols Difficulty: Hard 22.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the following compound?

A. B. C. D. E.

4,5,6-propyl-4-decanol 4-hydroxy, 4,5,6-propyloctane 4,5,6-dipropyl-4-decanol 4-hydroxy, 4,5,6-propyldecane 4,5,6-tripropyl-4-decanol

Answer: E

Learning Objective: alcohols Difficulty: Medium 23.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the following compound?

A. B. C. D. E.

1-ethyl-3-hydroxy-1-cyclohexene 3-ethyl-3-cyclohexenol 1-ethyl-3-hydroxycyclohex-1-ene 3-hydroxy-ethylcycylhexene 3-ethyl-1-hydroxycyclohex-3-ene

Answer: B Learning Objective: alcohols Difficulty: Medium 24.

A. B. C. D. E.

12.1 Describe the structure, properties, and nomenclature of

What is the correct structure for 2-methylphenol?

HO OH

III

I II III IV V

Answer: A Learning Objective: alcohols

12.1 Describe the structure, properties, and nomenclature of

Difficulty: Medium 25.

What is the correct structure for 2-bromo-5-isopropylphenol?

Br Br II

III

I II III IV V

Answer: B Learning Objective: alcohols Difficulty: Medium 26.

Br I

A. B. C. D. E.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

OH Br

Br A. B. C. D. E.

3,4-dibromophenol 2,4-dibromophenol 2,5-dibromophenol 3,6-dibromophenol 2,6-dibromophenol

Answer: C Learning Objective: alcohols Difficulty: Medium

12.1 Describe the structure, properties, and nomenclature of

27.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

1-sec-butyl-5-ethylphenol 1-sec-methylbutyl-5-ethylphenol 2-sec-butyl-5-ethyltoluene 2-tert-butyl-5-ethylhydroxybenzene 2-sec-butyl-5-ethylphenol

Answer: E Learning Objective: alcohols Difficulty: Medium 28.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

HOCH2CH2CH2OH A. B. C. D. E.

1,2-butanediol isopropyl alcohol 1-propanol 1,3-propanediol 1,2-ethanediol

Answer: D Learning Objective: alcohols Difficulty: Hard 29.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the compound shown?

OH OH

A. B. C. D. E.

cis-1,2-cyclopentanediol meso-1,2-cyclopentanediol (1R,2R)-1,2-cyclopentanediol (1R,2S)-1,2-cyclopentanediol (1S,2S)-1,2-cyclopentanediol

Answer: E Learning Objective: alcohols Difficulty: Hard 30.

12.1 Describe the structure, properties, and nomenclature of

What is the IUPAC name for the following compound?

A. 3,5-dimethyl-4,6-heptanediol B. 3,5-dimethyl-2,4-heptanediol C. 3,5-dimethyl-4,6-heptanol D. 1-ethyl-3,5-hydroxy-3-methylhexane E. 2,4-hydroxy-3,5-dimethylhexane Answer: B Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols Difficulty: Hard 31.

What is the structure for (2R,3S) -2-bromo-1,3-pentanediol?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: alcohols Difficulty: Hard

12.1 Describe the structure, properties, and nomenclature of

32.

What is the formal name for rubbing alcohol?

A. B. C. D. E.

methanol 2-propanol ethanol 1-butanol 1-propanol

Answer: B Learning Objective: alcohols Difficulty: Easy 33.

12.1 Describe the structure, properties, and nomenclature of

What is the formal name for grain alcohol?

A. B. C. D. E.

methanol 2-propanol ethanol 1-butanol 1-propanol

Answer: C Learning Objective: alcohols Difficulty: Easy

12.1 Describe the structure, properties, and nomenclature of

34.

What is the formal name for wood alcohol?

A. B. C. D. E.

methanol 2-propanol ethanol 1-butanol 1-propanol

Answer: A Learning Objective: alcohols Difficulty: Easy

12.1 Describe the structure, properties, and nomenclature of

35.

What is the formal name for the alcohol used in alcoholic drinks?

A. B. C. D. E.

methanol 2-propanol ethanol 1-butanol 1-propanol

Answer: C Learning Objective: alcohols Difficulty: Easy

12.1 Describe the structure, properties, and nomenclature of

36.

What type of bonding is present between molecules of alcohol?

A. B. C.

ion-ion van der Waals forces hydrogen bonding

D. E.

ion-dipole London dispersion

Answer: C Learning Objective: alcohols Difficulty: Easy

12.1 Describe the structure, properties, and nomenclature of

37.

Why does cyclohexanol have a pKa of 18 and phenol, despite its similarities in structure, have a pKa of 10?

Cycohexanol has a resonance-stabilized structure, which increases its stability and reduces the likelihood that it will react to form a conjugate base Cycohexanol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and inhibits its formation

B. C. D. E.

Answer: C Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Hard 38.

Rank the alcohols shown in decreasing order of acidity. OH Br

A. B. C. D. E.

OH F

III

II > I > III I > II > III I > III > II III > I > II III > II > I

Answer: A Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

Difficulty: Medium 39.

Which one of the alcohols shown is the most acidic?

I A. B. C. D.

OH II

III

I II III IV

Answer: A Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Medium 40.

Rank the alcohols shown in decreasing order of acidity.

F OH

F I A. B. C. D. E.

OH II

F III

II > I > III I > II > III I > III > II III > I > II III > II > I

Answer: C Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Medium

41.

Rank the alcohols shown in decreasing order of acidity. O2N

A. B. C. D. E.

OH II

III

II > I > III I > II > III I > III > II III > I > II III > II > I

Answer: C Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Medium 42.

Predict the product(s) for the reaction shown.

A. B. C. D. E.

I II III I and II II and III

Answer: B

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Medium

43.

Predict the product(s) for the reaction shown.

A. B. C. D. E.

I II III I and II III and IV

Answer: A

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Medium 44.

Predict the product for the reaction shown. OH 1. NaH 2. CH3CH2Br

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity Difficulty: Medium 45.

Which set of reagents is necessary to carry out the following conversion?

CH3CH2CH2CHCH3

CH3CH2CH2CH2CH2OH

Br A. B. C. D. E.

1. NaBH4; 2. MeOH 1. (CH)3COK; 2. BH3-THF; 3. H2O2/NaOH/H2O 1. H3O+; 2. H2O 1. (CH)3OH; 2. BH3-THF; 3. H2O2/NaOH/H2O 1. (CH)3OH; 2. H2O2/NaOH/H2O

Answer: B

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Medium 46.

Predict the product(s) for the reaction shown.

1. BH3 THF 2. H2O2/NaOH/H2O CH 2OH

OH OH + enantiomer I A. B. C. D. E.

OH + enantiomer II

III

I II III IV None of these

Answer: B Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Medium 47.

Predict the product for the reaction shown.

1. Hg(OAc)2, H2O 2. NaBH 4

CH 2OH

OH OH I A. B. C. D. E.

III

I II III IV None of these

Answer: C Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Medium 48.

What reagents are necessary to carry out the conversion shown?

(E)-3-methyl-3-hexene

3-methyl-3-hexanol

A. H3O+ B. 1. (CH)3COK; 2. BH3•THF; 3. H2O2/NaOH/H2O C. 1. Hg(OAc)2, H2O; 2. NaBH4 D. A and B E. A and C Answer: E Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Medium 49.

Predict the major product for the reaction shown. H 3O+

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Medium 50.

Predict the product for the reaction shown.

1. Hg(OAc)2, H 2O 2. NaBD 4

OH OH

I A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Medium 51.

Select the reagents suitable to carry out the conversion shown.

A. NaOH/H3O+ B. NaOH C. 1. Hg(OAc)2, H2O; 2. NaBH4 D. A and C E. C and D Answer: B Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Hard 52.

What reagents are suitable necessary to carry out the conversion shown?

OH Cl

A. B. C. D. E.

NaOH/H2O 1. NaOCH3; 2. H3O+ 1. (CH3)3COK; 2. BH3•THF; 3. H2O2/NaOH/H2O 1. (CH3)3COK; 2. H3O+ B and D

Answer: D Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Hard 53.

Identify the characteristics of the acid-catalyzed hydration of an alkene.

A. B. C. D.

Markovnikov, with rearrangement possible Markovnikov, with no rearrangement possible anti-Markovnikov, with rearrangement possible anti-Markovnikov, with no rearrangement possible

Answer: A Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Easy 54.

Identify the characteristics of the hydroboration-oxidation of an alkene.

A. B. C. D.

Markovnikov, with rearrangement possible Markovnikov, with no rearrangement possible anti-Markovnikov, with rearrangement possible anti-Markovnikov, with no rearrangement possible

Answer: D Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Easy 55.

Identify the characteristics of the oxymercuration-demercuration of an alkene.

A. B. C. D.

Markovnikov, with rearrangement possible Markovnikov, with no rearrangement possible anti-Markovnikov, with rearrangement possible anti-Markovnikov, with no rearrangement possible

Answer: B Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition Difficulty: Easy 56.

What are the oxidation states of carbon atoms I and II in the compound shown?

H O

I A. B. C. D. E.

I. +1, II. +2 I. +2, II. +2 I. +1, II. +3 I. +3, II. +2 I. +2, II. +1

Answer: E Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Easy 57.

What are the oxidation states of carbon atoms I and II in the reaction shown?

CH3CH

CH 3COH

A. B. C. D. E.

I. +1, II. +2 I. +2, II. +2 I. +1, II. +3 I. +3, II. +2 I. +2, II. +1

Answer: C

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium 58.

For the following conversion, has the starting material has been oxidized, reduced, a combination, or neither?

A. B. C. D. E.

Oxidized Reduced Oxidized and then reduced Reduced and then oxidized Neither oxidized nor reduced

Answer: A Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium 59.

For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither.

Cl A. B. C. D. E.

Oxidized Reduced Oxidized and then reduced Reduced and then oxidized Neither oxidized nor reduced

Answer: Oxidized. Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium

60.

For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither OH

A. B. C. D. E.

Oxidized Reduced Oxidized and then reduced Reduced and then oxidized Neither oxidized nor reduced

Answer: E Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium 61.

For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither.

O H O A. B. C. D. E.

Oxidized Reduced Oxidized and then reduced Reduced and then oxidized Neither oxidized nor reduced

Answer: A Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 62.

For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither.

OH O A. B. C. D. E.

O O

Oxidized Reduced Oxidized and then reduced Reduced and then oxidized Neither oxidized nor reduced

Answer: E Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 63.

What is the most likely product of the reaction shown?

O CH3CCH2CH 2CH3

NaBH 4/CH3OH

OH B. CH3CHCH2CH2CH 3 C. D. E. Answer: B

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium 64.

Predict the product for the reaction shown.

O H NaBH /CH OH 4

O OH

I A. B. C. D.

OH OH

OH IV

III

I II III IV

Answer: A Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium 65.

Which one of the compounds shown gives 5-methyl-3-heptanol when LiAlH4 is added followed by water?

O H

IV A. B. C. D. E.

I II III IV V

III

Answer: A Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 66.

What reagents can be used to carry out the following conversion?

OH HC

CCH2CH2CH 3

A. B. C. D. E.

1. Na, NH3; 2) 2 H3O+ 1. H2/Ni2B (OR Na, NH3); 2 H3O+ 1. H3O+/ HgSO4; 2. NaBH4/CH3OH A and B A, B, and C

CH3CHCH2CH2CH 3

Answer: E Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 67.

Predict the product for the reaction shown.

O H H Pd 2.

O OH I

A. B. C. D.

I II III IV

OH OH

OH II

III

OH IV

Answer: C Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 68.

Predict the product for the reaction shown. O COCH3 NaBH 4 / H 2O

A. B. C. D. E.

I II III I and II II and III

Answer: A Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 69.

Predict the product for the following reaction.

O COCH3 1. LiAlH4 2. H2O

A. B. C. D. E.

I II III I and II I and III

Answer: C Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Hard 70.

Predict the product for the following reaction.

H2O / H 2SO4 HgSO4

NaBH 4/CH3OH

A. B. C. D. E.

I II III I and II II and III

Answer: B Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Medium 71.

Provide the reactant (A) for the reaction shown.

1. LiAlH4 5-methyl-3-heptanol 2. H2O

A O

IV A. B. C. D. E.

I II III IV V

III O

Answer: A Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction Difficulty: Easy 72.

What reagents are suitable to carry out the following conversion?.

cyclohexene A. B. C. D. E.

cis-1,2-cyclohexanediol

KMnO4, NaOH,H2O,cold KMnO4, H3O+, 75oC H2SO4, heat 1. mCPBA 2. H3O+ none of these

Answer: A Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Medium 73.

What are the likely product(s) of the reaction shown.

3-hexyne

H2/Ni2B 1. OsO4 2. NaHSO3

HO A. B. C. D. E.

H II

H III

I II III I and II None of these

Answer: A Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Medium

74.

What reagents are suitable to carry out the conversion shown?

cyclohexene A. B. C. D. E.

trans-1,2-cyclohexanediol

KMnO4, NaOH,H2O KMnO4, H3O+, 75oC H2SO4, heat 1. mCPBA; 2. H3O+ none of these

Answer: D Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Medium 75.

Correctly label structures A, B, C, and D from the reaction sequence below.

Br2 hn

A. B.

CH3CH2ONa

A is I, B is II, C is III, and D is IV A is II, B is I, C is VI, and D is III

mCPBA

NaOH/H2O

C. D. E.

A is IV, B is II, C is III, and D is I A is III, B is II, C is IV, and D is I A is I, B is III, C is II, and D is I

Answer: D Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Hard 76.

What is the likely product of the reaction shown? O

O H

A. B. C. D. E.

excess NaBH4/CH 3OH

I II III IV V

Answer: C Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Medium

77.

What is the likely product of the reaction shown?

H3O+

OH OH I A. B. C. D. E.

H O OH

OH III

I II III IV none of these

Answer: C Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Medium 78.

What reagent(s) are suitable to carry out the conversion shown?

OH A. B. C. D. E.

1. mCPBA; 2. H3O+ 1. mCPBA; 2. NaOH/H2O H2SO4, heat A and B B and C

Answer: D Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Hard 79.

What reagent(s) are suitable to carry out the conversion shown?

OH OH

A. B. C. D. E.

1. O3; 2.1 equivalent of NaBH4/CH3OH 1. O3; 2. CH3)2S; 3. H3O+ 1. O3; 2. (CH3)2S; 3. excess NaBH4/CH3OH A and B B and C

Answer: C Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Hard 80.

Predict the product(s) for the reaction shown.

O O

1. excess LiAlH4 2. H2O

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols Difficulty: Hard 81.

What is the likely product of the reaction sequence shown?

1. CH 3CH2MgBr 2. H 2O

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Medium 82.

What is the most likely product for the reaction sequence given.

Mg/ether

2. H2O

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in Difficulty: Medium 83.

What reagent(s) are suitable to carry out the following conversion?

O O A. B. C. D. E.

1. 1 equivalent of CH3MgBr; 2. H2O 1. excess CH3Br/ether; 2. H2O 1. CH3MgBr; 2. H3O+ 1. excess CH3MgBr/ether; 2. H2O 1. CH3CH2MgBr/ether; 2. H2O

Answer: D

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Medium 84.

Predict the product for the reaction shown.

O 1. CH3CH 2CH2MgBr/ether 2. H 2O

OH HO

III A. B. C. D. E.

OH IV

I II III IV None of these

Answer: A Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Medium 85.

Predict the product for the following reaction.

A. B. C. D. E.

O Mg/ether

1. H H 2. H 2O

I II III IV V

Answer: A

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Medium 86. Which Grignard reaction shown could be used to could prepare the alcohol shown?

A. B. C. D. E.

I II III I and II II and III

Answer: C

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Medium 87.

Which Grignard reaction shown could be used to prepare the alcohol shown?

A. B. C. D. E.

I II III I and II II and III

Answer: D

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 88.

Which Grignard reaction shown could be used to prepare the alcohol shown?

A. B. C. D. E.

I II III I and II I, II, and III

Answer: E

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 89.

What reagents are appropriate to carry out the conversion shown?

O A.

1. Br2; 2. Mg/ether, 3 H

1. HBr, 2. ether, 3

H ; 4. H3O+ ; 4. H2O

O C.

1. HBr, 2. Mg/ether, 3 H

H ; 4. H2O

1. Br2, 2. Mg/ether, 3

; 4. H2O

1. HBr, 2. Mg/ether, 3

. 4. H3O+

Answer: C Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 90.

What reagent(s) are necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction?

A. B. C. D. E.

I II III I and II II and III

Answer: A

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 91.

What is the likely product of the reaction shown?

O OCH3

excess 1. CH3CH 2CH2MgBr 2. H 2O

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 92.

What is the most likely product of the following reaction?

O excess O 1. CH 3CH2MgBr 2. H 2O

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard

93.

What is the most likely product of the following reaction?

excess 1. CH3CH2MgBr

O O

A. B. C. D. E.

2. H2O

I II III IV V

Answer: D

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 94.

What is the best description of the curved arrow mechanism of the first step of the reaction shown?

excess 1. CH3CH2MgBr

O O

A. B. C. D. E.

2. H2O

I II III IV V

Answer: B

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols Difficulty: Hard 95.

What reagents are suitable to carry out the conversion shown?

O A.

1. (CH3)3SiCl / (CH3CH2)3N; 2.

; 2. H2O; 4. TBAF

O B.

1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg/ether; 3.

; 4. H2O; 5. TBAF

O C.

1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg/ether; 3.

; 4. H2O

1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg/ether; 3.

; 4. H2O; 5. TBAF

1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg; 3.

; 4. H2O

Answer: B Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome Difficulty: Hard 96.

What reagents are suitable to carry out the following conversion?

O HO

1. (CH3)3SiCl / (CH3CH2)3N; 2.

; 3. H2O; 4. TBAF

MgBr B.

1. (CH3)3SiCl; 2.

; 3. H2O

MgBr C.

1. (CH3)3SiCl / (CH3CH2)3N; 2.

; 3. H2O; 4. TBAF

Answer: C Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome Difficulty: Hard 97. For the following reaction sequence, what are the correct structures of products A through D?

OH 1. O Br (CH ) SiCl 33 (CH 3CH2)3N

Mg/ ether

2. H 2O

TBAF

A. B. C. D. E.

A is I, B is II, C is III, and D is IV A is II, B is I, C is VI, and D is III A is IV, B is II, C is III, and D is I A is III, B is II, C is IV, and D is I A is I, B is III, C is II, and D is I

Answer: A

Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome Difficulty: Hard 98.

What is the most likely product for the following reaction sequence?

1. O

OH (CH3)3SiCl Br (CH 3CH2)3N

Mg/ ether H H 2. H2O

TBAF

A. B. C. D. E.

2,4-heptanediol 1,4-heptanediol 2,5-octanediol 1,5-octanediol none of these

Answer: B Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome Difficulty: Hard 99.

HO A. B. C. D. E.

What reagents are suitable to carry out the conversion shown?

HO 1. (CH3)3SiCl / (CH3CH2)3N; 2. CH3CH2CH2Br; 3.TBAF 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2Br 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2CH2Br; 4.TBAF 1. (CH3)3SiCl / (CH3CH2)3N; 2.NaNH2; 3. CH3CH2CH2Br 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2Br; 4.TBAF

Answer: E Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and Grignard reagent is overcome Difficulty: Hard 100.

What are the correct structures for the products represented by A, B, and C?

A. B. C. D. E.

A is I, B is II, and C is III A is II, B is I, and C is III A is III, B is II, and C is I A is II, B is III, and C is I A is I, B is III, and C is II

Answer: C

Learning Objective: 12.8 Describe the industrial synthesis of phenols Difficulty: Hard 101.

2-Methyl-2-butanol reacts with hydrogen bromide via a(n) ___________.

A. B. C. D. E.

SN1 mechanism SN2 mechanism E1 mechanism E2 mechanism None of these.

Answer: A

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Easy 102.

3-Methyl-1-butanol reacts with hydrogen bromide via a(n) ___________.

A. B. C. D. E.

SN1 mechanism SN2 mechanism E1 mechanism E2 mechanism None of these.

Answer: B Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Easy 103.

3-Methyl-1-butanol reacts with thionyl chloride via a(n) ___________.

A. B. C. D. E.

SN1 mechanism SN2 mechanism E1 mechanism E2 mechanism None of these.

Answer: B Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Easy 104.

Which of the following reactions could be used to synthesize 1-bromopentane?

I II III IV V

CH3CH2CH2CH=CH2 + HBr ¾¾¾¾® CH3CH2CH2CH2CH2OH + PBr3 ¾¾¾¾® CH3CH2CH2CH2CH2OH + NaBr ¾¾¾¾® CH3CH2CH2CH2CH2OH + Br2 ¾¾¾¾® CH3CH2CH2CH=CH2 + Br2 ¾¾¾¾®

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

Difficulty: Medium 105.

Which reagents are suitable to convert 3-methyl-2-butanol to 2-bromo-3methylbutane.

A. B. C. D. E.

conc. HBr Br2 NaBr, H2SO4 PBr3 HBr, peroxide

Answer: D Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 106.

Predict the product for the following reaction.

OH PBr3

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Hard 107.

Identify the product of the reaction shown.

OH HBr

A. I B. II C. III D. IV E. I and II Answer: D Mechanism

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Hard 108.

What is the most likely major product of the reaction shown?

HCl

A. B. C. D. E.

I II III IV I and IV

Answer: D

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Hard 109.

What is the most likely product of the reaction shown.

SOCl2/pyridine OH

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 110.

What is the most likely major product for the reaction shown?

H OH

1. TsCl /pyridine

CH 3 2. NaI H

I A. B. C. D. E.

OTs

CH 3

CH3

CH 3

II H

III

I II III IV I and III

Answer: C Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 111.

What is the most likely product when cis-3-methylcyclopentanol is treated with TsCl/pyridine followed by sodium bromide.

A. B. C. D. E.

trans-1-bromo-3-methylcyclopentane cis-1-bromo-3-methylcyclopentane 1-methylcyclopentene 2-methylcyclopentene 3-methylcyclopentene

Answer: A Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 112.

The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2pentene proceeds via a(n) _____.

A. B. C. D. E.

SN1 mechanism SN2 mechanism E1 mechanism E2 mechanism None of these.

Answer: C Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Easy

113.

Explain why the following reaction will not produce an alcohol as product.

OH NaOH not produced

A. C l is not a good leaving group and therefore cannot be replaced by hydroxide. B. The primary methyl group is not sufficiently reactive to allow the reaction to begin. C. Steric hindrance at the tertiary halide prevents hydroxide from acting as a nucleophile in an SN2 reaction. D. NaOH is not a sufficiently strong base to initiate the reaction. E. Tertiary halides are not reactive. Answer: C Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 114.

What is the most likely major product of the following reaction.

1. TsCl/pyridine 2. CH3CH2ONa

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 115.

What is the most likely major product for the reaction shown.

OH H2SO4 D

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 116.

Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane..

A. B. C. D. E.

1. H2SO4, heat; 2. H2/Pd 1. H2SO4; 2. CH3CH2Ona; 3. H2/Pd 1. TsCl/pyridine; 2. CH3CH2Ona; 3. H2/Pd A and B A and C

Answer: C Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium

117. Which example best describes the stepwise curved arrow mechanism for the first step of the reaction shown?

HO CH2CH 3

CH 2CH 3 CH2CH3

A. B. C. D. E.

I II III IV I or II

Answer: A

H2SO4 D

CH 2CH3

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Hard 118.

Predict the product of the reaction shown.

OH OH

A. B. C. D. E.

I II III IV V

H2SO4 heat

O OH

H OH

S O

OH2 OH

+ O

Answer: E

Mechanism

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols Difficulty: Medium 119.

What is the likely product of the following reaction?

2-hexanol

PCC CH2Cl2

. A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 120.

What are the appropriate reagents to carry out the conversion shown?

A. B. C. D. E.

KMnO4/NaOH/H2O Na2Cr2O7/H2SO4/H2O H2, Pt Br2, CCl4 None of these

Answer: B Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 121.

Predict the product for the following reaction.

OH Na2Cr2O7/H2SO4/H 2O

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 122.

What is the most likely product of the following reaction?

OH PCC CH 2Cl2

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 123.

What are the appropriate reagents to carry out the following conversion?

O OH A. B. C. D. E.

KMnO4/NaOH/H2O Na2Cr2O7/H2SO4/H2O PCC/CH2Cl2 Br2, CCl4 None of these

Answer: C Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium

124.

What are the appropriate reagents to carry out the following conversion?

O OH A. B. C. D. E.

KMnO4/NaOH/H2O Na2Cr2O7/H2SO4/H2O PCC/CH2Cl2 Br2, CCl4 None of these

Answer: B Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 125.

What is the most likely product of the following reaction?

OH excess PCC/CH2Cl2

CH 2OH

A. B. C. D. E.

I II III IV III and IV

Answer: D

Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 126.

What is the most likely product of the following reaction?

PCC CH 2Cl2

A. B. C. D. E.

I II III IV No reaction.

Answer: E Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 127.

What is the most likely product of the following reaction?

cis-4-methylcyclohexanol

PCC CH2Cl2

A. B. C. D. E.

I II III IV No reaction

Answer: D . Learning Objective: 12.10 Describe the oxidation reactions of alcohols Difficulty: Medium 128.

Catalysts in living systems are called ________.

A. hormones B. enzymes C. reactive oxygen species D. cytoskeletal proteins E. lysosomal products Answer: B Learning Objective: systems Difficulty: Easy

12.11 Discuss the functions of NAD+ and NADH in biological

129.

NADH servers as a __________ delivery agent in living organisms.

A. B. C. D. E.

oxygen hydride hydroxide proton ozone

Answer: B Learning Objective: systems Difficulty: Easy 130.

12.11 Discuss the functions of NAD+ and NADH in biological

What is the most likely product of the following reaction?

OH Na2Cr2O7/H 2SO4/H2O

A. B. C. D. E.

I II III IV No reaction

Answer: C . Learning Objective: 12.12 Name the oxidation product of a phenol and explain the importance of this product Difficulty: Medium 131.

What is the structure for the final product (D), in the reaction sequence shown?

O CH3CH 2CHOH CH3

A. B. C. D.

I II III IV

PBr3

Mg H3C B ether

H2O

Answer: E

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Medium 132. Which series correctly shows structures A, B, and C labeled correctly and in order?

1. O CH3CH 2CHOH CH3

A. B. C. D. E.

I II III IV V

PBr 3

Mg ether

H3C

2. H2O

Answer: A Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 133.

What is the structure for the final product, (E), in the reaction sequence shown?

O OH

PBr 3

Mg ether

H2O

CH2Cl2

O H

O II

I A. B. C. D. E.

PCC

III

I II III IV V

Answer: C Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 134. Of the choices, which correctly matches a structure with one of the products in the reaction sequence shown?

1.O OH

PBr 3

Mg ether

2. H2O

PCC CH 2Cl2

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 135.

What is the structure for product (A) in the reaction sequence shown?

OH PBr 3

Mg ether

CH3CH2CH2CH3

D2O

B. C. D. E.

CH3CH2CHDCH3 CH3CH2CHODCH3 CH3CH2CH2CH2OD CH3CH2CH2CH2D

Answer: B Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 136.

What reagents are appropriate to carry out the conversion shown?

O OH

O A.

1. PBr3; 2. Mg/ether; 3.

H ; 4.

H2O; 5. PCC/CH2Cl2

H ; 4.

H2 O

O B.

1. PBr3; 2. Mg/ether; 3.

O C.

H ; 4. PCC/CH2Cl2

1. PBr3; 2. Mg/ether; 3.

O D.

1. BrMg/ether; 2.

1. PBr3; 2. Mg/ether; 3.

H ; 3. H2O; 4. PCC/CH2Cl2 O H ; 4.

H2O; 5. PCC/CH2Cl2

Answer: A Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 137. Which example shows the best choice of reactant for the first step in the synthesis shown?

A. B. C. D. E.

Cl2, hn H3O+ 1. CH3MgBr; 2. H2O H2SO4, heat PCC, CH2Cl2

Answer: A

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 138.

What is the likely product of the reaction sequence shown? MgBr

MgBr OH PCC CH 2Cl2

A. B. C.

I II III

H 2O K 2Cr2O7/H 2SO4/H 2O

H2O ether

ether

III

D. E.

IV V

Answer: C Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 139.

What is the likely product for the following reaction sequence shown?

3,4-dimethyl-1-hexanol

SOCl2

Mg/ether

pyridine

O H

2. H 3O+

CrO3/ H2SO4/H2O O

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 140.

What is the stepwise synthesis for the reaction shown?

A. 1. Br2, hn; 2. BH3-THF followed by H2O2/NaOH/H2O; 3. CH3CH2ONa; 4. PCC/CH2Cl2 B. 1. Br2, hn; 2. PCC/CH2Cl2; 3. CH3CH2ONa; 4. BH3-THF followed by H2O2/NaOH/H2O; C. 1. Br2, hn; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2 D. 1. CH3CH2ONa; 2. Br2, hn; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2 E. 1. BH3-THF followed by H2O2/NaOH/H2O; 2. Br2, hn; 3. CH3CH2ONa; 4. PCC/CH2Cl2 Answer: C

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 141.

What reagents are appropriate to carry out the conversion shown?

O O

A. B. C. D. E.

1. CH3CH2Ona; 2. KMnO4/NaOH; 3. H2O; 4. excess PCC/CH2Cl2 1. Cl2/hn; 2. CH3CH2Ona; 3. KMnO4/NaOH/H2O; 4. excess PCC/CH2Cl2 1. Cl2/hn; 2. CH3CH2Ona; 3. KMnO4/NaOH/H2O; 4. 1 equivalent PCC/CH2Cl2 1. CH3CH2Ona; 2. KMnO4/NaOH/H2O; 3. excess PCC/CH2Cl2 1. Cl2/hn; 2. KMnO4/NaOH/H2O; 3. H3O+; 4. excess PCC/CH2Cl2

Answer: B

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 142.

Provide the reagents necessary to carry out the following conversion.

HO HO

HO A. B. C. D. E.

1. (CH3)3SiCl/ (CH3CH2)3N; 2. CH3MgBr; 3. H3O+ 1. (CH3)3SiCl/ (CH3CH2)3N; 2. CH3MgBr 2. CH3MgBr; 2. H3O+ 1. (CH3)3SiCl/ (CH3CH2)3N; 2. H3O+ 1. (CH3)3SiCl/ (CH3CH2)3N; 2. KOH; 3. CH3MgBr; 4. H3O+

Answer: A Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 143.

Provide the reagents necessary to carry out the following conversion.

O Br

A. B. C. D. E.

1. NaOH; 2. H2O 1. NaOH; 2. H2SO4; 3. H2O 1. Na2Cr2O7/H2SO4; 2. H2O 1. NaOH; 2. Na2Cr2O7/H2SO4/H2O 1. KOH; 2. Na2Cr2O7; 3. NaOH

Answer: D Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard

144.

Choose the best stepwise synthesis to carry out the conversion shown.

A. 1. Br2, hn; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4/heat; 7. H2/Lindlar’s catalyst. B. 1. Br2, hn; 2. BH3-THF followed by H2O2/NaOH/H2O; 3. CH3CH2ONa; 4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4/heat; 7. H2/Pd. C. 1. Br2, hn; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4/heat; 7. H2/Pd. D. 1. HBr; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4; 6. H2/Pd. E. 1. CH3CH2ONa; 2. BH3-THF followed by H2O2/NaOH/H2O; 3. PCC/CH2Cl2; 4. CH3MgBr followed by H2O; 5. H2SO4/heat; 6. H2/Pd. Answer: C

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 145. Of the choices below, which is NOT a component of the stepwise synthesis needed to carry out the conversion shown?

O OH

B. C.

PBr 3

Mg/ether

Answer: C

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis Difficulty: Hard 146.

Which one of the following compounds is consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

OH OH II

A. B. C. D.

I II III IV

Answer: A Learning Objective: Spectroscopy Difficulty: Medium 147.

Which one of the compounds shown is consistent with the given IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH OH I A.

II I

O OH

III

B. C. D. E.

II III IV V

Answer: E Learning Objective: Spectroscopy Difficulty: Medium 148.

Which of the compounds shown is consistent with the given proton decoupled 13 C NMR spectrum?

40 PPM

III

HO I A. B. C. D. E.

II I II III IV none of these

Answer: B Learning Objective: Spectroscopy Difficulty: Hard

149.

Which of the compounds shown is consistent with the given proton decoupled 13 C NMR spectrum?

40 PPM

OH HO II

I A. B. C. D. E.

III

IV OH

I II III IV none of these

Answer: A Learning Objective: Spectroscopy Difficulty: Hard 150.

A compound with a molecular formula C9H12O has the 1H NMR spectrum shown. Which of the following structures is consistent with this spectrum?

3 2

1 exchanges with D2O

A. B. C. D. E.

4 PPM

III OH

I II III IV V

Answer: C Learning Objective: Spectroscopy Difficulty: Hard 151.

A compound with a molecular formula C6H14O exhibits the 1H NMR and 13C NMR spectra. Propose a structure for this compound.

A. B. C. D. E.

PPM

Answer: A

Learning Objective: Spectroscopy Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 13 1.

Which of the compounds shown is(are) classified as ethers?

A. B. C. D. E.

I II and IV III I and III all of these

Answer: E Learning Objective: 13.1 Describe the structure of ethers Difficulty: Easy 2.

What is the common name for CH3CH2CH2OCH2CH2CH3?

A. B. C. D. E.

dibutyl ether 1-propoxypropane 1-propoxyhexane dipropyl ether none of these

Answer: D Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Easy 3.

What is the common name for (CH3)2CHCH2OCH(CH3)2?

A. B. C. D. E.

diisobutyl ether isobutyl isopropyl ether sec-butyl isopropyl ether diisopropyl ether none of these

Answer: B Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Easy

What is the IUPAC name for CH3CH2CH2CH2OCH2CH3?

A. B. C. D. E.

1-ethoxybutane 1-butoxyethane ethyl butyl ether 1-ethoxyhexane none of these

Answer: A Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 5.

What is the common name for the compound shown?

A. B. C. D. E.

1-butoxybutane sec-butyl isopropyl ether sec-butyl t-butyl ether n-butyl isopropyl ether none of these

Answer: C Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 6.

What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3?

A. B. C. D. E.

1,4-ethoxyoctane diethoxy butyl ether 1,2-diethoxymethane 1,2-diethoxyhexane 1,4-diethoxybutane

Answer: E Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 7.

What is the correct structure for benzyl phenyl ether?

A. B. C. D. E.

I II III IV none of these

Answer: D Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 8.

What is the correct structure for dibenzyl ether?

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium

What is the IUPAC name for the compound shown?

A. B. C. D. E.

2-methyl-3-oxy—4-isopropyloctane 3-isopropoxy-2-methyloctane 2-methyl-4-isopropoxyloctane 2-methyl-3-oxy-4-tert-propyloctane 6-isopropyl-6-isopropoxyoctane

Answer: B Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 10.

What is the IUPAC name for the following compound?

A. B. C. D. E.

1-methoxy-2-methoxy-3-propylcyclohexane 3-ethoxy-3-methoxy-1-propylcyclohexane 1-ethoxy-1-methoxy-3-propylcyclohexane 3-ethoxy-3-methoxy-1-propylcyclohexone 1-oxyethyl-1-oxymethyl-3-propylcyclohexane

Answer: C Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 11.

What is the IUPAC name for the following compound?

A. B. C. D. E.

E-4-isopropoxy-4,5-dimethylhex-2-ene Z-4-isopropoxy-4,5-dimethylhex-2-ene E-1-methyl-2-oxo-3-isopropyl-3-methyl-5-heptene Z-4-isopropoxy-4,5-methylhex-2-ene E-4-isopropoxy-4,5-methylhex-2-ene

Answer: A Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 12.

What is the IUPAC name for the following compound?

A. B. C. D. E.

(1S,3R)-1-ethoxy-3-methylcyclohexane (1R,3S)-1-ethoxy-3-methylcyclohexane (1S,3S)-1-ethoxy-3-methylcyclohexane (1R,3R)-1-ethoxy-3-methylcyclohexane meso-ethoxy-3-methylcyclohexane

Answer: C Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 13.

What is the IUPAC name for the following compound?

A. B. C.

1,1,1-triethoxyethane 2,2,3-triethoxyethane 1,2,3-triethoxyethane

1,1,1-triethoxyethane

1,1,1-ethylether

Answer: D Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Hard 14.

Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Hard 15.

Provide an IUPAC name for the following compound.

A. B. C. D. E.

4-butyl-1-ethoxy-2-methylbenzene 1-t-butyl-4-ethoxy-3-methylbenzene 1-butyl-4-ethoxy-3-methylbenzene 4-t-butyl-1-ethoxy-2-methylbenzene 4-t-butyl-1-ethoxy-2-methylcyclohexane

Answer: D Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Hard 16.

Which choice shows the structure of (2S,5R)-5-ethoxy-2-octanol?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Hard

17.

Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Easy

18.

How many constitutional isomers with molecular formula C4H8O have an ether functional group?

A. B. C. D. E.

none one three six nine

Answer: E Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 19.

How many constitutional isomers with molecular formula C6H14O have an ether functional group?

A. B. C. D. E.

1 5 10 15 20

Answer: A Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers Difficulty: Medium 20.

Which the compounds shown has the highest boiling point?

A. B. C. D. E.

CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2OCH3 CH3CH2CH2Cl CH3CH2OCH2CH3

Answer: B Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Easy 21.

Which of the compounds shown has the highest boiling point?

A. B. C. D. E.

CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2OCH3 CH3CH2CH2Cl CH3CH2OCH2CH2OH

Answer: E Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Easy 22.

Which the compounds shown is the least soluble in water?

A. B. C. D. E.

diethyl ether methyl propyl ether 1-butanol 2-butanol pentane

Answer: E Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Easy 23.

Rank the given compounds in decreasing order of boiling points (from highest to lowest boiling point).

A. B. C. D. E.

II > IV > I > III I > IV > II > III IV > I > II > III III > II > I > IV IV > II > I > III

Answer: C Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Medium

24.

Rank the compounds shown in decreasing order of solubility in water (from highest to lowest solubility).

A. B. C. D. E.

II > IV > I > III I > IV > II > III IV > I > II > III III > II > I > IV IV > III > I > II

Answer: E Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Medium 25.

Which of the following compounds shown has highest boiling point?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Medium 26. What molecular interactions in ethers are primarily responsible for their elevated boiling point relative to equivalent alkanes? A. B. C. D.

dipole-dipole interactions ionic bonding hydrophilic interactions London dispersion forces

hydrogen bonding

Answer: A Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Easy 27. Ethers with larger alkyl groups have higher boiling points than equivalent ethers with smaller alkyl groups due to ___________ . A. B. C. D. E.

dipole-dipole interactions ionic bonding hydrophilic interactions London dispersion forces hydrogen bonding

Answer: D Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Easy 28.

Identify a common ether solvent that was once used as an anesthetic.

A. B. C. D. E.

diethyl ether ethanol methanol isopropyl alcohol dimethyl ether

Answer: A Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers Difficulty: Easy 29

What is the IUPAC name for the following compound?

A. B. C. D. E.

15-crown-5 15-crown-4 5-crown-15 15-crown-15 none of these

Answer: A Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Medium 30.

What is the correct IUPAC name for the following compound?

A. B. C. D. E.

12-crown-5 12-crown-4 4-crown-12 12-crown-12 none of these

Answer: B Learning Objective: 13.4 Discuss the structures and utility of crown ethers Section: 13.4 Difficulty: Medium 31.

Which of the following crown ether solvates lithium ions?

A. B. C. D. E.

12-crown-5 12-crown-4 15-crown-5 18-crown-6 none of these

Answer: B Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Easy

32.

Which of the following crown ether solvates potassium ions?

A. B. C. D. E.

12-crown-5 12-crown-4 15-crown-5 18-crown-6 none of these

Answer: D Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Easy 33.

Which of the following crown ether solvates sodium ions?

A. B. C. D. E.

12-crown-5 12-crown-4 15-crown-5 18-crown-6 none of these

Answer: C Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Easy 34.

Identify the missing reagent needed to carry out the reaction shown.

A. B. C. D. E.

12-crown-5 12-crown-4 15-crown-5 18-crown-6 none of these

Answer: C Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Medium 35.

Identify the missing reagent needed to carry out the reaction shown.

A. B. C. D. E.

12-crown-5 12-crown-4 15-crown-5 18-crown-6 none of these

Answer: B Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Medium 36.

Identify the missing reagent needed to carry out the reaction shown.

A. B. C. D.

15-crown-5 18-crown-6 12-crown-4 20-crown-3

Answer: B Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Hard 37.

Identify the missing reagent needed to carry out the reaction shown.

A. B. C. D.

18-crown-6 12-crown-4 20-crown-3 15-crown-5

Answer: A Learning Objective: 13.4 Discuss the structures and utility of crown ethers

Difficulty: Hard 38.

All crown ethers are examples_________.

A. B. C. D.

permanganates cyclic polyethers ionophones linear polyethers

Answer: B Learning Objective: 13.4 Discuss the structures and utility of crown ethers Difficulty: Easy 39.

Predict the product for the reaction shown.

A. B. C. D.

propene diethyl ether 1-hexanol 1-propoxypropane

Answer: D Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 40.

Predict the product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 41. Which illustration accurately shows the curved arrow mechanism for the initial step in the formation of the product shown?

B. C. D. E.

II III IV V

Answer: A

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 42.

Can you prepare diisopropyl ether as the major product by heating 2-propanol in the presence of sulfuric acid?

A. Yes, because these conditions promote the substitution reactions. B. Yes, because these conditions are highly favorable for C. No, because secondary and tertiary alcohols undergo elimination reactions in these conditions. D. No, because secondary and tertiary alcohols do not react in the presence of sulfuric acid. Answer: C Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 43.

Which one of the reactions shown would produce t-butyl methyl ether in high yield?

A. B. C. D.

t-butyl chloride + sodium methoxide t-butanol + methanol in presence of H2SO4 at 140°C t-butyl bromide + bromomethane in the presence of NaOH sodium t-butoxide + bromomethane

Answer: D Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 44.

Which one of the reactions shown would produce t-butyl methyl ether in high yield?

A. B. C. D.

CH3ONa + (CH3)3CBr CH3OH + (CH3)3COH in the presence of H2SO4 at 140°C CH3Cl + (CH3)3CBr in the presence of NaOH (CH3)3CONa + CH3Br

Answer: D Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 45.

Which one of the reactions shown would produce (S)-3-methoxyheptane in high yield?

A. B. C. D.

sodium (S)-3-heptoxide + bromomethane sodium (R)-3-heptoxide + bromomethane sodium methoxide + (S)-3-bromoheptane sodium methoxide + (R)-3-bromoheptane

Answer: A Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 46.

Predict the product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 47.

Provide the reagents necessary to carry out the following conversion.

1. PBr3; 2.

B. C.

1. Hg(OAc)2, toluene; 2. NaBH4 1. NaH; 2. bromobenzene

D. E.

1. MCBPA; 2. 1. Excess hBr, heat; 2: toluene

Answer: A Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 48.

Predict the product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 49.

Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis.

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 50.

Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Medium 51.

Predict the product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard

52.

Identify the mechanism for the Williamson ether synthesis.

A. B. C. D.

SN1 mechanism SN2 mechanism E1 mechanism E1 mechanism

Answer: B Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Easy 53.

Predict the product for the reaction shown.

A. B. C. D. E.

3-methyl-3-pentanol 3-ethoxy-3-methylpentane 3-methyl-2-pentanol 2-ethoxy-3-methylpentane 1-ethoxy-3-methylpentane

Answer: B Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 54.

Predict the product for the reaction shown.

A. B. C. D. E.

1-ethylcyclohexanol 2-ethoxy-1-ethylcyclohexane 1-ethoxy-1-ethylcyclohexane 2-ethoxy-3-ethylcyclohexane 1-ethoxy-2-ethylcyclohexane

Answer: C Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard

55.

Predict the product for the reaction shown.

A. B. C. D. E.

2-methyl-1-hexanol 2-methoxy-2-methylhexane 1-methoxy-2-methylhexane 2-methoxy-3-methylhexane 2-methyl-2-hexanol

Answer: B Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 56.

Predict the product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.5 Describe two methods for the preparation of ethers

Difficulty: Hard 57.

Predict the product for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 58.

What reagents are necessary to prepare the following compound using alkoxymercuration-demercuration?

A. B. C. D. E.

I II III I or II II or III

Answer: E

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 59.

Provide the reagents necessary to carry out the reaction shown.

A. B. C. D. E.

1. HBr; 2. H2, Pt; 3. NaOH 1. excess HBr; 2.(CH3)2Br 1. Hg(OAc)2, (CH3)2CHOH; 2. NaBH4 1. Br2, H2O; 2. NaOH; 3. (CH3)CBr 1. NaOH; 2. (CH3)CBr

Answer: C

Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 60.

Identify the conditions associated with oxymercuration-demercuration.

A. B. C. D.

anti-Markovnikov, rearrangement possible anti-Markovnikov, no rearrangement possible Markovnikov, rearrangement possible Markovnikov, no rearrangement possible

Answer: D Learning Objective: 13.5 Describe two methods for the preparation of ethers Difficulty: Hard 61.

Predict the product(s) for the reaction shown.

A. B. C. D. E.

ethanol + 1-bromopropane 1-propanol + bromoethane 1-propanol + ethanol 1-bromopropane + bromoethane none of these

Answer: D Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 62.

Predict the product(s) for the reaction shown.

A. B. C. D. E.

ethanol + phenol phenol + iodoethane iodobenzene + ethanol iodobenzene + iodoethane none of these

Answer: B Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 63.

Predict the product(s) for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 64.

Predict the product(s) for the reaction shown.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 65.

What is the expected product of the reaction shown? Provide a curved arrow mechanism for the formation of the product.

A. B.

I II

C. D. E.

III IV V

Answer: D

Mechanism

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 66.

Predict the product(s) for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Hard 67.

What is an accurate curved arrow mechanism for the formation of the product shown?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Hard

68.

What is the expected product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 69.

Predict the product(s) for the following reaction.

A. B. C. D. E.

I and II II and III III and IV I and IV II and V

Answer: D

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Hard 70.

Explain why long-term storage of ethers can be problematic.

A. Ethers degrade in storage and become unreactive. B. Ethers convert to esters during long periods of inertia. C. When exposed to atmospheric oxygen, ethers form hydroperoxides that can explode on heating. D. When isolated from atmospheric oxygen, ethers form highly explosive hydroperoxides. Answer: C Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen Difficulty: Medium 71.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

3-ethyl-2-methyloxirane 2-ethyl-3-methyloxirane 2-ethyl-1-methyloxypentane 1-ethyl-2-methyloxypentane none of these

Answer: B Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 72.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

2-ethyl-3-isopropyl-2-methyloxirane 1-ethyl-2-isopropyl-1-methyloxirane 2,4-dimethyloxyhexane 1-ethyl-2,4-dimethyloxyhexane 3-ethyl-2-isopropyl-3-methyloxirane

Answer: A Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 73.

What is the structure of tetrahydrofuran?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 74.

What is the structure for oxolane?

D. E. Answer: D

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 75.

What is the structure for oxane?

D. E. Answer: B

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 76.

What is the structure for oxetane?

D. E. Answer: A

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 77.

What is the IUPAC name for the compound shown?

A. (2R, 3S)-2-ethyl-3-isopropyloxirane B. (2S, 3S)-2-ethyl-3-isopropyloxirane C. (2S, 3R)-3-ethyl-2-isopropyloxirane D. (2S, 3S)-3-ethyl-2-isopropyloxirane Answer: B Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 78.

What is the IUPAC name for the compound shown?

A. (2S, 3R)-2-ethyl-3-phenyloxirane B. (2R, 3S)-2-ethyl-3-phenyloxirane C. (2S, 3S)-2-ethyl-3-phenyloxirane D. (2S, 3R)-3-ethyl-2-phenyloxirane Answer: A Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 79.

What is the common name for the compound shown?

A. B. C. D.

para-cyclodioxane cyclodioxane 1,4-dioxane meta-cyclodioxane

Answer: C Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 80.

What is the IUPAC name for the compound shown?

A. (1S,2R)-1-methyl-1,2-epoxycyclohexane B. (1R,2R)-1-methyl-1,2-epoxycyclohexane C. (1S,2R)-2-methyl-1,2-epoxycyclohexane D. (1R,2S)-2-methyl-1,2-epoxycyclohexane Answer: B Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 81.

What is the structure of (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 82.

What is the structure of (R)-2,2,3-trimethyl-3-phenyloxirane?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods Difficulty: Medium 83.

What is the expected product of the reaction shown?

(E)-2-pentene + mCPBA

A. B. C. D.

I II III IV

Answer: D Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 84.

What is the expected product of the reaction shown?

(Z)-3-hexene + mCPBA

A. B. C. D.

I II III IV

Answer: A Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 85.

What is the expected product of the reaction shown?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 86.

What is the expected product of the reaction shown?

1-methylcyclohexene + mCPBA

A. B. C. D.

I II III IV

Answer: B

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 87.

What reagent(s) are appropriate to carry out the reaction shown?

A. B. C. D. E.

mCPBA CH3CO3H NaOH A and B B and C

Answer: D Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 88.

What is the expected product of the reaction shown?

A. B. C.

I II III

Answer: D Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 89.

What is the expected product of the following reaction?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 90. What are the structure(s) of compounds A and B in the reaction sequence shown?

A. B. C. D. E.

A is I and B is II A is II and B is I A is III and B is IV A is VI and B is III A is I and B is III

Answer: D

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 91.

What is the expected product of the following reaction?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 92.

What reactants could be used to prepare the compound shown?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 93.

What reactants could be used to prepare the compound shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 94.

What reactants could be used to prepare the compound shown?

A. B. C. D E.

I II III IV V

Answer: D

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 95.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 96.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 97.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 98.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides Difficulty: Medium 99.

What is the expected product of the reaction shown?

A. B. C.

I II III

D. E.

IV none of these

Answer: C Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Easy 100.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Easy 101.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 102.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 103.

What is the likely product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 104.

What reagents are suitable to carry out the conversion shown?

A. B. C. D.

NaOH H2SO4 HCl H2O2

Answer: Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 105.

What reagents are necessary to carry out the conversion shown?

A. B. C. D.

H2SO4 HCl CH3OH/H2SO4 H3O+

Answer: C Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 106.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Easy 107.

Predict the product(s) of the reaction shown.

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 108.

What is the likely product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: D Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

Difficulty: Medium 109.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 110.

What is the expected product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium 111.

What reagents are appropriate to carry out the conversion shown?

A. B. C. D.

1. mCPBA; 2. CH3MgBr; 3. H2O 1. CH3MgBr; 2. H2O 1. mCPBA; 2. H2O mCPBA

Answer: A Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Hard 112.

What reagents are appropriate to carry out the conversion shown?

A. B. C. D.

1. LiAlH4; 2. H2O 1. mCPBA; 2. CH3MgBr; 3. H2O 1. H3O+; 2. NaOH 1. LiAlH4; 2. NaOH

Answer: A Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Hard 113.

What reagents are appropriate to carry out the conversion shown?

A. B. C. D.

Excess HI, heat MgBr, diethylether 1. mCPBA; 2. NH3 1. RCO3H; 2. H2O

Answer: C

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Hard 114.

What reagents are appropriate to carry out the conversion shown?

A. B.

1. CH3MgBr; 2. H2O 2. MCPBA; 2. H2O

; 2. H2O

; 2. MgBrCH3; 3. H2O

; 2. MgBr; 3. CH3CH3; 4. H2O

Answer: C Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Hard 115. What is an appropriate description of the curved arrow mechanism for the last step of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions Difficulty: Medium

116.

What is the correct structure for 3-methyl-1-hexanethiol?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 117.

What is the correct structure for phenylthiol?

A. B.

I II

C. D. E.

III IV V

Answer: D

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 118.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

2-sulfhydryl-5-methylheptane 5-methyl-2-heptanethiol 5-methyl-2-thiol-heptane 2-sulfhydryl-5-ethylhexane 2-mercapto-5-methylheptane

Answer: B Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 119.

What is the IUPAC name for the compound shown?

A. 2--mercapto-5-methyl-6-hexanol B. 1-hydroxy-2,5-methylhexanethiol C. 5-mercapto-2-methyl-1-hexanol D. 5-sulfhydryl-2-methyl-1-hexanol

Answer: C Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 120.

What is the common name for the compound shown?

A. B. C. D.

pentyl methyl sulfide methyl pentyl sulfhydryl methyl pentyl sulfide thio methyl pentyl

Answer: C Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 121.

What is the IUPAC name for the compound shown?

A. B. C. D.

3-sulfide-4-methyl-octane 2-ethylthiohexane 2-methylthiohexane 2-ethylsulfhydrylhexane

Answer: B Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 122.

What is the expected product of the following reaction?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 123.

What is the expected product for the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 124.

What is the expected product for the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 125.

What reagents are appropriate to carry out the following conversion?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 126.

What is the expected major product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 127.

What is the expected major product of the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 128.

What is the expected major product for the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium

129.

What is the expected major product for the reaction shown?

A. B. C. D. E.

I II III IV none of these

Answer: D Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium 130.

What is the expected major product for the reaction shown?

A. B. C. D. E.

I II III IV II and IV

Answer: D Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products Difficulty: Medium

131.

What is an appropriate first step of a stepwise synthesis for the reaction shown?

A. B.

Add Mg/ether Add H2O

C. D. E.

Add Add HCl Add PCC

Answer: A

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents Difficulty: Medium 132.

What is an appropriate stepwise synthesis for reaction shown?.

A. B. C. D. E.

1. NaOH; 2. H3O+ 1. HBr; 2. NaNH2 1. H3O+; 2. NaOH 1. HBr, peroxides; 2. NaOH; 3. H2, Pt 1. PCC; 2. H3O+

Answer: C

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

Difficulty: Hard 133.

What is an appropriate stepwise synthesis for the reaction shown?

A. B. C. D. E.

1. Br2, hn; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O 1. HBr; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O 1. Br2, hn; 2. CH3ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O 1. Br2, hn; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O 1. HBr; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2MgBr followed by H2O

Answer: D Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents Difficulty: Hard 134.

What is an appropriate stepwise synthesis for the reaction shown?

A. B. C. D.

1. mCPBA; 2. 1. mCPBA; 2. 1. PCC; 2. 1. HBr; 2.

followed by H2O followed by H2O followed by H2O followed by H2O

1. PCC; 2.

followed by H2O

Answer: A

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

Difficulty: Hard 135.

What is an appropriate stepwise synthesis for the reaction shown?

A. B. C. D. E.

1. HBr; 2. NaH; 3. CH3CH2I 1. BH3-THF followed by H2O2/NaOH/H2O; 2. CH3CH2I 1. BH3-THF followed by H2O2/NaOH/H2O; 2. NaH; 3. CH3CH2I 1. BH3-THF followed by H2O2; 2.. NaH; 3. CH3I 1. Br2 followed by H2O2/NaOH/H2O; 2. NaH; 3. CH3CH2I

Answer: C

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents Difficulty: Hard 136.

What is an appropriate stepwise synthesis for the reaction shown.

A. B.

1. H2SO4/heat; 2. mCPBA; 3. CH3CH2CH2ONa followed by H2O 1. CH3CH2CH2MgBr followed by H2O; 2. H2SO4/heat; 3. CH3CH2CH2ONa followed by H2O 1. PCC followed by H2O; 2. H2SO4/heat; 3. mCPBA; 4. CH3CH2CH2ONa followed by H2O 1. CH3CH2CH2MgBr followed by H2O; 2. H2SO4/heat; 3. mCPBA; 4. CH3CH2CH2ONa followed by H2O 1. CH3CH2MgBr followed by H2O; 2. H2SO4/heat; 3. mCPBA; 4. CH3CH2ONa followed by H2O

C. D. E.

Answer: D

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents Difficulty: Hard 137.

What is an appropriate stepwise synthesis for the reaction shown?

A. B. C. D. E.

1. (CH3)3COK; 2. HBr/CH3OOCH3; 3. NaSH 1. (CH3)3COK; 2. Br2/H2O; 3. NaSH 1. (CH3)3COK; 2. Br2/H2O; 3. NaSH 1. Hg(OAc)2, CH3OH; 2. NaBH4 1. HBr, CH3OOCH3; 2. NaSH; 3. NaOH/H2O/Br2

Answer: A

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents Difficulty: Medium 138.

What is an appropriate stepwise synthesis for the reaction shown?

A. B. C. D. E.

1. Br2, hn; 2. NaSH; 3. NaOH/H2O/Br2 1. HBr, CH3OOCH3; 2. NaSH; 3. NaOH/H2O/Br2 1. (CH3)3COK; 2. HBr/CH3OOCH3; 3. NaSH 1. NaOH/H2O/Br2; 2. HBr/CH3OOCH3 1. (CH3)3COK; 2. HBr; 3. NaSH

Answer: B

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents Difficulty: Medium

139.

A compound with molecular formula C6H14O displays the following IR, 1HNMR and 13CNMR spectra. What is a consistent a structure for this compound?

IR: 1200cm-1

9H, s

2H, q 3H, t

SDBS

A. B. C. D. E.

I II III IV I or III

Answer: D

Learning Objective: Spectroscopy Difficulty: Medium 140.

A compound with molecular formula C5H12O2 displays the following IR, 1H NMR and 13C NMR spectra. What is a consistent structure for this compound?

IR: 1200cm-1

A. B. C. D. E.

I II III IV I or II

Answer: B

Learning Objective: Spectroscopy Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 14 1.

Which of the statements given is not true about electromagnetic radiation?

A. B. C. D. E.

frequency is directly proportional to wavelength frequency is directly proportional to energy frequency is inversely proportional to wavelength wavelength is inversely proportional to energy frequency and wavelength are not related

Answer: A Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Easy 2.

Which of the types of electromagnetic radiation shown has the highest energy?

A. B. C. D. E.

UV X-ray IR microwave visible

Answer: B Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Easy 3. Which of the types of electromagnetic radiation shown has the longest wavelength? A. B. C. D. E.

UV X-ray IR microwave visible

Answer: D Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Easy

4. Which of the types of electromagnetic radiation shown has the highest frequency? A. B. C. D. E.

UV X-ray IR microwave visible

Answer: B Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Easy 5.

Arrange the given types of electromagnetic radiation in decreasing order of frequency (from highest frequency to lowest frequency).

A. B. C. D. E.

V > III > IV > II > I II > V > III > IV > I I > IV > III > V > II V > II > IV > III > I II > IV > V > III > I

Answer: B Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Medium 6.

Arrange the given types of electromagnetic radiation in decreasing order of wavelength (from highest to lowest wavelength).

A. B. C. D. E.

V > III > IV > II > I II > V > III > IV > I I > IV > III > V > II V > II > IV > III > I II > IV > V > III > I

Answer: E Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Medium 7.

Which of the information shown is primarily obtained from infrared spectroscopy?

A. B. C. D. E.

arrangement of carbon and hydrogen atoms in a compound molecular weight of a compound any conjugated π system present in a compound functional groups present in a compound all of these

Answer: D Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Easy 8.

Which of the information shown is primarily obtained from nuclear magnetic resonance spectroscopy?

A. B. C. D. E.

arrangement of carbon and hydrogen atoms in a compound molecular weight of a compound any conjugated π system present in a compound functional groups present in a compound all of these

Answer: A Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation Difficulty: Easy 9.

Which of the information shown is primarily obtained from UV-VIS spectroscopy?

A. B. C. D. E.

arrangement of carbon and hydrogen atoms in a compound molecular weight of a compound any conjugated π system present in a compound functional groups present in a compound all of these

Answer: C Learning Objective: 14.1 Describe the wave-like and particle-like nature of electromagnetic radiation, and define photon, ΔE, and vibrational excitation

Difficulty: Easy 10.

Absorption of _______ radiation results in vibrational excitation of the bonds in a compound.

A. B. C. D. E.

UV Microwave IR Visible x-ray

Answer: C Learning Objective: 14.2 Discuss the nature of the chemical analysis that can be accomplished with IR spectroscopy and describe how this is accomplished Difficulty: Easy 11.

Which of the given vibrations are observed in IR spectroscopy?

A. B. C. D. E.

stretching rotational bending A and B A and C

Answer: E Learning Objective: 14.2 Discuss the nature of the chemical analysis that can be accomplished with IR spectroscopy and describe how this is accomplished Difficulty: Easy 12.

Which of the given characteristics is currently most often used to indicate the location of a signal on an IR spectrum?

A. B. C. D. E.

wavelength wavenumber frequency A and B all of these

Answer: B Learning Objective: 14.2 Discuss the nature of the chemical analysis that can be accomplished with IR spectroscopy and describe how this is accomplished Difficulty: Easy

13. An object that feels warm is emitting ________ amounts of infrared radiation than an object that feels cool. A. B. C. D.

greater lower more variable less intense

Answer: IR Learning Objective: 14.2 Discuss the nature of the chemical analysis that can be accomplished with IR spectroscopy and describe how this is accomplished Difficulty: Easy 14.

Which of the choices given are units for wavenumber in IR spectroscopy?

A. B. C. D. E.

cm-1 cm J·s-1 mm J·s

Answer: A Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Easy 15.

Which of the wavenumbers given corresponds to the C=O double bond region on an IR spectrum?

A. B. C. D. E.

1500 – 4000 cm-1 400 – 4000 cm-1 400 – 1500 cm-1 2100 – 2300 cm-1 1600 – 1850 cm-1

Answer: E Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Easy

16.

Which of the wavenumbers given corresponds to the carbon/carbon triple bond region on an IR spectrum?

A. B. C. D. E.

1500 – 4000 cm-1 400 – 4000 cm-1 400 – 1500 cm-1 2100 – 2300 cm-1 1600 – 1850 cm-1

Answer: D Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Easy 17.

Which of the wavenumbers given corresponds to the fingerprint region on an IR spectrum?

A. B. C. D. E.

1500 – 4000 cm-1 400 – 4000 cm-1 400 – 1500 cm-1 2100 – 2300 cm-1 1600 – 1850 cm-1

Answer: C Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Easy 18.

Which of the given statement(s) is(are) true about the frequency of a stretching vibration according to Hooke’s law?

A. B. C.

it is directly proportional to strength of the bond and the reduced mass it is inversely proportional to strength of the bond and the reduced mass it is directly proportional to strength of the bond and inversely proportional to the reduced mass it is inversely proportional to the strength of the bond and proportional to the reduced mass it is not related to either the strength of the bond or the reduced mass

D. E.

Answer: C

Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Medium 19.

Rank the infrared absorption of the indicated bonds in order of decreasing wavenumber (from highest to lowest

wavenumber). A. B. C. D. E.

III > II > I I > II > III II > I > III III > I > II II > III > I

Answer: B Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Easy 20.

Rank absorption of the indicated bonds in order of decreasing wavenumber (from highest to lowest wavenumber).

A. B. C. D. E.

III > II > I I > II > III II > I > III III > I > II II > III > I

Difficulty: Easy 21.

Rank absorption of the indicated bonds in order of decreasing wavenumber (from highest to lowest wavenumber).

A. B. C. D. E.

III > II > I I > II > III II > I > III III > I > II II > III > I

Which of the given compounds has the lowest wavenumber for its carbonyl absorption?

A. B. C. D. E.

I II III IV V

Difficulty: Medium 23.

Which one of the given compounds has the lowest wavenumber for its carbonyl absorption?

A. B. C. D. E.

I II III IV V

Which one of the given compounds has the highest wavenumber for its C=C absorption?

A. B. C. D. E.

I II III IV V

Difficulty: Medium 25.

Which of the given compounds has the highest wavenumber for its carbonyl absorption?

A. B. C. D.

I II III II and III

Rank absorption of the indicated bonds in decreasing order of wavenumber (from highest to lowest wavenumber).

A. B. C. D. E.

I > V > II > IV > III IV > II > I > V > III II > I > V > III > IV IV > I > V > II > III IV > II > V > I > III

27.

Why is the expected stretching absorption of the C=O bond 1685 cm-1 for the structure I and 1715 cm-1 for structure II?

A. Having fewer double bonds results in lowering of all of the stretching absorptions. B. The C to O double bond of compound I has greater single bond character than the C to O double bond of compound II. C. The expected stretching absorption is lowered in all molecules with cyclohexane rings. D. Compound I lacks conjugation, whic his present in compound II. E. Compound II has a C to O double bond with considerable single bond character, lowering the expected stretching absorption. Answer: B

Why does the expected stretching absorption of the C=O bond in compounds I

and II differ, as shown below? A. Only compound I has resonance, causing it to have a higher stretching absorption. B. Only compound II has resonance, causing it to have a higher stretching absorption. C. Compound II has more possible resonance structures, increasing the single bond character of the carbonyl group.

D. Compound I has more possible resonance structures, increasing the single bond character of the carbonyl group. E. Compound I has a C to O bond with more single bond character than that of compound II, increasing the expected stretching absorption of the bond. Answer: D Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Hard 29.

The C—O absorption in carboxylic acids appears around 1250 cm-1. The C—O absorption in an alcohol appears around 1050 cm-1. Explain why.

A. Only compound I has resonance, causing it to have a higher stretching absorption. B. Only compound II has resonance, causing it to have a higher stretching absorption. C. Compound II has more possible resonance structures, increasing the single bond character of the carbonyl group. D. Compound I has more possible resonance structures, increasing the single bond character of the carbonyl group. E. Compound I has a C to O bond with more single bond character than that of compound II, increasing the expected stretching absorption of the bond. Answer: D Learning Objective: 14.3 Describe the factors that determine wavenumber, and then describe what can be learned from the signals in the diagnostic region and the fingerprint region of the IR spectrum Difficulty: Hard 30.

Which of the given statement(s) is(are) true for an IR-active bond?

the bond must be symmetrical

B. C. D. E.

a vibration must result in a change of bond length a vibration must result in a change of bond angle a vibration must result in a change of bond dipole a vibration must result in a change of isotope

Answer: D Learning Objective: 14.4 Discuss the factors that determine the strength of the signal in an IR spectrum and which bonds produce strong signals and which produce weaker ones Difficulty: Medium 31.

Which of the bonds shown has the weakest absorption?

A. B. C. D. E.

I II III I and IV I and III

Answer: E Learning Objective: 14.4 Discuss the factors that determine the strength of the signal in an IR spectrum and which bonds produce strong signals and which produce weaker ones Difficulty: Medium 32.

Which of the bonds shown has the weakest absorption?

A. B. C. D. E.

C=C O—H C=O sp3 C—H A and D

Answer: A Learning Objective: 14.4 Discuss the factors that determine the strength of the signal in an IR spectrum and which bonds produce strong signals and which produce weaker ones Difficulty: Medium

33.

Which of the bonds shown has the strongest absorption?

A. B. C. D. E.

C=N C≡C C=O sp2 C—H C—O

Answer: C Learning Objective: 14.4 Discuss the factors that determine the strength of the signal in an IR spectrum and which bonds produce strong signals and which produce weaker ones Difficulty: Medium 34.

3-Hexyne does not show absorption in the range of 2000-2200 cm-1, whereas 1hexyne does. What is a reasonable explanation for 3-hexyne’s absence of absorption?

A. B. C. D. E.

it is a symmetrical compound there is no change in bond dipole there is no bond dipole it is an unsymmetrical compound A, B and C

A. B. C. D.

I II III IV

Which of the alkene groups shown produces the stronger signal in an IR spectrum? Explain why.

A. Yes, compound I produces a stronger signal because fluorine is more electronegative than chlorine and produces a larger dipole moment B. Yes, compound II produces a stronger signal because chlorine is more electronegative than chlorine and produces a larger dipole moment C. No, the alkene groups produces similar signals because their structures are so similar D. No, the alkene groups produce similar signals because both have vinylic halogen atoms Answer: A Learning Objective: 14.4 Discuss the factors that determine the strength of the signal in an IR spectrum and which bonds produce strong signals and which produce weaker ones Difficulty: Hard 37.

Will one of the alkene groups shown produce a stronger signal in an IR spectrum?

A. Yes, compound I produces a stronger signal because it has a larger dipole moment B. Yes, compound II produces a stronger signal because it has a larger dipole moment

C. No, the alkene groups produce similar signals because they have similar double bonds D. No, the alkene groups produce similar signals because they both contain fluorine Answer: B Learning Objective: 14.4 Discuss the factors that determine the strength of the signal in an IR spectrum and which bonds produce strong signals and which produce weaker ones Difficulty: Hard 38.

Diluted alcohols show a _____absorption around 3600 cm-1, due to _____.

A. B. C. D.

sharp, hydrogen bonding broad, hydrogen bonding sharp, absence of hydrogen bonding broad, absence of hydrogen bonding

Answer: C Learning Objective: 14.5 Discuss the shape of signals from alcohols and amines Difficulty: Medium 39.

Concentrated alcohols show a _____absorption in the region of 3200-3600 cm1 due to _____.

A. B. C. D.

sharp, hydrogen bonding broad, hydrogen bonding sharp, polarity broad, polarity

Answer: B Learning Objective: 14.5 Discuss the shape of signals from alcohols and amines Difficulty: Medium 40.

Carboxylic acids show a very broad absorption for the OH group compared to alcohols because they can form a ______.

A. B. C. D.

dimer polymer trimer tetramer

Answer: A

Learning Objective: 14.5 Discuss the shape of signals from alcohols and amines Difficulty: Medium 41.

Primary amines show two medium absorption bands around 3400 cm-1 due to _______.

A. B. C. D.

symmetric stretching asymmetric stretching both symmetric and asymmetric stretching hydrogen bonding

Answer: C Learning Objective: 14.5 Discuss the shape of signals from alcohols and amines Difficulty: Medium 42.

How can you distinguish between cyclohexanol and cyclohexanecarboxylic acid using IR spectroscopy?

A. Cyclohexanecarboxylic acid shows a broader OH absorption associated with its carboxylic acid compared with the narrower OH absorption for the alcohol of cyclohexanol. B. Cyclohexanol shows a carbonyl absorption that will not be present in cyclohexanecarboxylic acid. C. Cyclohexanecarboxylic acid shows a carbonyl absorption that is not be present in cyclohexanol. D. A and B E. A and C Answer: E Learning Objective: 14.5 Discuss the shape of signals from alcohols and amines Difficulty: Medium

43.

Determine whether each of the IR spectra given is consistent with the structure of an alcohol, a ketone, an aldehyde, a carboxylic acid, a primary amine, or a secondary amine.

SDBS: National Institute of Advanced Industrial Science and Technology

II.

SDBS: National Institute of Advanced Industrial Science and Technology

A. Spectrum I is consistent with an aldehyde and spectrum II is consistent with an alcohol. B. Spectrum II is consistent with an aldehyde and spectrum II is consistent with an alcohol. C. Spectrum I is consistent with a primary amine and spectrum II is consistent with a secondary amine. D. Spectrum I is consistent with a ketone and spectrum II is consistent with a carboxylic acid. E. Spectrum I is consistent with a carboxylic acid and spectrum II is consistent with a primary amine. Answer: A Learning Objective: 14.6 Define the process for analyzing an IR spectrum

Difficulty: Medium 44.

Determine whether each of the IR spectra given is consistent with the structure of an alcohol, a ketone, an aldehyde, a carboxylic acid, a primary amine, a secondary amine, a primary amide, or a secondary amide.

I. SDBS: National Institute of Advanced Industrial Science and Technology

II.

A. Spectrum I is consistent with a carboxylic acid and spectrum II is consistent with an alcohol. B. Spectrum II is consistent with a primary amine and spectrum II is consistent with a secondary amine. C. Spectrum I is consistent with a primary amide and spectrum II is consistent with a ketone. D. Spectrum I is consistent with a secondary amide and spectrum II is consistent with a ketone. E. Spectrum I is consistent with an aldehyde and spectrum II is consistent with a ketone. Answer: C I: secondary amide II: ketone

Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 45.

Which of the given compounds shows a broad absorption near 3300 cm-1 and a sharp absorption at 1650 cm-1?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 46.

Which of the given compounds shows two sharp absorptions, one at 3300 cm-1 and one at 2150 cm-1?

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium

47.

Which of the given compounds shows two absorptions, one at 2700 cm-1 and one at 2800 cm-1, in addition to the carbonyl absorption?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 48.

Which of the given compounds shows an absorption at 2250 cm-1?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium

49.

Which of the given compounds has have the lowest wavenumber for the carbonyl absorption?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 50.

Which statement accurately describes the IR spectrum of the compound shown?

A. B. C. D. E.

absorptions at 1720 cm-1 and 2150 cm-1 absorptions at 1800 cm-1 and 2150 cm-1 absorptions at 1720 cm-1 and 2250 cm-1 absorptions at 1800 cm-1 and 2250 cm-1 absorptions at 1650 cm-1 and 2150 cm-1

Answer: B Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 51.

Which of the compounds give shows absorptions at 1640 cm-1, 2950 cm-1 and 3050 cm-1 on the IR spectrum?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 52.

What is a possible structure for a compound with molecular formula C6H10Othat shows absorptions at 1720 cm-1 and at 2980 cm-1 on the IR spectrum?

A. B. C. D. E.

I II III I and II I, II, and III

Answer: E

Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 53.

A compound with molecular formula C3H9N, shows absorptions at 3400 cm-1 (two), 2980 cm-1 and at 1100 cm-1 on the IR spectrum. Propose a possible structure for this compound.

CH3CH2CH2NH2

B. C. D. E.

(CH3)2CHNH2 CH3NHCH2CH3 A and B A and C

Answer: D Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 54.

A compound with molecular formula C4H8O2, shows absorptions at 2500-3300 cm-1 (broad), 1720 cm-1 and at 1200 cm-1 on the IR spectrum. Propose a possible structure for this compound.

A. B. C. D. E.

I II III I and II II and III

Answer: D

Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 55.

Which of the compounds shown has the highest wavenumber for carbonyl absorption?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Hard 56.

Which of the compounds shown has absorptions at 1700 cm-1 and 1320 cm-1?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Hard 57.

Which one of the given compounds has a structure consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 58.

Which one of the given compounds has a structure consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 59.

Which one of the given compounds has a structure consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 60.

Which one of the given compounds is consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D.

I II III IV

Answer: D Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 61.

Which one of the given compounds has a structure consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 62.

Which one of the given compounds has a structure is consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 63.

Which one of the given compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 14.6 Define the process for analyzing an IR spectrum Difficulty: Medium 64.

For the given reaction, which of the following change(s) in the IR spectrum is consistent with conversion of the reactant to the product?

A. B. C.

absorption at 2250 cm-1 should disappear absorption at 3200-3400 cm-1 and 1720cm-1 should appear absorption at 2250 cm-1 should disappear, new absorptions at 2600-2800 cm-1 and 1720 cm-1 should appear. absorption at 2250 cm-1 should disappear, a new absorption around 3400 cm-1 should appear.

none of these

Answer: C Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Medium 65.

For the given reaction, which of the following change(s) in the IR spectrum is consistent with conversion of the reactant to the product?

A. B. C.

absorption at 2150 cm-1 should disappear absorption at 3300 cm-1 and 2150 cm-1 should disappear absorption at 2250 cm-1 should disappear, a new absorption at 3300 cm-1 should appear absorption at 1650 cm-1 should disappear, a new absorption at 3300 cm-1 should appear absorption at 3300 cm-1 and 2150 cm-1 should disappear, a new absorption at 1720 cm-1 should appear

D. E.

Answer: E Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Medium 66.

For the given reaction, which of the following change(s) in the IR spectrum is consistent with conversion of the reactant to the product?

A. B. C.

absorption at 3200-3600 cm-1 should disappear absorption at 3200-3600 cm-1 and 1100 cm-1 should disappear absorption at 1100 cm-1 should disappear, a new absorption at 3100 cm-1 should appear absorption at 1650 cm-1 should disappear, a new absorption at 3300 cm-1 should appear none of these

D. E.

Answer: A Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Medium 67.

For the given reaction, which of the following change(s) in the IR spectrum is consistent with conversion of the reactant to the product?

A. B. C.

absorption at 3300 – 3400 cm-1 should disappear absorption at 3300 – 3400 cm-1 and 1100 cm-1 should disappear absorption at 1100 cm-1 should disappear, a new absorption at 3100 cm-1 should appear absorption at 1650 cm-1 should disappear, a new absorption at 3300 cm-1 should appear. absorption at 3300 – 3400 cm-1 should appear

D. E.

Answer: A Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Medium 68.

For the given reaction, explain how you can use IR spectroscopy to monitor the progress of the reaction.

Answer: The two absorptions at 3350 cm-1 and at 3450 cm-1 for the primary amine should disappear from the product and there should be a single absorption at around 3300 cm-1 for the secondary amine. Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Medium 69.

Predict the product for the reaction shown and explain how you can use IR spectroscopy to monitor the progress of the reaction.

Answer:

A new absorption for OH at 3200-3600 cm-1 would appear in the product’s IR spectrum. Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Medium 70.

Predict the product for the reaction shown and explain how you can use IR spectroscopy to monitor the progress of the reaction.

A. CH3CH2CH2C≡CCH2CH2CH3; absorptions at around both 3300 cm-1 and 2150 cm-1 will disappear from the product spectrum B. CH3C≡CCH2CH3; absorptions will remain the same but with smaller peaks C. CH3CH2CH2C≡CCH2CH2CH3; a single absorption at around 3300 cm-1 will disappear from the product spectrum D. CH3CH2C≡CCH2CH2CH2CH3; a single absorption at around 2150 cm-1 will disappear from the product spectrum E. CH3CH2CH2C≡CCH2CH2CH3; absorptions will remain the same but become broader Answer: A Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Hard 71.

Predict the product for the reaction shown and explain how you can use IR spectroscopy to monitor the progress of the reaction.

A. The product will be I, there will be a new absorption at 3200-3600 cm-1, and an absorption at 1720 cm-1 will disappear. B. The product will be I, there will be a new absorption at 1720 cm-1, and an absorption at 3200-3600 cm-1 will disappear. C. The product will be II, there will be a new absorption at 3200-3600 cm-1, and an absorption at 1720 cm-1 will disappear. D. The product will be III and an absorption at 1720 cm-1 will disappear. E. The product will be III and an absorption at 3200-3600 cm-1 will disappear. Answer: C

Learning Objective: 14.7 Describe how IR spectroscopy can be used to distinguish between two compounds Difficulty: Hard 72.

Mass spectrometry is primarily used to determine:

A. B. C. D. E.

molecular formula of a compound molecular weight of a compound conjugation in a compound A and B A and C

Answer: D Learning Objective: 14.8 Describe both the type of information that can be determined with mass spectrometry and how a mass spectrometer works Difficulty: Easy

73.

Which of the choices given is initially produced when a compound is bombarded with high energy electrons?

A. B. C. D. E.

anions free radicals radical cations cations isotopes

Answer: C Difficulty: Easy 74. Which of these statements is not true about the molecular ion in mass spectrometry? A. B. C. D.

The molecular ion is produced by loss of one electron from the molecule. The mass of the molecular ion is equivalent to the mass of the molecule. The ion is produced by a loss of pair of electrons from the molecule. The molecular ion is often unstable and can undergo fragmentation.

Answer: C Learning Objective: 14.8 Describe both the type of information that can be determined with mass spectrometry and how a mass spectrometer works Difficulty: Easy 75. Which of the statements given is always true about the base peak in a mass spectrum? A. B. C. D. E.

the peak corresponding to molecular ion the peak corresponding to the most abundant ion the peak corresponding to lowest m/z the peak corresponding to the cation the peak corresponding to the lowest fragment

Answer: B Learning Objective: 14.8 Describe both the type of information that can be determined with mass spectrometry and how a mass spectrometer works Difficulty: Easy 76.

The separation of ions in the mass spectrometer is done by their ______.

electrons to protons ratio

B. C. D. E.

mass to neutrons ratio protons to neutrons ratio mass to charge ratio protons to electrons ratio

Answer: D Learning Objective: 14.8 Describe both the type of information that can be determined with mass spectrometry and how a mass spectrometer works Difficulty: Easy 77.

In mass spectrometry using the electron impact ionization technique, a beam of high-energy electrons initially ejects one electron from the compound being studied. This produces a positively charged ion called the ____________________.

A. B. C. D. E.

proton molecular ion central fragment base peak central peak

Answer: B Learning Objective: 14.8 Describe both the type of information that can be determined with mass spectrometry and how a mass spectrometer works Difficulty: Easy 78.

In mass spectrometry, the tallest peak is assigned an intensity of 100% and is referred to as the ______________.

A. B. C. D. E.

molecular peak primary peak central fragment base peak central peak

Answer: D Learning Objective: 14.8 Describe both the type of information that can be determined with mass spectrometry and how a mass spectrometer works Difficulty: Easy 79.

Which of the statements given is true about CH3CH3+•?

it is the parent ion of ethane

B. C. D. E.

it is a molecular ion of ethane with m/z = 30 it is a fragment of propane it is a fragment of butane A and B

Answer: E Learning Objective: 14.9 Explain what is indicated by the M⁺• peak and what is indicated by an odd or even molecular weight Difficulty: Easy 80.

Which of the m/z values corresponds to the base peak in the mass spectrum shown?

A. B. C. D. E.

45 44 29 15 30

Answer: C Learning Objective: 14.9 Explain what is indicated by the M⁺• peak and what is indicated by an odd or even molecular weight Difficulty: Easy 81.

Which of the m/z values correspond to the molecular ion peak in the mass spectrum shown?

A. B. C. D. E.

45 44 29 15 30

Answer: B Learning Objective: 14.9 Explain what is indicated by the M⁺• peak and what is indicated by an odd or even molecular weight Difficulty: Easy 82.

Which of the m/z values correspond to the molecular ion for the compound shown?

A. B. C. D. E.

18 82 100 102 103

Answer: D Learning Objective: 14.9 Explain what is indicated by the M⁺• peak and what is indicated by an odd or even molecular weight Difficulty: Medium 83.

Which of the m/z values shown corresponds to the base peak for 2-chloro-2methylpropane?

A. B. C. D. E.

15 92 77 47 57

Answer: E Learning Objective: 14.9 Explain what is indicated by the M⁺• peak and what is indicated by an odd or even molecular weight Difficulty: Medium

84.

Which of the compounds shown has an odd m/z value for the molecular ion?

A. B. C. D. E.

I II III IV all of them

Answer: B Learning Objective: 14.9 Explain what is indicated by the M⁺• peak and what is indicated by an odd or even molecular weight Difficulty: Medium 85.

Which of the statements given is true about the molecular weight and the M+•m/z value for the compound shown?

A. B. C. D. E.

odd molecular weight, m/z = 115 odd molecular weight, m/z = 121 even molecular weight, m/z = 96 even molecular weight, m/z = 132 even molecular weight, m/z = 116

Answer: B Learning Objective: 14.10 Describe how the number of carbon atoms in a compound is determined using the (M+1)⁺• peak Difficulty: Medium 86.

Which of the statements given is true about the (M+1)+• peak on the mass spectrum of a hydrocarbon?

A. B.

it is always the most abundant peak it is due to the 13C isotope of carbon

C. D. E.

it has a m/z value lower than the molecular ion it is useful in calculating number of carbon atoms B and D

Answer: E Learning Objective: 14.10 Describe how the number of carbon atoms in a compound is determined using the (M+1)⁺• peak Difficulty: Medium 87.

Which molecular formula is consistent with the given mass spectral data? M+• at m/z = 84, relative height = 10.0% (M+1)+• at m/ z = 85, relative height = 0.56%

A. B. C. D. E.

C5H10O C5 H8 O C5H24 C6H12 C4H6O2

Answer: B Learning Objective: 14.10 Describe how the number of carbon atoms in a compound is determined using the (M+1)⁺• peak Difficulty: Medium 88.

Which molecular formula is consistent with the given mass spectral data? M+• at m/z = 72, relative height = 73.0% (M+1)+• at m/z = 73, relative height = 3.3%

A. B. C. D. E.

C4H10O C4 H9 N C5H12 C4 H8 O none of these

Answer: D Learning Objective: 14.10 Describe how the number of carbon atoms in a compound is determined using the (M+1)⁺• peak Difficulty: Medium 89.

Provide a molecular formula that is consistent with the given mass spectral data. M+• at m/z = 73, relative height = 86.1% (M+1)+• at m/z = 74, relative height = 3.2%

A. B. C. D. E.

C3H7NO

Answer: B Learning Objective: 14.10 Describe how the number of carbon atoms in a compound is determined using the (M+1)⁺• peak Difficulty: Medium 90.

Provide a molecular formula that is consistent with the given mass spectral data. M+• at m/z = 136, relative height = 65.6% (M+1)+ • at m/z = 137, relative height = 6.2%

A. B. C. D. E.

C9H20O C9H12O C8H16O C8H12O C9H14O

Answer: B Learning Objective: 14.10 Describe how the number of carbon atoms in a compound is determined using the (M+1)⁺• peak Difficulty: Hard 91.

Provide a molecular formula that is consistent with the given mass spectral data. M+• at m/z = 167, relative height = 50.0% (M+1)+ • at m/z = 168, relative height = 4.4%

A. B. C. D. E.

C8H9NH2 C9H18NO3 C9H9Br C8H9NO3 C8H18NO3

Answer: D Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Hard 92.

Compounds containing chlorine or bromine usually show a strong _____ peak.

A. B. C.

molecular ion base M+1

D. E.

M+2 all of these

Answer: D Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 93. Which of the chemicals shown produces M+• and (M+2)+• peaks of equal intensity? A. B. C. D. E.

nitrogen chlorine bromine oxygen B and C

Answer: C Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 94.

Which of the chemicals shown produce an (M+2)+ • peak one third the intensity of the M+• peak?

A. B. C. D. E.

nitrogen chlorine bromine oxygen B and C

Answer: B Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 95.

Why does bromine produce M+• and (M+2)+• peaks of equal intensity on a mass spectrum?

A. B. C. D.

The 81Br isotope has higher natural abundance than 79Br isotope The 79Br and 81Br isotopes have almost equal natural abundance The 79Br isotope has higher natural abundance than 81Br isotope none of these

Answer: B Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 96.

Which molecular formula is consistent with the given mass spectral data? M+• at m/z = 78, relative height = 23.5% (M+1)+• at m/z = 79, relative height = 0.78% (M+2)+• at m/z = 80, relative height = 7.5%

A. B. C. D. E.

C6 H6 C3H7Cl C6 H8 C6H9Cl none of these

Answer: B Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 97.

Which molecular formula is consistent with the given mass spectral data? M+• at m/z = 108, relative height = 61.5% (M+1)+• at m/z = 109, relative height = 1.5% (M+2)+• at m/z = 110, relative height = 61.3%

A. B. C. D. E.

C2H5Br C5H12Cl C8H12 C2H7Br none of these

Answer: A Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 98.

For which of the given compounds will the (M+2)+• peak intensity be around one third the intensity of the molecular ion peak?

A. B.

CH3CH2CH2Br CH3CH2CH2OH

C. D. E.

CH3CH2CH2Cl CH3CH2CH2NH2 none of these

Answer: C Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 99.

For which of the given compounds will the (M+2)+• peak intensity be equal to the intensity of the molecular ion peak?

A. B. C. D. E.

CH3CH2CH2Br CH3CH2CH2OH CH3CH2CH2Cl CH3CH2CH2NH2 none of these

Answer: A Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 100. I

Which of the four mass spectra shown is consistent with the presence of bromine in a compound?

III

Four spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology

B. C. D. E.

II III IV none of these

Answer: A Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 101. I

III

Which of the four mass spectra is consistent with the presence of chlorine in a compound?

Four spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV none of these

Answer: E Learning Objective: 14.11 Describe how the height of the (M+2)⁺• peak is affected by the presence of bromine or chlorine atoms Difficulty: Medium 102.

Which of the given compounds produces a prominent (M-18) peak in the mass spectrum?

A. B.

2-methylheptane 1-heptanol

C. D. E.

heptanamine heptanal none of these

Answer: B Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 103.

Which of the given compounds produces a prominent (M-15) peak in the mass spectrum?

A. B. C. D. E.

2-methylheptane 1-heptanol heptanamine 1-chloroheptane none of these

Answer: A Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 104.

Which of the choices is not a prominent peak in the mass spectrum of 2-methyl2-pentanol?

A. B. C. D. E.

(M-15) (M-18) (M-29) (M-16) none of these

Answer: D Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 105.

Which of the given compounds has a prominent peak at (M-127)?

A. B. C. D.

CH3CH2CH2I (CH3CH2)3CCH2Cl (CH3)3CCH2CH2Br (CH3)2CHCH(CH3)2

none of these

Answer: A Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 106.

Which of the given compounds has a base peak at m/z = 43?

A. B. C. D. E.

CH3CH2CH2CH2CH2CH3 (CH3CH2)2CHCH3 (CH3)3CCH2CH3 (CH3)2CHCH(CH3)2 none of these

Answer: D Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 107.

Which of the choices given is the base peak in the mass spectrum of 2,2,4trimethylpentane?

A. B. C. D. E.

114 57 42 29 none of these

Answer: B Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 108.

Which of the choices given is expected to be the base peak in the mass spectrum of CH3(CH2)4OH?

A. B. C. D. E.

88 55 42 31 none of these

Answer: C Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 109.

Which of the choices given is expected to be the base peak in the mass spectrum of 2-methyl-2-butanol?

A. B. C. D. E.

73 55 43 31 59

Answer: E Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 110.

Which of the choices given is expected to be the base peak in the mass spectrum of CH3CH2NH2?

A. B. C. D. E.

15 28 30 45 none of these

Answer: C Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 111. Provide the structures of the fragments that result when the molecular ion of 2heptanone undergoes fragmentation via McLafferty rearrangement.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 112.

Provide the structure of the major fragment that results when the molecular ion of (CH3)2CHCH2CH2NH2 undergoes fragmentation.

A. B.

I II

C. D. E.

III IV V

Answer: B

Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 113.

Provide the structure of the major fragment that results when the molecular ion of CH3CH2CH2CH2OH undergoes fragmentation via alpha cleavage.

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 114.

Which of the choices given is expected to be the base peak in the mass spectrum of pentanal?

A. B. C. D. E.

29 41 44 58 86

Answer: C Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 115.

Which one of the given compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

CH3CH2CH(CH3)2 CH3CHOHCH2CH3 CH3CH2OCH2CH3 CH3CH2NHCH2CH3 CH3CH2CH2CH3

Answer: D Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 116.

Which one of the given compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

CH3CH2CH(CH3)2 CH3CHOHCH2CH3 CH3CH2OCH2CH3 CH3CH2NHCH2CH3 CH3CH2CH2CH3

Answer: B Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 117.

Which one of the given compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

CH3CH2CH(CH3)2 CH3CHOHCH2CH3 CH3CH2OCH2CH3 CH3CH2NHCH2CH3 CH3CH2CH2CH3

Answer: A Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 118.

Which one of the given compounds is consistent with the mass spectrum below?

SDBS:

A. B. C. D. E.

(CH3CH2CH2)2CH CH3CH2CHOHCH2CH2CH3 (CH3CH2CH2)2O (CH3CH2CH2)2NH CH3CH2CH2CH3

Answer: D Learning Objective: 14.12 Describe the characteristic fragmentation patterns of alkanes, alcohols, amines, aldehydes, and ketones Difficulty: Medium 119.

High-resolution mass spectrometry is used to determine the _____ of a compound.

A. B. C. D. E.

degree of unsaturation molecular formula molecular weight B and C none of these

Answer: D

Learning Objective: 14.13 Identify the characteristic of an organic compound that can be determined with high resolution mass spectrometry Difficulty: Easy 120.

How can you distinguish between the given compounds using high-resolution mass spectrometry?

A. B. C. D. E.

Compound I: m/z at 103.0678; Compound II: m/z at 103.0235 Compound I: m/z at 102.0678; Compound II: m/z at 102.0235 Compound I: m/z at 102.0235; Compound I: m/z at 102.0678 Compound I: m/z at 103.0235; Compound II: m/z at 102.0678 Compound I: m/z at 102.0678; Compound II: m/z at 103.0235

Answer: B Learning Objective: 14.13 Identify the characteristic of an organic compound that can be determined with high resolution mass spectrometry Difficulty: Medium 121.

How can you distinguish between the given compounds using high-resolution mass spectrometry?

A. B. C. D. E.

Compound I: m/z at 98; Compound II: m/z at 99 Compound I: m/z at 99.1092; Compound II: m/z at 99.0729 Compound I: m/z at 99.0729; Compound II: m/z at 99.1092 Compound I: m/z at 98.1092; Compound II: m/z at 98.0729 Compound I: m/z at 98.0729; Compound II: m/z at 98.1092

Answer: E Learning Objective: 14.13 Identify the characteristic of an organic compound that can be determined with high resolution mass spectrometry

Difficulty: Medium 122.

GC-mass spectrometry is used to find the _________ of each compound in a __________.

A. B. C. D. E.

molecular formula, mixture of alkanes molecular weight, mixture of compounds molecular formula, mixture of compounds B and C none of these

Answer: B Learning Objective: 14.14 Describe the functions of a gas chromatograph–mass spectrometer (GC-MS) Difficulty: Medium 123.

A stationary phase separates the components of a mixture based on their _____________ and __________ .

A. B. C. D. E.

boiling points, their affinity for the stationary phase melting points, their repulsion for the stationary phase molecular weights, melting points solubility in water, in methanol heat of vaporization, heat of sublimation

Answer: A Learning Objective: 14.14 Describe the functions of a gas chromatograph–mass spectrometer (GC-MS) Difficulty: Easy 124.

Define retention time.

A. B. C. D. E.

the amount of time that the substance takes to boil the amount of time that the substance takes to melt the amount of time required to exit from the mass spectrometer the amount of time required to exit from the gas chromatograph the amount of time required to set up the GC-MS

Answer: D Learning Objective: 14.14 Describe the functions of a gas chromatograph–mass spectrometer (GC-MS) Difficulty: Easy

125.

Electrospray ionization is used to obtain mass spectra of proteins because:

A. B. C. D.

it allows for faster fragmentation of the molecular ion the molecular ion usually does not undergo fragmentation it allows for slow fragmentation of the molecular ion the proteins are liquids

Answer: B Learning Objective: 14.15 Explain how large biomolecules are ionized for analysis by mass spectrometry Difficulty: Medium 126.

Identify the medical application that does not use mass spectrometry.

A. B. C. D. E.

cancer detection metabolic defects in babies pathogenic bacteria drug analysis all of these applications use mass spectrometry

Answer: E Learning Objective: 14.15 Explain how large biomolecules are ionized for analysis by mass spectrometry Difficulty: Easy 127.

Calculate the degree of unsaturation for C9H11N.

A. B. C. D. E.

4 6 2 5 3

Answer: D Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Easy 128.

Calculate the degree of unsaturation for C14H14N2O.

A. B.

4 6

C. D. E.

8 10 9

Answer: E Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Easy 129.

Calculate the degree of unsaturation for C11H8ClBrO.

A. B. C. D. E.

4 6 7 8 10

Answer: C Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Easy 130.

Calculate the degree of unsaturation for C5H5Br2NO.

A. B. C. D. E.

4 6 2 3 7

Answer: D Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Medium 131.

Which of the compounds shown have the same degree of unsaturation?

A. B.

I and II I and III

C. D. E.

III and IV II and III none of these

Answer: B Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Medium 132.

Propose a possible structure for a compound with molecular formula C6H5Br.

A. B. C. D. E.

I II III IV V

Answer:

Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Medium 133.

Propose all possible structures for a compound with molecular formula C4H9N that shows two medium absorptions at 3400 cm-1 and no absorption in the range of 1600 – 1800 cm-1 in its IR spectrum.

A. B. C.

I II III

D. E.

I and II I, II, III, and IV

Answer: C

Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Medium 134.

Propose possible structure(s) for a compound with molecular formula C4H7N that shows absorption at 2250 cm-1 in its IR spectrum.

A. B. C. D. E.

CH3CH2CH2C≡N CH3NHC≡CCH3 (CH3)2CHC≡N A and B A and C

Answer: E Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Medium 135.

Propose a possible structure for a compound with molecular formula C7H12O2 that shows absorption at 1720 cm-1 and no absorption in the range of 1500 – 1700 cm-1 or 2600 – 2800 cm-1 in its IR spectrum.

A. B. C. D. E.

I II III I and II II and III

Answer: A

Learning Objective: 14.16 Discuss the degree of unsaturation of a compound and explain the HDI and how it is useful Difficulty: Medium 136.

Based on the given IR spectrum and mass spectrum of an unknown compound, what is a possible structure for the unknown compound?

SDBS:

A. B. C. D. E.

(CH3CH2CH2)3C (CH3CH2)2NH (CH3CH2CH2)2NH CH3C(O)CH2NH CH3CH2CH2CH2CH2CH2NH

Answer: C Learning Objective: Integrated Spectroscopy

Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 15 1.

NMR is an abbreviation for ____________ ____________ __________.

A. B. C. D. E.

Nuclide magnetic resonance Nuclear magnetic resonance Nuclear magnetic repetition Nuclide manipulation resonance Nuclear manipulation repetition

Answer: B Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Easy 2.

List the most common nuclei that are used in NMR.

A. B. C. D. E.

H and 14C 1 H and 13C 2 H and 14C 3 H and 13C 3 H and 14C

Answer: D Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Easy 3.

Identify the nuclei that cannot be analyzed by NMR.

A. B. C. D. E.

N C 19 F 31 P 1 H 14

Answer: B Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Easy

Which of the nuclei given cannot be analyzed by an NMR spectrometer?

A. B. C. D. E.

nucleus with odd number of protons & odd number of neutrons nucleus with odd number of protons &even number of neutrons nucleus with even number of protons & odd number of neutrons nucleus with even number of protons & even number of neutrons none of these

Answer: D Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Easy 5.

How many nuclear spin states are possible for the 1H nucleus?

A. B. C. D. E.

1 2 4 5 none of these

Answer: B Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Easy 6. Which of the types of electromagnetic radiation shown is used in NMR spectroscopy? A. B. C. D. E.

UV IR visible γ-rays radio wave

Answer: E Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Easy 7. A.

_______ protons experience a net magnetic field strength that is smaller than the applied magnetic field. Deshielded

B. C. D. E.

Shielded Paramagnetic Diamagnetic none of these

Answer: B Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Medium 8.

_______ protons experience a net magnetic field strength that is higher than that experienced by _____ protons.

A. B. C. D. E.

Deshielded, shielded Shielded, deshielded Paramagnetic, diamagnetic Shielded, diamagnetic none of these

Answer: A Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible Difficulty: Medium 9.

Which of the statements given is true about the relationship between the energy gap (∆E) between the spin states for a 1H nucleus and the strength of the external magnetic field?

A. B. C. D. E.

they are inversely proportional they are directly proportional there is no relationship the magnetic field is slightly less none of these

Answer: B Learning Objective: 15.2 Describe how NMR spectrometers work and the process of preparing a sample for NMR spectral analysis Difficulty: Medium 10.

The strength of the magnetic field is a determining factor for the range of _______that must be used for NMR spectrometer.

temperature

B. C. D. D.

frequencies tesla spin states none of these

Answer: B Learning Objective: 15.2 Describe how NMR spectrometers work and the process of preparing a sample for NMR spectral analysis Difficulty: Medium 11.

Which of the solvents given is not commonly used for acquiring a 1H NMR spectrum?

A. B. C. D. E.

CDCl3 CCl4 CD3CN CH3OH D2 O

Answer: D Learning Objective: 15.2 Describe how NMR spectrometers work and the process of preparing a sample for NMR spectral analysis Difficulty: Easy 12.

Which of the statements given is true about the number of signals in a 1H NMR spectrum?

A. B. C. D. E.

it indicates the number of neighboring protons it indicates the electronic environment of neighboring protons it indicates the number of different kinds of protons it indicates the electronic environment of absorbing protons it indicates the number of protons in the signal

Answer: C Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum Difficulty: Easy 13.

Which of the statements given is true about the location of signals in a 1H NMR spectrum?

A. B.

it indicates the number of neighboring protons it indicates the electronic environment of neighboring protons

C. D. E.

it indicates the number of different protons it indicates the electronic environment of absorbing protons it indicates the number of protons in the signal

Answer: D Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum Difficulty: Easy 14.

Which of the statements given is true about the area under each signal in a 1H NMR spectrum?

A. B. C. D. E.

it indicates the number of neighboring protons it indicates the electronic environment of neighboring protons it indicates the number of different protons it indicates the electronic environment of absorbing protons it indicates the relative number of protons in the signal

Answer: E Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum Difficulty: Easy 15.

Which of the statements given is true about the shape (multiplicity) of the signal in a 1H NMR spectrum?

A. B. C. D. E.

Answer: A Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum Difficulty: Easy 16.

In an NMR spectrometer, the receiver coil records a complex signal, called a ________________, which is converted into a spectrum via a mathematical technique called a ____________________.

A. B.

free induction decay; NMR transformation free induction decay; Fourier transformation

C. D. E.

continuous wave induction; Fourier transformation chemically equivalent induction, NMR transformation chemically equivalent induction, Fourier transformation

Answer: B Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum Difficulty: Easy 17.

Which of the type(s) of protons given are chemically non-equivalent?

A. B. C. D. E.

homotopic enantiotopic diastereotopic A&B B&C

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 18.

Which of the type(s) of protons give are chemically equivalent?

A. B. C. D. E.

homotopic enantiotopic diastereotopic A&B B&C

Answer: D Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Easy 19.

Protons Ha and Hb in compound given are _________.

A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: A Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Easy 20.

Protons Ha and Hb in the compound given are _________.

A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: B Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 21.

Protons Ha and Hb in the compound given are _________.

Ha Hb

A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 22.

Protons Ha and Hb in the compound given are _________.

Ha A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 23.

Protons Ha and Hb in the compound given are _________.

Hb A.

homotopic

B. C. D. E.

enantiotopic diastereotopic mesotopic none of these

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 24.

Protons Ha and Hb in the compound given are _________.

Ha Hb

A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 25.

Protons Ha and Hb in the compound given are _________.

NH 2 Ha Hb

A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 26.

Protons Ha and Hb in the compound given are _________.

Hb O

O A. B. C. D. E.

homotopic enantiotopic diastereotopic mesotopic none of these

Answer: A Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 27.

How many signals would you expect in the 1H NMR spectrum of CH3OCH2CH3?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

Difficulty: Medium 28.

How many signals would you expect in the CH3OCH2CH2OCH3?

A. B. C. D. E.

1 2 3 4 5

H NMR spectrum of

Answer: B Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 29.

How many signals would you expect in the (CH3)2CHCH2CH2CH3?

A. B. C. D. E.

1 2 3 4 5

H NMR spectrum of

Answer: E Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 30.

How many signals would you expect in the HOCH2CH2CH2CH2OH?

A. B. C. D. E.

1 2 3 4 5

Answer: C

H NMR spectrum of

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 31.

How many signals would you expect in the 1H NMR spectrum of the compound shown?

A. B. C. D. E.

4 5 6 7 8

Answer: D Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 32.

How many signals would you expect in the 1H NMR spectrum of the compound shown?

O O A. B. C. D. E.

4 5 6 7 8

Answer: B

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 33.

How many signals would you expect in the 1H NMR spectrum of the compound shown?

A. B. C. D. E.

4 5 6 7 9

Answer: D Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 34.

How many signals would you expect in the 1H NMR spectrum of the compound shown?

O O

A. B. C. D. E.

3 4 5 6 7

Answer: A Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 35.

How many signals would you expect in the 1H NMR spectrum of the compound given?

O Cl

Answer: 6 Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium 36.

How many signals would you expect in the 1H NMR spectrum of the compound given?

A. B. C. D. E.

3 4 5 6 7

Answer: A Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent Difficulty: Medium

37.

The 1H NMR spectrum of bromoethane shows a signal at 3.5 ppm when the spectrum is recorded using a 60 MHz spectrometer. Where do you expect to see the signal if a 300 MHz instrument is used instead?

A. B. C. D. E.

3.5 ppm 7.5 ppm 6.8 ppm 5.8 ppm none of these

Answer: A Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 38.

______is used as a reference for recording NMR spectra and is assigned a chemical shift value of zero.

A. B. C. D. E.

Tetramethylsilene 13 C Benzene CCH4 CCl4

Answer: A Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Easy 39.

Which of the indicated protons in the following compound would appear farthest downfield in the 1H NMR spectrum given?

III OH I II A. B. C.

I II III

Answer: D Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 40.

Which of the indicated protons in the following compound would appear farthest upfield in the 1H NMR spectrum given?

III OH I II A. B. C. D.

I II III IV

Answer: A Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 41.

Which of the indicated protons in the compound given would appear farther downfield in the 1H NMR spectrum?

III

H H

IV CH3

V H

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Hard 42.

Which of the indicated protons in the following compound would appear farthest upfield in the 1H NMR spectrum?

O O

I A. B. C. D. E.

I II III IV I and III

Answer: A

F III

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Hard 43.

Which of the following is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the compound shown?

HO II A. B. C. D. E.

III

I = 3.7 ppm, II = 2.7 ppm, III = 1.9 ppm I = 3.7 ppm, II = 2.2 ppm, III = 1.9 ppm I = 3.9 ppm, II = 2.7 ppm, III = 1.9 ppm I = 3.9 ppm, II = 2.2 ppm, III = 2.4 ppm none of these

Answer: C Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 44.

Which of the choices given is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound?

II O

O I A. B. C.

III

I = 3.9 ppm, II = 4.2 ppm, III = 2.2 ppm, IV = 3.4 ppm I = 3.4 ppm, II = 2.2 ppm, III = 2.2 ppm, IV = 3.4 ppm I = 3.4 ppm, II = 2.2 ppm, III = 4.2 ppm, IV = 3.4 ppm

D. E.

I = 3.4 ppm, II = 4.2 ppm, III = 4.2 ppm, IV = 3.4 ppm none of these

Answer: D Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 45.

Which of the choices given is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound?

III

O O

II A. B. C. D. E.

I = 0.9 ppm, II = 1.8 ppm, III = 4.2 ppm, IV = 1.9 ppm I = 0.9 ppm, II = 1.2 ppm, III = 3.7 ppm, IV = 1.9 ppm I = 0.9 ppm, II = 1.7 ppm, III = 3.4 ppm, IV = 2.4 ppm I = 0.9 ppm, II = 1.7 ppm, III = 3.4 ppm, IV = 1.9 ppm none of these

Answer: A Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 46.

Which of the choices given is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound?

III

O II IV

A. B. C. D. E.

I=0.9 ppm, II=2.7 ppm, III=1.2 ppm, IV=0.9 ppm I=1.1 ppm, II=3.2 ppm, III=1.4 ppm, IV=0.9 ppm I=0.9 ppm, II=1.7 ppm, III=1.2 ppm, IV=1.1 ppm I=0.9 ppm, II=1.9 ppm, III=3.4 ppm, IV=0.9 ppm none of these

Answer: B Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 47.

Predict the chemical shifts for the signals in the 1H NMR spectrum for the given compound.

O O O I

A. B. C. D. E.

I II III IV V

Answer: V

III

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Hard Predict the chemical shifts for the signals in the 1H NMR spectrum for the following compound.

48.

O O

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Hard 49.

Aromatic protons produce signals in the range of 7 – 8 ppm, due to the _________effect of p electrons

A. B. C. D. E.

diamagnetic anisotropy paramagnetic anisotropy diamagnetic isotropy paramagnetic isotropy none of these

Answer: A Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium 50.

Which of the protons shown appear farthest upfield in the 1H NMR spectrum?

III

H IV I

A. B. C. D. E.

I II III IV none of these

Answer: D Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups Difficulty: Medium

51. A compound with molecular formula C8H14 has the 1H NMR spectrum shown. Which choices shows the correct number of protons giving rise to each signal?

I III

A. B. C. D.

4 PPM

I – 3H, II – 9H, III – 2H I – 2H, II – 9H, III – 3H I – 4H, II – 6H, III – 4H I – 3H, II – 6H, III – 2H

Answer: A Learning Objective: 15.6 Define integration, and explain what it indicates Difficulty: Medium 52.

A compound with molecular formula C6H11N has the 1H NMR spectrum shown. Which choices shows the correct number of protons giving rise to each signal?

I II III

I – 6H, II – 3H, III – 2H

4 PPM

B. C. D.

I – 5H, II – 4H, III – 2H I – 6H, II – 4H, III – 1H I – 1H, II – 4H, III – 6H

Answer: C Learning Objective: 15.6 Define integration, and explain what it indicates Difficulty: Medium 53.

A compound with molecular formula C8H10O has the 1H NMR spectrum shown. Which of the choices shows the correct number of protons giving rise to each signal?

I III

SDBS: National Institute of Advanced Industrial Science and Technology

Answer: I – 3H, II – 2H, III – 3H, IV – 2H Learning Objective: 15.6 Define integration, and explain what it indicates Difficulty: Medium 54.

What is the structure of a molecule with that has an integration of 6H, 2H, 1H, and 1H?

A. B. C. D. E

CH3CH(OH)CH(CH3)2 CH3CH2OCH2CH3 CH3C(O)CH2CH2CH3 (CH3)2C(OH)CH3 (CH3)2CHCH2OH

Answer: E Learning Objective: 15.6 Define integration, and explain what it indicates Difficulty: Medium

55.

What is the structure of a molecule with that has an integration of 9H, 3H, 1H?

A. B. C. D. E.

CH3CH2CH2CH2CH2CH2CH2CH2NH2 CH3)3CH2COOH (CH3)3CH2COOH (CH3)3CNHCH3 (CH3)2CHOCH2CH3

Answer: D Learning Objective: 15.6 Define integration, and explain what it indicates Difficulty: Medium 56.

What is the structure of a molecule that has an integration of 3H, 2H, 2H, and 2H?

A. B. C. D. E.

CH3CH2COOCH2Br CH3CH(Br)CH2CH3 BrCH2CH(CH3)CH2COOH CH3CH2CH2CH2Br ClCH2CH2CH2Br

Answer: D Learning Objective: 15.6 Define integration, and explain what it indicates Difficulty: Medium 57.

Which of the compounds shown gives a 1H NMR spectrum consisting of only a singlet?

A. B. C. D. E.

1,1-dichloropropane 1,3-dichloropropane 1,2-dichloropropane 2,2-dichloropropane 1-chloropropane

Answer: D Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 58.

How many 1H NMR signals does 2-chloro-3-methyl-2-butene exhibit?

B. C. D. E.

2 3 4 5

Answer: C Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 59.

Which of the compounds shown displays two triplets and a singlet in its 1H NMR spectrum?

A. B. C. D. E.

CH3CH(OCH3)2 CH3OCH2CH2OCH3 CH3OCH2CH(OH)CH3 CH3OCH2CH2CH2CH2OCH3 CH3CH2OCH2CH3

Answer: D Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 60.

Which of the compounds shown displays only two singlets in its 1H NMR spectrum?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 61.

Which of the compounds shown displays only three singlets in its 1H NMR spectrum?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 62.

Which of the compounds shown displays a singlet, a triplet and a quartet in its 1H NMR spectrum?

A. B. C. D. E.

2-chloro-4-methylpentane 3-chloro-2-methylpentane 3-chloropentane 1-chloro-2,2-dimethylbutane 3-chloro-3-methylpentane

Answer: E Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 63.

Determine the multiplicity of each signal in the expected 1H NMR spectrum of the compound shown.

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 64.

Determine the multiplicity of each signal in the expected 1H NMR spectrum of the compound shown.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 65.

Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 66.

Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 67.

Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 68.

Predict the multiplicity of each signal in the expected 1H NMR spectrum of 2,3dimethyl-2-pentanol.

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 69.

Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 70.

The coupling constant (J) for bromoethane is 7 Hz when the 1H NMR spectrum is acquired at 250 MHz. What is the coupling constant between these protons when the spectrum is acquired at 500 MHz?

A. B. C. D. E.

3.5 Hz 7 Hz 14 Hz 21 Hz 1 Hz

Answer: B Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 71.

Which of the following is the maximum multiplicity observed for Hc protons in the compound shown? Assume that the Jcd and Jcb values are different.

A. B. C. D. E.

5 6 8 12 none of these

Answer: B Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 72.

Which of the following is the maximum multiplicity observed for Hb protons in the compound shown? Assume that the Jab and Jbc values are different.

A. B. C. D. E.

9 12 21 24 none of these

Answer: A Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 73.

Which of the following Jab values is consistent with the structure shown?

A. B. C. D. E.

1.2 Hz 6.5 Hz 17 Hz 20 Hz 11 Hz

Answer: B Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 74.

Which of the following Jac values is consistent with the structure shown?

A. B. C. D. E.

1.2 Hz 6.5 Hz 17 Hz 20 Hz 11 Hz

Answer: C Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 75.

Which of the following Jbc values is consistent with the structure shown?

A. B. C. D. E.

1.2 Hz 6.5 Hz 14 Hz 20 Hz none of these

Answer: A Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 76.

Presence of which of the following protons is confirmed by D2O exchange?

A. B. C. D. E.

OH NH2 CH A&B none of these

Answer: D Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 77.

The 1H NMR spectrum of 1-propanol displays a singlet for the OH proton instead of a triplet. Explain why.

A. This is typical of all protons bound to oxygen.

B. 1-propanol is too small for coupling to occur. C. 1-propanol molecules rapidly exchange the OH proton, which prevents splitting D. The signal for the OH proton is out of the normal range of the 1H NMR spectrum, meaning that it is not usually visible. E. OH does not generate a proton signal due to the highly electronegative nature of oxygen. Answer: C A rapid exchange of the OH proton between 1-propanol molecules does not allow for splitting of the signal. Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Medium 78.

Ethanamine (CH3CH2NH2) experiences a rapid exchange of NH2 protons. How do you predict that this affects the 1H NMR spectrum? of ethanamine?

A. Like other molecules with nitrogen, the electronegativity of nitrogen prevents NH2 protons from producing a signal. B. NH2 protons are exchanged too rapidly for splitting to occur, so a singlet is produced. C. Like many other molecules with NH2, ethanamine is highly unstable and produces a variable proton NMR signal. D. The NH2 protons should produce a standard NMR signal despite this rapid exchange. E. The effects on the NMR spectrum depend on whether an oxygen is nearby, so it is impossible to predict whether the rapid exchange would affect their signal. Answer: C Learning Objective: 15.7 Describe spin-spin splitting and multiplicity Difficulty: Hard 79.

How would the 1H NMR spectrum of an alcohol be affected by the addition of D2O to replace the OH protons with D atoms?

A. B. C. D. E.

The chemical shift of the absorption would move to the left. The chemical shift of the absorption would move to the right. The OH absorption would disappear. The absorption would become a narrow, rather than a broad, peak. The absorption would become a broad, rather than a narrow, peak.

Answer: C Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

Difficulty: Hard 80.

Determine the multiplicity and predict the chemical shifts of the four signals in the expected 1H NMR spectrum of the following compound.

A. B. C. D.

I II III IV

Answer: A

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound Difficulty: Medium

81.

Determine the multiplicity and predict the chemical shifts of each signal in the expected 1H NMR spectrum of the following compound.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound Difficulty: Medium 82.

Determine the multiplicity and predict the chemical shifts of each signal in the expected 1H NMR spectrum of the following compound.

A. B. C. D.

I II III IV

Answer: D

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound Difficulty: Medium 83.

How would you use 1H NMR spectroscopy to distinguish between the two compounds shown?

A. B. C. D. E.

I = 3 and II = 2 signals I = 4 and II = 3 signals I = 5 and II = 3 signals I = 5 and II = 4 signals I = 3 and II = 4 signals

Answer: B Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy Difficulty: Medium 84.

How would you use 1H NMR spectroscopy to distinguish between the two compounds shown?

A. B. C. D. E.

The compounds will have different numbers of signals. Compound II will have a singlet with a higher chemical shift. Compound I will have a triplet, a quartet, and a singlet. Compound II will have a singlet, a triplet, and a quintet. C and D are correct.

Answer: E Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy Difficulty: Medium 85.

How would you use 1H NMR spectroscopy to distinguish between the following compounds?

A. The compounds will have different numbers of signals. B. Compound I will have a doublet, a septet, two triplets, and a sextet. singlet with a higher chemical shift. C. Compound I will have two doublets, two triplets, and a multiplet. D. Compound II will have a doublet, a multiplet, a quartet, and a triplet. E. Both compounds will have almost identical signals but only compound I will have a multiplet. Answer: B Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy Difficulty: Medium 86.

How would you use 1H NMR spectroscopy to distinguish between the following compounds?

A. The compounds will have different numbers of signals. B. The proton bonded to C bonded to 2 CH3 to the right will be farther downfield in the spectrum of compound I versus the spectrum of compound II. C. The proton bonded to C bonded to 2 CH3 to the right will be farther downfield in the spectrum of compound I versus the spectrum of compound II. D. The entire spectrum of compound I will be shifted downfield from the spectrum of compound II. E. The spectra will be identical, so the compounds cannot be distinguished based solely on their NMR spectra. Answer: B Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 87.

A compound with a molecular formula C9H12 has the 1H NMR spectrum below. Which structures given is consistent with this spectrum?

A. B. C. D. E.

4 PPM

I II III IV none of these

Answer: C Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 88. Which of the structures given is consistent with this 1H NMR spectrum?

5 1

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 89.

A compound with a molecular formula C9H10O2 has the 1H NMR spectrum shown. Which of the structures given is consistent with this spectrum?

A. B. C. D. E.

PPM

I II III IV none of these

Answer: B Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 90.

A compound with a molecular formula C8H15ClO3 has the 1H NMR spectrum given. The IR spectrum shows a strong absorption at 1800 cm-1. Which of the structures shown is consistent with this spectrum?

A. B. C. D. E.

PPM

I II III IV none of these

Answer: D Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 91. A compound with a molecular formula C5H11NO has the 1H NMR spectrum given. The IR spectrum shows an absorption at around 3400 cm-1. Which of the structures given is consistent with this spectrum?

3 2

1 exchanges with D2O

A. B. C. D. E.

PPM

I II III IV none of these

Answer: B Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 92. A compound with a molecular formula of C5H10O has the 1H NMR spectrum shown. Which structure shown is consistent with this spectrum?

1 10

PPM

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 93.

Propose a structure for a compound, with molecular formula C5H11Cl, that fits the following spectroscopic data:

H NMR: 0.9 d (triplet, 3H), 1.3 d (sextet, 2H), 1.5 d (quartet, 2H), 1.6 d (doublet, 3H), 3.6 d (sextet, 1H) 1

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 94.

Propose a structure for a compound, with molecular formula C8H14O3, that fits the following spectroscopic data:

IR: 1820cm-1, 1760cm-1 1 H NMR: 1.0 d (triplet, 6H), 1.6 d (sextet, 4H), 2.2 d (triplet, 4H)

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 95.

Propose a structure for a compound, with molecular formula C10H12O, that fits the following spectroscopic data:

IR: 1680 cm-1 1 H NMR: 1.0 d (triplet, 3H), 1.5 d (sextet, 2H), 2.6 d (triplet, 2H), 7.4 d (triplet, 2H), 7.5 d (triplet, 1H), 7.9 d (doublet, 2H)

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 96.

A compound with a molecular formula of C8H16O has the following 1H NMR spectrum. Provide a structure that is consistent with this spectrum.

3 2

A. B. C. D. E.

PPM

I II III IV V

Answer: E Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium

97.

A compound with a molecular formula of C10H12O2 has the following 1H NMR spectrum. Which of the structures shown is consistent with this spectrum?

3 2

A. B. C. D. E.

I II III IV none of these

Answer: C

6 PPM

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum Difficulty: Medium 98.

The broadband decoupling in 13C NMR suppresses ________ splitting.

A. B. C. D. E.

C-13C C-1H 13 C-13C 13 C-1H none of these 12

Answer: D Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy Section: 15.11 Difficulty: Easy 99.

The off-resonance decoupling in 13C NMR allows for ________ splitting.

A. B. C. D. E.

C-13C C-1H 13 C-13C 13 C-1H none of these 12

Answer: D Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy Difficulty: Easy 100.

Identify the splitting pattern for a CH3 in an off-resonance decoupled 13C NMR spectrum.

A. B. C. D. E.

no peak singlet doublet triplet quartet

Answer: E Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy Difficulty: Easy

101.

Identify the splitting pattern for a CH2 in an off-resonance decoupled 13C NMR spectrum.

A. B. C. D. E.

no peak singlet doublet triplet quartet

Answer: D Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy Difficulty: Easy 102.

Identify the splitting pattern for a CH in an off-resonance decoupled 13C NMR spectrum.

A. B. C. D. E.

no peak singlet doublet triplet quartet

Answer: C Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy Difficulty: Easy 103.

Identify the splitting pattern for a C in a carbonyl group in an off-resonance decoupled 13C NMR spectrum.

A. B. C. D. E.

no peak singlet doublet triplet quartet

Answer: B Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy Difficulty: Easy

104.

How many signals would you expect to find in the 13C NMR spectrum of the compound shown?

A. B. C. D. E.

6 7 8 9 10

Answer: B Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Easy

105.

How many signals would you expect to find in the 13C NMR spectrum of the compound shown?

A. B. C. D. E.

2 3 4 5 6

Answer: C Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Medium 106.

How many signals would you expect to find in the 13C NMR spectrum of the compound shown?

A. B. C. D. E.

6 7 8 9 10

Answer: D Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Medium 107.

How many signals would you expect to find in the 13C NMR spectrum of the compounds shown?

A. B. C. D. E.

I – 5, II – 8 I – 3, II – 6 I – 4, II – 8 I – 5, II – 6 I – 3, II – 3

Answer: D Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Easy 108.

Which of the carbon atoms shown displays the signal that is the most downfield in the 13C NMR spectrum?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Medium 109.

Which of the compounds shown displays four signals in its 13C NMR spectrum?

A. B. C. D. E.

2,6-dimethylheptane 2,4-dimethylheptane 3,5-dimethylheptane 4,4-dimethylheptane 3,4-dimethylheptane

Answer: A Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Medium 110.

Which of the compounds shown displays five signals in its 13C NMR spectrum?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Medium 111.

Which of the 13C NMR chemical shifts shown corresponds to Ca in the given compound?

A. B. C. D. E.

100 – 150 ppm 200 – 220 ppm 60 – 90 ppm 45 – 60 ppm 45 – 80 ppm

Answer: A Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Medium 112. Which of the compounds shown is consistent with the given 13C NMR spectrum?

200

A. B. C. D. E.

180

160

140

120

100 PPM

I II III IV V

Answer: A Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Hard 113. Which of the compounds shown is consistent with the 13C NMR spectrum given?

A. B. C. D. E.

40 PPM

I II III IV V

Answer: D Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Hard 114. Which of the compounds shown is consistent with the 13C NMR spectrum given?

A. B. C. D. E.

30 PPM

I II III IV V

Answer: C Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Hard 115. Which of the compounds shown is consistent with the 13C NMR spectrum given?

A. B. C. D. E.

40 PPM

I II III IV V

Answer: C Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum Difficulty: Hard 116.

Which of the atoms or compounds shown displays a signal in the DEPT-90 13C NMR spectroscopy?

A. B. C. D. E.

CH3 CH2 CH C none of these

Answer: C Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Easy

117.

Which of the following atoms or compounds displays a negative signal in the DEPT-135 13C NMR spectroscopy?

A. B. C. D. E.

CH3 CH2 CH C none of these

Answer: B Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Easy 118.

Which of the following compounds or atoms does not display a signal in the DEPT-135 13C NMR spectroscopy?

A. B. C. D. E.

CH3 CH2 CH C none of these

Answer: D Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Easy 119.

Which of the following atoms or compounds does not display a signal in the DEPT-90, but displays a positive signal in DEPT-135 13C NMR spectroscopy?

A. B. C. D. E.

CH3 CH2 CH C none of these

Answer: A Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Easy

120.

Which of the compounds shown does not display a carbonyl carbon signal in the DEPT-90 and DEPT-135 13C NMR spectroscopy?

A. B. C. D. E.

I II III II and III I and II

Answer: D Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Medium 121.

A compound with the molecular formula C5H10Br2 displays the 13C NMR spectrum along with DEPT-90 and DEPT-135 13C NMR spectra. What is the structure for this compound?

DEPT-90 DEPT-135

Broadband decoupled

A. B. C. D. E.

Br2CHCH2CH2CH2CH3 BrCH2CH2CH2CH2CH2Br (CH3)3CCHBr2 (CH3)2CHCH2CBr2 BrCH2CH(Br)CH2CH2CH3

Answer: B Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Hard 122. A compound, with molecular formula C7H7Br, displays the 13C NMR spectrum shown along with the DEPT-90 and DEPT-135 13C NMR spectra. What is the structure for this compound?

DEPT-90 DEPT-135

Broadband decoupled

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy Difficulty: Hard 123.

A compound, with molecular formula C4H9Br, displays the 1H NMR spectrum shown and 13C NMR spectra. Propose a structure for this compound.

PPM

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: Integrated Spectroscopy Difficulty: Medium 124.

Which of the compounds shown, all with the molecular formula C9H18O2, is consistent with the 1H NMR and 13C NMR spectra given?

180

A. B. C. D. E.

160

140

120

100 PPM

I II III IV None of these

Answer: A Learning Objective: Integrated Spectroscopy Difficulty: Medium 125. Which of the given compounds, all with molecular formula C9H12O, is consistent with the 1H NMR and 13C NMR spectra shown?

3 2

1 exchanges with D2O

160

A. B. C. D. E.

140

I II III IV None of these

Answer: C

120

4 PPM

100

80 PPM

Learning Objective: Integrated Spectroscopy Difficulty: Medium 126. A compound with molecular formula C11H14O displays the following IR, 1H NMR and 13C NMR spectra. Which of the given structures is consistent with this data?

220

200

180

160

140

120 100 PPM

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: Integrated Spectroscopy Difficulty: Hard 127. A compound with molecular formula C7H14O2 displays the following IR, 1H NMR and 13C NMR spectra. What is a likely structure for this compound?

3 1

180

A. B. C. D. E.

160

I II III IV V

Answer: C

140

120

100 PPM

Learning Objective: Integrated Spectroscopy Difficulty: Medium 128.

A compound, with molecular formula C5H7NO2, displays the following IR, 1H NMR and 13C NMR spectra. What is a likely structure for this compound?

SDBS: National Institute of Advanced Industrial Science and Technology

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: Integrated Spectroscopy Difficulty: Hard 129.

Which compound with the molecular formula C5H10O fits the spectroscopic data given?

IR: 1720 cm-1 1 H NMR: 1.1 d (doublet, 6H), 2.1 d (singlet, 3H), 2.7 d (septet, 1H) 13 C NMR: 15, 22, 45, 210

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: Integrated Spectroscopy Difficulty: Medium 130.

Which compound with the molecular formula C8H19N fits the spectroscopic data given?

IR: 3400 cm-1 1 H NMR: 0.9 d (triplet, 6H), 1.1 d (singlet, 1H, exchanges with D2O), 1.3 d (sextet, 4H), 1.4 d (quintet, 4H), 2.6 d (triplet, 4H) 13 C NMR: 13.7, 20.5, 30.4, 49.2

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: Integrated Spectroscopy Difficulty: Medium 131.

What is a structure for a compound with molecular formula C5H12O2, that fits the following spectroscopic data?

IR: 1200 cm-1 1 H NMR: 1.4 d (singlet, 6H), 3.2 d (singlet, 6H) 13 C NMR: 28, 45, 100

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: Integrated Spectroscopy Difficulty: Hard 132.

What is an appropriate structure for structure for a compound with molecular formula C6H10O that fits the following spectroscopic data?

IR: 3400 cm-1(broad), 3250 cm-1(sharp), 2150 cm-1 1 H NMR: 1.0 d (triplet, 3H), 1.5 d (singlet, 3H), 1.6 d (quartet, 2H), 2.0 d (singlet, 1H), 2.5 d (singlet, 1H)

C NMR: 4.1, 26, 35, 67.6, 69.4

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: Integrated Spectroscopy Difficulty: Hard 133.

What is an appropriate structure for a compound with molecular formula C8H15ClO3 that fits the following spectroscopic data?

IR: 1780 cm-1, 1150 cm-1 1 H NMR: 1.1 d (triplet, 6H), 1.9 d (quartet, 2H), 2.8 d (triplet, 2H), 3.4 d (quartet, 4H), 4.2 d (triplet, 1H) 13 C NMR: 15, 31, 38, 57, 100, 173

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: Integrated Spectroscopy Difficulty: Hard 134. What is an appropriate structural formula for a compound with the molecular formula C3H6O2 that displays the following IR, 1H NMR and 13C NMR spectra?

DEPT-90

DEPT-135

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: Integrated Spectroscopy Difficulty: Medium 135.

What is an appropriate structure for a compound with the molecular formula C6H12O that displays the following IR, 1H NMR and 13C NMR spectra?

DEPT-90

DEPT-135

Broadband decoupled

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: Integrated Spectroscopy Difficulty: Medium 136.

What is an appropriate structure for a compound with the molecular formula C6H4Cl2O that displays the following IR, 1H NMR and 13C NMR spectra?

DEPT-90

DEPT-135

Broadband decoupled

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: Integrated Spectroscopy Difficulty: Medium 137.

What is an appropriate structure for a compound with the molecular formula C10H14 that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: Integrated Spectroscopy Difficulty: Medium 138. What is an appropriate structure for a compound with the molecular formula C8H11N that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

140

A. B. C. D. E.

I II III IV V

120

100

80 PPM

Answer: B

Learning Objective: Integrated Spectroscopy Difficulty: Medium 139.

SDBS

What is an appropriate structure for a compound with the molecular formula C8H14O3 that displays the following IR, 1H NMR, 13C NMR spectra?

180

A. B. C. D. E.

160

140

120

100 PPM

I II III IV V

Answer: E Learning Objective: Integrated Spectroscopy Difficulty: Medium 140. What is an appropriate structure for a compound with molecular formula C7H14O2 that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

180

160

140

120

100 PPM

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: Integrated Spectroscopy Difficulty: Hard 141. An unknown compound displays the following IR, 1H NMR, 13C NMR and mass spectra. What is a reasonable structure for this compound?

SDBS

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: Integrated Spectroscopy Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 16 1.

Dienes with p bonds separated by exactly one σ bond are classified as ______.

A. B. C. D. E.

isolated cumulated skipped conjugated terminal

Answer: D Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 2.

Dienes with adjacent p bonds are classified as ______.

A. B. C. D. E.

isolated cumulated skipped conjugated terminal

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 3.

Dienes with p bonds separated by two or more σ bonds are classified as ______.

A. B. C. D. E.

isolated cumulated skipped conjugated terminal

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 4.

Identify from the following compounds the isolated diene.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 5.

Identify from the following compounds the conjugated diene.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 6.

Identify from the following compounds those having conjugated double bonds.

II and V

B. C. D. E.

II, IV, and V I and III II and IV I, III, and IV

Answer: C Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 7.

Identify from the following compounds those having isolated double bonds.

A. B. C. D. E.

II and IV III and V I, III, and V I and V I and III

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 8.

Classify the double bonds in the following compounds as cumulated, conjugated or isolated.

A. B. C. D. E.

I = cumulated; I = cumulated; I = conjugated; I = isolated; I = conjugated;

II = conjugated II = isolated II = isolated II = cumulated II = cumulated

Answer: E Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy

Identify the cumulated diene from the following options.

A. B. C. D. E.

4-methyl-1,3-heptadiene 3-methyl-1,5-heptadiene 2-methyl-2,4-heptadiene 4-methyl-1,4-heptadiene 5-methyl-2,3-heptadiene

Answer: E Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 10.

Identify the conjugated diene from the following options.

A. B. C. D. E.

4-methyl-1,3-heptadiene 3-methyl-1,5-heptadiene 2-methyl-2,5-heptadiene 4-methyl-1,4-heptadiene 5-methyl-2,3-heptadiene

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 11.

Identify the isolated diene from the following options.

A. B. C. D. E.

4-methyl-1,3-heptadiene 3-methyl-1,5-heptadiene 2-methyl-2,4-heptadiene 4-methyl-1,2-heptadiene 5-methyl-2,3-heptadiene

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 12.

Zingiberene, a terpene found in ginger, has the structure shown below. Classify the p bonds in zingiberene as conjugated, cumulated or isolated.

A. B. C. D. E.

I = cumulated; I = isolated; I = conjugated; I = isolated; I = cumulated;

II = conjugated II = isolated II = isolated II = conjugated II = cumulated

III = cumulated III = conjugated III = cumulated III = conjugated III = isolated

Answer: D Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 13.

Vitamin D3 has the structure shown below. Classify the p bonds in vitamin D3 as conjugated, cumulated or isolated.

A. B. C. D. E.

I = isolated; I = conjugated; I = isolated; I = isolated; I = cumulated;

II = conjugated II = conjugated II = isolated II = conjugated II = cumulated

III = conjugated III = conjugated III = isolated III = conjugated III = cumulated

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 14.

What is the IUPAC name for the following compound?

A. B. C. D. E.

1-chloro-1-methyl-2,5-cyclohexadiene 3-chloro-3-methyl-1,4-cyclohexadiene 6-chloro-6-methyl-1,4-cyclohexadiene 2-chloro-2-methyl-1,3-cyclohexadiene 5-chloro-5-methyl-1,3-cyclohexadiene

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 15.

What is the IUPAC name for the following compound?

A. B. C. D. E.

(2Z,4E)-2,4-hexadiene (2E,4Z)-1,4-dimethyl-1,3-butadiene (2Z,4Z)-1,4-dimethyl-1,3-butadiene (2Z,4Z)-2,4-hexadiene (2E,4Z)-5-methyl-2,4-pentadiene

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Hard 16.

What is the IUPAC name for the following compound?

A. B. C. D. E.

(2E,4Z,6E)-3,4,7,8-tetramethyl-2,4,6-heptatriene (2Z,4E)–3,4,7-trimethyl-2,4,6-octatriene (2E,4Z,6E)-2,5,6,7-tetramethyl-3,5,7-heptatriene (2E,4Z)-2,5,6-trimethyl-3,5,7-octatriene (4E,6E)-2,5,6-trimethyl-2,4,6-octatriene

Answer: E Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Hard 17.

What is the IUPAC name for the following compound?

A. B. C. D. E.

1-isopropyl-4-methyl-1,3-cyclopentadiene 2-isopropyl-5-methyl-2,4-cyclopentadiene 4-isopropyl-2-methyl-1,3-cyclopentadiene 3-isopropyl-5-methyl-1,2-cyclopentadiene 1-isopropyl-3-methyl-1,3-cyclopentadiene

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 18.

Which of the following is the correct structure of (E)-2-methyl-1,3-pentadiene.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium 19.

Which of the following is the correct structure of (Z)-2-methyl-2,4-hexadiene.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Medium

20.

Which of the following is the correct structure of (1E,3Z)-1-methoxy-2-methyl-1,3pentadiene.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Hard 21.

Identify the structure for (S,E)-3-tert-butyl-4-methyl-1,4-hexadiene.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Hard 22.

Predict the major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Easy 23.

Predict the major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Easy 24.

Classify the following compounds as having cumulated, conjugated or isolated double bonds?

A. B. C. D. E.

I = cumulated; I = cumulated; I = conjugated; I = isolated; I = conjugated;

II = isolated II = conjugated II = isolated II = conjugated II = cumulated

Answer: D Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy 25.

Predict the major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Easy 26.

Identify the reagents necessary to carry out the following transformation.

1. Br2

2. Mg

3. H2O

B. C. D. E.

1. H2, Pd catalyst 1. HBr 1. MCPBA 1. NBS, heat

2. NBS, heat 2. (CH3)3COK 2. H3O+ 2. (CH3)3COK

Answer: E Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 27.

Identify the reagents necessary to carry out the following transformation.

A. B. C. D. E.

1. H2SO4, heat 1. PBr3 1. 1 eq. H2, Pd/C 1. SOCl2/pyridine 1. NBS, heat

2. NBS, heat 2. (CH3)3COK 2. BH3 2. Mg in ether 2. (CH3)3COK

3. (CH3)3COK 3. Br2/H2O 3. H2O2, NaOH 3. H2O

Answer: A Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 28.

Identify the reagents necessary to carry out the following transformation.

A. B. C. D. E.

1. H2, Pd/C 1. PBr3 1. Br2, hn 1. SOCl2/pyridine 1. (CH3)3COK

2. (CH3)3COK 2. (CH3)3COK 2. Mg in ether 2. NBS, heat

3. NBS, heat 3. H2O 3. (CH3)3COK

4. (CH3)3COK 4. (CH3)3COK

Answer: B Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium

29.

Which of the following indicated C—C bonds is the shortest?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Easy 30.

Which of the following indicated C—C bonds is the longest?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 31.

Which of the following dienes is most stable?

A. B. C. D. E.

CH3CH=CHCH=CHCH3 CH3CH=CHCH2CH=CH2 CH2=CHCH2CH2CH=CH2 CH2=CHCH(CH3)CH=CH2 CH3CH=C=CHCH2CH3

Answer: A Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Easy 32.

Which of the following dienes is least stable?

A. B. C. D. E.

CH3CH=CHCH=CHCH3 CH3CH=CHCH2CH=CH2 CH2=CHCH2CH2CH=CH2 CH2=CHCH(CH3)CH=CH2 CH3CH=C=CHCH2CH3

Answer: E Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Easy 33.

Which of the following dienes is least stable?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 34.

Rank the following dienes in order of increasing stability (least to most).

I < III < II

B. C. D. E.

III < II < I II < III < I II < I < III III < II < I

Answer: C Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 35.

Which one of the following dienes is most stable?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 36.

Which one of the following dienes will have the lowest heat of hydrogenation?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium

37.

Which one of the following dienes is the most stable stereoisomer in its most stable conformation?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 38.

Rank the following dienes in order of decreasing heat of hydrogenation (highest to lowest).

A. B. C. D. E.

III > I > II > IV IV > II > III > I II > III > I > IV I > II > IV > III IV > III > II > I

Answer: B Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 39.

Rank the following dienes in order of decreasing heat of hydrogenation (highest to lowest).

A. B. C. D. E.

III > I > II > IV IV > III > II > I II > III > I > IV I > II > IV > III IV > II > I > III

Answer: E Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 40.

Both s-cis and s-trans conformers of 1,3-butadiene have a continuous conjugated p system. Which of the following statements is true about the s-cis conformer?

A. B. C. D. E.

The s-cis conformer is lower in energy than the s-trans conformer The s-cis conformer is higher in energy than the s-trans conformer The s-cis conformer has equal energy as the s-trans conformer The s-cis conformer cannot be converted into the s-trans conformer The equilibrium favors the s-cis conformer

Answer: B Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 41.

Which one of the following represents the lowest energy p-bonding molecular orbital of 1,3-butadiene?

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Medium 42.

Which one of the following represents the highest energy p-antibonding molecular orbital of 1,3-butadiene?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Medium 43.

How many p -bonding molecular orbitals does 1,3-pentadiene have?

A. B. C. D. E.

1 2 3 4 5

Answer: B Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Medium 44.

How many electrons does the HOMO of 1,3-pentadiene have in its excited state?

A. B. C.

1 2 3

D. E.

4 5

Answer: A Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Medium 45.

How many electrons does the HOMO of 2,4-hexadiene have in its ground state?

A. B. C. D. E.

1 2 3 4 0

Answer: B Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Medium 46.

How many electrons does the LUMO of 2,4-hexadiene have in its ground state?

A. B. C. D. E.

1 2 3 4 0

Answer: E Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Medium 47.

Which one of the following represents the HOMO of 1,3,5-hexatriene?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Hard 48.

Which one of the following represents the LUMO of 1,3,5-hexatriene?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.3 Explain the circumstances under which a p electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs Difficulty: Hard 49.

Identify the major products possible from the following reaction?

A. B. C. D. E.

I and V II and IV III and IV I, III and VI II, IV and V

Answer: D Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 50.

Which one of the following compounds is not a product of the reaction between 1,3-butadiene and HBr?

A. B. C. D. E.

(S)-3-bromo-1-butene (R)-3-bromo-1-butene (E)-1-bromo-2-butene (Z)-1-bromo-2-butene (Z)-2-bromo-2-butene

Answer: E Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 51.

Identify the products of the 1,2-addition for the following reaction.

A. B. C. D. E.

I and III II and IV II and III I and II III and IV

Answer: D Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 52.

Identify the products of the 1,2-addition for the following reaction.

A. B. C. D. E.

I and III II and IV II and III I and II III and IV

Answer: C Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 53.

Identify the products of the 1,2-addition for the following reaction.

A. B. C. D. E.

I and III II and IV II and III I and II III and IV

Answer: D Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 54.

Identify the products of the 1,4-addition reaction of 1,3-hexadiene with Br2/CCl4.

A. B. C. D. E.

I II III I and III II and IV

Answer: A Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 55.

Identify the products of the 1,2-addition for the following reaction.

A. B. C. D. E.

I I and II III IV III and IV

Answer: A Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 56.

A thermodynamically-controlled process describes a reaction that

A. B.

generates the most stable product. generates the product whose formation requires the smallest energy of activation. generates the product requiring the fewest steps. generates the product formed at the fastest rate. generates the product favored at low temperatures.

C. D. E.

Answer: A Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Easy 57.

A kinetically-controlled process describes a reaction that

A. B.

generates the most stable product. generates the product whose formation requires the smallest energy of activation. generates the product requiring the fewest steps. generates the product formed at the slowest rate. generates the product favored at high temperatures.

C. D. E.

Answer: B Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Easy 58.

The reaction of 1,3-butadiene with a hydrohalide at 0°C will undergo a ____________ under ____________ control.

A. B C. D. E.

1,2-addition; 1,4-addition; 1,2-addition; 1,3-addition; 1,4-addition;

kinetic thermodynamic thermodynamic kinetic kinetic

Answer: A Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Easy 59.

The reaction of 1,3-butadiene with a hydrohalide at 40°C will undergo a ____________ under ____________ control.

A. B C. D. E.

1,2-addition; 1,4-addition; 1,2-addition; 1,3-addition; 1,4-addition;

kinetic thermodynamic thermodynamic kinetic kinetic

Answer: B Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Easy 60.

Identify the major product(s) for the following reaction.

A. B. C. D. E.

I II III I and II II and III

Answer: A Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Medium 61.

Identify the major product(s) for the following reaction.

A. B. C. D. E.

I II III I and II II and III

Answer: B Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Medium 62.

Identify the structure for 1,2-addition product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Medium 63.

Identify the expected major product(s) for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Medium 64.

Identify the expected major product for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Medium 65.

The polymerization of isoprene to produce synthetic rubber is a special case of ____________.

A. B C. D. E.

1,1-addition 1,2-addition 1,3-addition 1,4-addition 2,2-addition

Answer: D Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Easy 66.

The addition of a _____________ bond improves the elasticity in synthetic rubber.

A. B

ionic disulfide

C. D. E.

pi sigma hydrogen

Answer: B Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Easy 67.

Which of the following is true of pericyclic reactions?

A. B. C. D. E.

they are concerted reactions proceed via a cyclic transition state no intermediates are formed the polarity of the solvent generally does not impact the reaction rate all of these

Answer: E Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 68.

Identify the pericyclic reaction in which two pi bonds are broken and two sigma bonds are formed.

A. B. C. D. E.

sigmatropic rearrangement cycloaddition reaction electrolytic reaction Woodward-Fieser reaction polymerization reaction

Answer: B Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 69.

Identify the pericyclic reaction in which two sigma bonds are broken and two pi bonds are formed.

A. B. C. D. E.

sigmatropic rearrangement cycloaddition reaction electrolytic reaction this is not a pericyclic reaction Woodward-Fieser reaction

Answer: D Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 70.

Identify the pericyclic reaction in which one pi bond is broken and one sigma bond is formed.

A. B. C. D. E.

sigmatropic rearrangement cycloaddition reaction electrolytic reaction Woodward-Fieser reaction polymerization reaction

Answer: C Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 71.

Identify the pericyclic reaction in which no pi bonds are broken and no sigma bonds are formed.

A. B. C. D. E.

sigmatropic rearrangement cycloaddition reaction electrolytic reaction Woodward-Fieser reaction polymerization reaction

Answer: A Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 72.

What is the correct classification of the following pericyclic reaction?

A. B. C. D. E.

electrophilic addition sigmatropic rearrangement cycloaddition electrocyclic reaction nucleophilic substitution

Answer: B Learning Objective: 16.6 Identify three types of pericyclic reactions

Difficulty: Easy 73.

What is the correct classification of the following pericyclic reaction?

A. B. C. D. E.

electrophilic addition sigmatropic rearrangement cycloaddition electrocyclic reaction nucleophilic substitution

Answer: D Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 74.

What is the correct classification of the following pericyclic reaction?

A. B. C. D. E.

electrophilic addition sigmatropic rearrangement cycloaddition electrocyclic reaction nucleophilic substitution

Answer: C Learning Objective: 16.6 Identify three types of pericyclic reactions Difficulty: Easy 75.

Which statement is NOT true about the Diels-Alder reaction?

A. B. C. D. E.

It is a [4+2] cycloaddition reaction. The diene must be in the s-cis conformation to react. Most Diels-Alder reactions are reversible. It is a sigmatropic rearrangement. Electron donating groups on the diene and electron withdrawing groups on the dienophile favor product formation.

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

Difficulty: Medium 76.

The Diels Alder reaction is a concerted reaction. Define concerted.

A. B. C.

A reaction where the product contains a cyclic ring. A reaction where the diene must be in the s-cis conformation to react. A reaction where all changes in bonding (bond making and bond breaking) occur simultaneously. Another term for an endothermic reaction. A reaction where both exo and endo products are formed.

D. E.

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Easy 77.

Which of the following dienes can undergo a Diels-Alder reaction?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Easy 78.

Which of the following dienes cannot undergo a Diels-Alder reaction?

A. B. C.

I and II II and III III and IV

D. E.

I and III II and IV

Answer: E Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 79.

Which of the following dienophiles is least reactive in a Diels-Alder reaction?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 80.

Which of the following dienophiles is most reactive in a Diels-Alder reaction?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium

81.

The following diene does not undergo Diels Alder reaction because _____.

A. B. C. D. E.

it does not have an electron donating group it does not have an electron withdrawing group the bicyclic ring does not function as a diene it cannot adopt the s-cis conformation the double bonds are not in the same cyclic ring

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Easy 82.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 83.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 84.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 85.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 86.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium

87.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 88.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 89.

Identify the expected major product of the following Diels-Alder reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 90.

Compound A is one of the intermediate products in the synthesis of the corticoid hormone cortisone. Identify the structure of compound A.

B. C. D. E.

II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 91.

Identify the expected major products of the following Diels-Alder reaction.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 92.

Identify the expected major products of the following intramolecular Diels-Alder reaction.

A. B. C. D. E.

I and II III IV V and VI I, II, V and VI

Answer: A Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 93.

The following Diels-Alder reaction product is an intermediate in the synthesis of estrone. Identify the structure of the products.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: E Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 94.

The following Diels-Alder reaction product is an intermediate in the synthesis of cholesterol. Identify the structure of the product.

A. B. C. D. E.

I and II II and III III and IV I and III II and IV

Answer: B Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 95.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 96.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 97.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 98.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D.

I II III IV

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 99.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Medium 100.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 101.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 102.

Classify the following compounds as having cumulated, conjugated or isolated double bonds?

A. B. C. D. E.

I = isolated; I = cumulated; I = conjugated; I = cumulated; I = conjugated;

II = conjugated II = isolated II = isolated II = conjugated II = cumulated

Answer: A Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy

103.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 104.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 105.

The following product shown in the box is formed by an intramolecular DielsAlder reaction. Identify the structure of the starting compound.

A. B. C. D.

I II III IV

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 106.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 107.

Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 108.

Identify the Molecular Orbitals that react to form cyclohexene in a Diels-Alder reaction.

A. B. C. D. E.

HOMO of 1,3-butadiene and LUMO of ethylene LUMO of 1,3-butadiene and LUMO of ethylene HOMO of 1,3-butadiene and HOMO of ethylene LUMO of 1,3-butadiene and LUMO of 1,3-butadiene HOMO of 1,3-butadiene and HOMO of 1,3-butadiene

Answer: A Learning Objective: 16.8 Describe the Diels-Alder and other cycloaddition reactions in terms of molecular orbitals Difficulty: Medium

109.

Classify the following compounds as having cumulated, conjugated or isolated double bonds?

A. B. C. D. E.

I = isolated; I = cumulated; I = conjugated; I = cumulated; I = conjugated;

II = conjugated II = conjugated II = isolated II = isolated II = cumulated

Answer: B Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes. Difficulty: Easy

110.

Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

A. B. C. D. E.

disrotatory; conrotatory: disrotatory: conrotatory; disrotatory;

cis-3,4-diethylcyclobutene cis-3,4-diethylcyclobutene trans-3,4-diethylcyclobutene trans-3,4-diethylcyclobutene 3,3-diethylcyclobutene

Answer: D Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Hard 111.

Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

A. B. C. D. E.

disrotatory; conrotatory; disrotatory; conrotatory; conrotatory;

cis-3,4-diethylcyclobutene cis-3,4-diethylcyclobutene trans-3,4-diethylcyclobutene trans -3,4-diethylcyclobutene 3,3-diethylcyclobutene

Answer: A Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Hard 112.

Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

A. B. C. D. E.

disrotatory; conrotatory; disrotatory; conrotatory; disrotatory;

cis-5,6-diethyl-1,3-cyclohexadiene cis-5,6-diethyl-1,3-cyclohexadiene trans-5,6-diethyl-1,3-cyclohexadiene trans -5,6-diethyl-1,3-cyclohexadiene 5,5-diethyl-1,3-cyclohexadiene

Answer: D Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Hard 113.

Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

A. B. C. D. E.

disrotatory; conrotatory; disrotatory; conrotatory; conrotatory;

cis-5,6-diethyl-1,3-cyclohexadiene cis-5,6-diethyl-1,3-cyclohexadiene trans-5,6-diethyl-1,3-cyclohexadiene trans -5,6-diethyl-1,3-cyclohexadiene 5,5-diethyl-1,3-cyclohexadiene

Answer: A Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Hard 114.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 115.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

Difficulty: Medium 116.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 117.

Identify the expected product of the following Claisen rearrangement.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Medium

sigmatropic

118.

Identify the expected major product of the following Cope rearrangement.

A. B. C. D. E.

I II III IV V

Answer: C Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Medium 119.

Identify the expected product of the following Claisen rearrangement.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Hard

120.

Identify the expected product of the following Claisen rearrangement.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Medium

sigmatropic

121.

Identify the expected major product of the following Cope rearrangement.

A. B.

I II

C. D. E.

III IV V

Answer: E Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Medium

sigmatropic

122.

Identify the reagents necessary to carry out the following transformation.

A. B. C. D. E.

1. H2SO4, heat 1. TsCl, pyr 1. 1 eq. H2, Pd/C 1. SOCl2/pyridine 1. NBS, heat

2. HBr 2. (CH3)3COK 2. BH3 2. Mg in ether 2. (CH3)3COK

3. (CH3)3COK 3. Br2 3. H2O2, NaOH 3. H2O

4. (CH3)3COK

Answer: B Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Hard

123.

Identify the expected product labeled B in the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Hard

sigmatropic

124.

Which of the following best describes a Cope rearrangement?

[2,2] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms [2,2] sigmatropic rearrangement with heteroatoms [3,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms [2,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms [2,3] sigmatropic rearrangement with heteroatoms

B. C. D. E.

Answer: C Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Easy

sigmatropic

125.

Which of the following best describes a Claisen rearrangement?

[2,2] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms [2,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms [2,3] sigmatropic rearrangement with heteroatoms [3,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms [3,3] sigmatropic rearrangement with heteroatoms

B. C. D. E.

Answer: E Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Easy

sigmatropic

126.

Absorption of UV-visible radiation by a molecule results in ___________ transitions.

A. B.

electronic nuclear

C. D. E.

rotational vibrational atomic

Answer: A Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Easy 127.

Which is the most energetically favorable UV transition for 1,3-butadiene?

A. B. C. D. E.

n ¾¾¾® s* n ¾¾¾® p* p2 ¾¾¾® p3* s ¾¾¾® s* p1 ¾¾¾® p4*

Answer: C Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 128.

Which of the following is primarily suited to the study of conjugation in organic compounds?

A. B. C. D. E.

IR spectroscopy NMR spectroscopy Mass spectroscopy UV-Vis spectroscopy Raman spectroscopy

Answer: D Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Easy 129.

Which of the following symbols is used to represent the molar absorptivity of a given compound in the UV-Vis region?

A. B. C.

l e n

D. E.

g a

Answer: B Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Easy 130.

Which of the following compounds has the longest lmax?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 131.

Which of the following compounds has the shortest lmax?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 132.

Which of the following compounds has the longest lmax?

A. B. C. D. E.

(E)-2-pentene (Z)-2-pentene 1-pentene 1,3-hexadiene 1,3,5-hexatriene

Answer: E Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 133.

Which of the following compounds has the longest lmax?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 134.

Which of the following compounds has the longest lmax?

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 135.

Using the Woodward-Fieser rules identify the best estimate for the lmax of the following compound.

A. B. C. D. E.

232 nm 237 nm 217 nm 222 nm 242 nm

Answer: B Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 136.

Using the Woodward-Fieser rules identify the best estimate for the lmax of the following compound.

A. B. C. D. E.

247 nm 262 nm 267 nm 272 nm 277 nm

Answer: D Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 137.

Using the Woodward-Fieser rules identify the best estimate for the lmax of the following compound.

A. B. C. D. E.

232 nm 256 nm 267 nm 271 nm 286 nm

Answer: D Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 138.

A compound that absorbs yellow light would be expected to have which of the following colors.

A. B. C. D. E.

orange green red blue violet

Answer: E Learning Objective: 16.12 Identify the origin of color for organic compounds Difficulty: Medium 139.

A compound that absorbs blue light would be expected to have which of the following colors.

A. B. C. D. E.

orange green red blue yellow

Answer: A Learning Objective: 16.12 Identify the origin of color for organic compounds Difficulty: Medium

140.

Identify the type(s) of light-sensitive cells that function as photoreceptors.

A. B. C. D. E.

rods cones disks A and B B and C

Answer: rods and cones Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision Difficulty: Easy 141.

Identify the light-sensitive compound in rods.

A. B. C. D. E.

rhodopsin cis-retinal lycopene trans-retinal vitamin A

Answer: A Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision Difficulty: Easy 142.

Which of the following dienes is most stable?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium

143. Which one of the following dienes is the least stable stereoisomer in its most stable conformation?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 144.

Which one of the following dienes is the most stable stereoisomer in its least stable conformation?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 145.

Which one of the following dienes is the least stable stereoisomer in its least stable conformation?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes Difficulty: Medium 146.

Which one of the following compounds is not an expected product of the reaction between 1,3-butadiene and HBr?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 147.

Identify the products of the 1,4-addition for the following reaction.

A. B. C. D. E.

I and III II and IV II and III I and II III and IV

Answer: E Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 148.

Identify the products of the 1,4-addition for the following reaction.

A. B. C. D. E.

I and III I and IV II and III II and IV III and IV

Answer: B Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 149.

Identify the products of the 1,4-addition for the following reaction.

A. B.

I and III II and IV

C. D. E.

II and III I and II III and IV

Answer: E Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 150.

Identify the products of the 1,2-addition reaction of 1,3-hexadiene with Br2/CCl4.

A. B. C. D. E.

I II II and III III I and IV

Answer: C Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 151.

Identify the products of the 1,4-addition for the following reaction.

A. B. C.

I I and II I and IV

D. E.

IV III and IV

Answer: E Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene Difficulty: Medium 152.

Which of the following provides the best explanation for why the 1,2-addition product of the following reaction is favored.

This reaction is under thermodynamic control, which favors the formation of the more stable trisubstituted double bond. The reaction is under kinetic control which always gives the 1,2-addition product. The reaction is under thermodynamic control which always gives the 1,2-addition product. The 1,4-adduct is more stable and these conditions favor the less substituted alkene The 1,2-adduct is less stable and thus is formed faster under the reaction conditions.

B. C. D. E.

Answer: A Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Hard 153.. Identify the structure of the expected product for the following reaction under thermodynamic control.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control Difficulty: Hard

154.

Identify the expected major product(s) for the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B 155.

Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 156.

Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 157.

Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 158.

Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 159.

The following product shown in the box is formed by an intramolecular DielsAlder reaction. Identify the structure of the starting compound.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.7 Predict the product of a Diels-Alder reaction Difficulty: Hard 160.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium

161.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 162.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 163.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 164.

Identify the expected major product of the following electrocyclic reaction.

A. B. C.

I II III

D. E.

IV V

Answer: B Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 165.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 166.

Identify the expected major product of the following electrocyclic reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions Difficulty: Medium 167.

Identify the expected product labeled A in the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 16.10 Describe the defining features of rearrangement, and compare the Cope and Claisen rearrangements Difficulty: Medium 168.

Which of the following compounds has the shortest lmax?

sigmatropic

B. C. D. E.

II III IV V

Answer: E Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 169.

Which of the following compounds has the shortest lmax?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 16.11 Describe the relationship between lmax and the extent of conjugation, and use Woodward-Fieser rules to predict the lmax of simple compounds Difficulty: Medium 170.

Lack of what compound is responsible for the condition known as night blindness?

A. B. C. D. E.

rhodopsin cis-retinal lycopene trans-retinal vitamin A

Answer: E Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision Difficulty: Easy

171.

A diet rich in what compound can help prevent the condition known as night blindness and improve vision?

A. B. C. D. E.

lycopene cis-retinal trans-retinal b-carotene vitamin A

Answer: D Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision Difficulty: Easy

Klein, Organic Chemistry 4e Chapter 17 1.

Identify the common name for toluene.

A. B. C. D. E.

hydroxybenzene aminobenzene methylbenzene ethylbenzene methoxybenzene

Answer: C Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 2.

Identify the common name for anisole.

A. B. C. D. E.

hydroxybenzene aminobenzene methylbenzene ethylbenzene methoxybenzene

Answer: E Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 3.

Identify the common name for phenol.

A. B. C. D. E.

hydroxybenzene aminobenzene methylbenzene ethylbenzene methoxybenzene

Answer: A Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium

Other than an arene, identify the other key functional group found in acetophenone.

A. B. C. D. E.

ether alkene carboxylic acid aldehyde ketone

Answer: E Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 5.

Other than an arene, identify the other key functional group found in styrene.

A. B. C. D. E.

ether alkene carboxylic acid aldehyde ketone

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 6.

Identify the common name for o-xylene.

A. B. C. D. E.

hydroxybenzene aminobenzene 1,2-dimethylbenzene ethylbenzene 1,3-dimethylbenzene

Answer: C Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 7.

Identify the IUPAC name for the following compound.

A. B. C. D. E.

5-bromophenol 3-bromophenol 5-bromoaniline 3-bromoaniline 1-bromophenol

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 8.

Which of the following is another name for 4-chlorobenzaldehyde?

A. B. C. D. E.

o-chlorobenzaldehyde m-chlorobenzaldehyde p-chlorobenzaldehyde m-chlorobenzenecarbaldehyde anisole

Answer: C Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 9.

What is the IUPAC name for the following compound?

A. B. C. D. E.

5-bromo-4-nitroaniline 5-bromo-p-nitroaniline 1-bromo-2-nitroaniline 3-bromo-4-nitroaniline p-nitro-m-bromoaniline

Answer: D

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 10.

Identify the correct structure for 4-amino-2-chlorophenol.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 11.

What is the correct order of the names for the following compound?

A. B. C. D. E.

I = naphthalene; I = naphthalene; I = phenanthrene; I = phenanthrene; I = anthracene;

II = anthracene; II = phenanthrene; II = anthracene; II = naphthalene; II = phenanthrene;

III = phenanthrene III = anthracene III = naphthalene III = anthracene III = naphthalene

Answer: C Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 12.

What is the IUPAC name for the following compound?

A. B. C. D. E.

3,4-dichloroaniline 2,4-dichloroaniline 2,5-dichloroaniline 3,6-dichloroaniline 2,6-dichloroaniline

Answer: C Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 13.

What is the IUPAC name for the following compound?

A. B. C. D. E.

4-butylphenol 1-sec-butylphenol 4-propylphenol 4-sec-butylphenol 1-isobutylphenol

Answer: D Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 14.

What is the IUPAC name for the following compound?

A. B. C.

6-ethyl-3-nitrobenzoic acid 2-ethyl-5-nitrobenzoic acid 1-ethyl-4-nitrobenzoic acid

D. E.

2-ethyl-5-nitrobenzaldehyde 4-nitro-3-carboxyethylbenzene

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 15.

Identify the structure of 4-amino-2-bromophenol.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy 16.

In nomenclature when the benzene ring is treated as a substituent, it is named a(n) _________ group.

A. B. C. D. E.

phenol benzenyl benzyl aryl phenyl

Answer: E Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy

17.

Identify the structure of acetophenone.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy 18.

What is the common name for the following compound?

A. B. C. D. E.

m-toluene p-toluene o-styrene m-xylene o-xylene

Answer: D Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 19.

Identify the structure of 1,3-diphenylbutane.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 20.

Identify the structure of p-aminobenzoic acid (PABA).

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 21.

What is the IUPAC name for the following compound?

A. B. C. D. E.

5-ethyl-4-fluoro-3-methylbenzaldehyde 2-ethyl-4-fluoro-5-methylbenzaldehyde 3-carbaldehyde-4-ethyl-6-fluorotoluene o-ethyl-p-fluoro-m-methylbenzaldehyde 1-ethyl-3-fluoro-4-methyl-6-benzaldehyde

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 22.

What is the IUPAC name for the following compound?

A. B. C. D. E.

3-(chloromethyl)-6-methoxy-2-nitrobenzene 4-methoxy-3-nitro-chlorotoluene p-(chloromethyl)-o-nitroanisole 3-(chloromethyl)-1-nitroanisole 4-(chloromethyl)-2-nitroanisole

Answer: E Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 23.

What is the IUPAC name for the following compound?

A. B. C.

benzene phenanthrene napththalene

D. E.

xylene anthracene

Answer: B Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 24.

Identify the structure of styrene.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy 25.

Identify the structure of 3-isobutyl-5-isopropylaniline.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Medium 26.

Identify the scientist credited with proposing the structure of benzene.

A. B. C. D. E.

Erich Hückel Victor Grignard Vladimir Markovnikov Robert Woodward August Kekulé

Answer: E Learning Objective: 17.3 Describe the structure of benzene, and explain why the structure cannot be shown in a single drawing Difficulty: Easy 27.

Which of the following describes the current view of the two Kekulé structures for benzene?

A. B. C. D. E.

they are both correct structures for benzene the two structures are in equilibrium the two are conformational isomers of benzene the true structure of benzene is a resonance hybrid of the two structures the two structures represent constitutional isomers of benzene

Answer: D Learning Objective: 17.3 Describe the structure of benzene, and explain why the structure cannot be shown in a single drawing Difficulty: Easy 28.

The carbon-carbon bonds in benzene are _________.

A. B. C. D. E.

of equal length and are longer than an isolated double bond of equal length and are midway between a single bond and a double bond of equal length and are shorter than a typical single bond of unequal length and alternate as single and double bonds in fluctuation of length between that of a double bond and a single bond

Answer: B Learning Objective: 17.3 Describe the structure of benzene, and explain why the structure cannot be shown in a single drawing Difficulty: Easy

29.

The difference between the amount of heat actually released upon the hydrogenation of benzene and that calculated for the hydrogenation of an imaginary cyclohexatriene is called the _________ of benzene.

A. B. C. D. E.

stabilization energy hydrogenation energy Hückel number antibonding MO nonbonding MO

Answer: A Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy 30.

Molecular orbitals of equal energy are referred to as _________ orbitals.

A. B. C. D. E.

nonbonding degenerate antibonding hybridized bonding

Answer: B Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy 31.

According to the molecular orbital theory how many molecular orbitals are formed when the six p-orbitals of benzene combine?

A. B. C. D. E.

6 5 4 3 2

Answer: A Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium

32.

According to molecular orbital theory, how many p-bonding molecular orbitals does benzene have?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium 33.

According to molecular orbital theory, how many p-antibonding molecular orbitals does benzene have?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium 34.

According to molecular orbital theory, how many non-bonding molecular orbitals does benzene have?

A. B. C. D. E.

0 1 2 3 4

Answer: A Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium

35.

For a compound to be aromatic, it must have a planar cyclic conjugated p system along with a(n) _________ number of electron pairs/p-bonds.

A. B. C. D. E.

even odd whole prime integer

Answer: B Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy 36.

Which one of the following statements is not true for a compound to be considered as aromatic?

A. B. C. D. E.

The compound must be cyclic and planar. The compound must be monocyclic. The compound contains a ring comprised of continuously overlapping p orbitals. The compound must satisfy Hückel’s rule – must have (4n + 2) p electrons. May contain both E and Z bonds within the ring.

Answer: B Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy 37.

What is the main difference between an aromatic and antiaromatic compound?

Aromatic compounds must be cyclic and planar, but not antiaromatic compounds. Aromatic compounds must be monocyclic. Antiaromatic compounds must contain a ring comprised of continuously overlapping p orbitals. Aromatic compounds must satisfy Hückel’s rule. Antiaromatic compounds tend to be more stable that aromatic compounds.

B. C. D. E.

Answer: D Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy

38.

Identify the number of p electrons present in an antiaromatic compound.

A. B. C. D. E.

4n + 2 2n + 2 4n 3n 2n – 2

Answer: C Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy 39.

Identify the number of p electrons present in an aromatic compound.

A. B. C. D. E.

4n + 2 2n + 2 2n 3n 4n

Answer: A Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Easy 40.

Identify the molecular orbital energy diagram for the cyclopropenyl anion, shown in the box below, and predict if it is aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

molecular orbital energy diagram (I); molecular orbital energy diagram (II); molecular orbital energy diagram (I); molecular orbital energy diagram (II); molecular orbital energy diagram (I);

aromatic aromatic antiaromatic antiaromatic nonaromatic

Answer: C Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium 41.

Identify the molecular orbital energy diagram for the cyclopentadienyl anion, shown in the box below, and predict if it is aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

molecular orbital energy diagram (I); molecular orbital energy diagram (II); molecular orbital energy diagram (I); molecular orbital energy diagram (II); molecular orbital energy diagram (I);

aromatic aromatic antiaromatic antiaromatic nonaromatic

Answer: B Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium

42.

Identify the molecular orbital energy diagram for the tropylium anion, shown in the box below, and predict if it is aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

molecular orbital energy diagram (I); molecular orbital energy diagram (II); molecular orbital energy diagram (I); molecular orbital energy diagram (II); molecular orbital energy diagram (I);

aromatic aromatic antiaromatic antiaromatic nonaromatic

Answer: A Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability Difficulty: Medium

43.

Identify the structure of phenol.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy 44.

Identify from the following compounds which one is aromatic.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 45.

Identify from the following compounds which one is antiaromatic.

A. B. C.

I II III

D. E.

IV V

Answer: B Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 46.

Identify from the following compounds which one is nonaromatic.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 47.

Identify from the following compounds which one is aromatic.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium

48.

Identify from the following compounds which one is nonaromatic.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 49.

Identify from the following compounds which one is aromatic.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 50.

Identify from the following compounds which one is antiaromatic.

B. C. D. E.

II III IV V

Answer: C Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 51.

Identify from the following compounds which one is aromatic.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 52.

Identify from the following compounds which one is antiaromatic.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium

53.

Identify which of the following annulenes is not aromatic.

A. B. C. D. E.

[6]-annulene [14]-annulene [16]-annulene [18]-annulene [22]-annulene

Answer: C Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 54.

Identify the structure that is not an annulene.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Easy 55.

Identify the structure that is an annulene.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Easy

56.

For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

I = aromatic; I = nonaromatic; I = antiaromatic; I = nonaromatic; I = aromatic;

II = antiaromatic II = aromatic II = nonaromatic II = antiaromatic II = nonaromatic

Answer: D Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 57.

For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

I = aromatic; I = nonaromatic; I = antiaromatic; I = nonaromatic; I = aromatic;

II = antiaromatic II = aromatic II = nonaromatic II = antiaromatic II = nonaromatic

Answer: E Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 58.

For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

I = aromatic; I = nonaromatic; I = antiaromatic; I = nonaromatic; I = aromatic;

II = antiaromatic II = aromatic II = nonaromatic II = antiaromatic II = nonaromatic

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 59.

For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

I = aromatic; I = nonaromatic; I = antiaromatic; I = nonaromatic; I = aromatic;

II = antiaromatic II = aromatic II = aromatic II = antiaromatic II = nonaromatic

Answer: C Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 60.

For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

I = aromatic; I = nonaromatic; I = antiaromatic; I = aromatic; I = nonaromatic;

Answer: D

II = antiaromatic II = aromatic II = nonaromatic II = nonaromatic II = antiaromatic

Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 61.

For the following molecule classify it is as aromatic, antiaromatic, or nonaromatic, and identify the best supporting explanation.

A. B. C. D.

nonaromatic; antiaromatic; aromatic; nonaromatic;

antiaromatic;

there are only two conjugated double bonds It only has 2 p bonds there are two p bonds and a lone pair on the nitrogen atom the protonated nitrogen is sp3 hybridized so there is no continuous p orbital system the compound has 4n p electrons

Answer: D It is cyclic, but there is not a planar continuous system of p-orbitals because one of the nitrogen atoms is sp3 hybridized. Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Hard 62.

For the following molecule classify it is as aromatic, antiaromatic, or nonaromatic, and identify the best supporting explanation.

A. B. C. D.

aromatic; antiaromatic; aromatic; antiaromatic;

nonaromatic;

cylic conjugated system with Hückel’s number of p electrons It only has 3 p bonds there is a p orbital on every atom in the ring the compound has 4n p electrons when counting the lone pair on the nitrogen atom the nitrogen is sp3 hybridized to avoid the instability associated antiaromaticity

Answer: E Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Hard

63.

For the following molecule classify it is as aromatic, antiaromatic, or nonaromatic, and identify the best supporting explanation.

A. B. C. D. E.

aromatic; antiaromatic; nonaromatic; antiaromatic; aromatic;

cylic conjugated system with Hückel’s number of p electrons It only has 4 p bonds there is not a continous system of p electrons due to the NH the compound has 4n p electrons there is a p orbital on every atom in the rings

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Hard 64.

For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A. B. C. D. E.

I = aromatic; I = aromatic; I = antiaromatic; I = nonaromatic; I = aromatic ;

II = antiaromatic II = aromatic II = nonaromatic II = nonaromatic II = nonaromatic

Answer: B Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium

65.

Identify the structure of anisole.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy 66.

Identify which of the following compounds is most acidic.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 67.

Identify the structure of aniline.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names Difficulty: Easy

68.

Identify which of the following compounds is most acidic.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 69.

Identify which of the following compounds is most acidic along with the best supporting explanation.

A. B. C. D. E.

(I) is more acidic as the resulting conjugate base is an aromatic anion. (II) is more acidic as the resulting conjugate base is an aromatic anion. (I) is more acidic becase the compound has two pi bonds. (II) is more acidic due to the large angle strain in the cyclopropene. (I) is more acidic due to less angle strain in the cyclopentadiene.

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 70.

Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms a hydrochloride salt, whereas pyrrole is unreactive. Which of the following is not a valid explanation for this observed reactivity?

A. B. C. D. E.

The lone pair on pyridine is not part of the aromatic system. The lone pair on pyridine can be protonated without disrupting the aromatic stability. The lone pair on pyrrole is sp3 hybridized and is less prone to protonation. Protonation of pyrrole leads to a nonaromatic cation, which is less stable. The lone pair on pyrrole is involved in making the compound aromatic and thus is less susceptible to protonation.

Answer: C Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 71.

The pKa of cyclopentadiene (I) and cycloheptatriene (II) are around 16 and 36 respectively. Which of the following is not a valid explanation for the large difference in the two pKa values?

A. B. C. D. E.

The conjugate base of cyclopentadiene (I) is an aromatic anion. The conjugate base of cycloheptatriene (I) is a nonaromatic anion. If the conjugate base of cycloheptatriene (II) was flat it would be antiaromatic. The conjugate base of cycloheptatriene (II) is less stable due to aromaticity. The conjugate base of cyclopentadiene (I) is more stable due to aromaticity.

Answer: D Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 72.

Identify which of the following molecules would undergo the fastest SN1 reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 73.

Identify which of the following compounds would undergo the fastest SN1 reaction along with the best supporting explanation.

(I) would undergo the fastest SN1 reaction because it would form a stable aromatic carbocation intermediate. (II) would undergo the fastest SN1 reaction because it has less angle strain than the cyclopropene. (III) would undergo the fastest SN1 reaction because it forms a resonance stabilized carbocation intermediate. (I) would undergo the fastest SN1 reaction because it has the greatest amount of angle strain. (III) would undergo the fastest SN1 reaction because it has the no angle strain since it is acyclic.

B. C. D. E.

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 74.

Identify the hydrocarbon with the highest total aromatic stabilization energy.

A. B. C. D. E.

phenanthrene benzene naphthalene anthracene cyclopentadiene

Answer: A Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 75.

Identify the hydrocarbon with the highest aromatic stabilization energy per ring.

A. B.

phenanthrene benzene

C. D. E.

naphthalene anthracene cyclopentadiene

Answer: B Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 76.

Provide the reagent(s) necessary to convert toluene to benzoic acid.

A. B. C. D. E.

Na2Cr2O7/H2SO4/H2O 1. NBS, D; 2. NaOH 1. LiAlH4; 2. H3O+ H2, Pd 1. CO2; 2. H3O+

Answer: A Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 77.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 78.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 79.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 80.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 81.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 82.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium

83.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 84.

Identify the expected major product of the following reaction.

A. B. C.

I II III

D. E.

IV V

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 85.

Identify the reagents, in correct order, expected to accomplish the following transformation.

A. B. C. D. E.

1. PCC 1. KCN 1. NBS/D 1. H2SO4/D 1. Na2Cr2O7/H2SO4/H2O

2. NaCN 2. Br2 2. NaCN 2. HCN 2. KCN

Answer: C Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 86.

Identify the reagents, in correct order, expected to accomplish the following transformation.

A. B. C. D. E.

1. H2SO4 1. NBS/D 1. NaOEt 1. NBS/D 1. Na2Cr2O7/H2SO4/H2O

2. HBr/ROOR 2. NaOEt 2. Br2 2. NaOH 2. NaOH

3. HOEt 3. HOEt 3. EtBr

Answer: B Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium

87.

Identify the reagents, in correct order, expected to accomplish the following transformation.

A. B. C. D. E.

1. H2SO4 1. NBS/D 1. NaOH 1. CH3OH 1. NBS/D

2. HBr/ROOR 2. NaOCH3 2. CH3OH 2. Br2 2. CH3OH, 25°C

3. CH3OH

Answer: E Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 88.

Identify the reagents, in correct order, expected to convert ethylbenzene to styrene.

A. B. C. D. E.

1. H2SO4 1. NaOH 1. TsCl, pyr 1. NBS/D 1. NBS/D

2. HBr/ROOR 2. Br2 2. t-BuOK 2. NaOCH2CH3 2. CH3CH2OH, 25°C

3. NaOCH2CH3

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 89.

Identify the reagents, in correct order, expected to accomplish the following transformation.

A. B. C. D. E.

1. NBS/D 1. TsCl, pyr 1. NBS/D 1. HBr 1. H2SO4

2. NaOCH2CH3 2. t-BuOK 2. CH3CH2OH, 25°C 2. t-BuOK

Answer: A Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 90.

Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A. B. C. D. E.

I then II then III then IV then V V then I then II then IV then III I then III then V then II then IV IV then II then IV then III then I V then IV then II then I then III

Answer: B Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 91.

Identify the structure of intermediate A expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 92.

Identify the structure of intermediate A expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Medium 93.

Identify the expected product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 94.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 95.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 96.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium

97.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 98.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: B

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 99.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 100.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

Difficulty: Medium 101.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 102.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 103.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Hard 104.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 105.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 106.

Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A. B. C. D. E.

I then II then IV then V then III V then III then I then IV then II III Then IV then II then V then I V then II then I then III then IV II then V then I then IV then III

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 107.

Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A. B. C. D. E.

I then II then IV then III II then IV then III then I I then IV then II then III II then I then III then IV III then I then II then IV

Answer: A Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Hard 108.

Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A. B. C. D. E.

I then II then IV then III II then IV then III then I I then IV then II then III II then I then III then IV III then I then II then IV

Answer: D Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Hard 109.

The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers are difficult to distinguish using 1H NMR, but are readily identified using 13C NMR. Which of the following observations is correct in identifying an isomer of xylene using 13C NMR?

A. B. C. D. E.

In the proton-decoupled 13C NMR spectra o-xylene will display 5 peaks. In the proton-decoupled 13C NMR spectra m-xylene will display 4 peaks. In the proton-decoupled 13C NMR spectra p-xylene will display 3 peaks. In the proton-decoupled 13C NMR spectra p-xylene will display 4 peaks. In the proton-decoupled 13C NMR spectra o-xylene will display 3 peaks.

Answer: C Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium

110.

Which one of the following compounds would exhibit seven signals in its 13 C NMR spectrum?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 111.

Which of the following isomers of tribromoaniline will show two doublets with 7.5 Hz coupling constants in an 1H NMR spectrum?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 112.

Identify the structure with molecular formula C8H9Br that is consistent with the following 1H NMR spectroscopic data. 1

H NMR: 2.8 ppm (multiplet, I = 5H)

(triplet, I = 2H),

4.65 ppm

(triplet, I = 2H),

7.2 ppm

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 113.

Identify the structure with molecular formula C9H9ClO that is consistent with the following spectroscopic data. IR: 1680 cm−1 1 H NMR: 3.5 ppm (triplet, I = 2H), 4.0 ppm (triplet, I = 2H), (triplet, I = 2H), 7.6 ppm (triplet, I = 1H), 7.9 ppm (doublet, I = 2H)

A. B. C. D. E.

7.4 ppm

I II III IV V

Answer: A Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 114.

Identify the structure with molecular formula C9H12 that is consistent with the following spectroscopic data.

H NMR: 1.2 ppm (multiplet, I = 5H)

A. B. C. D. E.

(doublet, I = 6H),

3.0 ppm

(septet, I = 1H),

7.1 ppm

I II III IV V

Answer: B Learning Objective: Spectroscopy Section: 18.8 Difficulty: Medium 115.

Identify the structure with molecular formula C10H12O2 that is consistent with the following spectroscopic data. IR: 1680 cm−1, 2750 cm−1, 2850 cm−1 1 H NMR: 1.1 ppm (triplet, I = 3H), 3.5 ppm (quartet, I = 2H), 4.5 ppm (singlet, I = 2H), 7.3 ppm (doublet, I = 2H), 7.7 ppm (doublet, I = 2H), 9.9 ppm (singlet, I = 1H)

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy

Difficulty: Hard 116.

The following compound shows signals at 190.7, 140.9, 134.8, 130.9 and 129.5 ppm in its broadband decoupled C-13 spectrum. Assign the signals to the indicated carbon atoms in the structure below.

A. B. C. D. E.

I = 109.7 I = 190.7 I = 134.8 I = 129.5 I = 140.9

II = 130.9 II = 134.8 II = 130.9 II = 140.9 II = 129.5

III = 134.8 III = 129.5 III = 129.5 III = 190.7 III = 130.9

IV = 140.9 IV = 130.9 IV = 140.9 IV = 130.9 IV = 134.8

V = 129.5 V = 140.9 V = 190.7 V = 134.8 V = 190.7

Answer: E Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Hard 117.

A compound with molecular formula C9H12O displays the following 1H NMR and 13 C NMR spectra. Identify the structure consistent with this information.

3 2

1 exchanges with D2O

4 PPM

160

A. B. C. D. E.

140

120

100

80 PPM

I II III IV V

Answer: C Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 118.

A compound with molecular formula C10H14 displays the following IR, 1H NMR, 13 C NMR spectra. Identify the structure consistent with this information.

SDBS

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium

119.

Identify which of the following compounds is least acidic along with the best supporting explanation.

A. B. C. D. E.

(I) is less acidic as the resulting conjugate base is an antiaromatic anion. (II) is less acidic as the resulting conjugate base is an antiaromatic anion. (I) is less acidic becase the compound has two pi bonds. (II) is less acidic due to the large angle strain in the cyclopropene. (I) is less acidic due to less angle strain in the cyclopentadiene.

Answer: B Learning Objective: 17.5 Identify aromatic compounds other than benzene Difficulty: Medium 120.

Identify the structure of intermediate B expected from the following reaction sequence.

A. B. C. D.

I II III IV

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 121.

Identify the structure of intermediate C expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 122.

Identify the structure of the product D expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 123.

Identify the structure of intermediate B expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

Difficulty: Hard 124.

Identify the structure of intermediate C expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 125.

Identify the structure of the product D expected from the following reaction sequence.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position Difficulty: Hard 126.

Identify the expected major product of the following reaction.

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction Difficulty: Medium 127.

Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A. B. C. D. E.

I then II then III III then II then I I then III then II II then I then III III then I then II

Answer: D Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Hard 128.

A. B. C. D. E.

In the proton-decoupled 13C NMR spectra p-xylene will display 5 peaks. In the proton-decoupled 13C NMR spectra m-xylene will display 4 peaks. In the proton-decoupled 13C NMR spectra o-xylene will display 3 peaks. In the proton-decoupled 13C NMR spectra o-xylene will display 4 peaks. In the proton-decoupled 13C NMR spectra p-xylene will display 5 peaks.

Answer: D Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 129.

A. B. C. D. E.

In the proton-decoupled 13C NMR spectra m-xylene will display 5 peaks. In the proton-decoupled 13C NMR spectra p-xylene will display 4 peaks. In the proton-decoupled 13C NMR spectra o-xylene will display 3 peaks. In the proton-decoupled 13C NMR spectra p-xylene will display 4 peaks. In the proton-decoupled 13C NMR spectra o-xylene will display 5 peaks.

Answer: A Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 130.

The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers can be readily identified using 13C NMR. How many signals would be expected in the proton-decoupled 3C NMR spectra of p-xylene?

A. B. C. D. E.

1 peak 2 peaks 3 peaks 4 peaks 5 peaks

Answer: C Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium 131.

A. B. C. D. E.

1 peak 2 peaks 3 peaks 4 peaks 5 peaks

Answer: E Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium

132.

A. B. C. D. E.

1 peak 2 peaks 3 peaks 4 peaks 5 peaks

Answer: D Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1 H NMR, and 13C NMR spectroscopy Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 18 1.

Which of the reagents shown could be used as the basis for a simple chemical test that would distinguish between ethylbenzene and styrene?

A. B. C. D. E.

NaI/acetone Br2/CCl4 NaOH/H2O NaBH4/CH3OH HCl/H2O

Answer: B Learning Objective: 18.1 Describe the difference between an addition reaction and an electrophilic aromatic substitution reaction Difficulty: Easy 2.

Why does benzene undergo a substitution reaction with benzene, whereas cyclohexene undergoes an addition reaction with benzene?

A. Benzene has delocalized p electrons not present in cyclohexene and adding bromine would result in a less stable, nonaromatic product. B. Cyclohexene has delocalized p electrons that make it too stable to underego an addition reaction. C. Cyclohexene has a mix of localized and delocalized p electrons, so substitution would disrupt this pattern and make the ring less stable. D. Benzene is highly unstable due to its lack of localized p electrons and this makes an addition reaction impossible. E. Benzene localized p electrons and this forms a structure that is stable and very unreactive, preventing an addition reaction from occurring. Answer: A Learning Objective: 18.1 Describe the difference between an addition reaction and an electrophilic aromatic substitution reaction Difficulty: Medium 3.

What is the mechanism by which benzene reacts with bromine?

A. B. C. D. E.

Unimolecular nucleophilic addition Electrophilic aromatic addition Electrophilic aromatic substitution Biomolecular nucleophilic substitution Aromatic nucleophilic substitution

Answer: C Learning Objective: 18.1 Describe the difference between an addition reaction and an electrophilic aromatic substitution reaction Difficulty: Medium 4.

A. B. C. D. E.

Which illustration shows all of the resonance structures of the sigma complex that is formed when benzene reacts with an electrophile (E+)?

III

I, II, and III I, III, and IV I, II, and V II, III, and IV III, IV, and V

Answer: C Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Medium 5.

What is the rate-determining step in the electrophilic aromatic substitution of benzene?

A. B. C. D. E.

Formation of an electrophile Formation of a sigma complex. Loss of a proton from the sigma complex. Addition of an electrophile & loss of a proton None of these

Answer: B Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Easy

The electrophilic bromination or chlorination of benzene requires ______ along with the halogen.

A. B. C. D. E.

UV light a Brønsted base a Lewis base a Lewis acid none of these

Answer: D Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Easy 7.

What is the electrophile in the bromination of benzene?

A. B.

Br2

C. D.

FeBr3 FeBr2

E. Answer: B Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Easy 8.

What is the electrophile in the chlorination of benzene?

A. B.

Cl2

C. D.

AlCl3 AlCl2

What is the electrophile in the iodination of benzene?

B. C. D.

CuI3 CuI2

E. Answer: E Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Easy 10.

What reagents are used to carry out the chlorination of benzene?

A. B. C. D. E.

Cl2/CCl4 Cl2/FeCl3 Cl2/AlCl3 NaCl/Fe both B and C

Answer: E Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Medium 11.

What reagents are used to carry out the iodination of benzene?

I2/CCl4

B. C. D. E.

I2/FeCl3 I2/AlCl3 I2/CuCl2 NaI/Acetone

In order, what are the major steps involved in an electrophilic aromatic substitution reaction?

A. 1) Reaction of an electrophile with an aromatic ring to form a sigma complex; 2) Deprotonation of the aromatic ring to form the aromatic product B. Deprotonation of the aromatic ring to increase its reactivity; Addition of the electrophile to form the sigma product; 3) Loss of the leaving group to form the product C. 1) Deprotonation of the aromatic ring to form a sigma complex; 2) Reaction of the sigma complex with the electrophile D. 1) Formation of an electrophile; 2) Reaction of the electrophile with an aromatic ring to form the sigma complex; 3) Deprotonation of the sigma complex to restore aromaticity E. 1) Polarization of a dihalide, yielding a nucleophile; 2) Reaction of the nucleophile with the aromatic ring to form an electrophile; 3) Loss of the leaving group to restore aromaticity Answer: D Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Medium 13.

What is the first step in the curved arrow mechanism for the chlorination of benzene in the presence of FeCl3?

A. I B. II C. III D. IV E. II or III Answer: C Learning Objective: 18.2 Describe the conditions under which benzene reacts with bromine, write the mechanism of the reaction, and describe the role of a Lewis acid in the reaction Difficulty: Medium 14.

Identify the electrophile in the sulfonation reaction of benzene.

A. B. C. D. E.

SO2+ H2SO4 SO3+ H2SO3 SO3

Answer: E Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring Difficulty: Easy

15.

Predict the product of reaction shown.

fuming H 2SO4

A. B. C. D. E.

SO3H

SO2

SO3

III

I II III IV V

Answer: A Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring Difficulty: Easy 16.

What is the predicted product of the reaction shown?

SO3H H3O+ D

SO3

OH O

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring Difficulty: Easy 17.

Predict the product for the reaction shown.

SO3H H3O+ D

A. B. C. D. E.

I II III IV V

Answer: B

III

Learning Objective: 18.3 Draw the mechanism of sulfonation of an aromatic ring Difficulty: Easy 18.

Which of the species shown acts as an electrophile in the nitration of benzene?

A. B. C. D. E.

NO2+ HNO3 NO3+ H2SO4 NO2

Answer: A Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring Difficulty: Easy 19.

Which of the species shown acts as an electrophile in the nitration of benzene.

A. B. C. D. E.

sulfonium ion nitrogen dioxide nitronium ion nitrous oxide nitrogen dioxide

Answer: C Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring Difficulty: Easy 20.

Predict the product for the reaction shown.

HNO3 H 2SO4

SO3H

NO3

NO2

SO3

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring Difficulty: Medium 21.

What is the first step in the curved arrow mechanism of the reaction shown?

HNO 3/H 2SO4

NO2

O I

O OH

+ H

A. B. C. D. E.

O OH

+ H

S O O

+ H

S O

O V

S O

O IV

O III

O II

O OH

+ H

S O

I II III IV V

Answer: A Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring Difficulty: Easy 22.

What is the product from the reaction of nitrobenzene with iron and hydrochloric acid, followed with base?

A. B. C. D. E.

nitrobenzene benzene aniline 1,3-dinitrobenzene 1,4-dinitrobenzene

Answer: C Learning Objective: 18.4 Draw the mechanism of nitration of an aromatic ring Difficulty: Easy 23.

What is the electrophile in a Friedel-Crafts alkylation?

A. B. C. D. E.

aluminum chloride carbocation aluminum tetrachloride ion carbanion radical

Answer: B Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Easy 24.

Predict the major product for the reaction shown.

(CH 3)2CHCH2Cl AlCl3

CH 3

CH3

CH 2CH CH 3

CHCH 2CH3

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Medium 25.

Which one of the reactions shown is most likely to give a polysubstituted product?

A. B. C. D. E.

Friedel-Crafts alkylation Friedel-Crafts acylation nitration sulfonation halogenation

Answer: A Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Medium 26.

Which one of the compounds shown does not undergo a Friedel-Crafts reaction?

A. B. C. D. E.

benzene chlorobenzene nitrobenzene toluene t-butylbenzene

Answer: C

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Medium 27.

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.

A. B. C. D. E.

chlorobenzene sec-butylbenzene ethylbenzene isopropylbenzene t-butylbenzene

Answer: B Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Medium 28.

Which of the halides shown cannot be used for a Friedel-Crafts alkylation reaction?

A. B. C. D. E.

bromobenzene vinylchloride 2-chloropropane chloroethane both A and B

Answer: E Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Medium 29.

Aryl and vinyl halides cannot be used in the Friedel-Crafts alkylation reaction, because they __________.

A. B. C. D. E.

are exceptionally stable due to electron delocalization do not have suitable leaving groups are not very electrophilic do not form stable cations are not sufficiently nucleophilic

Answer: D

Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 30.

Predict the major product for the reaction shown.

Cl AlCl3 Cl

III

A. B. C.

I II III

D. E.

IV V

Answer: C Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 31.

Predict the major product for the reaction shown.

(CH 3)3CCH 2Cl AlCl3

A. B. C. D. E.

I II III IV V

III

Answer: B Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 32.

Provide the structures of the intermediate products and final product in the reaction sequence shown.

CH3Cl AlCl3

Cl2

C AlCl3

Al II

III

A A. B. C. D.

I II III I and II

II and III

Answer: A Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 33.

Predict the major product for the reaction shown.

Cl AlCl3

O I A. B. C. D. E.

OH II

CH2CH 2Cl

excess 1. KMnO4/NaOH/H2O 2. H3O+

AlCl3

III

OH IV

I II III IV V

Answer: B Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 34.

Predict the major product for the reaction shown.

H2SO4

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 35. What is the first step of the stepwise, curved arrow mechanism for the reaction shown?

Cl AlCl3

AlCl3

III

AlCl3

Cl3Al

AlCl3

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard

36.

Predict the major product for the reaction shown.

H 2SO4

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 37.

Predict the major product for the reaction shown.

AlCl3

+ Cl

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 38.

Predict the structure of the major product for the reaction shown.

OH +

H2SO4

III

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 39.

Which of the reactions shown would produce isopropylbenzene as the major product?

AlCl3

H 2SO4

A. B. C. D. E.

I II III IV all of these

Answer: E Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 40.

Which of the reactions shown would produce t-butylbenzene as the major product?

AlCl3

H2SO4

A. B. C. D. E.

I II III IV all of these

Answer: E Learning Objective: 18.5 Predict the products of a Friedel-Crafts alkylation considering limitations on the choice of the alkyl halide and ring substituents Difficulty: Hard 41. Which of the choices is the electrophile for the Friedel-Crafts acylation of benzene? A. B. C. D. E.

aluminum tetrachloride anion aluminum chloride acylium ion carbocation carbanion

Answer: C Learning Objective: 18.6 Predict the products of a Friedel-Crafts acylation considering limitations on the choice of ring substituents, and describe the product that results from a subsequent reduction reaction Difficulty: Easy 42.

In a Clemmensen reduction, an aryl ketone is reduced to _____________.

A. B. C. D. E.

an aryl aldehyde an aryl alkane an aryl carboxylic acid an aryl ester an aryl anhydride

Answer: B Learning Objective: 18.6 Predict the products of a Friedel-Crafts acylation considering limitations on the choice of ring substituents, and describe the product that results from a subsequent reduction reaction Difficulty: Easy 43.

Predict the structure of the major product for the reaction shown?

O CH 3CH 2CCl AlCl3

O O III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 18.6 Predict the products of a Friedel-Crafts acylation considering limitations on the choice of ring substituents, and describe the product that results from a subsequent reduction reaction Difficulty: Medium

44.

Predict the structure of the major product for the reaction shown.

O Cl AlCl3 O

A. B. C. D. E.

III

I II III IV V

Predict the structure of the major product for the reaction shown.

O O CH 3CH 2CH2COCCH2CH 2CH3 AlCl3

A. B. C. D. E.

III

I II III II and III III and IV

Provide the structure of the major products formed in each step of the reaction sequence shown.

O CH 3CH 2CH2CCl AlCl3

Zn(Hg) HCl, D

III

A. B. C. D.

I II III I and II

III and IV

What sequence of reagents could be used to carry out the conversion shown.

A. B.

1. Fuming H2SO4; 2. Excess NBS 1. Br2, 2. AlBr2; 2. Zn(Hg), HCl, heat

O Cl

/ AlCl3

; 2. Zn(Hg), HCl, heat

Predict the structure of the product for the reaction shown.

O +

1. AlCl3

2. H3O+

O OH

O II

O O III

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 18.6 Predict the products of a Friedel-Crafts acylation considering limitations on the choice of ring substituents, and describe the product that results from a subsequent reduction reaction Difficulty: Hard 49.

Predict the structure of the product for the reaction shown.

O Cl AlCl3

O I

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 18.6 Predict the products of a Friedel-Crafts acylation considering limitations on the choice of ring substituents, and describe the product that results from a subsequent reduction reaction

Difficulty: Medium 50.

Predict the structure of the product for the reaction shown.

O Cl Zn(Hg) AlCl3

HCl, D

A. B. C. D. E.

III

I II III IV V

An alkyl group ___________ the benzene ring to make it __________ reactive than benzene.

A. B. C. D. E.

activates, less blocks, less deactivates, less activates, more deactivates, more

Answer: D Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Easy 52.

Which of the substituents shown will not direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A. B. C. D. E.

-CH2CH3 -CF3 -OCH3 -NHCH3 -Br

Answer: B Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Easy 53.

Which of the substituents shown will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A. B. C. D. E.

-CH2CH3 -CF3 -OCH3 -COOCH3 both A and C

Answer: E Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Medium 54.

Which one of the compounds shown will be most reactive towards an electrophilic aromatic bromination reaction?

nitrobenzene

B. C. D. E.

anisole acetanilide benzene benzaldehyde

Answer: B Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Medium 55.

Which of the compounds shown will yield the ortho substituted compound as the major product for a nitration reaction?

A. B. C. D. E.

toluene ethylbenzene cumene t-butylbenzene none of these

Answer: A Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Medium 56.

Which of the structures shown are resonance structures of the sigma complex produced when aniline reacts with an electrophile (E+) to yield the parasubstituted product?

NH2

H I

NH2

III

NH2

H IV

A. B. C. D. E.

NH2

H V

I and II II and III II, III, and IV I, III, IV and V I, II, IV, and V

Answer: E Learning Objective: 18.7 Describe how the presence of an activator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Medium 57.

A nitro group ___________ the benzene ring to make it __________ reactive than benzene.

A. B. C. D. E.

activates, less blocks, less deactivates, less activates, more deactivates, more

Answer: C Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction

Difficulty: Easy 58.

Which one of the substituents shown will direct the incoming group to the meta position during electrophilic aromatic substitution?

A. B. C. D. E.

-NO2 -CºN -CCl3 -COOH all of these

Answer: E Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Easy 59.

Which one of the substituents shown will not direct the incoming group to the meta position during electrophilic aromatic substitution?

A. B. C. D. E.

-NO2 -CºN -OCH3 -COOH all of these

Answer: C Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Easy 60.

Which one of the compounds shown will be least reactive towards a FriedelCrafts reaction?

A. B. C. D. E.

nitrobenzene anisole phenol benzene chlorobenzene

Answer: A Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Medium

61.

Which of the structures shown are major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position?

III

E H

H IV

A. B. C. D. E.

I II III I, III, and IV V

Answer: Learning Objective: 18.8 Describe how the presence of a deactivator affects the rate and regiochemical outcome of an electrophilic aromatic substitution reaction Difficulty: Easy 62.

A halogen ___________ the benzene ring; the ring is __________ reactive than benzene.

A. B. C. D. E.

activates, less blocks, less deactivates, less activates, more deactivates, more

Answer: C Learning Objective: 18.9 Describe how the presence of a halogen affects the rate and regiochemical outcome of an electrophilic aromatic substitution Difficulty: Easy 63.

What are the preferred products from the nitration of bromobenzene?

A. B. C. D. E.

I and II II and III I and III III and IV II and IV

Answer: D Learning Objective: 18.9 Describe how the presence of a halogen affects the rate and regiochemical outcome of an electrophilic aromatic substitution Difficulty: Easy 64.

Which of the substituents shown directs the incoming group to the ortho/para position during electrophilic aromatic substitution?

A. B. C. D. E.

-NO2 -CF3 -Br -COOCH3 none of these

Answer: C Learning Objective: 18.9 Describe how the presence of a halogen affects the rate and regiochemical outcome of an electrophilic aromatic substitution Difficulty: Easy 65.

Which one of the compounds shown is the most reactive toward electrophilic aromatic substitution?

NH 2

I A. B. C. D. E.

III

CF3

I II III IV V

Answer: A Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Easy

66.

A. B. C. D. E.

Which one of the compounds shown is the least reactive toward electrophilic aromatic substitution?

NO2

III

CF3

I II III IV V

Answer: A Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 67.

Arrange the compounds shown in order of decreasing reactivity towards electrophilic aromatic substitution.

I A. B. C. D. E.

V > II > I > III > IV II > V > III > I > IV IV > I > III > V > II III > II > I > IV > V IV > V > II > I > III

NH 3

III

Answer: C Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 68.

Predict the major product for the reaction shown.

Cl2/FeCl3

Cl Cl Cl

Cl I Cl A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 69.

What reagent(s) are necessary to carry out the conversion shown?

t-butylbenzene ¾¾® 1-t-butyl-4-chlorobenzene A. B.

Cl2, heat Cl2, FeCl3

C. D. E.

SOCl2, pyridine HCl PCl3

Answer: B Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 70.

What is the predicted major product for the reaction shown?

OCH3 fuming H 2SO4

OCH3

OCH3 SO3H

SO3H

SO3H SO3H II

I A. B. C. D. E.

SO3H III

I II III IV I and II

Answer: B Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 71.

What is the predicted major product for the reaction shown?

O CH2

C CH2

A. B. C. D. E.

Br2/AlBr 3

I II III IV V

Answer: B Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 72.

What is the predicted major product for the reaction shown?

O OCCH 3 Br2/ FeBr3

OCCH 3

Br I A. B. C. D. E.

Br II

III

I II III IV I & IV

Answer: D Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 73.

What is the predicted major product for reaction shown?

OCH 3

HNO3/ H2SO4

OCH3

OCH 3

NO2 NO 2 NO 2 I

II OCH 3

III OCH 3

NO2

NO2 IV A. B. C. D. E.

O2N

NO2 V

I II III IV V

Answer: C Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Easy 74.

What is the predicted major product for the reaction shown?

O CCH3 CH3Cl/AlCl3 NO 2

I A. B. C. D. E.

CCH3

CCH 3

NO2

III

NO2

I II III IV no reaction

Answer: E Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 75.

What is the predicted major product for the reaction shown?

Cl2/AlCl3

Cl OH

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 18.10 Predict the directing effects of strong, medium, and weak activators, and strong, medium, and weak deactivators Difficulty: Medium 76.

What is the predicted major product for the reaction shown?

HNO 3/H2SO 4

NO2

NO2 I

NO2

III

NO2

O2N

NO2 IV

A. B. C. D. E.

I II III IV V

What is the predicted major product for the reaction shown?

Fuming H 2SO4

OCH3

SO3H

SO3H OCH3

OCH3

III

SO3H

A. B. C. D. E.

OCH3

I II III IV V

Answer: V Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Medium 78.

What is the predicted major product for the reaction shown?

O COCH 3 (CH3)3CCl AlCl3 OCH3

COCH3

COCH3 (H3C)3C

C(CH3)3 OCH3

C(CH3)3

OCH3

III

O COCH3

C(CH3)3 (H3C)3C

C(CH3)3

A. B. C. D. E.

I II III IV V

OCH3

Predict the major product for the reaction shown.

OCH3 HNO3/H2SO4 OCH 3

OCH3

NO2 OCH3

OCH3

NO2

III

NO2

OCH3

OCH3 O N

OCH3

A. B. C.

I II III

D. E.

IV V

Answer: B Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Medium 80.

What are the predicted structures of the major intermediate (A) and product (B) of the reaction sequence shown?

Br2/FeBr3

CH 3CH2Cl B AlCl3

III

O O

O Br A. B. C. D. E.

O Br

I II III IV V

Answer: D Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Hard

81.

What is (are) the predicted major product(s) for the reaction shown?

HNO3/H2SO4

O I

O2N O II

O2N

NO2 O

III

O2N NO2 O IV

O2N A. B. C. D. E.

I II III II and III IV and V

What is the predicted major product for following reaction shown?

H N

O Br2 / FeBr3

H N

Br I

A. B. C. D. E.

I II III IV V

Predict the major product for the following reaction.

O NHCCH3

CH 3Cl/AlCl3

NHCCH3

III

O NHCCH3

A. B. C. D. E.

I II III IV V

What is the predicted major product for the reaction shown?

CCl3 H 3CO

OCH 3

Fuming H 2SO4

CCl3

CCl3 H3CO

H3CO

OCH3

SO3H

SO3H I

CCl3

SO3H

H3CO

OCH3

SO3H IV

III

CCl3 HO3S

SO3H

A. B. C.

I II III

D. E.

IV V

Answer: C Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Medium 85.

What is the predicted major product for the reaction shown?

O Cl AlCl3

O O

A. B. C. D. E.

I II III IV V

What is the predicted major product for the reaction shown?

O2N

O 2N

CH2 I

CH 3CH2Cl

CH2

AlCl3

O2N

CH 2 II

B. C. D. E.

II III IV no reaction

Answer: D Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Medium 87. Which of the following series of reagents could be used to carry out the conversion shown?

A. B. C. D. E.

1. Fuming H2SO4; 2. Excess NBS 1. Br2; 2. AlBr2; 2. Zn(Hg), HCl, heat 1. Br2; 2. FeBr3 1. Fuming H2SO4; 2. Br2/FeBr3; 3. Dilute H2SO4 1. Br2; 2. AlBr3

Answer: D Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Medium 88. Which of following reagents or series of reagents could be used to carry out the conversion shown?

(CH 3)3N A. B. C. D. E.

(CH 3)3N

1. Fuming H2SO4; 2. CH3CH2Cl/AlCl3; 3. H2O, heat 1. CH3CH2Cl/AlCl3 1. Cl2; 2. AlBr3; 1. CH3CH2Cl/AlCl3 1. Dilute H2SO4; 2. CH3CH2Cl/AlCl3 1. Dilute H2SO4; 2. CH3CH2CH2Cl/AlCl3

Answer: A Learning Objective: 18.11 Predict the regiochemical outcome of an electrophilic aromatic substitution reaction when multiple substituents are present on an aromatic ring Difficulty: Medium 89. Which of the following series of reagents could be used to carry out the conversion shown?

NO2

Br A. B. C. D. E.

1. HNO3/H2SO4; 2. Br2/FeBr3 1. Br/AlBr3; 2. HNO3; 3. H3O+ 1. Br/AlBr; 2. Fuming H2SO4; 3. H2O, heat; 4. HNO3/H2SO4 1. Br2/FeBr3; 2. HNO3, H3O+ 1. FeBr3; 2. HNO3; 3. H3O+

Answer: A Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Easy

90. Which of the following series of reagents could be used to carry out the conversion shown?

NO2

Cl A. B. C. D. E.

1. HNO3/H2SO4; 2. Fuming H2SO4; 3. Excess NBS; 4. Cl2/FeCl3 1. Cl2; 2. HNO3; 3. H3O+ 1. HNO3, H2SO4; 2. Cl/FeCl3 1. Cl2/FeCl3; 2. HNO3, H2SO4 1. FeCl3; 2. HNO3; 3. H3O+

Answer: D Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Easy 91.

What series of reagents necessary to carry out the following conversion.

O CCH3

Br O

1. CH3CCl / AlCl3 ; 2. Br2/FeBr3 O

B. C.

1. Br2, FeBr3; 2. H3O+; 3. CH3CCl / AlCl3 1. CH3CH2CH2Cl; 2. PCC, CH2Cl2; 3. Br2FeBr3

/AlCl3; 2. Br2/FeBr3

1. Br2/FeBr3; 2. Fuming H2SO4; 3. CH3CCl / AlCl3 ; 4. H3O+

Answer: A Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 92. What reagent or series of reagents could be used to carry out the conversion shown?

A. B. C. D. E.

1. Br2/FeBr3; 2. H3O+, heat; 3. CH3CH2Cl/AlCl3 1. Fuming H2SO4; 2. Br2/AlBr3; 3. H3O+, heat; 4. CH3CH2Cl/AlCl3 1. Fuming H2SO4; 2. Br2/FeBr3; 3. H3O+, heat; 4. CH3CH2Cl/AlCl3 1. CH3CH2Cl/AlCl3; 2. Fuming H2SO4; 3. Br2/ FeBr3; 4. H3O+, heat 1. CH3CH2Cl/AlCl3; 2. Br2/ FeBr3; 3. H3O+, heat

Answer: D Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 93.

What series of reagents could be used to carry out the conversion shown?

O COH

Cl A. B. C. D. E.

1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. KMnO4, H2O, heat 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. PCC, CH2Cl2 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. Na2Cr2O7/H2O 1. CH3CH2Cl/AlCl3; 2. KMnO4, H2O, heat; 3. Cl2/FeCl3 1. CH3CH2Cl/AlCl3; 2. NaOH; 3. Cl2/FeCl3

Answer: A Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 94.

What series of reagents could be used to carry out the conversion shown?

A. B.

1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. KMnO4, H2O, heat 1. CH3CH2Cl/AlCl3; 2. (CH3)2CH2OH/AlCl3Cl2/FeCl3; 3. 3. H2O, heat O

1. (CH3)2CH2Cl/AlCl3; 2. CH3CH2CCl / AlCl3; 3. Zn(Hg)/HCl, heat O

1. CH3CH2CCl / AlCl3; 2. CH3CH2Cl/AlCl3; 3. H2O, heat

; NaOH; 2. (CH3)2CH2Cl/AlCl3; 3. H2O, heat

Answer: C ( Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 95.

What series of reagents could be used to carry out the conversion shown?

SO3H A. B. C. D. E.

1. CH3CH2Cl/AlCl3; 2. NBS; 3. NaCN; 4. fuming H2SO4 1. CH3CH2Cl/AlCl3; 2. fuming H2SO4, heat; 3. NBS, heat; 4. NaCN 1. Fuming H2SO4; 2. NBS, heat; 3. NaCN; 4. CH3CH2Cl/AlCl3 1. Fuming H2SO4; 2. NBS, heat; 3. CH3CH2Cl/AlCl3; 4. NaCN; 1. CH3CH2Cl/AlCl3; 2. NBS; 3. fuming H2SO4; 4. NaCN

Answer: B Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 96.

What series of reagents could be used to carry out the conversion shown?

A. B. C. D. E.

1. (CH3)2(CH2Cl/AlCl3; 2. NaOH; 3. excess Br2/FeBr3; 3. fuming H2SO4 1. CH3CH2Cl/AlCl3; 2. Br2; 3. H2O, heat 1. (CH3)2CH2Cl/AlCl3; 2. Zn(Hg)/HCl, heat; 3. excess Br2/FeBr3; 4. H3O+, heat 1. excess Br2/FeBr3; 2. H3O+, heat; 3. (CH3)2CH2Cl/AlCl3; 4. fuming H2SO4 1. (CH3)2CH2Cl/AlCl3; 2. fuming H2SO4; 3. excess Br2/FeBr3; 4. H3O+, heat

Answer: E Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 97.

What series of reagents could be used to carry out the conversion shown?

O COH Br

A. 1. excess Br2/FeBr3; 2. CH3CH2Cl/AlCl3; 3. fuming H2SO4; 4. dilute H2SO4, heat; 5. NaCr2O7/H2SO4/H2O B. 1. CH3CH2Cl/AlCl3; 2. fuming H2SO4; 3. excess Br2/FeBr3; 4. dilute H2SO4, heat; 5. NaCr2O7/H2SO4/H2O C. 1. excess Br2/FeBr3; 2. CH3CH2CH2Cl/AlCl3; 3. fuming H2SO4; 4. CH3CH2Cl/AlCl3; 5. fuming H2SO4; D. 1. excess Br2/FeCl3; 2. H3O+, heat; 3. (CH3)2CH2Cl/AlCl3; 4. fuming H2SO4 E. 1. CH3CH2Cl/AlCl3; 2. fuming H2SO4; 3. excess Br2/FeBr3; 4. NaCr2O7/H2SO4/H2O Answer: B Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 98.

What series of reagents could be used to carry out the conversion shown?

CCl3

Cl A. B. C. D. E.

1. Cl2/FeCl3; 2. CH3Cl/AlCl3; 3. excess Cl2, heat 1. CH3Cl/AlCl3; 2. Cl2/FeCl3; 3. excess Cl2, heat 1. excess Cl2/FeCl3; 2. H3O+; 3. CH3Cl/AlCl3; 1. Excess Cl2; 2. CH3Cl/AlCl3 1. Cl2/FeBr3; 2. CH3Cl/AlCl3; 3. H3O+, heat

Answer: A Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 99.

What series of reagents could be used to carry out the conversion shown?

Cl A. B. C. D. E.

1. Cl2/FeBr3; 2. CH3Cl/AlCl3CH3MgBr/ether; 3. H2O 1. Cl2/FeCl3; 2. CH3Cl/AlCl3CH3MgBr/ether; 3. H2O 1. excess Cl2/FeCl3; 2. CH3MgBr/ether; 3. H2O, heat 1. Cl2/FeCl3; 2. CH3MgBr/ether; 3. H2O; 4. H3PO4, heat 1. CH3MgBr/ether; 2. Cl2/FeCl3; 3. H2O; 4. H3PO4, heat

Answer: D Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium

100.

What reagents are necessary to prepare 1-bromo-3-isobutylbenzene from benzene?

1. Excess Br2; 2. CH3CH2CH2CH2Cl; 3. Zn(Hg), HCl, heat; O

1. Br2/FeBr3; 2. Zn(Hg), HCl, heat; 3. (CH3)2CHCCl/AlCl3 O

1. (CH3)2CHCCl/AlCl3 ; 2. Br2/FeBr3; 3. Zn(Hg), HCl, heat O

1. Br2/FeBr3; 2. (CH3)2CHCCl/AlCl3 ; 3. Zn(Hg), HCl, heat O

1. Zn(Hg), HCl, heat; 2. Br2/FeBr3; 3. (CH3)2CHCCl/AlCl3

Answer: C Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 101.

What is the structure of the major product when anisole is treated with the reagents shown?

1. 2.

Br2, FeBr3 HNO3, H2SO4

OCH3

OCH3 Br

NO2

III

OCH3

A. B. C. D. E.

OCH3 NO2

NO2

I II III IV V

Answer: B Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 102.

What series of reagents could be used to carry out the conversion shown?

Cl O

1. CH3CCl /AlCl3; 2. Cl2/FeCl3; 3. CH3MgBr; 4. H2O O

1. Cl2/FeCl3; 2. CH3MgBr; 3. H2O; 4. CH3CCl /AlCl3 O

1. CH3CCl /AlCl3; 2. CH3CH2Cl/AlCl3; 3. excess Cl2; 4. H3O+, heat O

1. CH3CCl /AlCl3; 2. CH3CH2Cl/AlCl3; 3. H3O+, heat

1. CH3COOH; 2. Cl2; 3. CH3MgBr; 4. H2O

Answer: A Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Medium 103.

What series of reagents could be used to carry out the conversion shown?

OCH3 Br

NO 2 A. B. C. D. E.

1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. CH3ONa; 4. excess Br2/FeBr3 1. HNO3/H2SO4; 2. CH3ONa; 3. excess Br2/FeBr3; 4. Cl2/FeCl3 1. Excess Cl2; 2. HNO3/H2SO4; 3. excess NBS 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. CH3ONa; 4. excess Br2/FeBr3 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. CH3ONa

Answer: D Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 104.

What series of reagents could be used to carry out the conversion shown?

O COH Cl

NO2 A. B. C. D. E.

1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. KMnO4/NaOH/H2O 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. KMnO4/NaOH/H2O; 4. H3O+ 1. HNO3/H2SO4; 2. CH3CH2Cl/AlCl3; 3. Cl2/FeCl3; 4. KMnO4/NaOH/H2O; 5. H3O+ 1. CH3CH2Cl/AlCl3; 2. Cl2/FeCl3; 3. KMnO4/NaOH/H2O; 4. HNO3/H2SO4; 5. H3O+ 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. KMnO4/NaOH/H2O; 5. H3O+

Answer: E Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 105. What reagent or series of reagents could be used to carry out the conversion shown?

OH Br

Br A.

1. Cl2/FeCl3; 2. H3O+ ; 3. excess Br2/FeBr3

B. C. D. E.

1. Cl2/FeCl3; 2. NaOH, heat; 3. H3O+ ; 4. excess Br2/FeBr3 1. Br2/FeBr3; 2. NaOH, heat; 3. H3O+ ; 4. excess Br2/FeBr3 1. Br2/FeBr3; 2. NaOH, heat; 3. H3O+ 1. excess Cl2/FeCl3; 2.H3O+ ; 3. excess Br2/FeBr3

Answer: B Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 106. What would be an appropriate first step for a stepwise synthesis to convert benzene to the compound shown?

CH2CH2Br

O2N

NO 2

O CH3CCl

AlCl3 NaBH4

CH3OH excess HNO3

III

H2SO4

HBr

ROOR H3PO4

heat

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 107. What would be a good choice for the first reagent to begin a series of reactions to convert benzene to the product shown?

OH SO3H

NO 2

A. B. C. D. E.

H3O+ HNO3/H2SO4 NaOH, heat Cl2/FeCl3 Fuming H2SO4

Answer: D Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 108. What series of reagents could be used to carry out the conversion of benzene to the product shown?

CH 2CH 2CN

Br CH3CH 2ONa

Br HBr/CH 3OOCH 3

CH=CH2

Br NaCN

CH 2CH 2Br

CH2CH 2CN

A. 1. CH3CH2Cl/AlCl3; 2. Br2FeBr3; 3. NBS, heat; 4. NaCN; 5. CH3CH2ONa; 6. HBr/CH3OOCH3 B. 1. CH3CH2Cl/AlCl3; 2. NBS, heat; 3. CH3CH2ONa; 4. HBr/CH3OOCH3; 5. NaCN C. 1. CH3CH2Cl/AlCl3; 2. NBS, heat; 3. Br2FeBr3; 4. CH3CH2ONa; 5. HBr/CH3OOCH3; 6. NaCN D. 1. Br2FeBr3; 2. CH3CH2Cl/AlCl3; 3. NBS, heat; 4. CH3CH2ONa; 5. HBr/CH3OOCH3; 6. NaCN E. 1. Br2FeBr3; 2. NBS, heat; 3. CH3CH2ONa; 4. HBr/CH3OOCH3; 5. CH3CH2Cl/AlCl3; 6. NaCN Answer: D Learning Objective: 18.12 Design a synthesis for a substituted benzene ring Difficulty: Hard 109.

Which of the criteria listed is necessary for a nucleophilic aromatic substitution reaction?

A. B. C. D. E.

the ring must contain a very strong electron withdrawing group the ring must contain a leaving group the leaving group must be ortho or para to the electron withdrawing group the leaving group must be meta to the electron withdrawing group A, B and C

Answer: E Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Easy 110.

Which of the compounds listed will not undergo nucleophilic aromatic substitution?

A. B. C. D.

1-chloro-2,4-dinitrobenzene 1-bromo-4-nitrobenzene o-chloronitrobenzene m-chloronitrobenzene

p-chloronitrobenzene

Answer: D Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Easy 111.

What is the predicted product of the following reaction?

NO2

OCH3 II

H3CO

III

NO2

A. B. C. D. E.

CH 3ONa

H3CO

OCH3

NO2

I II III IV V

Answer: E Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Medium 112.

What is the predicted product of the reaction shown?

O2N

NH 3

NH2

O2N

Cl O2N

III

O2N

NO2

O2N

NH2 NH2

Cl NH2

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Medium 113.

What is the predicted product for the reaction shown?

Cl NO2

NO 2 O

N NO2

I Cl

III

NO2 NO2

O NO2

NO2 NO2 A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Medium 114.

What is the predicted product for the reaction shown?

Br CH 3NH2

NO 2

NH2

CH3

NHCH3 I

NO2

III

NO2 NO2

NHCH3 V

NO2 A. B. C. D. E.

I II III IV V

NO2

NHCH3

Answer: D Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Medium 115.

What is the expected product of the reaction shown?

NO2 Br2/AlCl3

NO2

III

NO2

NO2 Br NO2

NO2

O2N

NO2

Br V

Br Br A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism

Difficulty: Medium 116.

Which structure(s) are major resonance contributors for the intermediate that results when p-chloronitrobenzene is treated with NaOH?

O HO

III

O A. B. C. D. E.

I and II I and III I, II, and IV I, III, IV, and V I, II, IV, and V

Answer: E Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Hard 117.

What is the predicted product of the reaction shown?

Cl CH3ONa

NO 2

OCH3

NO2

III

Cl H3CO

OCH3

A. B. C. D. E.

NO2

OCH3

I II III IV V

Answer: B Learning Objective: 18.13 Identify the requirements for a nucleophilic aromatic substitution reaction, and draw its mechanism Difficulty: Medium

118.

What is(are) the predicted product(s) of the reaction shown?

Cl 1. NaOH, heat 2. H3O+

Cl OH

OH I

III

Cl IV

A. B. C. D. E.

I II I and III I and IV III and IV

Answer: E Learning Objective: 18.14 Predict the products of an elimination-addition reaction

Difficulty: Easy 119.

What is(are) the predicted product(s) of the reaction shown?

Cl 1. NaNH 2, NH3 2. H3O+

Cl NH2

NH2

Cl NH2

A. B. C.

NH2

I III II and III

III

NH2

D. E.

IV and V II and V

Answer: C Learning Objective: 18.14 Predict the products of an elimination-addition reaction Difficulty: Easy 120.

What is the mechanism by which the following reaction occurs?

Cl Cl2/FeCl3

A. B. C. D.

elimination-addition nucleophilic aromatic substitution electrophilic aromatic substitution both B and C

Answer: C Learning Objective: 18.15 Predict the mechanism of an aromatic substitution reaction Difficulty: Easy 121.

What

O2N

the

mechanism

which

Br NaOCH3

O2N

the

following

reaction

occurs? A. B. C. D. D.

elimination-addition nucleophilic aromatic substitution electrophilic aromatic substitution addition-elimination both B and C

Answer: B Learning Objective: 18.15 Predict the mechanism of an aromatic substitution reaction Difficulty: Medium 122.

What is the mechanism by which the following reaction occurs?

Cl 1. NaNH 2, NH3 2. H 3O+

A. B. C. D. E.

elimination-addition nucleophilic aromatic substitution electrophilic aromatic substitution addition-elimination both B and C

Answer: A Learning Objective: 18.15 Predict the mechanism of an aromatic substitution reaction Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 19 1.

Name the aldehyde or ketone that is found in nail polish remover.

A. B. C. D. E.

ethanol 2-butanone acetone formaldehyde diethyl ether

Answer: C Learning Objective: 19.1 Compare the structures of an aldehyde and a ketone Difficulty: Easy 2.

Name the aldehyde or ketone that is used as a preservative.

A. B. C. D. E.

ethanol 2-butanone acetone formaldehyde diethyl ether

Answer: D Learning Objective: 19.1 Compare the structures of an aldehyde and a ketone Difficulty: Easy 3.

What is the IUPAC name for the compound shown?

O A. B. C. D. E.

2-methyl-5-heptanone 7-methyl-4-octanone 6-isopropyl-4-octanone isobutyl propyl ketone 1,1-dimethyl-4-heptanone

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

Difficulty: Medium 4.

What is the correct structure for 5-methyl-4-octanone?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 5.

What is the IUPAC name for the compound shown?

A. 3,3,-dimethyl-6-heptanone B. 3,3-methyl-6-heptanone C. 3-dimethyl-6-heptanone D. 5,5-dimethyl-2-heptanone E. 5,5-methyl-2-heptanone Answer: D

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 6.

What is the IUPAC name for the compound shown?

O H A. B. C. D. E.

2,5-dimethyl-6-hexanal 2,5-dimethylhexanal 1,4-dimethylpentanal 1,4-dimethylhexanal none of these

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 7.

What is the structure of 4-methylbenzaldehyde? O

O H

III

A. B. C.

I II III

D. E.

IV V

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 8.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

5,5-dimethyl-2-heptanone 5,5-dimethylcycloheptanone 4,4-dimethylcycloheptanone 3,3-dimethylcycloheptanone 1,1-dimethyl-4-cycloheptanone

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 9.

What is the IUPAC name for the compound shown?

A. B. C.

2,4-dimethyl-2-pentenone 2,5-dimethylcyclopenten-3-one 2,4-dimethylcyclopent-2-enone

D. E.

3,5-dimethylcyclopent-2-enone 2-methyl-5-methylcyclopent-2-enone

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 10.

What is the structure of 2,3-dimethyl-2-octen-4-one?

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

Difficulty: Hard 11.

What is the IUPAC name for the compound shown?

O H

A. B. C. D. E.

4-benzylbutanal 3-phenylpropanal 3-benzylpropanal 4-phenylbutanal 2-benzylethanal

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 12.

What is the structure for 5-hydroxy-2-phenyl-3-hexanone?

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 13.

What is the IUPAC name for the compound shown?

O H Cl

A. B. C. D. E.

4-chloro-3-methylbenzaldehyde 4-chloro-3-methylcyclohexan-1-one 1-chloro-2-methyl-4-benzaldehyde 1-chloro-2-methylbenzaldehyde 4-chloro-3-methylcyclahexanone

Answer: A Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium

14.

What is the structure of m-nitroacetophenone?

NO2 O2N NO2 II

III

OH O2N NO2 IV

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 15.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

(S)-2-methyl-2-bromobutanone (S)-2-bromo-2-methylcyclobutanone (R)-2-bromo-2-methylcyclobutanone (S)-1-bromo-1-methyl-2-cyclobutanone (R)-1-bromo-1-methyl-2-cyclobutanone

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 16.

What is the structure of (S)-3-chlorocyclohexanone?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 17.

What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

H I

Cl Cl

O H

H III

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 18.

What is the structure of 7-bromo-1-octyn-4-one?

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 19.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

4-oxo-5-phenyl-2-hexanol 5-hydroxy-2-phenyl-3-hexanone 2-hydroxy-5-phenyl-4-hexanone 2-hydroxypropyl-1-phenylethyl ketone 5-hydroxy-3-keto-2-phenylhexane

Answer: B Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 20.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

(2R,3R)-2-isopropyl-3-methylcyclohexanone (2S,3S)-2-isopropyl-3-methylcyclohexanone (2S,3R)-2-isopropyl-3-methylcyclohexanone (2R,3S)-2-isopropyl-3-methylcyclohexanone (2R)-2-isopropyl-3-methylcyclohexanone

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 21.

A. B. C. D. E.

What is the IUPAC name for the compound shown?

(R)-6-bromo-2-heptanal (S)-6-bromo-2-heptanal (R)-6-bromo-2-heptanone (S)-6-bromo-2-heptanone (R)-2-bromo-6-heptanone

Answer: C Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard

22.

What is the IUPAC name for the compound shown?

O A. B. C. D. E.

5-cyclohexyl-2-hexanal 5-cyclohexyl-2-hexanone 5-cyclohexyl-5-methyl-2-pentanone 5-(1-methylcyclohexyl)-2-pentanone 4-(1-methylcyclohexyl)-2-butanone

Answer: E Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 23.

What is the structure of benzophenone?

III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 24.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

(2R,4S)-2,4-methylpentanedial (2S,4R)-2,4-dimethylpentanedial (2R,4S)-2,4-dimethylpentanedial (2S,4S)-2,4-dimethylpentanedial (2R,4R)-2,4-dimethylpentanedial

Answer: E Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 25.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

(3R,5R)-3,5-dimethyl-2,6-heptanone (3S,5S)-3,5-dimethyl-2,6-heptanone (3S,5R)-3,5-dimethyl-2,6-heptanedione (3R,5S)-3,5-dimethyl-2,6-heptanedione (3R,5R)-3,5-dimethyl-2,6-heptanedione

Answer: E Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Hard 26.

What is the IUPAC name for the compound shown?

O O

A. B. C. D. E.

1,2-cyclohexanediol 1,2-hexanodione 1,2-cyclohexanone 1,2-cyclodihexanone 1,2-cyclohexanedione

Answer: E Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature Difficulty: Medium 27.

What is the predicted product of the reaction shown?

1-hexanol A. B. C. D. E.

PCC CH2Cl2

hexanal hexanoic acid 2-hexanone 2-chlorohexane 1-hexanol

Answer: A Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 28.

What is the predicted product of the reaction shown?

1-hexanol A. B.

DMP CH2Cl2

hexanal hexanoic acid

C. D. E.

2-hexanone 2-chlorohexane 1-hexanol

Answer: A Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 29.

What is the predicted product of the reaction shown?

1-hexanol A. B. C. D. E.

1. DMSO, (COCl)2 2. Et3N

hexanal hexanoic acid 2-hexanone 2-chlorohexane 1-hexanol

Answer: A Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 30.

What is the predicted product of the reaction shown?

2-hexanol A. B. C. D. E.

PCC CH2Cl2

hexanal hexanoic acid 2-hexanone 2-chlorohexane 1-hexanol

Answer: C Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 31.

What is the predicted product for the reaction shown?

Na2Cr 2O7 H2SO4, H2O

2-hexanol A. B. C. D. E.

hexanal hexanoic acid 2-hexanone 2-chlorohexane 1-hexanol

Answer: C Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 32.

What is the predicted product for the reaction shown?

N CrO3 Cl H CH 2Cl2

A. B. C. D. E.

I II III IV V

Answer: D

O H II

Cl OH

III

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 33.

What is the predicted product for the reaction shown?

Na2Cr 2O7 H2SO4, H 2O

A. B. C. D. E.

O H II

Cl OH

III

I II III IV V

Answer: D Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 34.

What is the predicted product for the reaction shown?

3-methyl-1-octanol A. B. C. D. E.

PCC CH2Cl2

3-methyloctanone 3-methyloctanal 2-methyloctanone 2-methyloctanal 2-methyloctanoic acid

Answer: B Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 35.

What is the predicted product for the reaction shown?

3-methyl-1-octanol A. B. C. D. E.

DMP CH2Cl2

3-methyloctanone 3-methyloctanal 2-methyloctanone 2-methyloctanal 2-methyloctanoic acid

Answer: B Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 36.

What is the predicted product of the reaction shown?

3-methyl-1-octanol

1. DMSO, (COCl)2 2. Et3N

A. B. C. D. E.

3-methyloctanone 3-methyloctanal 2-methyloctanone 2-methyloctanal 2-methyloctanoic acid

Answer: B Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 37.

What is the predicted product of the reaction shown?

OH PCC , excess

CH 2OH

CH2Cl2 O

O O

C OH

A. B. C. D. E.

C H

III

I II III IV V

Answer: B Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 38.

Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?

Compound A

1. O3 2. (CH3)2S

acetophenone + propanal

A. B. C. D.

2-phenyl-2-pentene 1-phenyl-1-hexene 1-phenyl-2-pentene 2-phenyl-2-hexene

Answer: A Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 39.

Compound A on ozonolysis yields the two products shown. What is the structure of compound A?

O Compound A

1. O3

2. (CH3)2S

A. B. C. D.

I II III IV

none of these

Answer: A Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 40.

Compound A on ozonolysis yields 2,6-heptanedione. What is the structure of compound A?

Compound A A. B. C. D. E.

1. O3 2. (CH3)2S

2,6-heptanedione

1,2-dimethylcyclohexene 2,6-dimethylcyclohexene 1,5-dimethylcyclopentene 1,2-dimethylcyclopentene 2-methyl-1-cyclopentene

Answer: D Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 41.

What is the predicted product of the reaction shown?

1. excess O3 2. (CH 3)2S

O H

H I

III

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 42.

What is the predicted product of the reaction shown?

1.O3 2. (CH3)2S A. B. C. D. E.

cyclopentene cyclopentanol cyclopentanal cyclopentanone none of these

Answer: D Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 43.

Provide the reagents necessary to carry out the conversion shown.

(CH3)2CHCH2C A. B. C. D.

CCH2CH(CH3)2

1. H2O; 2. O3; 3. (CH3)2S 1. LiAlH3; 2. H3O+; 3. (CH3)2S 1. H2/Ni2B or Na/NH3; 2. O3 1. H2/Ni2B; 2. (CH3)2S

3-methylbutanal

1. H2/Ni2B or Na/NH3; 2. O3; 3. (CH3)2S

Answer: E Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 44.

What is the predicted product for the reaction shown?

(CH3)2CHCH2C

CCH2CH(CH3)2

Na/NH3

1. O3 2. DMS

O (CH3)2CHCH2CH3

(CH3)2CHCH2CH

(CH3)2CHCH2CCH3 III

O (CH3)2CHCH2CCH2(CH3) IV

A. B. C. D. E.

(CH3)2CHCH2CH2CH2(CH3) V

I II III IV V

Answer: B Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 45.

Provide the reagents necessary to carry out the conversion shown.

O H A. 9-BBN; H2O2/NaOH/H2O B. H3O+; LiAlH3; H2O C. PdCl2; O2, H2O D. 9-BBN; O3, H2O E. H2/Ni2B; H2/Pd; H3O+ Answer: A Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 46.

What is the predicted product for the reaction shown?

H2O / H 2SO4 HgSO4

OH I

A. B. C. D. E.

I II III IV V

Answer: D

H II

III

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 47.

Predict the product for the reaction shown.

H 2O / H2SO4 HgSO4

III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 48.

Provide the reagents necessary to carry out the conversion shown.

H O A. B. C. D. E.

1. H2O/ H2SO4, 2. PCC/CH2Cl2 PCC/ CH2Cl2 1. 9-BBN, 2. H2O2/NaOH/H2O 1. O3, 2. Zn/acetic acid 1. 9-BBN 2. H2O2/NaOH/H2O 3. CrO3/H2SO4/H2O

Answer: C Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 49.

What reagents are necessary to carry out the conversion shown?

A. B. C. D. E.

1. BH3; 2. H2O2/NaOH/H2O; 3. CrO3/H2SO4/H2O or PCC/CH2Cl2 2. H2/Pt; 2. H2O2; 3. H2O 1. H2O2/NaOH/H2O; 2. PCC/CH2Cl2 1. BH3; 2. PCC/CH2Cl2 1. O3; 2. H2O2/NaOH/H2O; 3. H3O+

Answer: A

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 50.

Predict the major product for the reaction shown.

O CH3CH 2CCl AlCl3

O O

O O Cl O I A. B. C. D. E.

III

I II III IV none of these

Answer: C Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 51.

What is the predicted product of the reaction shown?

AlCl3

Cl O

III

IV A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard

52.

What reagents are necessary to carry out the conversion shown?

/H3O+

A. B.

/AlCl3 O

/ AlCl3

, AlCl3

, H3 O+

Answer: C

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 53.

What is the predicted major product for the reaction shown?

O Cl O

AlCl3

O I

III

O V

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Medium 54.

Which of the following reactions will produce acetophenone as a major product?

O Cl

PCC

AlCl3

A. B. C. D. E.

CH 2Cl2

I II III IV all of these

Answer: E Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones Difficulty: Hard 55.

Which of the following compounds is most reactive towards a nucleophilic addition reaction?

O H

H I

A. B. C. D. E.

I II III IV V

Answer: A

H II

III

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions Difficulty: Easy 56.

Which of the following compounds is least reactive towards a nucleophilic addition reaction?

O H

I A. B. C. D. E.

III

I II III IV V

Answer: E Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions Difficulty: Easy 57.

Which of the following compounds is least reactive towards a nucleophilic addition reaction?

O H

A. B. C. D. E.

I II III IV Both I & IV

H I

III

Answer: A Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions Difficulty: Easy 58.

Rank the following compounds in decreasing order (most to least) of reactivity towards a nucleophilic addition reaction.

O H

H I

A. B. C. D. E.

H II

III

I > II > III > IV > V II > IV > V > III > I III > I > V > IV > II I > III > II > IV > V V > IV > II > III > I

Answer: D Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions Difficulty: Medium 59.

Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.

A. There is a steric effect in which the carbonyl group of the aldehyde produces a more sterically hindered transition state and an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic. B. There is a steric effect in which the carbonyl group of the aldehyde produces a less sterically hindered transition state and an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic. C. There is a steric effect in which the carbonyl group of the aldehyde produces a less sterically hindered transition state and an electronic effect because the carbonyl carbon of the aldehyde is less electrophilic. D. There is a steric effect in which the carbonyl group of the aldehyde produces a less sterically hindered transition state, but this is counteracted by an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic.

E. There is a steric effect in which the carbonyl group of the aldehyde produces a more sterically hindered transition state, but this is counteracted by an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic. Answer: B Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions Difficulty: Medium 60.

Benzaldehyde is less reactive than ethanal towards nucleophilic addition reactions. Explain why using words as well as structural drawings.

A. The carbonyl carbon of bezaldehyde is more electrophilic than the ethanal because of the delocalization of the positive charge on the carbonyl carbon via resonance. B. The carbonyl carbon of bezaldehyde is less electrophilic than the ethanal, because of the localization of the positive charge on the carbonyl carbon via resonance. C. The carbonyl carbon of bezaldehyde is less electrophilic than the ethanal because of the delocalization of the negative charge on the carbonyl carbon via resonance. D. The carbonyl carbon of bezaldehyde is more electrophilic than the ethanal, because of the delocalization of the negative charge on the carbonyl carbon via resonance. E. The carbonyl carbon of bezaldehyde is less electrophilic than the ethanal because of the delocalization of the positive charge on the carbonyl carbon via resonance. Answer: E

Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under basic conditions?

A. B. C.

a proton transfer followed by a nucleophilic attack a nucleophilic attack followed by a proton transfer nucleophilic attack is the only step

proton transfer is not required

Answer: B Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions Difficulty: Medium 62.

Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under acidic conditions?

A. B. C. D.

a proton transfer followed by a nucleophilic attack a nucleophilic attack followed by a proton transfer nucleophilic attack is the only step proton transfer is not required

A compound with two OH groups attached to the same carbon is known as ______.

A. B. C. D. E.

an acetal a hemiacetal a hydrate a vicinal hydrate none of these

Answer: C Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Easy 64.

A compound with an OH and an OR group attached to the same carbon is known as ______.

A. B. C.

an acetal a hemiacetal a hydrate

D. E.

a vicinal hydrate none of these

Answer: B Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Easy 65.

A compound with two OR groups attached to the same carbon is known as ______.

A. B. C. D. E.

an acetal a hemiacetal a hydrate a vicinal hydrate none of these

Answer: A Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Easy 66.

Which of the compounds shown can be classified as an acetal?

I A. B. C. D. E.

III

I II III IV none of these

Answer: D Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Easy

67.

Which of the compounds shown can be classified as a hemiacetal?

I A. B. C. D. E.

III

I II III IV none of these

What is the predicted product of the following reaction?

excess H2O H

H2SO4

OCH 3

OCH3

H I A. B. C. D. E.

I II III IV none of these

What is the predicted product of the following reaction?

excess CH 3CH2OH H2SO4

A. B. C. D. E.

OCH 2CH 3

I II III IV none of these

What is the predicted product of the following reaction?

O H

excess CH 3OH H 2SO4

H 3CO OH

A. B. C. D. E.

OCH3 H

I II III IV V

What is the predicted product formed when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid?

O O

O II

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Hard 72.

What reagents are needed to carry out the conversion shown?

1 mole

B. C. D.

2 moles CH3CH2CH2CH2CH2CH2OH and H2SO4 CH3CH2CH2CH2CH2OH and H2SO4

/H2SO4

Answer: A 1 mol

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Medium 73.

What is the predicted product of the conversion shown?

O O O

H3O+ 1 equi.

OH HO

OH I

III

O HO

A. B. C. D. E.

O V

I II III IV V

What is the predicted product of the reaction shown?

O HO

H2SO4

OH OH

I A. B. C. D. E.

III

O V

I II III IV V

What is the predicted product of the reaction shown?

O excess CH3CH2OH H2SO4 HO

A. B. C. D. E.

I II III IV V

What is the predicted product for the reaction shown?

O H2SO4 HO

O O O O I

III

O O O O

A. B. C. D. E.

O V

I II III IV V

What is the predicted product for the reaction shown?

O H

H2SO4

OH I A. B. C. D. E.

IV OH

III

I II III IV V

Which one of the following pairs of compounds will yield the product shown in the presence of sulfuric acid?

O O

HO + I

H II

HO +

A. B. C. D. E.

I II III IV V

Predict the product for the following reaction.

O HOCH2CH 2OH H2SO4

O O

III

A. B. C. D. E.

I II III IV V

Answer: C

80.

What reagents are needed to carry out the conversion shown?

O 1. HOCH2CH2OH, H2SO4; 2. CH3CH2AlCl3 (2 eq.); 3. H3O+ 1 HOCH2CH2CH2OH, H2SO4; 2. CH3MgBr (4 eq.); 3. H3O+ 1. HOCH2CH2CH2CH2CH2CH2OH, H2SO4; 2. H3O+ 1. HOCH2CH2OH, H2SO4; 2. CH3CH2MgBr (2 eq.); 3. H3O+ 1. HOCH2CH2CO3H; 2. H3O+

A. B. C. D. E.

Answer: D 1. Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups Difficulty: Hard 81.

What reagents are needed to carry out the conversion shown?

O O

A. B. C. D. E.

1. HOCH2CH2OH/H2SO4; 2. LiAlH4; 3. H3O+ 1. HOCH2CH2OH/H2SO4; 2. AlCl3; 3. H3O+ 1. HOCH2CH2OH; 2. AlCl3; 3. H3O+ 1. HOCH2CH2CH2CH2OH; 2. LiAlH4; 3. H2SO4 1. HOCH2CH2CH3/H2SO4; 2. LiAlH4; 3. H3O+

What is the predicted product when pentanal reacts with CH3NH2 in the presence of an acid catalyst?

NH 2

NH HO

H IV A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 83.

What is the predicted product when 4-methyl-2-hexanone reacts with hydrazine in the presence of an acid catalyst?

H 2N HO

H2N

N H2N

III

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 84.

What is the predicted product when 4-methyl-2-hexanone reacts with methylamine in the presence of an acid catalyst?

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 85.

What is the predicted product of the reaction shown?

O NH2OH H2SO 4

NH2

I A. B. C. D. E.

ONH2

NOH

NHOH

III

I II III IV V

Answer: D Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 86.

What is the predicted product for the reaction shown?

O CH3CH 2NH2 H2SO4

NH 2 HO

I A. B. C. D. E.

H2N

III

I II III IV V

Answer: E Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 87.

What is the predicted product when cyclopentanecarbaldehyde reacts with phenylhydrazine (PhNHNH2) in the presence of an acid catalyst?

NNHPh

NNH2

NHNHPh

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 88.

What is the predicted product for the reaction shown?

O H

NH 2OH H 2SO4

NH2

NOH

NH2

III

NO2

NH2

A. B. C. D. E.

I II III IV V

Answer: C Mechanism

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Hard 89.

What is the predicted product of the following reaction?

NH2NHCNH2 H2SO4 O

H2N

A. B. C. D. E.

NCNHNH2

CNHNH 2

O HO

NNHCNH 2

III

I II III IV V

Answer: D Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 90.

What reagents are needed to carry out the conversion shown?

NH 2

propanone / H2SO4

B. C. D. E.

propanal/ H2SO4 1-propanol/H2SO4 2-propanol/ H2SO4 ethanal/ H2SO4

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 91.

What is the predicted product for the reaction sequence shown?

CH 2CH 2OH (CH 3)2NH

PCC

H2SO4 N N N III

OH N IV A. B. C. D. E.

I II III IV V

Answer: B

N V

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 92.

What is the predicted product of the reaction sequence shown?

O (CH3CH 2)2NH H 2SO4

A. B. C. D. E.

III

N H

I II III IV V

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 93.

What is the predicted product of the reaction sequence shown?

H N O H2SO4 O

NH2

SO2

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 94.

What is the predicted product of the reaction shown?

H N +

H2SO4

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 95.

What are reactants will form the enamine shown?

OH CH3CH2NHCH3

H2SO4

CH3CH2NHCH3

H2SO4 IV

III

O CH3CH2NHCH3 H2SO4 V

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 96.

What reactants will form the enamine shown?

NH2 O +

H N

OH III

O IV

H N

H2SO4

H3O+

H2SO4

O V

H3O+

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 97.

Predict the product for the following reaction.

NH 2

H 2SO4

+ NH 2 N

O O

N III

NH2

NH2 O

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Hard 98.

What reactant(s) is(are) necessary to prepare the compound shown?

NH2 H3O+

NH2 NH2 H2SO4

O NH2 H2SO4

III

OH NH2 H2SO4

NH2 NH2 H3O+

A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Hard 99.

What is the predicted product for the reaction shown?

O 1.NH2NH2/ H+ 2. KOH/H2O/D A. B. C. D. E.

3-methylhexane 3-methyl-4-hexanol 4-methyl-2-hexene 3-methyl-4-hexene 3-methyl-3-hexene

Answer: A Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 100.

What is the predicted product for the reaction shown?

O 1.NH2NH 2/ H + H A. B. C. D. E.

2. KOH/H2O/D

3-methylhexane 4-methyl-1-hexanol 4-methyl-2-hexene 3-methyl-4-hexene 3-methyl-3-hexene

Answer: A Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

Difficulty: Medium 101.

What is the predicted product for the reaction shown?

O OH 1. NH2NH2/ H+ 2. KOH/H2O/D 3. H3O+

NNH2

OH O

NNH 2

O NH2

OH III

O OH V A. B. C. D. E.

I II III IV V

Answer: C

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 102.

Which of the possible reagent(s) could not be used to carry out the transformation shown?

A. B. C. D.

Zn(Hg), HCl LiAlH4, ether HSCH2CH2SH, BF3; then Raney Ni (H2) 1. NH2NH2/H+ 2. KOH/H2O/heat

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 103.

What is the predicted product for the reaction shown?

H excess 1. NH2NH2/H+ 2. KOH/ H2O/ D

NNH2 CH

A. B. C. D. E.

NNH2 I

HO H NHNH2 C

NHNH2

III

NH 2

I II III IV V

Answer: A Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 104.

What is the predicted product for the reaction shown?

excess 1. NH2NH2/H+ 2. KOH/ H2O/ D O

NNH2 CH

CH NNH2 I A. B. C. D. E.

HO H NHNH2 C

III

NHNH2

NH 2

I II III IV V

Answer: A Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 105.

What reagents are needed to carry out the conversion shown?

O A. B. C. D.

NaBH4/CH3OH 1. NH2NH2/H+ 2. KOH/H2O/heat H2/Ni 1. LiAlH4 , 2. H2O

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Hard 106.

What is the major product of the reaction sequence shown?

O Cl

1. NH 2NH2/ H+ 2. KOH/H 2O/D

AlCl3

O I

H 2NN

III

B. C. D. E.

II III IV V

Answer: B Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction Difficulty: Medium 107.

What is the predicted product(s) for the reaction shown?

H 3O+ excess D H3CO

OCH3

HO HO

OCH3 I

A. B. C. D. E.

OH II

O III

OH IV

I II III IV none of these

Answer: C Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Hard

108.

What is the predicted product for the reaction shown?

NaOH D, H 2O H 3CO

OCH 3

HO HO

OCH3 I

A. B. C. D. E.

O III

OH IV

I II III IV none of these

Answer: E Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Hard 109.

What are the predicted products of the reaction shown?

O O

H3O+ D

HO + I

A. B. C. D. E.

HO +

I II III IV V

Answer: A Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Hard 110.

What are the predicted products for the reaction shown?

O O

H 3O+ D

HO + I

A. B. C. D. E.

I II III IV V

Answer: C

H II

HO +

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Hard 111.

What is(are) the predicted product(s) of the reaction shown?.

H3O+

O I

OH O

III

OH O

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Hard 112.

What is (are) the predicted product(s) of the reaction shown?

NaOH O

H 2O O

OH O

III

OH O

No reaction will occur

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Hard 113.

What are the predicted products of the reaction shown?

N H3O+ D

NH +

NH3

O +

III

O IV

NH3

NH2 V

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Medium 114.

What are the predicted products for the reaction shown.

N H3O+ D NH +

NH +

NH3

O +

III

O IV

NH3

NH2 V

A. B.

I II

C. D. E.

III IV V

Answer: D Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Medium 115.

What are the predicted products of the reaction shown?

N H3O+ D

O I

N H

O II

N H

NH2 III

OH IV

No reaction will occur, so there will be no products.

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Medium

116.

What are the predicted products for the reaction shown?

N H3O+ D

H N

+ O

H N

+ NH2 O

III

+ O H N

A. B. C.

H +

I II III

D. E.

IV V

Answer: B Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Medium 117.

What are the predicted products of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis Difficulty: Medium 118.

What is the predicted product of the reaction shown?

propanal +

Raney

H2SO4 SH

HO S

S S

A. B. C. D. E.

SH III

I II III IV V

Answer: E Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals Difficulty: Medium 119.

What is the predicted product of the reaction shown?

HO S

S S

A. B. C. D. E.

SH III

I II III IV V

Answer: A Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals Difficulty: Medium 120.

What is the predicted product of the reaction sequence shown?

O Cl 1. NH 2NH 2/ H + AlCl3

2. KOH/H2O/D

HSCH2CH 2SH Raney Ni H 2SO4

O I

S IV

A. B. C. D. E.

III

SH V

I II III IV V

Answer: B Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals Difficulty: Medium 121.

What is the predicted product for the reaction shown?

excess CH3CH 2SH H 2SO4

O I

S II

S III

O V

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals Difficulty: Medium 122.

What is the predicted product of the reaction shown?

excess CH3CH 2SH

Raney

H 2SO4

OH I

O II

III

O IV

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals Difficulty: Medium 123.

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water?

O H

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents Difficulty: Medium 124.

What would be the product of the reaction shown?

O H NaBH /CH OH 4

OH OH

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents Difficulty: Medium 125.

What is the predicted product of the reaction shown?

O H

1. LiAlH 4 2. H2O

OH OH

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents Difficulty: Medium 126.

What is the predicted product of the reaction sequence shown? O

NaBH4/CH 3OH

AlCl3 O

III

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents Difficulty: Hard 127.

What is the predicted product of the reaction shown?

O OCH3 NaBH4/CH 3OH

OCH3 I

A. B. C. D.

I II III IV

Answer: A

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents Difficulty: Hard 128.

What reagents are necessary to carry out the conversion shown?

A. B. C. D. E.

NaBH4/CH3OH 1. HOCH2CH2OH/H2SO4 2. NaBH4/CH3OH 3. H3O+, D 1. HOCH2CH2OH/H2SO4, 2. LiAlH4/ether 3. NaOH, H2O + H3 O none of the above

Answer: E Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents Difficulty: Hard 129.

What is the predicted product of the reaction sequence shown?

OH A. B. C. D. E.

6,7-dimethyl-3-nonanol 6,7-dimethyl-3-nonanone 6,7-dimethyl-3-nonanal 3,4-dimethyl-7-nonanol 3,4-dimethyl-7-nonanone

Answer: B

PBr3

Mg/ether

2. H3O+

PCC

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 130.

What is the predicted product of the reaction sequence shown?

PBr3

Mg/ether

H CrO / 3 + H2SO4/H2O 2. H O 3

A. B. C. D. E.

6,7-dimethyl-3-nonanol 6,7-dimethyl-3-nonanone 6,7-dimethyl-3-nonanal 3,4-dimethyl-7-nonanol 3,4-dimethyl-7-nonanone

Answer: B Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 131.

What reagents are necessary to carry out the conversion shown?

O Br

O H ; 3. H3O+; 4. PCC/CH2Cl2 O

1. MgBr; 2.

B. C.

H ; 3. H3O+; 4. PCC/CH2Cl2 1. Mg/ether; 2. 1. LiAlH; 2. H3O+; 3. PCC/CH2Cl2

; 3. H3O+

1. CrO3, H2SO4; 2.

O E.

H ; 3. H3O+; 4. AlCl3

1. Mg/ether; 2.

Answer: B Answer: 1. Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 132.

What reagents are necessary to carry out the conversion shown?

A. B. C. D.

1. 2. 1. 2. 1. 2. 1. 2.

CH3CH2ONa H2 O CH3CH2MgBr H2 O CH3CH2CH2ONa H2 O CH3CH2CH2MgBr H2 O

Answer: B Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 133.

What is the predicted product of the reaction shown?

H3O+

Mg/ether Br HOCH2CH 2OH 2. H2O H 2SO4 HO

O I

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 134.

What reagents are necessary for the conversion shown?

A. B. C. D.

1. NaBH4/CH3OH 2. CH3CH2MgBr CH3CH2MgBr/ether 1. H3O+ 2. CH3CH2MgBr/ ether 1. CH3CH2MgBr/ ether 2. H3O+,D

Answer: B Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Medium 135.

Which one of the compounds shown will yield 1-hexanol when treated with butylmagnesium bromide followed by acid workup?

A. B. C. D. E.

1-hexanol formaldehyde propanal oxirane hexanal

Answer: D Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 136.

What is the predicted product of the reaction sequence shown?

MgBr

MgBr H

H2O ether

PCC/CH2Cl2

H2O ether

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 137.

What reagents are necessary to carry out the conversion shown?

A. B. C. D. E.

1. PCC/CH2Cl2; 2. KCN/HCN 1. H2SO4; 2. KCN/HCN 1. CrO3, H2SO4; 2. H2O; 3. KCN/HCN 1. PCC/CH2Cl2; 2. H2O; 3. CH3CH2CN 1. CrO3, H2SO4; 2. H2O; 3. CH3CH2CN

Answer: A Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Medium 138.

What is the predicted product of the reaction sequence shown?

O NaCN HCN

H2N HO

H2N

H 2N I A. B. C. D. E.

NH 2

III

I II III IV V

Answer: B Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 139.

What is the predicted product of the reaction sequence shown?

O NaCN HCN

1. LiAlH 4 2. H2O

H2N

NH2

H 2N

H2N I

A. B. C. D. E.

NH 2

III

I II III IV V

Answer: C Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 140.

What are the reagents necessary to carry out the conversion shown?

O O

OH OH

A. B. C. D. E.

1. PCC/CH2Cl2; 2. KCN/HCN 1. PCC/CH2Cl2; 2. H3O+ 1. CrO3, H2SO4; 2. CH3CH2CN 1. CrO3, H2SO4; 2. H2O; 3. CH3CH2CN 1. KCN/HCN; 2. H3O+

Answer: E Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Easy

141.

Which reactants are the best choice to prepare the alkene shown using the Wittig reaction?

A. B. C. D. E.

ethanal and 2-bromopentane/PPh3 propanal and 2-bromopentane/PPh3 2-pentanone and 1-bromopropane/PPh3 2-pentanone and 2-bromopropane/PPh3 butanal and 2-bromopentane/PPh3

Answer: C Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Medium 142.

What ylide is needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction?

A. B. C. D. E.

Ph3P=CH(CH2CH3)2 Ph3P=CHCH2CH3 Ph3P=CHCH2CH2CH3 Ph3P=CH2 Ph3P=CHCH2(CH3)2

Answer: C Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Medium 143.

What is the reactant for the reaction shown?

Ph3P=CHCH 3

A. B.

cyclohexanone cyclohexanecarbaldehyde

C. D.

cyclohexylpropanone 3-cyclohexylpropanal

Answer: B Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Medium 144.

What is the predicted product for the reaction sequence shown?

Br Ph3P

CH3CH2CH 2CH2Li CH3CCH2CH 3 ether

A. B. C. D. E.

I II III IV V

Answer: D

O II

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 145.

Provide the structures of X, Y and Z in the following reaction sequence.

Br + Ph3P

CH 3CH2CH2CH 2Li

ether

CH3CCH2CH3

A. B. C. D. E.

X is III, Y is I, and Z is II X is I, Y is II, and Z is IV X is III, Y is I or II, and Z is IV X is V, Y is III, and Z is I or II X is II, Y is I, and Z is V

Answer: C Answer:

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Hard 146.

Provide the structure of the reactants necessary to prepare the following compound using the Wittig reaction.

OH I

+ OH PPh3

+ O PPh3

III

PPh3

O PHPh3

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent Difficulty: Medium

147.

What is the predicted product of the reaction shown?

O CH3COOH

O O I

A. B. C. D.

O II

I II III IV

Answer: C Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation Difficulty: Medium 148.

What is the predicted product of the reaction shown?

O CH 3COOH

I A. B. C. D. E.

O III

O V

I II III IV V

Answer: B Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation Difficulty: Medium 149.

Predict the product of the following reaction.

O O H

CH3COOH

O OH

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation Difficulty: Medium 150.

What is the correct order of the migration rate in the Baeyer–Villiger oxidation reaction for the groups shown?

A. B. C. D. E.

phenyl > methyl > t-butyl > H phenyl > t-butyl > methyl > H H > phenyl > methyl > t-butyl H > t-butyl > phenyl > methyl methyl > t-butyl > phenyl > H

Answer: D Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation Difficulty: Easy

151.

What is an appropriate stepwise synthesis for 1-pentanol from butanal?

1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4.

1. NaBH4/CH3OH; 2. Mg/ether; 3.

1. NaBH4; 2. PBr3; 3. Mg/ether; 4.

, 5. H3O+

; 5. H3O+

; 4. H3O+

, 4. H3O+

Answer: B Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 152. What is an appropriate stepwise synthesis for pentanal from butanal? Answer:

1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4.

; 5. PCC

1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4.

1. NaBH4/CH3OH; 2. Mg/ether; 3.

1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 3.

1. NaBH4; 2. PBr3; 3. Mg/ether; 4.

; 5. H3O+

; 4. H3O+

; 4. H3O+; 5. PCC

Answer: D Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 153. What is an appropriate stepwise synthesis for 3-phenylpropanal from benzyl alcohol? Answer:

OH PBr

O OH

PCC

1. PBr3; 2. Mg/ether; 3.

; 4. H3O+; 5. PCC

1. PBr3; 2. Mg/ether; 3.

; 4. H3O+

1. PBr3; 2. Mg/ether; 3.

; 4. H3O+

1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 3.

1. PBr3; 2. Mg/ether; 3.

; 4. H3O+; 5. PCC

; 4. H3O+

Answer: A Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 154.

What is an appropriate stepwise synthesis for the reaction shown.

H O

1. CrO3/H2O; 2.

1. CrO3/H2SO4/H2O; 2.

1. PCC; 2.

1. CrO3/H2SO4; 2.

1. CrO3/H2SO4/H2O; 2.

; 3. H2O; 4. H2O2/NaOH/H2O ; 3. H2O; 4. 9-BBN; 5. H2O2/NaOH/H2O ; 3. 9-BBN; 4. H2O2/NaOH/H2O ; 3. H2O; 4. 9-BBN; 5. NaOH ; 3. H2O; 4. H2O2

Answer: C Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 155.

What is an appropriate stepwise synthesis for 4-methyl-1-pentanamine from 3methyl-1-butanol?

A. B.

1. PBr3; 2. NaCN; 3. CrO3/H2O 1. PBr3; 2. NaCN; 3. LiAlH4

C. D. E.

1. PBr3; 2. LiAlH4; 3. PCC; 4. 1. PBr3; 2. NaCN; 3. NaOH 1. LiAlH4; 2. NaCN; 3. CrO3/H2O

; 5. H2O

Answer: B

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 156. What is an appropriate stepwise synthesis for 5-methylhexanal from 3-methyl-1bromobutane? A. B.

1. ; 2. 9-BBN; 3. H2O2/NaOH/H2O 1. PBr3; 2. NaCN; 3. LiAlH4

1. PBr3; 2. LiAlH4; 3. PCC; 4.

D. E.

1. ; 2. PBr3; 3. NaOH 1. LiAlH4; 2. NaCN; 3. CrO3/H2O

Answer: C

; 5. H2O

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 157.

What is an appropriate stepwise synthesis for 5-methyl-2-hexanone from 3methyl-1-bromobutane?

1. PBr3; 2.

1. PBr3; 2. LiAlH4; 3. PCC; 4.

D. E.

1. ; 2. PBr3; 3. NaOH 1. LiAlH4; 2. NaCN; 3. CrO3/H2O

; 2. H2O/H2SO4/HgSO4 ; 3. LiAlH4 ; 5. H2O

Answer: D Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 158.

What is an appropriate stepwise synthesis for the conversion shown?

OH O A. B. C. D. E.

1. PBr3; 2. PCC; 3. H2O 1. PBr3; 2. H2SO4; 3. PCC; 4. H2O 1. KMnO4; 2. CrO3; 3. H2O 1. KMnO4/NaOH/H2O (hot); 2. H2O 1. KMnO4/NaOH/H2O (cold); 2. CrO3/H2SO4/H2O

Answer: E

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 159.

What is an appropriate stepwise synthesis for the conversion shown?

1. Mg/ether; 2.

; 3. H3O+; 4. PCC/CH2Cl2

1. Mg/ether; 2.

; 3. H3O+; 4. PCC/CH2Cl2

C. D. E.

1. Mg/ether; 2. ; 3. PCC/CH2Cl2 1. MgBr; 2. H3O+; 3. PCC/CH2Cl2 1. MgBr; 2. H3O+; 3. H2SO4

Answer: A

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 160. In the reaction below, what are the structures for the intermediates and final product?

PBr3

Mg/ether

A. B. C. D. E.

X is I, Y is III, Z is II, and A is V X is II, Y is I, Z is V, and A is III X is III, Y is II, Z is I, and A is IV X is I, Y is II, Z is III, and A is IV X is IVI, Y is III, Z is I, and A is II

Answer: A

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 161. In the reaction below, what are the structures for the intermediates and final product?

O Br

HOCH2CH2OH H2SO4

Mg /ether

A. B. C. D. E.

X is I, Y is III, Z is II, and A is V X is II, Y is I, Z is V, and A is III X is III, Y is II, Z is I, and A is IV X is I, Y is II, Z is III, and A is IV X is IVI, Y is III, Z is I, and A is II

Answer: C Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard

162. In the reaction below, what are the structures for the intermediates and final product?

O HO

TMSCl (CH 3CH2)3N

A. B. C. D. E.

X is I, Y is III, and Z is II. X is II, Y is I, and Z is V X is III, Y is II, and Z is I X is I, Y is II, and Z is III X is IVI, Y is III, and Z is I

Answer: B Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard

163.

What is an appropriate stepwise synthesis for the conversion shown?

A. B. C. D. E.

1. PCC; 2. CH3CH2NH2/H2SO4 1. CrO3; 2. H2O; MgBrCH3; H2O 1. CH3CH2NH2/H2SO4 1. H2SO4; 2. Mg/ether; 3. PCC 1. MgBrCH3 2. H2O

Answer: A

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 164.

What is a complete stepwise synthesis for 3-hexanone that uses 1-propanol as the only source of carbon and using any other reagents as appropriate?

A. 1. Mg/ether; 2. CH3CH2CH2MgBr; 3. H2O; 4. PCC/CH2Cl2 B. 1. PBr3; 2. Mg/ether; 3. PCC/CH2Cl2; 4. CH3CH2CH2MgBr; 5. H2O; 6. PCC/CH2Cl2 C. 1. PBr3; 2. Mg/ether; 3. PCC/CH2Cl2; 4. CH3CH2CH2MgBr; 5. H2O D. 1. PBr3; 2. PCC/CH2Cl2; 3. H2SO4; 4. CH3CH2CH2MgBr; 5. H2O; 6. PCC/CH2Cl2 E. 1. PBr3; 2. Mg/ether; 3. PCC/CH2Cl2; 4. CH3CH2CH2CH2CH2MgBr; 5. H2O; 6. PCC/CH2Cl2 Answer: B

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions Difficulty: Hard 165.

A compound with formula C5H10O shows only two singlets, in its 1H NMR spectrum. Which one of the compounds shown could produce this spectrum?

CH3CH2CCH2CH 3 (CH 3) 2CHCCH3 (CH3)3CCH I

III

O CH3CH 2CHCH

O (CH3)2CHCH 2CH

CH3 IV A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones Difficulty: Medium 166.

The 1H NMR spectrum of a compound with formula C7H14O shows only two signals. Which one of the choices is a possible structure for this compound?

A. B. C. D. E.

2-heptanone 3-heptanone 2,4-dimethyl-3-pentanone 2,2-dimethyl-3-pentanone Two of the above

Answer: C

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones Difficulty: Medium 167.

The 13C NMR spectrum of a compound with formula C7H14O shows five signals. Which one of the choices is a possible structure for this compound?

A. B. C. D. E.

2-heptanone 3-heptanone 2,2-dimethyl-3-pentanone 2,4-dimethyl-3-pentanone none of these

Answer: C Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones Difficulty: Medium 168.

The 1H NMR spectrum of a compound with formula C7H14O shows a singlet at 9.2 ppm. Which one of the choices is a possible structure for this compound?

A. B. C. D. E.

2-methyl-3-hexanone 2-methylhexanal 2,2 -dimethylpentanal 2,2-dimethyl-3-pentanone B&C

Answer: E Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones Difficulty: Medium 169.

Provide a structure for the compound with molecular formula C5H10O and with the following spectroscopic data. IR: 1720 cm−1 1 H NMR: 0.9 d (triplet, 3H), 1.7 d (sextet, 2H), 2.1 d (singlet, 3H), 2.4 d (triplet, 2H)

O I

CH3CH2CH2CCH3 O

CH3CH2CH2CH2CH

III

CH3CH2O

CHCH3

H V

CH3CH2CH2O

CH2

H A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones Difficulty: Medium 170.

Provide a structure for the compound with molecular formula C9H10O and with the following spectroscopic data. IR: 1680 cm−1 1 H NMR: 1.25 d (triplet, 3H), 3.0 d (quartet, 2H), 7-8 d (multiplet, 5H)

OH I

O O III

O IV

OH V

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 20 1.

What is the IUPAC name for the compound shown?

O OH A. B. C. D. E.

2-methylpentanoic acid 3-methylpentanoic acid 2-methylhexanoic acid 3-methylhexanoic acid None of these

Answer: D Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 2.

What is the common name for the compound shown?

O OH

A. B. C. D. E.

3-fluorobutanoic acid 2-fluorobutanoic acid β-fluorobutyric acid α-fluorobutyric acid none of these

Answer: C Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 3.

What is the IUPAC name for the compound shown?

O OH

A. B. C. D. E.

3-fluorobutanoic acid 2-fluorobutanoic acid β-fluorobutyric acid α-fluorobutyric acid none of these

Answer: A Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 4.

What is the IUPAC name for the compound shown?

HO A. B. C. D. E.

OH 2,4-dimethylheptanedioic acid 3,5-dimethylheptanedioic acid 2,4-dimethylpentanedioic acid 3,5-dimethylpentanedioic acid 2,4-dimethylheptanoyl acid

Answer: B Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 5.

What is the correct structure for trichloroacetic acid?

O Cl OH

OH II

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 6.

What is the correct structure for succinic acid?

OH I

A. B. C. D. E.

I II III IV none of these

Answer: C

OH II

Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 7.

What is the IUPAC name for the compound shown?

O OH A. B. C. D. E.

(Z)-5-ethyl-3-methyl-3-heptenoic acid (E)-2-ethyl-5-methyl-4-hepten-7-oic acid (Z)-2-ethyl-5-methyl-4-hepten7-oic acid (E)-5-ethyl-3-methyl-3-heptenoic acid (Z)-5-ethyl-3-methyl-3-heptanoic acid

Answer: D Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Hard 8.

What is the IUPAC name for the compound shown?

O OH

A. B. C. D. E.

1-ethylcyclohexane-3-carboxylic acid (2-ethyl)-1-cyclohexylmethanecarboxylic acid 1-(2-ethyl)-cyclohexylmethanecarboxylic acid 3-ethylcyclohexanoic acid 3-ethylcyclohexanecarboxylic acid

Answer: E Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Hard

What is the structure of 5-chloro-3-isopropyloctanoic acid?

A. B. C. D. E.

I II III IV V

O OH

III

O OH

Cl O

O OH

Answer: B Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Hard 10.

What is structure of (3S,4S)-3-hydroxy-4-phenylnonanoic acid?

A. B. C. D. E.

I II III IV V

III

OH V

O OH

Answer: C Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Hard 11.

What is the IUPAC name for the compound shown?

C(CH3)3 O

(CH 2)3CHCH2CHCH 2 C

CH2CH(CH 3)2 A. B. C. D. E.

3-t-butyl-5-isobutylnonanedioic acid 3-t-butyl-5-isobutyl-1,9-nonanoic acid 3-t-butyl-5-isobutylnonanoic acid 5-butyl-3-isobutylnonanedioic acid 3,5-butyl-nonanedioic acid

Answer: A Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Hard 12.

What is the IUPAC name for the compound shown?

O OH

A. B. C. D. E.

(3-isobutyl)-benzene-methanoic acid 3-isobutylbenzene methanoic acid Isobutylbenzenzne-3-methanoic acid 3-isobutylbenzoic acid 3-isopropylbenzoic acid

Answer: D Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Medium 13.

Methanoic acid is commonly known as ________.

A. B. C. D. E.

formic acid acetic acid malonic acid glutaric acid oxalic acid

Answer: A Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Easy 14.

Ethanoic acid is commonly known as ________.

A. B. C. D. E.

formic acid acetic acid malonic acid glutaric acid oxalic acid

Answer: B Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Easy 15.

What is the IUPAC name for oxalic acid?

A. B. C. D. E.

ethanedioic acid propanedioic acid butanedioic acid pentanedioic acid benzoic acid

Answer: A Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Easy

16.

What is the IUPAC name for malonic acid?

A. B. C. D. E.

ethanedioic acid propanedioic acid butanedioic acid pentanedioic acid benzoic acid

Answer: B Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Easy 17.

What is the IUPAC name for glutaric acid?

A. B. C. D. E.

ethanedioic acid propanedioic acid butanedioic acid pentanedioic acid benzoic acid

Answer: D Learning Objective: 21.2 Assign a name for a carboxylic acid or a diacid using the IUPAC system of nomenclature Difficulty: Easy 18.

Which one of the compounds shown has the highest boiling point?

O H

A. B.

I II

OH II

III

C. D. E.

III IV V

Answer: D Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Easy 19.

Which one of the compounds shown has the highest boiling point?

A. B. C. D. E.

butanoic acid 1-butanol 2-butanone methoxyethane butanal

Answer: A Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Easy 20.

Which of the compounds shown is the strongest acid?

O OH

Cl I

A. B. C.

I II III

O OH

F II

Br III

D. E.

IV V

Answer: B Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Medium 21.

Which of the compounds shown is the weakest acid?

O OH

Cl I

A. B. C. D. E.

O OH

F II

Br III

I II III IV V

Answer: D Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Medium 22.

Which one of the compounds shown is the strongest acid?

OH F

A. B. C. D. E.

OH II

I II III IV V

Answer: E Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Easy 23.

Which one of the choices is the strongest acid?

A. B. C. D. E.

benzoic acid 4-nitrobenzoic acid 4-ethylbenzoic acid 4-chlorobenzoic acid 4-hydroxybenzoic acid

Answer: B

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Easy 24.

Which one of the choices is the weakest acid?

A. B. C. D. E.

benzoic acid 4-nitrobenzoic acid 4-ethylbenzoic acid 4-chlorobenzoic acid 4-hydroxybenzoic acid

Answer: E Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Easy 25.

Rank the acids shown in decreasing (strongest to weakest) order of acidity.

O OH

Cl I

A. B. C. D. E.

V > III > I > II > IV II > I > III > V > IV IV > III > I > II > V IV > V > III > I > II V > I > III > II > IV

Answer: B

O OH

F II

Br III

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Medium 26.

D. B. C. E. A.

Rank the acids shown in decreasing (strongest to weakest) order of acidity.

COH

OCH3

NO2

CH3

III

IV > V > III > I > II II > IV > III > 1 IV > III > I > II > V V > I > III > II > IV V > III > I > II > IV

Answer: B Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Medium 27.

Which one of the choices is the strongest acid?

A. B. C. D. E.

2,2-dichlorobutanoic acid 2,3-dichlorobutanoic acid 3,3-dichlorobutanoic acid 3,4-dichlorobutanoic acid 4,4-dichlorobutanoic acid

Answer: A Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Hard

28.

Which one of the choices is the strongest acid?

A. B. C. D. E.

2,3-dimethylheptanoic acid 3,3-dichlorohexanoic acid 4-bromo-3-iodohexanoic acid 4-bromo-3-chloroheptanoic acid 4-bromo-2-fluorohexanoic acid

Answer: E Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity Difficulty: Hard 29.

What is the predicted product of the reaction shown?

1. O3 2. DMS 3. Na2Cr2O7/HgSO4/H2O OH

OH I

A. B. C. D. E.

I II III IV V

OH OH

OH II

III

Answer: B Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard 30.

What is the predicted product of the reaction shown?

1. O3 2. H 2O

OH OH

O I

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Medium 31.

What is the predicted product of the reaction shown?

Na2Cr2O7/H 2SO4/H 2O

OH H

O I

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Medium 32.

Which of the reagent(s) shown can be used to carry out the given conversion?

O OH

A. B. C. D.

PCC/CH2Cl2 CO2 followed by H3O+ mCPBA Na2Cr2O7/H2SO4/H2O

both A and D

Answer: D Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Medium 33.

Provide the reagents necessary to carry out the conversion shown.

O +

HO A. B. C. D. E.

OH HO

1. H2O; 2. KMnO4 1. O3; 2. DMS; 3. Na2Cr2O7/H2SO4/H2O 1. NaOH, Br2; 2. DMS; 3. H2O/heat 1. O3; 2. DMS; 3. KMnO4 1. DMS; 2. H2O2/heat

Answer: B 1. Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard 34.

What is the predicted product of the reaction shown?

Br OH Na2Cr 2O7/H2SO4/H2O

Br OH I

O O OH II

O Br

O OH

III

COOH

COOH OH V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.4 Identify three methods of producing carboxylic acids

Difficulty: Medium 35.

What is the predicted product of the reaction shown?

excess Na2Cr 2O7/H2SO4/H2O

O H I

H O SO3H

II HO S 3

O OH III

HO O

O IV

O O

HO O

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Medium 36.

What is the predicted product of the reaction shown?

Br 1. NaCN 2. H3O+, heat

O OH I

O H II

CN III

OH V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Medium 37.

What is the predicted product of the reaction shown?

1. NaCN Br

A. B. C. D. E.

2. H3O+, heat

(CH3)2CHCH2COOH (CH3)2CHCH2CH2COOH (CH3)2CHCH2CN (CH3)2CHCH2CH2CN (CH3)2CHCH2OH

Answer: A Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Medium 38.

Provide the reagents necessary to carry out the conversion shown.

Br O A. B. C. D. E.

1. Mg/ether 2. CO2 3. H3O+ 1. NaOH 2. KMnO4/NaOH/H2O 3. H3O+ 1. NaCN 2. H3O+, heat A and C all of these

Answer: D Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard

39.

What is the predicted product of the reaction sequence shown?

2-methyl-1-propanol PBr3

Mg/ether 1. CO2 2. H 3O+ O

A. B. C. D. E.

Br OH II

III

I II III IV V

Answer: C Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard 40.

What reagents are necessary to carry out the conversion shown?

O Br

O A.

; 2. Mg/ether; 3. KMnO4

O B. C. D.

1. ; 2 H3O+; 3. KMnO4 1. Mg/ether; 2. CH3CH2CH2Br; 3. H3O+; 4. KMnO4 KMnO4/H2O/heat

O E.

1. Mg/ether; 2.

; 3. H3O+; 4. Na2Cr2O7/H2SO4/H2O

Answer: E Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard 41.

What reagents are needed to carry out the conversion shown?

O OH Cl A. B. C. D. E.

1. Cl2/heat; 2. MgBr; 3. Mg/ether; 4 KMnO4 1. Cl2/FeCl3; 2. Na2Cr2O7/H2SO4/H2O 1. LiAlH4; 2. H2O; 3. HCl 1. Mg/ether; 2. CO2; 3. H3O+ 1. Mg/ether; 2. CH3CH2CH2Cl; 3. H3O+; 4. KMnO4

Answer: B Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard 42.

What reagents are needed to carry out the conversion shown?

Br O

A. B. C. D. E.

1. Br2/heat; 2. MgBr; 3. Mg/ether; 4 KMnO4 1. Br2/FeBr3; 2. Na2Cr2O7/H2SO4/H2O 1. LiAlH4; 2. H2O; 3. HCl 1. Mg/ether; 2. CO2; 3. H3O+ 1. Mg/ether; 2. CH3CH2CH2Cl; 3. H3O+; 4. KMnO4

Answer: D Learning Objective: 20.4 Identify three methods of producing carboxylic acids Difficulty: Hard 43.

What is the predicted product of the reaction shown?

O OH A. B. C. D. E.

1. LiAlH 4 2. H 2O

3-methyl-2-pentanone 3-methyl -1-propanol 2-methyl-1-butanol 3-methyl-2-pentanol none of these

Answer: C Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Medium 44.

What reagents are necessary to carry out the conversion shown?

OH O A.

1. 2.

LiAlH4 H2 O

B. C. D. E.

NaBH4/CH3OH LiAl[OC(CH3)3]H BH3·THF C and D

Answer: B Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Hard 45.

What reagents are necessary to carry out the conversion shown?

OH O A. B. C. D. E.

1. LiAlH4 2. H2 O NaBH4/CH3OH LiAl[OC(CH3)3]H BH3·THF C and D

Answer: D Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Hard 46.

What reagents are necessary to carry out the conversion shown?

HO O

A. B. C. D. E.

1. LiAlH4; 2. H3O+ NaBH4/CH3OH LiAl[OC(CH3)3]H BH3·THF C and D

Answer: A Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Hard 47.

What reagents are necessary to carry out the conversion shown?

OH Br

A. B. C. D. E.

1. LiAlH4; 2. H3O+ 1. Mg/ether; 2. H2C=O; 3. H2O 1. Mg/ether; 2. CO2; 3. H3O+; 4. LiAlH4; 5. H2O A and B B and C

Answer: E A. 1. LiAlH4; 2. H3O+ B. 1. Mg/ether; 2. H2C=O; 3. H2O C. 1. Mg/ether; 2. CO2; 3. H3O+; 4. LiAlH4; 5. H2O D. A and B E. B and C Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Hard 48.

What reagents are necessary to carry out the conversion shown?

OH OH A. B.

1. PBr3; 2. Mg/ether; 3. H2C=O; 4. H2O 1. PBr3; 2. Mg/ether; 3. CH3CH2COOH; 4. H3O+; 5. LiAlH4; 6. H2O

C. D. E.

1. PBr3; 2. Mg/ether; 3. CO2; 4. H3O+; 5. LiAlH4; 6. H2O A and B A and C

Answer: E Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Hard 49.

What is the predicted product of the reaction sequence shown?

Mg/ether

2. H 3O+

Br A. B. C. D. E.

1. CO2

1. LiAlH4 2. H2O

2,2-dimethylpropanoic acid 3,3-dimethyl-2-butanone 2,2-dimethyl-1-propanol 2,2-dimethylbutanoic acid 2,2-dimethylethanoic acid

Answer: C Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols Difficulty: Hard 50.

What is the IUPAC name for the compound shown?

O Cl A. B. C. D. E.

a-methylbutyryl chloride b-methylbutyryl chloride g-methylbutyryl chloride 2-methylbutanoyl chloride 3-methylbutanoyl chloride

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Medium 51.

What is the common name for the compound shown?

O Cl A. B. C. D. E.

a-methylbutyryl chloride b-methylbutyryl chloride g-methylbutyryl chloride 2-methylbutanoyl chloride 3-methylbutanoyl chloride

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 52.

What is the common name for the compound shown?

O Br Br A. B. C. D. E.

a-bromoacetyl bromide b-bromoacetyl bromide 1-bromoethanoyl bromide 2-bromoethanoyl bromide 1,2-dibromoacetic acid

Answer: A Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 53.

What is the IUPAC name for the compound shown?

O Br Br A. B. C. D. E.

bromoacetyl bromide b-bromoacetyl bromide 1-bromoethanoyl bromide bromoethanoyl bromide 1,2-dibromoacetic acid

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 54.

What is the IUPAC name for the compound shown?

O Cl A. B. C. D. E.

g-methylvaleryl chloride 2-methylpentanoyl chloride 3-methylhexanoyl chloride 3-methylpentanoyl chloride 2-methylhexanoyl chloride

Answer: C Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 55.

What is the IUPAC name for the compound shown?

O Cl Br A. B. C. D. E.

a-bromobutyryl chloride b-bromobutyryl chloride 1-bromobutanoyl chloride 2-bromobutanoyl chloride 2-bromopropanoyl chloride

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 56.

What is the common name for the compound shown?

O Cl Br A. B. C. D. E.

a-bromobutyryl chloride b-bromobutyryl chloride 1-bromobutanoyl chloride 2-bromobutanoyl chloride 2-bromopropanoyl chloride

Answer: A Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 57.

What is the IUPAC name for the compound shown?

O Cl

A. B. C. D. E.

3-ethyl-2,4-dimethylpentanoyl chloride 4-ethyl-3,5-dimethylpentanoyl chloride 3-ethyl-2,4-dimethylhexanoyl chloride 4-ethyl-3,5-dimethylhexanoyl chloride 3,4,5-trimethylhexanoyl chloride

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 58.

What is the structure of 4-ethylbenzoyl chloride?

O Cl

O I

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Medium 59.

What is the structure for cyclopentanecarbonyl chloride?

OCl

Cl I

III

Cl O

Cl IV

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 60.

Provide the structure for benzoyl chloride.

Cl Cl I

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 61.

What is the IUPAC name for the compound shown?

O H A. B. C. D. E.

O O

methanoic anhydride ethanoic anhydride acetic anhydride formic anhydride propanoic anhydride

Answer: A Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium

62.

What is the common name for the compound shown?

O H A. B. C. D. E.

O O

methanoic anhydride ethanoic anhydride acetic anhydride formic anhydride propanoic anhydride

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 63.

What is the IUPAC name for the compound shown?

O O

A. B. C. D. E.

propanoic anhydride butanoic anhydride propionic anhydride pentanoic anhydride butyric anhydride

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 64.

What is the common name for the compound shown?

O O

propanoic anhydride

B. C. D. E.

butanoic anhydride propionic anhydride pentanoic anhydride butyric anhydride

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 65.

What is the IUPAC name for the compound shown?

O O

A. B. C. D. E.

methanoic propanoic anhydride formic propionic anhydride ethanoic propionic anhydride acetic butyric anhydride butanoic ethanoic anhydride

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 66.

What is the common name for the compound shown?

O O

A. B. C. D. E.

methanoic propanoic anhydride formic propionic anhydride ethanoic propionic anhydride acetic butyric anhydride butanoic ethanoic anhydride

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Medium 67.

What is the structure of acetic formic anhydride?

O O

III

O H

O IV

A. B. C. D. E.

O V

I II III IV V

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 68.

What is the IUPAC name for the compound shown?

O O

A. B. C. D. E.

hexanoic anhydride septanoic anhydride propanoic anhydride dipropanoic carboxyl ether dipropanone

Answer: C Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Medium 69.

Provide the structure for benzoic ethanoic anhydride.

O O

III

O O

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 70.

What is the IUPAC name for the compound shown?

O O A. B. C. D. E.

sec-butyl ethanoate ethyl 3-methylpentanoate 3-methylbutyl ethanoate ethyl 3-methylbutanoate none of these

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 71.

What is the IUPAC name for the compound shown?

O O A. B. C. D. E.

2-methylbutyl 3-methylbutanoate 3-methylbutyl 3-methylbutanoate 2-methylbutyl isovalerate 2-methylbutyl 2-methylbutanoate isopentyl isovalerate

Answer: A Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 72.

What is the IUPAC name for the compound shown?

O H A.

O 2-methylbutyl acetate

B. C. D. E.

3-methylbutyl acetate 2-methylbutyl methanoate 3-methylbutyl methanoate isopentyl formate

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 73.

What is the common name for the compound shown?

O H A. B. C. D. E.

O 2-methylbutyl acetate 3-methylbutyl acetate 2-methylbutyl methanoate 3-methylbutyl methanoate isopentyl formate

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 74.

What is the IUPAC name for the following compound?

O O

A. B. C. D. E.

3-cyclohexyl-2-oxy-tert-butanone butyl cyclohexanecarboxylate butyl cyclohexanone t-butyl cyclohexanone t-butyl cyclohexanecarboxylate

Answer: E

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 75.

Provide the structure for benzyl propionate.

O O

O OH III

O O

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Medium 76.

What is the structure of N-phenyl-N-propyl-2,3-dimethylbutanamide?

H N

A. B. C. D. E.

O II

I II III IV V

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Hard 77.

What is the structure of N-methylcyclohexanecarboxamide?

NH2 O

N H

III

O N H

N H

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Hard 78.

What is the IUPAC name for the compound shown?

O N

A. B. C. D. E.

N,N-diethylbenzamine N,ethylbenzamine N-ethylbenzamide 1-benzyl, 1-aminodiethyl ketone N,N-diethylbenzamide

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 79.

What is the common name for the compound shown?

O N

A. B. C. D. E.

benzaldehyde N,N-diethylacetamide benzylamine ketobenzylamide N,N-carboxyamide

Answer: N,N-diethylacetamide Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 80.

What is the IUPAC name for the compound shown?

O N

A. B.

N,N-diethylethanamine N,N-diethylethanamide

C. D. E.

N,ethylpropylamide N-ethylpropylamine N-ethylethanamide

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 81.

What is the IUPAC name for the compound shown?

CN A. B. C. D. E.

2,3-dimethylbutanenitrile a,b-dimethylbutyrnitrile b,g-dimethylbutyrnitrile 3,4-dimethylbutanenitrile 3,4-dimethylpentanenitrile

Answer: E Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 82.

What is the IUPAC name for the compound shown?

CN A. B. C. D. E.

2,2-dimethylbutanenitrile 3,3-dimethylbutanenitrile a,a-dimethylbutyronitrile b,b-dimethylbutyronitrile g,g-dimethylbutyronitrile

Answer: B Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

Difficulty: Medium 83.

What is the common name for the compound shown?

CN A. B. C. D. E.

2,2-dimethylbutanenitrile 3,3-dimethylbutanenitrile a,a-dimethylbutyronitrile b,b-dimethylbutyronitrile g,g-dimethylbutyronitrile

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 84.

What is the structure of 3-ethylbenzonitrile?

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 85.

What is the IUPAC name for the compound shown?

Br A. B. C. D. E.

2-cyanobenzylcyclohexane 2-bromo-1-cyanocyclohexane 2-bromocyanocyclohexane 2-bromocyclohexanecarbonitrile 2-bromocyclohexanenitrile

Answer: D Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named Difficulty: Medium 86.

Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

O O I

A. B. C. D. E.

O NH2

O O

III

I > IV > III > II II > III > IV > I I > III > II > IV III > IV > II > I IV > I > III > II

Answer: E Learning Objective: 20.7 Compare the reactivity of carboxylic acid derivatives, and describe the mechanism of a nucleophilic acyl substitution reaction Difficulty: Medium

87.

Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

O Cl

NH2

A. B. C. D. E.

I > IV > III > II II > III > IV > I I > III > II > IV III > IV > II > I IV > I > III > II

Answer: C Learning Objective: 20.7 Compare the reactivity of carboxylic acid derivatives, and describe the mechanism of a nucleophilic acyl substitution reaction Difficulty: Medium 88.

What is the predicted product of the reaction shown?

O OH

SOCl2 pyridine

SO2Cl

Cl I

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium 89.

What is the predicted product of the reaction shown?

SOCl2 OH

A. B. C. D. E.

pyridine

3-methylbutanoyl chloride 2-methylbutanoyl chloride 2-methylpropanoyl chloride 3-methylbutanoic acid 2-methylbutanoic acid

Answer: A Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride

from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium 90.

What is the predicted product of the reaction shown?

O OH A. B. C. D. E.

SOCl2

CH3CH 2OH

pyridine

ethyl 3-methylbutanoate ethyl 2-methylpropanoate isobutyl ethanoate 5-methyl-3-hexanone none of these

What is the predicted product of the reaction shown?

1. KMnO4/NaOH/H2O SOCl2 2. H 3O+

pyridine

(CH 3)2CHCH2OH A pyridine

A. B. C. D. E.

I II III IV V

What is the predicted product of the reaction shown?

O Cl

OH pyridine

O II

III

O OH

A. B. C. D. E.

I II III IV V

What is the predicted product of the reaction shown?

O OH

1. SOCl2/pyridine 2. LiAl[OC(CH 3) 3]H

O Cl

A. B. C. D. E.

OCH3

I II III IV V

Answer: D Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium 94.

What reagents are necessary to carry out the conversion shown?

4-ethylheptanoyl chloride A.

CH3Li

5-ethyl-2-octanone

B. C. D. E.

CH3MgBr (CH3)2CuLi 1. Mg/ether 2. CH3Br CH3OH

Answer: C Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium 95.

What reagents are necessary to carry out the conversion shown?

5-cyclopentyl-1-pentanol

5-cyclopentylpentanoic acid C

5-cyclopentylpentanoyl chloride A. B. C. D. E.

8-cyclopentyl-4-octanone

A. Na2Cr2O7/H2SO4 B. SOCl2; C. CuLi A. Na2Cr2O7/H2SO4/H2O; B. SOCl2; C. (CH3CH2CH2CH2)2CuLi A. Na2Cr2O7/H2SO4/H2O; B. H2SO4; C. (CH3CH2CH2)2CuLi A. Na2Cr2O7; B. H2O; C. (CH3CH2CH2)2CuLi A. Na2Cr2O7/H2SO4/H2O; B. SOCl2; C. (CH3CH2CH2)2CuLi

Answer: E Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Hard 96.

What reagents are necessary to carry out the conversion shown?

CH2CH 3 CH2CH 3

A. B.

1. Na2Cr2O7/H2SO4/H2O; 2. CH3CH2CH2CH2MgBr; 4. H2O 1. Na2Cr2O7/H2SO4/H2O; 2. SOCl2; 3. excess CH3CH2CH2CuLi; 4. H2O

C. D. E.

1. Na2Cr2O7/H2SO4; 2. excess CH3CH2MgBr; 4. H3O+ 1. Na2Cr2O7/H2SO4/H2O; 2. SOCl2; 3. excess CH3CH2MgBr; 4. H2O 1. Na2Cr2O7; 2. SOCl2; 3. CH3CH2MgBr; 4. H2O

What is an appropriate stepwise synthesis for the given compound using benzyl alcohol as the only source of carbon and using any other reagents necessary.

OH CH 2 CH 2

1. PBr3; 2. Mg/ether; 3. Na2Cr2O7/H2SO4/H2O; 4. SOCl2; 5. excess H2 O

1. PBr3; 2. Na2Cr2O7/H2SO4/H2O; 3. SOCl2; 4. excess

1. PBr3; 2. Mg/ether; 3. Na2Cr2O7/H2SO4/H2O; 4. SOCl2; 5. excess

1. Mg/ether; 2. Na2Cr2O7/H2SO4/H2O; 3. SOCl2; 4. 1 equiv.

Answer: A

; 6.

; 5. H2O ; 6. H2O

; 5. H2O ; 5. H2O

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Hard 98.

What is the predicted product of the reaction shown?

O OH

1. SOCl2 2. CH3CH2NH 2 2 equi.

SO2H

N H II

O N H

NH2

III

SO2H O N H V

A. B. C. D. E.

I II III IV V

What reagents are needed to convert 4,5-dimethyl-1-hexanol into N-cyclopentyl4,5-dimethylhexanamide? 1. Na2Cr2O7/H2SO4/H2O; 2.

NH 2 2 equi.

1. SOCl2; 2. K2Cr2O7/H2SO4/H2O; 3.

NH 2 2 equi.

1. K2Cr2O7/H2SO4/H2O; 2. SOCl2; 3.

NH 2 2 equi.

D. E.

2 equi. ; 2. K2Cr2O7/H2SO4/H2O; 3. SOCl2 1. 1. K2Cr2O7/H2SO4/H2O; 2. SOCl2

NH 2

What is the predicted product of the reaction shown?

COH

COH D

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Hard 101.

What is the predicted product of the reaction shown?

O Cl

ONa

O I

A. B. C. D. E.

I II III IV V

What is the predicted product of the reaction shown?

O Cl

O ONa

O O II

O O

III

O O

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium

103.

Which of the reactions shown would not yield isopropyl acetate as major product?

O I

(CH3C)2O + (CH 3)2CHOH

O II

(CH 3C)2O + CH 3CH2CH2OH

O III

CH3CCl + (CH3)2CHOH

pyridine

O IV

CH3COH + (CH 3)2CHOH

A. B. C. D. E.

I II III IV I and III

H2SO4

What is the predicted product of the reaction shown?

O OH

O O

HO O I

O O

III

O HO

O O V

A. B. C. D. E.

I II III IV V

Answer: D

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Hard 105.

What is the predicted product of the reaction shown?

O CH3CH2OH

O O

O I

A. B. C. D. E.

O II

I II III IV V

106.

What is the predicted product of the reaction sequence shown?

H 3O+

SOCl2

CH 3CH2OH pyridine

AlCl3

O O

O O O

O IV

III

O O O V

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with

water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Hard 107.

What is the predicted product of the reaction shown?

O NH2

O O O O

A. B. C. D. E.

OH H N

N I

HO II

NH O III

I II III IV V

Answer: C Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride

from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Hard 108.

What is the predicted product of the reaction shown?

O excess H 2O

O O

OH II

OH III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride

from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium 109.

What reagent is necessary to carry out the conversion shown?

O +

A. B. C. D. E.

SOCl2 CH3Br CH3CH2MgBr LiAlH4 [(CH3)2CH]2CuLi

Answer: E Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent Difficulty: Medium 110.

What reagents are necessary to carry out the reaction sequence shown?

A. B. H2 O

A. K2Cr2O7/H2SO4/H2O; B. high heat; C. excess CH3CH2MgBr followed by H2O A. K2Cr2O7/H2SO4/H2O; B. ultraviolet light; C. excess CH3CH2MgBr followed by

C. D. E.

A. K2Cr2O7/H2SO4/H2O; B. high heat; C. 1 equiv. CH3MgBr followed by H2O A. PBr3; B. high heat; C. excess CH3MgBr followed by H2O A. Excess LiAlH4; B. high heat; C. excess CH3Br followed by H2O

What is the predicted product of the reaction shown?

OH O

H 2SO4

+ OH O

O O I

B. C. D. E.

II III IV V

Answer: A Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides Difficulty: Medium 112.

What is the predicted product of the reaction shown?

O OH

H2SO4

O I

III

OH IV

A. B. C. D. E.

I II III IV V

OH V

Answer: A Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides Difficulty: Hard 113.

What is the predicted product of the reaction shown?

O O

CH 3OH H 2SO4

OH O

O O

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides Difficulty: Hard 114.

Which of the reactions shown would not yield propyl butanoate as its major product?

O I

H2SO4

OH O II

Cl O

III

pyridine

O +

IV A. B. C. D.

H 2SO4

NH2 I II III IV

Answer: D Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides Difficulty: Hard 115.

What is(are) the predicted product(s) of the reaction shown?

O NH 3 excess

H2N

NH2

A. B. C. D. E.

HO II

HO III

I II III A and B A and C

Answer: D Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Hard 116.

What is(are) the predicted products of the reaction shown?

O OCH2CH 3

excess KOH D

O OK

OH OH

O I

A. B. C. D. E.

CH3CH2OH

O II

III

I II III A and B A and C

Answer: E Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Hard 117.

What reagents are necessary to carry out the conversion shown?

O O A. B. C. D. E.

NaBH4/CH3OH Na/NH3 1. LiAlH4 2. H2 O H3O+/heat A and C

Answer: C Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Medium 118.

What is the predicted product of the reaction shown?

O O

1. DIBAH 2. H 2O

H II

A. B. C. D.

I II III IV

Answer: B Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Medium 119.

What reagents are necessary to carry out the conversion shown?

HO OCH3

(CH3)2CuLi

B. C. D.

2. H2 O 1. excess DIBAH 2. H2 O 1. excess CH3MgBr 2. H2 O Both A and C

Answer: C Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Hard 120.

What is(are) the predicted products of the reaction shown?

O CH2OC(CH 2) 14CH3 NaOH excess

O CHOC(CH 2)16CH3

O CH2OC(CH 2) 14CH3

O 2 CH3(CH2)14CONa

CH3(CH2)16CONa

HOCH2CHCH2OH OH

A. B. C. D. E.

III

I II III A and B A, B, and C

Answer: E Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Hard

121.

What reagent(s) is(are) required to carry out the conversion shown?

O O

COCH(CH 3)2

O A. B.

(CH3)2CHOH only (CH3)2CHOH/H2SO4

C. D. E.

CH3CH2OH/H2SO4 CH3CH2OH only H2SO4 only

Answer: A Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Hard 122.

Barbital, used as a sedative, is synthesized from diethyl 2,2-diethyl malonate (A) and urea (B). What is the structure of barbital?

O C C O

OCH 2CH3 OCH 2CH3 A

H 2N O

+ H 2N B

NH O

III

NH O

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent Difficulty: Hard 123.

What is the predicted product of the reaction sequence shown?

Mg/ether

1. CO2

SOCl2

2. H3O+

Pyridine

excess CH 3NH2

O NHCH 3

NHCH 3

NHCH3

O I

III

O NH2

NHCH3 IV A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Hard 124.

What is the predicted product of the reaction shown?

O C

O O NHCH3

CH 3COCCH 3 excess

NHCH3

CH3

NHCH3

III

O C

NH2

NHCH3

CH3

NHCH3

O IV

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Medium 125.

What reagents are necessary to carry out the conversion shown?

NH 2

A. B.

1. H3O+/heat; 2. SOCl2/pyridine; 3. CH3OH/pyridine 1. PBr3; 2. CH3CH2MgBr; 3.H2O; 4. acetone O

1. PBr3; 2. CH3CH2MgBr; 3.H2O; 4. NaO O

1. H3O+/heat; 2. SOCl2/pyridine; 3. NaO O

1. H3O+/heat; 2. pyridine; 3. NaO

Answer: D Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Hard 126.

What reagents are necessary to carry out the conversion shown?

O O

H2N A. B. C. D. E.

1. H3O+, heat; 2. CH3CH2OH, H2SO4 1. H3O+; 2. CH3OH, H2SO4 1. SOCl2; 2. heat; 3. CH3CH2OH, H2SO4 1. LiAlH4; 2. SOCl2; 3. CH3CH2OH, H2SO4 1. H2SO4, heat; 2. CH3OH, H2SO4

Answer: A Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Medium

127.

What is the predicted product of the reaction shown?

O N

1. LiAlH 4 (excess) 2. H 3O+

O OH

O I

A. B. C. D. E.

H II

I II III IV I and II

Answer: C Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Hard 128. Aspartame is an artificial sweetener used in Equal® and diet soft drinks. What is(are) the predicted product(s) of the reaction shown?

NH2

H N

O COH

excess H3O+

O OCH3

Aspartame

NH3 O

NH3 HO

COH

CH3OH

A. B. C. D. E.

III

I II III A and B A, B, and C

Answer: E Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Hard 129.

What reagents are necessary to carry out the conversion shown?

O O

A. B.

1. NH3; 2. LiAlH4; 3. H2O 1. (CH3)2NH; 2. LiAlH4; 3. H2O

C. D. E.

1. SOCl2; 2. (CH3)2NH; 3. H2O 1. (CH3)2NH; 2. heat; 3. H2O 1. CH3NH; 2. LiAlH4; 3. H2O

Answer: A Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines Difficulty: Hard 130.

What reagents are necessary to carry out the conversion shown?

A. B. C.

D. E.

1. CH3Cl/AlCl3 2. Br2/hn 3. NaCN 1. CH3Cl/AlCl3 2. HCN 1. Br2/FeBr3 2. Mg/ether 3. CO2 4. H3O+ 5. SOCl2 6. excess NH3 7. SOCl2 A and C A and B

Answer: A Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Hard 131.

What is the predicted product of the reaction shown?

NH2 O

SOCl2

O CH

O I

III

CN V

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Hard 132.

What is the predicted product of the reaction sequence shown?

Na2Cr2O7/H 2SO4/H2O SOCl2

H N

NH2

N H I

A. B. C. D. E.

III

I II III IV V

Answer: D Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Hard 133.

What reagents are necessary to carry out the conversion shown?

CN O A. B. C. D. E.

1. (CH3)2CH2CH2MgBr; 2. H3O+ 1. (CH3)2CHMgBr; 2. H3O+ 1. (CH3)2CHBr; 2. H3O+ 1. LiAlH4; 2. (CH3)2CHMgBr 1. (CH3)2CHMgBr

Answer: B

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Hard 134.

What reagents are necessary to carry out the conversion shown?

NH2

A. B. C. D. E.

1. NH3; 2. H3O+ 1. LiAlH4; 2. H2O 1. H2SO4; 2. H3O+ 1. LiAlH4; 2. NH3 1. LiAlH4; 2. KCN

Answer: B Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Medium 135.

What is the predicted product of the reaction shown?

H 3O+ heat

III

O CN

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Medium 136.

What is the predicted product of the reaction shown?

CH 3(CH2)3C

1. CH3CH2MgBr 2. H3O+

O CH3(CH2)3CCH3

CH3CH2CCH2CH3

CH3(CH2)3CCH2CH3

III

CH3(CH2)3CCH2CH3

A. B. C. D. E.

CH2

I II III IV V

Answer: D Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines Difficulty: Hard 137.

What is an appropriate stepwise synthesis for the conversion shown?

A. B. C.

1. Mg/ether; 2. CO2; 3. H3O+; 4. SOCl2; 5. (CH3CH2)2CuLi 1. Mg/ether; 2. H3O+; 3. (CH3CH2)2CuLi 1. Mg/ether; 2. CH3CH2CN; 3. H3O+

D. E.

A or B A or C

Answer: E

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives Difficulty: Hard 138.

What is an appropriate stepwise synthesis for the following synthesis that uses ethyl 3-methylbutanoate as the only source of carbon and using any other reagents necessary.

HO O

A. B. C. D. E.

1. PBr3; 2. Mg/ether; 3. SOCl2; 4. 2 equiv. CH3CH2MgBr; 5. H2O 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. SOCl2; 5. 2 equiv. CH3CH2MgBr; 6. H2O 1. PBr3; 2. H3O+/heat; 3. H2SO4; 4. MgBr; 5. SOCl2; 6. CH3CH2MgBr; 7. H2O 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. SOCl2; 5. 2 equiv. CH3MgBr; 6. H2O 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. 2 equiv. CH3CH2MgBr; 5. H2O

Answer: B

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives Difficulty: Hard

139.

What is an appropriate stepwise synthesis for the following synthesis that uses ethyl 3-methylbutanoate as the only source of carbon and using any other reagents necessary.

O O

A. B. C. D. E.

1. PBr3; 2. 2 Li; 3. CuI; 4. SOCl2; 5. 1 mole (CH3CH2)2CuLi 1. H3O+/heat; 2. PBr3; 3. 2 Li; 4. CuI; 5. SOCl2; 6. 1 mole (CH3CH2)2CuLi 1. H3O+/heat; 2. PBr3; 3. Li; 4. SOCl2; 5. 1 mole (CH3CH2)2CuLi; 6. H2O 1. H3O+/heat; 2. Mg/ether; 3. SOCl2; 4. CH3CH2MgBr; 5. H2O 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. SOCl2; 5. 2 equiv. CH3CH2MgBr; 6. H2O

Answer: B

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives Difficulty: Hard 140.

What is an appropriate stepwise synthesis for N-propylbutanamide that uses only 1-propanol and/or carbon dioxide as the only source(s) of carbon and any other reagents necessary?

1. PBr3; 2. Mg/ether; 3. CO2; 4. SOCl2; 5. Na2Cr2O4/H2SO4/H2O; 6. NH3; 7.

excess LiAlH4; 8. H2O; 9. 2 equiv. of product of step 8 plus B. 1. Mg/ether; 2. CO2; 3. Na2Cr2O4/H2SO4/H2O; 4. H3O+; 5. SOCl2; 6. NH3; 7. excess LiAlH4; 8. H2O; 9. 2 equiv. of product of step 8 plus C.

1. PBr3; 2. Mg/ether; 3. CO2; 4. H3O+; 5. SOCl2; 6. Na2Cr2O4/H2SO4/H2O; 7.

SOCl2; 8. NH3; 9. excess LiAlH4; 10. H2O; 11. 2 equiv. of product of 10 plus from an earlier step D. 1. PBr3; 2. MgBr; 3. CH3CH2Br; 4. SOCl2; 5. Na2Cr2O4/H2SO4/H2O; 6. SOCl2; 7. NH3; 8. 2 equiv. of product of 7 plus E. Answer: C

from an earlier step

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives Difficulty: Hard 141.

What is an appropriate stepwise synthesis for 2-phenylethanoyl chloride that uses toluene and/or carbon dioxide as the only source(s) of carbon and any other reagents necessary.

A. B. C. D. E.

1. Br2/hv; 2. MgBr; 3. CO2; 4. H3O+; 5. SOCl2 1. HBr; 2. MgBr; 3. CO2; 4. H3O+; 5. SOCl2 1. HBr; 2. Mg/ether; 3. CO2; 4. H3O+; 5. SOCl2 1. Br2/hv; 2. Mg/ether; 3. CO2; 4. H3O+; 5. SOCl2 1. Br2/hv; 2. Mg/ether; 3. CO2; 4. SOCl2

Answer: D

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives Difficulty: Hard 142.

A compound with molecular formula C6H12O2 exhibits two singlets in its 1H NMR spectrum, at d 1.4 (9H) and d 2.0 (3H). Its IR spectrum shows a strong absorption band near 1740 cm-1. What is the structure for this compound?

O O

O I

O O III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy Difficulty: Hard 143.

A compound with molecular formula C8H14O4 exhibits a triplet at d 1.3 (6H), a singlet at d 2.6 (4H) and a quartet at d 4.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows a strong absorption band near 1740 cm-1. What is the structure for this compound?

O O

O I

A. B. C. D. E.

O II

I II III IV none of these

Answer: B Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy Difficulty: Hard 144.

A compound with molecular formula C9H10O2 exhibits a triplet at d 1.2 (3H), a

quartet at d 2.6 (2H), a doublet at d 7.3 (2H), a doublet at d 8.0 (2H) and a singlet at d 11 (1H) in its 1H NMR spectrum. What is the structure for this compound?

O OH OH

OH II

III

O OH V

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy Difficulty: Hard 145.

A compound with molecular formula C8H14O3 exhibits a triplet at d 1.0 (6H), a sextet at d 1.6 (4H) and a triplet at d 2.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm-1. What is the structure for this compound?

O O

O II

O O O O

O III

O IV

O O

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 21 1.

Which one of the compounds shown is most acidic?

A. B. C. D. E.

ethyl acetoacetate 2-butanone ethyl pentanoate 1-butanol 3-pentanone

Answer: A Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Medium 2.

How many alpha hydrogens are in 2-pentanone?

A. B. C. D. E.

1 2 3 4 5

Answer: E Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Easy 3.

How many beta hydrogens are in 2-pentanone?

A. B. C. D. E.

1 2 3 4 5

Answer: B Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Easy 4.

How many gamma hydrogens are in 2-pentanone?

B. C. D. E.

2 3 4 5

Answer: C Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Easy 5.

Which of the indicated a-hydrogens is most acidic?

A. B. C. D. E.

CH3CH 2CH

CH 3CH2CCH2CCH2CH3

CH3CH2CCH2COCH 2CH3

III

I II III IV V

Which is the most acidic hydrogen in the compound shown?

I CN H

H IV

H III

A. B. C. D. E.

I II III IV V

Which is the most acidic hydrogen in the compound shown?

IV O

O I A. B. C. D. E.

III

I II III IV V

Which is the most acidic hydrogen in the compound shown?

H V

O O

IV A. B. C. D. E.

H H

III

I II III IV V

Which carbon atom has the most acidic hydrogen in the compound shown?

III

O II O O

IV A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

Difficulty: Medium 10.

Which one of the indicated hydrogens is the most acidic?

O H

O I

A. B. C. D. E.

III

I II III IV V

Answer: D Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Medium 11.

Arrange the indicated hydrogens in decreasing order (most to least) of acidity.

O H

O II

I > II > III > IV

O O

O I

III

B. C. D. E.

IV > II > III > I III > II > I > IV II > I > III > IV III > I > II > IV

Which of the choice(s) shows a keto-enol tautomeric pair(s)?

CH3C CH H

CH3CH CH

CH3C CH 2

CH 3CCH 3

A. B. C. D. E.

I II III I and II I and III

Which of the choices is a keto-enol tautomeric pair?

A. B. C. D. E.

I II III IV V

Which of the choices is a keto-enol tautomeric pair?

A. B. C. D. E.

I II III IV None of these

Which one of the compounds shown is most likely to favor the enol tautomer over the ketone tautomer?

O H

A. B. C. D. E.

III

I II III IV V

16.

Which one of the compounds shown is most likely to favor the enol tautomer over the ketone tautomer?

O H

O O

I A. B. C. D. E.

O III

I II III IV V

Which of the given statements explains the keto-enol equilibrium shown below?

A. B. C. D. E.

simple enols are more stable the enol tautomer is stabilized by the conjugated p system the enol tautomer is stabilized by the intramolecular hydrogen bonding the diketone is less coplanar both B and C

Explain why the equilibrium shown favors the enol tautomer.

A. The enol tautomer is stabilized by the intramolecular hydrogen bonding between the OH and the carbonyl group. B. The enol tautomer is stabilized by the conjugated p system. C. The enol tautomer is stabilized by lacking a conjugated p system. D. A and B E. A and C Answer: D Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Medium 19.

Explain why the equilibrium shown favors the enol tautomer.

A. The enol tautomer is stabilized by the intramolecular hydrogen bonding. B. The enol tautomer is stabilized by the conjugated p system of the aromatic system. C. The enol tautomer is stabilized by lacking a conjugated p system. D. A and B E. A and C Answer: B Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Medium 20.

What is the structure of the enol produced when 3,3,6-trimethyl-4-heptanone is treated with acid?

III

A. B. C. D. E.

I II III IV V

Provide the structure of the enolate when acetophenone is treated with a strong base.

OH III

OH IV

A. B. C. D. E.

I II III IV V

22.

Which of the bases shown will completely convert 1,4-cyclohexanedione into an enolate?

A. B. C. D. E.

sodium hydroxide sodium ethoxide LDA sodium hydride both C and D

Which of the compounds shown represents an enolate?

O I A. B. C. D. E.

III

I II III IV both B and C

Which one of the compounds shown would undergo racemization at the astereocenter in the presence of a base?

III

A. B. C. D. E.

I II III IV none of these

What are the resonance structures of the enolate formed when the given ketone is treated with a base?

O I

O III

O IV

O V

A. B. C. D. E.

I and II I and IV II and III I and III II and V

What are the resonance structures of the enolate formed when the given ketone is treated with a base?

O I

O IIH

O IIHI

O IV

O V

A. B. C. D. E.

I and II I and IV II and III I and III II and V

Answer: E

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Medium 27.

What are the resonance structures of the enolate formed when the given ester is treated with a base?

O O

O I

O II

O III

O IV

A. B. C. D. E.

I and II I and IV II and III I and III II and V

Answer: A Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate Difficulty: Medium

28.

Which of the compounds shown would NOT undergo racemization in the presence of a base?

A. B. C. D. E.

III

CH3

I II III IV II and III

What is the predicted major product of the reaction shown?

O H 3O+ Cl2 O

O Cl

Cl I

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 30.

What is the predicted major product of the reaction shown?

O H3O+ Cl2 O

O Cl

Cl I A. B. C. D. E.

III

I II III IV none of these

Answer: E Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

Difficulty: Medium 31.

What is the predicted major product of the reaction shown?

O H3O+ Cl2 O Cl

I A. B. C. D. E.

III

I II III IV none of these

Answer: B Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 32.

What are the predicted products of the reaction shown?

PCC CH2Cl2

H 3O+ Br 2 O

Br I

III

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 33.

What reagents are needed to carry out the conversion shown?

OH O A. B. C. D. E.

1. PCC/CH2Cl2; 2. H3O+/Br2; 3. NaCN 1. PCC/CH2Cl2; 2. H2O/HBr; 3. NaOCH3 1. NaOEt; 2. H3O+ 1. PCC/CH2Cl2; 2. H3O+/Br2; NaOCH2CH3 1. NaOH; 2. heat

Answer: D Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 34.

What reagents are needed to carry out the conversion shown?.

O CN

A. B. C. D. E.

1. PCC/CH2Cl2; 2. H3O+/Br2; 3. NaCN 1. PCC/CH2Cl2; 2. NaCN; 3. H3O+ 1. NaOEt; 2. H3O+ 1. PCC/CH2Cl2; 2. H3O+/CN; NaOCH2CH3 1. NaOH; 2. NaCN; 3. heat

Answer: A Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 35.

What is the predicted major product of the reaction shown?

O H3O+ Br2

pyridine

+ I

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 36.

What is the predicted major product of the reaction shown?

O H3O+ Br2

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 37.

What is the predicted major product of the reaction shown?

1. Br2/PBr3 OH

2. H2O

O Br

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 38.

What is the predicted major product of the reaction shown?

1. Br2/PBr3 OH 2. H2O

O Br

I A. B. C. D. E.

OH II

I II III IV none of these

Answer: E

O OH

III

Br IV

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 39.

What is the predicted major product of the reaction shown?

Na2Cr2O7/H 2SO4/H 2O

1. Br2/PBr 3 2. H2O

Br H

A. B. C. D. E.

O OH

Br II

III

I II III IV V

Answer: C Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 40.

What reagents are needed to carry out the conversion shown?

O CN OH Br

A. B. C. D. E.

1. H3O+/heat; 2. Br2PBr3; 3. H2O 1. Br2PBr3; 2. H2O 1. HBr; 2. H2SO4; 3. H3O+ 1. NaOH/Br2; 2. H3O+ 1. NaOH/heat; 2. HBr

Answer: A Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 41.

What is the name of the reaction in which a carboxylic acid can undergo alpha halogenation?

A. B. C. D. E.

Haloform reaction Hell-Volhard-Zelinsky reaction Claisen reaction Williamson synthesis Stork reaction

Answer: B Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Easy 42.

Which of the given ketones will give a positive haloform test?

A. B. C. D. E.

3-heptanone 3-hexanone cyclohexanone 2-pentanone 2-methyl-3-hexanone

Answer: D Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 43.

Which of the given aldehydes and ketones will give a positive haloform test?

A. B. C. D. E.

3-heptanone 4-decanone acetone 3-pentanone 3-hexanone

Answer: C

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Easy 44.

What is the organic by-product in a haloform reaction?

A. B. C. D. E.

an ether a haloform an alcohol an ester an amide

Answer: B Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Easy 45.

What is the predicted major product of the reaction shown?

O 1. NaOH/Br2 2. H3O+ O Br

A. B. C. D. E.

I II III IV V

Answer: E

Br Br

Br III

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 46.

Provide the reagents necessary to convert acetophenone to benzoic acid.

A. B.

PCC/CH2Cl2 1. NaOH/Br2 2. H3O+ 1. KMnO4/NaOH/H2O 2. H3O+ 1. Br2/PBr3 2. H2 O both B and C

C. D. E.

Answer: E Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 47.

What is the predicted major product of the reaction shown?

O 1. NaOH/I2 2. H3O+ O

O I

I I

A. B. C. D.

I II III IV

I III

Answer: B Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 48.

What is the predicted major product of the reaction sequence shown?

OH KMnO4/NaOH/H2O

O O

O III

O I

OH O

A. B.

I II

CH3

1. NaOH/I2

CH3OH

2. H 3O+

H2SO4

C. D. E.

III IV V

Answer: A Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 49.

What reagents are necessary to carry out the conversion shown?

O Br

O N H

1. NaOH/Br2; 2. H3O+; 3. CH3NH2 1. NaOH; 2. H3O+; 3. Br2/PBr3; 4. NH3 1. NaOH/I2; 2. H3O+; 3. Br2/PBr3; 4. CH3NH2 1. NaOH/I2; 2. H3O+; 3. HBr; 4; H3O+; 5. CH3NH2 1. NaOH/Br2; 2. H3O+; 3. NaOH/H2O; 4.NH3

A. B. C. D. E.

Answer: C Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Hard 50.

Which reactant would yield m-chlorobenzoic acid using the haloform reaction?

CCH3

CCH2CH 3

COH

Cl I A. B. C. D. E.

Cl II

I II III IV V

III

CH2Cl

Answer: A Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction Difficulty: Medium 51.

Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?

A. B. C. D. E.

butanal 2-methylbutanal 3-methylpentanal 2,2-dimethylbutanal pentanal

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Easy 52.

In an aldol mechanism, the ___________ attacks the aldehyde.

A. B. C. D. E.

carbonyl carbon hydroxide ion alkoxide ion enolate proton

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Easy 53.

What is the predicted major product of the reaction shown?

O NaOH/H2O H

A. B. C. D. E.

OH OH

III

I II III IV V

Answer: B Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Medium 54.

What is the predicted major product of the reaction shown?

butanal + 2,2-dimethylpentanal NaOH, H2O OH H I

H II

III

A. B. C. D. E.

I II and IV III I and III V

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Medium 55.

What is the predicted major product of the reaction shown?

1. LDA H

O H

3. H2O

A. B. C. D. E.

O H

H I

III

I II III IV V

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard

56.

What is the predicted product when cyclohexanone reacts with aqueous sodium hydroxide at 100°C?

III

IV A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Medium 57.

What is the predicted product of the reaction shown?

O H

NaOH/H2O D

O H

II O

O H

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 58.

What is the predicted product of the reaction shown?

O H +

O O

NaOH/H2O D

O I

A. B. C. D. E.

I II III IV no reaction

Answer: A Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 59.

Which one of the following is not a possible product when a crossed aldol addition reaction is carried out with ethanal and butanal as reactants?

OH H

O I

A. B.

I II

III

C. D. E.

III IV V

Answer: B Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 60.

What is the predicted product of the reaction shown?

A. B. C. D. E.

NaOH/H2O D

III

I II III IV V

Answer: B Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 61.

What is the predicted product of the reaction shown?

O H + O O

H OH

NaOH/H2O

H III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 62.

What is the predicted product of the reaction shown?

O H +

NaOH/H2O H

H II

O H

III

O H V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 63.

What is the predicted product of the reaction shown?

O H +

NaOH/H2O D

Answer:

III

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 64.

What reactants would give the aldol condensation product shown?

O H +

H O

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 65.

What reactants would give the aldol condensation product shown?

O H

H +

O I

A. B. C. D. E.

I II III IV none of these

Answer: A

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard

66.

What reactants would give the aldol condensation product shown?

OH O I

H + O

H O

O OH + OH O III

OH O

H + O

H O

O H + O V

H + I II III IV V

Answer: E

H O

A. B. C. D. E.

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Medium 67.

What reactant would give the aldol condensation product shown?

H I

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 68.

What is the predicted product of the reaction shown?

O NaOH/H 2O D

O O O

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 69.

What reactants would give the aldol condensation product shown?

O H

A. B. C. D. E.

O HO

III

I II III IV V

Answer: A Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 70.

What reactant would give the possible aldol condensation product shown?

O H

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 71.

What reactant(s) would give the possible aldol condensation product shown?

Answer:

III

A. B. C. D. E.

I and II I and III II and III I and IV II and V

Answer: D Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 72.

What reactant would give the possible aldol condensation product shown?

O I

III

O V

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation Difficulty: Hard 73.

Which of the choices is a major product in a Claisen condensation?

A. B. C. D. E.

a-keto ester b-keto ester b-hydroxy ester g-hydroxyester b-diketone

Answer: B Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Easy 74.

Which of the choices is a reactive starting material in the Claisen condensation?

A. B. C. D. E.

3-pentanone butanal ethyl butanoate 1-propanol propanoic anhydride

Answer: C Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Easy 75.

Why shouldn’t CH3ONa be used for Claisen condensation of ethylbutanoate?

A. B. C. D. E.

The reaction will proceed too quickly. Using CH3ONa will yield a transesterification product. There will be no reaction. The starting ester will undergo hydrolysis. Ammonium chloride would be required for the reaction to take place.

Answer: B Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Easy 76.

What is the major predicted product of the reaction shown?

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Medium 77.

What is the major predicted product of the reaction shown?

O O

1. NaOCH 2CH 3 2. H3O+

Answer:

O O

III

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Medium 78.

What is the major predicted product of the reaction shown?

ethyl benzoate + ethyl butanoate

1. NaOCH2CH 3 2. H3O+ O

O O

A. B. C. D. E.

I II III IV none of these

Answer: D Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 79.

What is the structure of reactant (X) in the following reaction?

O O +

2. H 3O+

O O

1. NaOCH3

O O

O II

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 80.

What is(are) the predicted product(s) of the reaction shown?

1. NaOCH3

methyl acetate + methyl propanoate O

2. H3O+ O

O I

A. B. C. D. E.

O II

I II III IV all of these

Answer: E Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard

81.

What reactants will yield the given compound as a crossed Claisen condensation product?

1. NaOCH2CH3

1. NaOH

O O

2. H3O+

1. NaOCH2CH3 O

2. H3O+

A. B. C. D. E.

O H

1. NaOCH2CH3

H3C

2. H3O+

III

2. H3O+

1. NaOCH3 O

2. H3O+

I II III IV V

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard

82.

What is the predicted product of the reaction shown?

O O O +

1. NaOCH 3 2. H3O+

O O

III

IV O

A. B. C. D. E.

I II III IV All of these

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 83.

What reactant(s) will yield the given Claisen condensation product?

O I

O II

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 84.

An intermolecular Claisen condensation is called a _____________.

A. B. C. D. E.

Crossed Claisen condensation Direct Claisen condensation Dieckmann cyclization Cyclic Claisen condensation Asymmetrical Claisen condensation

Answer: C Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Easy 85.

Which cannot be used in a Claisen condensation?

A. B. C. D. E.

two esters, both without alpha hydrogens one ester with an alpha hydrogen and one ester without an alpha hydrogen two esters, both with alpha hydrogens all of these none of these

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation

Difficulty: Easy 86.

What is the predicted product of the reaction shown?

O 1. NaOCH 2CH3

2. H3O+

O O

O O I

A. B. C. D. E.

O III

I II III IV V

Answer: B Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 87.

What is the predicted product of the reaction shown?

diethyl heptanedioate

1. NaOCH2CH3 2. H3O+

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Medium 88.

Which of the compounds shown can be prepared using the Dieckmann condensation?

O I A. B. C. D. E.

HO II

III

I II III IV II and IV

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard

89.

What is the predicted product of the reaction shown?

O O

1. NaOCH 2CH 3 O

2. H3O+

O O O

O I

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard

90.

What is(are) the predicted products of the reaction shown?

1. NaOCH2CH 3

O O

2. H3O+ O

O II

A. B. C. D. E.

I II III I and IV I and III

Answer: E Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 91.

Provide a stepwise synthesis for the following compound starting with cycloheptene and using the Dieckmann cyclization.

O O

A. 1. O3; 2. DMS; 3. excess Na2Cr2O7/H2SO4/H2O; 4. excess CH3CH2OH/H2SO4; 5. NaOCH2CH3; 6. H3O+ B. 1. H2/Pd; 2. Br2; 3. excess CH3CH2OH/H2SO4; 5. NaOCH2CH3; 6. H3O+ C. 1. O3; 2. excess Na2Cr2O7/H2SO4/H2O; 3. excess CH3CH2OH/H2SO4; 4. NaOCH2CH3; 5. H3O+ D. 1. O3; 2. DMS; 3. excess Na2Cr2O7/H2SO4/H2O; 4. excess CH3OH/H2SO4; 5. NaOCH2CH3; 6. H2O E. 1. Br2/hv; 2. DMS; 3. NaOH; 4. excess CH3CH2OH/H2SO4; 5. NaOCH2CH3; 6. + H3 O Answer: A Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 92.

What is the predicted product for the Dieckmann-like cyclization shown?

O O

1. NaOCH 2CH3 2. H3O +

O O

O O I

A. B.

I II

O II

III

C. D. E.

III IV V

Answer B Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 93.

What is the predicted major product of the reaction sequence shown?

O 1. NaOCH 2CH3

2. H3O+ O

III

O OH O

A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 20.4 Predict the products and draw a mechanism for a Claisen condensation Difficulty: Hard 94.

What is the predicted product of the reaction shown?

O 1. LDA, -78oC 2. CH 3CH 2Br O

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Medium 95.

What is the predicted product of the reaction shown?

O 1. NaH, 25oC 2. CH 3CH 2Br O

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Medium 96.

What is the predicted product of the reaction shown?

2-methyl-3-pentanone

1. LDA, -78oC 2. CH 3CH2I

A. B. C. D. E.

I II III IV V

What is the predicted product of the reaction shown?

2-methyl-3-pentanone

1. NaH, 25oC 2. CH 3CH2I

A. B. C. D. E.

I II III IV V

What reagents are needed to carry out the conversion shown?

A. B. C. D. E.

1. LDA; 2. CH3CH2Br; 3. NaBH4/CH3OH 1. LDA; 2. CH3Br; 3. NaBH4/CH3OH 1. LDA; 2. CH3CH2CH2Br; 3. CH3OH 1. LDA; 2. CH3CH2Br; 3. CH3OH 1. LDA; 2. CH3CH2CH2Br; 3. NaBH4/CH3OH

Answer: E Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Hard 99.

What is the predicted product of the reaction shown?

O 1. LDA, -78oC 2. CH3CH2Br

A. B. C. D. E.

III

I II III IV V

What is the predicted product of the reaction shown?

O 1. NaH, 25oC 2. CH3CH2Br

A. B. C. D. E.

III

I II III IV V

Will the following reaction yield the product shown and why or why not?

O 1. NaH 2. 2-iodo-2-methylbutane

A. Yes, the reaction will yield the product shown because an SN2 reaction is favored under these conditions. B. Yes, the reaction will yield the product shown because an E2 reaction is favored under these conditions. C. No, because the tertiary alkyl halide is too sterically hindered for an SN2 reaction to occur. D. No, because iodine is not a good leaving group. E. No, because no electrophile is present. Answer: Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Hard 102.

What is the predicted product of the reaction shown?

O O O

Answer: D

2. CH3CH 2CH2Br 3. H 3O+

O I

I II III IV V

1. NaOCH 2CH3

A. B. C. D. E.

OH II

III

Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Medium 103.

What is the predicted product of the reaction sequence shown?

O 1. NaOCH2CH 3 1. NaOCH2CH3

2. CH3CH 2I

O O

O II

A. B. C. D. E.

2. CH 3CH2I

H3O+ D

III

I II III IV V

Answer: D Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Hard 104.

What is the predicted product of the reaction sequence shown?

O O

1. NaOCH2CH 3

1. NaOCH 2CH3

2. CH3CH2I

2. CH3I

O OH

A. B. C. D. E.

O OH

III

I II III IV V

What is the predicted final product of the reaction sequence shown?

diethyl malonate

A. B. C. D. E.

1. sodium ethoxide

2. 1-bromopentane

2. bromomethane

2-methylheptanoic acid 3-methylhexanoic acid 3-methylpentanoic acid 2-methylpentanoic acid ethyl 2-methylheptanoate

Answer: A

H 3O+ D

What is the predicted product of the reaction sequence shown?

O O

A. B. C. D. E.

Br O

OH HO

H3O+ D

1. NaOCH 2CH 3 1. NaOCH2CH 3

III

I II III IV V

107.

Provide the reagents necessary to carry out the following conversion using a malonic ester synthesis.

O O

OH O

Br A.

; 5. H3O+,

1. NaOCH2CH3; 2. CH3CH2CH2Br; 3. NaOCH2CH3; 4. heat

Br B.

1. LDA; 2.

; 4. H3O+, heat

1. LDA; 2.

; 4. H3O+, heat

Br D. 1. NaOCH2CH3; 2. (CH3)2CHCH2Br; 3. NaOCH2CH3; 4. H3O+/heat E.

1. NaOCH2CH3; 2. (CH3)2CHCH2Br; 3. NaOCH2CH3; 4.

; 5.

; 5. H3O+, heat

What is the predicted final product of the reaction sequence shown?

O 1. NaOCH2CH 3 NaOCH2CH 3

H3O+ D

O OH

O O

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis Difficulty: Hard 109.

What is the predicted final product of the reaction sequence shown?

O 1. NaOCH 2CH3

2. Br(CH 2)5Br

OH I

NaOCH2CH 3

H3O+ D

O O

OH III

A. B. C. D. E.

I II III IV V

Provide the structures of the intermediates and the final product in the following reaction sequence.

O O

1. NaOCH2CH 3 O

A. B. C. D. E.

X is I, Y is II, and Z is III X is II, Y is I, and Z is III X is I, Y is III, and Z is IV X is II, Y is III, and Z is V X is I, Y is IV, and Z is C

Which of the following ketones cannot be prepared using an acetoacetic ester synthesis?

I A. B. C. D. E.

III

I II III IV A and C

What is the predicted final product of the reaction shown?

O O O

1. NaOCH2CH 3

H3O+

2. CH 3CH2CH2I

O HO

III

A. B. C. D. E.

I II III IV V

What is the predicted product of the reaction sequence shown?

O O

1. NaOCH2CH3

H 3O+

O HO

Br O

O HO

III

B. C. D. E.

II III IV V

What is the predicted product of the reaction sequence shown?

O 1. NaOCH2CH3 1. NaOCH2CH 3

2. CH3CH 2I

2. CH3CH2I

H I

A. B. C. D. E.

III

I II III IV V

115.

What reagents are needed to carry out the following conversion?

O O

O 2.

1. NaH

D O

1. NaOCH2CH3

3. H3O+ D

2. III

3. H 3O+

2. II

1. NaOCH2CH3

3. H 3O+ D

2. IV A. B. C. D. E.

1. NaOCH2CH3

3. H3O+ D

I II III IV all of them

What reagents are needed necessary to prepare the following compound starting with ethyl acetoacetate?

O O

O A.

; 3. H3O+, heat

NaOH; 2.

O B.

NaOCH3; 2.

NaOCH2CH3; 2.

; 3. H3O+, heat ; 3. H3O+, heat

O D.

NaOCH2CH3; 2.

NaOCH3; 2.

; 3. H3O+, heat ; 3. H3O+, heat

Which of the following nucleophiles will undergo conjugate addition in a Michael reaction?

O MgBr I A. B. C. D. E.

CN II

N III O

(CH 3CH2)2CuLi IV

I I and II III I and IV II and IV

Answer: E Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

Difficulty: Easy 118.

Which one of the choices is the most reactive Michael acceptor?

O NO2

O I

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Easy 119.

What is(are) the predicted product(s) of the reaction shown?

O 1. (CH 3CH 2CH2)2CuLi 2. H 3O+ O

O I

A. B. C. D. E.

I II III IV I and IV

Answer: A Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Medium 120.

What is(are) the predicted product(s) of the reaction shown?

O 1. CH3CH 2CH2MgBr 2. H3O+ O

O I

A. B. C.

I II III

D. E.

IV I and IV

Answer: D Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Medium 121.

What is the predicted product of the reaction shown?

1. KOH 2.

3. H3O+ O O

HO O

O I

A. B. C. D. E.

I II III IV V

Answer: B

III

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 122.

What is the predicted product of the reaction shown?

1. NaOCH 3 2. Br 3. H 3O+

OH O

A. B. C. D. E.

III

I II III IV V

Answer: C Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 123.

What reagents are needed to carry out the conversion shown?

O CN O

1. (CH3)2NH; 2.

O CN ; 3. H3O+

1. LDA; 2.

CN ; 3. H3O+

1. LDA; 2.

; 3. H3O+

1. LDA; 2.

1. LDA; 2. (CH3)2NH; 3.

; 3. H3O+ ; 3. H3O+

Answer: B Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 124.

What is the predicted product of the reaction shown?

A. B. C. D. E.

H 3O+

1. NaOCH 3

III

I II III IV V

Answer: A Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard

125.

Which of the compounds shown can be prepared using the Michael reaction?

O O

HO II

I A. B. C. D. E.

III

I II III IV none of these

Answer: C Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Medium 126.

What is the predicted product of the reaction shown?

1. NaOCH3 O

OH HO

HO I

A. B.

I II

III

C. D. E.

III IV V

Answer: B Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 127.

Which of the amines shown will form an enamine with aldehydes and ketones?

H NH 2

H N

III

I A. B. C. D. E.

I II III IV II and III

Answer: E Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Easy 128.

Which of the amines shown will form an enamine with aldehydes and ketones?

N H I A. B. C. D. E.

I II III IV I and III

Answer: E

N II

N H

III

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Easy 129.

Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis.

O O

O A.

; 3. H3O+

CH3NH/H2SO4; 2.

O ; 3. H3O+

NaOCH3; 2.

(CH3)2NH/H2SO4; 2.

; 3. H3O+

O D.

(CH3)2NH/H2SO4; 2.

CH3NH/H2SO4; 2.

; 3. H3O+ ; 3. H3O+

Answer: D Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 130.

What is the predicted product of the reaction shown?

O 1.

(CH3)2NH H2SO4

2. H 3O+

N(CH3)2

N(CH 3)2

A. B. C. D. E.

O HO

III

I II III IV V

Answer: D Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 131.

What is the predicted product of the reaction shown?

O 1.

(CH 3)2NH

H2SO4

2. H 3O+

(CH 3)2N

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 132. Provide the reactants necessary to synthesize the following compound using a Stork enamine synthesis.

O H

O I

2. H3O+ 1.

O II

(CH3)2NH H2SO4

III

CH3NH2 H2SO4

2. H3O+ 1.

A. B. C. D. E.

(CH3)2NH H2SO4

2. H3O+

I II III IV V

Answer: B Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 133.

What is the predicted product of the reaction sequence shown?

O 1. (CH3)2NH H 2SO4

O O

1. LiAlH4

2. H 3O+

O OH

O II

OH III

OH OH

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard

134.

What is the predicted major product of the reaction shown?

O O

NaOH D

+ O O

A. B. C. D. E.

III

I II III IV V

Answer: E Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Medium 135.

What is(are) the predicted product(s) of the reaction shown?

O + O

NaOH D

O OH I

A. B. C. D. E.

III

I II and III III and IV IV II and V

Answer: E Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 136.

What reactants are needed to prepare the given compound using Robinson annulation?

O I

O III A. B. C. D. E.

I II III IV I and III

Answer: A Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 137.

What reactants are needed to prepare the given compound using Robinson annulation?

O O

+ I

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis Difficulty: Hard 138.

What are the structures of the intermediates and the final product in the reaction sequence shown?

O (CH 3CH2)2NH H2SO4

2. H3O+

NaOH D

O O N(CH2CH3)2

III

O O

A. B. C. D. E.

X is I, Y is II, and Z is III X is II, Y is I, and Z is III X is I, Y is III, and Z is IV X is II, Y is III, and Z is V X is I, Y is IV, and Z is C

Answer: A Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Medium 139.

What reagents are needed to carry out the conversion shown?

O H

A. B.

1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. Zn(Hg)/HCl 1. (CH3CH2)2CuLi; 2. CH3I; 3. KCr2O7/H2SO4/H2O; 4. CH3OH/H2SO4

C. D. E.

1. (CH3CH2)2CuLi; 2. CH3Br; 3. Zn(Hg)/HCl 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. KCr2O7/H2SO4/H2O; 4. CH3OH 1. (CH3CH2)2CuLi; 2. KCr2O7/H2SO4/H2O; 3. NaOH; 4. CH3OH/H2SO4

Answer: B Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Medium 140.

What reagents are needed to carry out the conversion shown?

O H

A. B. C. D. E.

1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. Zn(Hg)/HCl 1. (CH3CH2)2CuLi; 2. CH3I; 3. KCr2O7/H2SO4/H2O; 4. CH3OH/H2SO4 1. (CH3CH2)2CuLi; 2. CH3Br; 3. Zn(Hg)/HCl 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. KCr2O7/H2SO4/H2O; 4. CH3OH 1. LDA; 2. (CH3CH2O)2C=O; DIBAH

Answer: A Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Medium 141.

Provide the reagents necessary to carry out the following conversion.

O H

A. B. C. D. E.

1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. Zn(Hg)/HCl 1. (CH3CH2)2CuLi; 2. CH3I; 3. KCr2O7/H2SO4/H2O; 4. CH3OH/H2SO4 1. LDA; 2. (CH3CH2O)2C=O; DIBAH 1. LDA; 2. (CH3O)2C=O; DIBAH 1. LDA; 2. (CH3CH2O)2C=O; DIBAH

Answer: E Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard

142.

What is the structure of the reactant (X) necessary to carry out the conversion shown?

O O

O NaOH H

/ heat

/ heat IV

III

/ heat V

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard 143.

What is an appropriate stepwise synthesis for the conversion shown?

O H O

1. Cl2/FeCl3; 2.

/NaOCH3; 3. H3O+; 4. SOCl2

1. HCl/AlCl3; 2.

/NaOCH3; 3. SOCl2; 4. NaOH

1. Cl2/FeCl3; 2.

/NaOCH3; 3. H3O+; 4. SOCl2

1. HCl/AlCl3; 2.

; 3. SOCl2; 4. NaOH

/NaOCH3; 3. H3O+; 4. SOCl2

Answer: A Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard 144.

Which one of the reaction sequences shown will yield 2,2-dimethylcyclohexane1,3-dione?

O excess 1. CH3MgBr 2. H3O+ O

A. B. C. D. E.

I II III IV II and IV

Answer: B Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard 145.

What reagents are needed to carry out the conversion shown?

O O O

O O

A. 1. NaOCH2CH3; 2. CH3Br B. 1. NaOCH2CH3; 2. CH3I; 4. H3O+, heat C. 1. NaOCH2CH3; 2. NaOCH2CH3; 3. CH3CH2Br; 4. H2SO4 D. 1. NaOCH2CH3; 2. NaOCH2CH3; 3. CH3Br; 4. H3O+, heat E. 1. NaOCH2CH3; 2. CH3Br; 3. H3O+, heat Answer: D Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard 146.

What reagents are necessary to carry out the conversion shown?

O O

O O O

A. B. C. D. E.

1. Na2Cr2O7/H2SO4/H2O; 2. H3O+/EtOH; 3. H3O+, heat 1. HOCH2CH2OH; 2. NaOCH2CH3; 3. excess H3O+, heat 1. HOCH2CH2OH, H2SO4; 2. NaOCH3; 3. excess H3O+, heat 1. NaOCH2CH3; 2. NaOCH2CH3; 3. CH3Br; 4. H3O+, heat 1. Na2Cr2O7/H2SO4/H2O; 2. H3O+/EtOH; 3. NaOEt; 4. H3O+, heat

Answer: C Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard 147.

What is an appropriate stepwise synthesis for the following synthesis that uses 1propanol as the only source of carbon and any other reagents as needed?

CH3CH 2CH2OH

CH 3CH2CH 2CHCH2OH CH3

A. 1-propanol reacts with PCC/CH2Cl2 to yield an intermediate that reacts with LDA to yield intermediate X, which has a resonance form Y. 1-propanol also reacts with PCl3 to yield an intermediate Z that reacts with intermediate X, which undergoes the following series of reactions to yield the product: 1. Na2Cr2O7/H2SO4/H2O; 2. Excess CH3CH2CH2OH/H2SO4. B. 1-propanol reacts with PCC/CH2Cl2, then the product reacts with LDA to produce intermediate X, which has resonance forms. 1-propanol reacts with PCl3, then the product reacts with intermediate X to yield intermediate Y. Intermediate Y reacts with NaBH4/CH3OH to yield the product. C. 1-propanol reacts with PCl3 to yield intermediate X. 1-propanol also undergoes the following reaction sequence: 1. Na2Cr2O7/H2SO4/H2O; 2. excess CH3CH2CH2OH/H2SO4; 3. LDA; 4. Intermediate X. This yields the product.

D. E.

A or B B or C

Answer: B Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard 148.

What is an appropriate stepwise synthesis for the following synthesis that uses 1propanol as the only source of carbon and any other reagents as needed?

O CH3CH 2CH2OH

CH 3CH2CH2CHCOCH2CH2CH 3 CH 3

Answer: E Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds Difficulty: Hard

Klein, Organic Chemistry 4e Chapter 22 1.

Which of the choices is a primary amine?

A. B. C. D. E.

CH3CH2CH2CH2NH2 CH3CH2NHCH2CH(CH3)2 (CH3CH2)2NCH2CH(CH3)2 (CH3CH2)4N+ OH(CH3CH2)3N

Answer: A Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines Difficulty: Easy 2.

Which of the choices is a secondary amine?

A. B. C. D. E.

CH3CH2CH2CH2NH2 CH3CH2NHCH2CH(CH3)2 (CH3CH2)2NCH2CH(CH3)2 (CH3CH2)4N+ OH(CH3CH2)3CNH2

Answer: B Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines Difficulty: Easy 3.

Which of the choices is a tertiary amine?

A. B. C. D. E.

CH3CH2CH2CH2NH2 CH3CH2NHCH2CH(CH3)2 (CH3CH2)2NCH2CH(CH3)2 (CH3CH2)4N+ OH(CH3CH2)3CNH2

Answer: C Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines Difficulty: Easy 4.

Which of the choices is a quaternary ammonium salt?

CH3CH2CH2CH2NH3+ Cl(CH3CH2)2NH2+ Cl(CH3CH2)3NH+ Cl(CH3CH2)4N+ Cl(CH3CH2)2NCH3

A. B. C. D. E.

Answer: D Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines Difficulty: Medium 5.

Classify each of the compounds as a primary, secondary or tertiary amine.

H N

NH2 N

O II

III

A. I is a primary amine, II is a secondary amine, and II is a tertiary amine B. I is a secondary amine, II is a tertiary amine, and III is a primary amine C. I is tertiary amine, II is a secondary amine, and III is a primary amine D. I is a secondary amine, II is a primary amine, and III is a tertiary amine E.I is a tertiary amine, II is a primary amine, and III is a primary amine Answer: B Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines Difficulty: Easy 6.

What is the structure for 1-butanamine?

A. B. C. D. E.

CH3CH2CH2CH2NH2 CH3CH2NHCH2CH(CH3)2 (CH3CH2)2NCH2CH(CH3)2 (CH3CH2)4N+ OH(CH3CH2)3CNH2

Answer: A Learning Objective: 22.2 Describe two methods of naming amines

Difficulty: Medium 7.

What is the common name for the compound shown?

A. B. C. D. E.

ethylmethylisobutylamine diethylisobutylamine sec-butyldiethylamine 2-diethylaminobutane sec-butyldimethylamine

Answer: C Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 8.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

N,N,1-diethyl-1-ethanamine N,N-diethyl-1-methyl-1-propanamine 2,2-diethyl-2-butanamine N,N-dimethyl-2-butanamine N,N-diethyl-2-butanamine

Answer: E Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 9.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

ethylisobutylisopropylamine ethylisopropylbutylamine sec-butylethylpropylamine sec-butylethylisopropylamine none of these

Answer: A Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 10.

What is the common name for the compound shown?

H N

A. B. C. D. E.

dibenzylamine diphenylamine dibenzeneamine phenylbenzeneamine none of these

Answer: B Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 11.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

N-ethylhexanamine N-ethylcyclohexanamine N-cyclohexylethanamine N-ethylcyclopentanamine N-ethylaniline

Answer: B Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 12.

What is the common name for the compound shown?

A. B. C. D. E.

cyclopentylmethylamine ethylhexylamine cyclohexylethylamine cyclohexylmethylamine ethylhexylmethylamine

Answer: C Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 13.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

N-cyclopentyl-N-methylcyclohexanamine N-cyclohexyl-N-methylcyclohexanamine N-cyclopentyl-N-methylcyclopentanamine cyclohexylcyclopentylmethylamine N-pentyl-N-methylhexanamine

Answer: A

Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 14.

What is the common name for the compound shown?

A. B. C. D. E.

N-cyclopentyl-N-methylcyclohexanamine N-cyclohexyl-N-methylcyclohexanamine N-cyclopentyl-N-methylcyclopentanamine cyclohexylcyclopentylmethylamine N-pentyl-N-methylhexanamine

Answer: D Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 15.

What is the IUPAC name for the compound shown?

H N

A. B. C. D. E.

1-methyl-N-propyl-1-butananmine 4-methyl-5-octanamine 1-ethyl-N-propyl-1-pentanamine N-butyl-2-pentanamine N-methylpropyl-1-butanamine

Answer: D Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 16.

What is the IUPAC name for the compound shown?

NH2

A. B. C. D. E.

1-cyclopropyl-1-ethyl-6-hexamine 3-cyclopropyl-7-heptamine 5-cyclopropyl-1-heptanamine 1-ethyl-1-cyclopropyl-6-hexamine 3-cyclopropylheptamine

Answer: C Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 17.

What is the IUPAC name for the compound shown?

NH 2 A. B. C. D. E.

(1R,2S)-2-methylcyclopentanamine (1S,2R)-2-methylcyclopentanamine (1S,2S)-1-methyl-3cyclopentanamine (1R,2R)-1-methyl-3cyclopentanamine (1S,2S)-2-methylcyclopentanamine

Answer: E Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 18.

What is the structure for 3-chloro-N-ethyl-1-pentanamine?

H N

NH2

Cl I

N H

Cl IV

III

H N Cl V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 19.

What is the structure for N-ethylbenzylamine?

NH2

NH2 II

NH2 N H III

NH2 V

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 20.

What is the structure for N,N-diethylaniline?

H N

III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 21.

What is the IUPAC name for the compound shown?

OH A. B. C. D. E.

NH2

7-amino-5-isopropyl-3-octanol 7-amino-5-(dimethyl)-3-octanol 2-amino-5-isopropyl-6-octanol 2-amino-5-(dimethyl)-3-octanol 1-ethyl-3-isopropyl-5-amino-1-octanol

Answer: A

Answer: A Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Hard 22.

What is the IUPAC name for the compound shown?

NH2 HO O A. B. C. D. E.

4-amino-2,2-ethylhexanoic acid 4-amino-2-diethylhexanoic acid 3-amino-5,5-ethyl-6-hexanoic acid 3-amino-5,5-diethyl-6-hexanoic acid 4-amino-2,2-diethylhexanoic acid

Answer: E Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Hard 23.

What is the IUPAC name for the compound shown?

HO O A. B. C. D. E.

NH2

7-amino-5-ethyl-hydroxyoctanone 7-amino-5-ethyl-1-hydroxy-3-octanone 2-amino-4-ethyl-8-hydroxy-6-octanone 2-amino-4-methyl-8-hydroxy-6-octanone 7-amino-1-hydroxy-5-ethyl-6-octanone

Answer: B Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Hard 24.

What is the IUPAC name for the compound shown?

A. B. C. D. E.

4-amino-4-ethyloctane 5-amino-5-ethyloctane N-propylethyl-1-butanamine N-ethylpropyl-1-butanamine N-ethyl-N-propyl-1-butanamine

Answer: E Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Hard 25.

What is the common name for the compound shown?

A. B. C. D. E,

N-ethylbutylpropylamine N-butylethylpropylamine butylethylpropylamine propylethylbutylamine butylpropylethylamine

Answer: B Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Medium 26.

What is the IUPAC name for the compound shown?

NH 2

A. B. C. D. E.

1-amino-6-ethylcyclohexan-3-one 3-amino-4-ethylcyclohexanone 2-amino-1-ethylcyclohexan-5-one p-ethyl-m-aminocyclohexanone 1-ethyl, 6-aminocyclohexan-4-one

Answer: B Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Hard 27.

What is the IUPAC name for the compound shown?

NH 2

A. B. C. D. E.

(1R,6S)-6-methylcyclohex-2-enamine (1S,6R)-6-methylcyclohex-2-enamine (1S,6S)-6-methylcyclohex-2-enamine (1R,6R)-6-methylcyclohex-2-enamine (1R,6S)-6-methylcyclohex-2-amine

Answer: D Learning Objective: 22.2 Describe two methods of naming amines Difficulty: Hard 28.

Arrange the compounds shown in decreasing (highest to lowest) order of boiling point.

CH3CH2CH2CH2NH2

I A. B. C. D. E.

CH3CH2N(CH3)2

CH3CH2CH2NHCH3 III

II > III > I I > III > II II > III > I III > II > I I > II > III

Answer: B Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction Difficulty: Medium 29.

Arrange the compounds shown in decreasing (highest to lowest) order of boiling point.

1-pentanol I A. B. C. D. E.

hexane II

1-pentanamine III

butyl methyl ether IV

III > I > IV > II I > III > IV > II I > IV > III > II I > III > II > IV III > I > II > IV

Which of the compounds shown is most soluble in water?

NH 2

N H I A. B.

I II

N III

C. D. E.

III both I and II all of these

Which of the compounds shown is least soluble in water?

NH 2

N H

I A. B. C. D. E.

N III

I II III both I and III none of these

Answer: C Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction Difficulty: Medium 32.

Which of the compounds shown is the strongest base?

NH2

NH 2

NH2

O 2N I

III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction Difficulty: Medium 33.

Rank the compounds shown in decreasing (strongest to weakest) order of basicity.

NH2

O 2N I A. B. C. D. E.

III

NH 2

I > III > II > IV II > III > I > IV IV > II > III > IV IV > III > II > I III > II > I > IV

Arrange the compounds shown in decreasing (strongest to weakest) order of basicity.

A. B. C. D. E.

CH3CH2NH2

(CH3CH2)3N

NH3

(CH3CH2)2NH

III

I > III > II > IV II > III > I > IV IV > II > I > III IV > III > II > I II > I > IV > III

Arrange the compounds shown in decreasing (strongest to weakest) order of basicity.

p-methylaniline I A. B. C. D. E.

aniline

p-nitroaniline

p-methoxyaniline

III

I > III > II > IV II > III > I > IV IV > III > II > I IV > I > II > III II > I > IV > III

Arrange the compounds shown in decreasing (strongest to weakest) order of basicity.

NH 2

NH2

CF3

OCH3 II

I A. B. C. D. E.

NH2

III

NH2

I > III > II > IV II > III > I > IV IV > III > II > I IV > I > II > III II > IV > I > III

Answer: E Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction Difficulty: Medium 37.

Which of the choices is the weakest base?

A. B. C. D. E.

4-chloroaniline 4-nitroaniline 4-aminobenzonitrile aniline 4-aminoanisole

Which of the choices is the strongest base?

A. B. C. D.

4-chloroaniline 4-nitroaniline 4-aminobenzonitrile aniline

4-aminoanisole

Arrange the compounds shown in increasing (weakest to strongest) order of basicity.

NH 2 H N

NH 2 N

NO2 A. B. C. D. E.

III

IV < II < I < III III < II < IV < I II < I < III < IV II < III < I < IV None of the above

Which one of the compounds shown, if either, is a stronger base and why?

NH I

N H

A. I is a stronger base because the nonbonding electrons on N are not involved in resonance in the aromatic ring. B. I is a stronger base because the nonbonding electrons on N are involved in resonance in the aromatic ring. C. II is a stronger base because the nonbinding electrons on N are involved in resonance on the aromatic ring. D. II is a stronger base because the nonbinding electrons on N are not involved in resonance on the aromatic ring. E. I and II are equivalent bases because both have nonbinding electrons that are involved resonance. Answer: B Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction Difficulty: Medium 41.

Pyridoxamine, aka vitamin B6, has the structure shown. Which nitrogen is more basic and why?

1 CH 2NH2 HO

CH 2OH

H 3C

N 2

A. B. C. D. E.

N2 is more basic because it is sp hybridized. N2 is more basic because it is sp3 hybridized. N1 is more basic because it is sp hybridized and more electronegative than N2. N1 is more basic as it is sp3 hybridized and is less electronegative than N2. N1 is more basic as it is sp2 hybridized and more electronegative than N2.

42.

Nicotine, present in tobacco, has the structure shown. Which nitrogen is more basic and why?

N CH 3

1 A. B. C. D. E.

N2 is more basic as it is sp3 hybridized and less electronegative than N1. N2 is more basic as it is sp2 hybridized and less electronegative than N1. N2 is more basic as it is sp3 hybridized and more electronegative than N1. N1 is more basic as it is sp3 hybridized and more electronegative than N2. N1 is more basic as it is sp hybridized and more electronegative than N2.

Answer: A Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction Difficulty: Hard 43.

Chloroquine is used as an antimalarial drug. Rank the three nitrogen atoms in decreasing (strongest to weakest) order of basicity.

III

I HN

N II

A. B. C.

III > I > II I > III > II II > I > III

D. E.

I > II > III III > II > I

What is the predicted product of the reaction shown?

H2/Ni

NH 2

NH2

NH V A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 45.

What is the predicted product of the reaction shown?

1. NaCN 2. LiAlH4 3. H2O NH2

NH 2 I

III

NH2

O IV A. B. C. D. E.

O V

I II III IV V

Answer: C Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 46.

What reagents are needed to carry out the conversion shown?

NO2

A. B. C. D. E.

H2 and Ni 1. LiAlH4 2. H2 O Fe and HCl Zn and HCl all of these

Answer: E

NH2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 47.

What is the predicted product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 48.

What is the predicted product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 49.

What is the predicted product of the reaction shown?

O 1. LiAlH4

NH 2

2. H2O OH NH 2 I

NH2

NH2 II

III

H 2N

H2N IV A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 50.

What is the predicted product of the reaction shown?

O NH

1. LiAlH 4 2. H2O

OH NH

NH 2 I

A. B. C. D. E.

I II III IV V

III

Answer: A Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 51.

What reagents are necessary to carry out the conversion shown?

A. B. C. D. E.

H2 and Ni 1. LiAlH4; 2. H2O Fe and HCl Zn and HCl Fe and H2O

Answer: B Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 52.

What is the predicted product of the reaction sequence shown?

SOCl2 pyridine

CH3NH 2

1. LiAlH 4 2. H 2O

O I

H N

III

H N

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Hard 53.

What reagents are needed to convert (S)-3-methyl-3-phenylpentanoic acid to (S)3-methyl-3-phenylpentanamine?

A. B. C. D. E.

1. NaCN; 2. LiAlH4; 2. H2O 1. HNO3/H2SO4; 2. H2/Pt 1. NaN3; 2. LiAlH4; 3. H2O 1. SOCl2/pyridine; 2. NH3; 3. LiAlH4; 4.H2O 1. SOCl2/pyridine; 2. LiAlH4; 3.H2O

Answer: E Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium

54.

What reagents are needed to carry out the conversion shown?

CH 2Br

A. B. C. D. E.

CH 2CH2NH2

1. NaCN; 2. LiAlH4; 2. H2O 1. HNO3/H2SO4; 2. H2/Pt 1. NaN3; 2. LiAlH4; 3. H2O 1. SOCl2/pyridine; 2. NH3; 3. LiAlH4; 4.H2O 1. SOCl2/pyridine; 2. LiAlH4; 3.H2O

Answer: A Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Medium 55.

What reagents are needed to carry out the conversion shown?

COOH

A. B. C. D. E.

CH2NH2

1. NaCN; 2. LiAlH4; 2. H2O 1. HNO3/H2SO4; 2. H2/Pt 1. NaN3; 2. LiAlH4; 3. H2O 1. SOCl2; 2. excess NH3; 3. excess LiAlH4; 4.H2O 1. SOCl2/pyridine; 2. LiAlH4; 3.H2O

Answer: D Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids Difficulty: Hard

56.

What is the predicted product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: substitution reaction Difficulty: Medium

22.5 Identify three methods for preparing an amine via a

57.

What is the predicted product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: substitution reaction Difficulty: Medium 58.

22.5 Identify three methods for preparing an amine via a

What is the predicted product of the reaction shown?

1. NaN3 2. LiAlH4 3. H 2O

NHNH 2

NH 2

NNH2

III

O N

NH V

IV A. B. C. D. E.

I II III IV III and IV

Answer: B Learning Objective: substitution reaction Difficulty: Medium 59.

22.5 Identify three methods for preparing an amine via a

What is the predicted product of the reaction shown?

Br 1. NaN3 2. H 2, Pd

NH2 NH

A. B. C. D. E.

NH2

I II III IV V

Answer: E

III

Learning Objective: substitution reaction Difficulty: Medium 60.

22.5 Identify three methods for preparing an amine via a

What is the predicted product of the reaction shown?

1. LiAlH4 2. H 2O Li

NH2 N

NH2

III

NH2

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: substitution reaction Difficulty: Hard 61.

22.5 Identify three methods for preparing an amine via a

What is the predicted product of the reaction sequence shown?

mCPBA

NaN3

1. LiAlH 4 2. H2O

NH 2

+ enantiomer

III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: substitution reaction Difficulty: Hard

22.5 Identify three methods for preparing an amine via a

62.

Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?

A. B. C. D. E.

1-bromopentane 1-bromo-3-methylbutane 2-bromo-3-methylpentane 1-bromo-2,3-dimethylbutane 2-bromo-2,3-dimethylbutane

Answer: E Learning Objective: substitution reaction Difficulty: Medium

22.5 Identify three methods for preparing an amine via a

63.

What is(are) the predicted product(s) of the reaction shown?

O NH O I

1. KOH 2. CH3CH2CH 2CH2Br 3. H3O+

O OH OH O

NH2

NH NH

NH2

O A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: substitution reaction Difficulty: Hard

22.5 Identify three methods for preparing an amine via a

64.

Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.

1. KOH; 2.

; 3. H3O+

1. KOH; 2.

1. LiAlH4; 2.

; 3. H3O+

1. LiAlH4; 2.

; 3. H3O+

1. KOH; 2.

; 3. H3O+

Answer: B Learning Objective: substitution reaction Difficulty: Hard 65.

22.5 Identify three methods for preparing an amine via a

Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.

O NH O

O KOH

NK O

1. KOH; 2.

; 3. H3O+

1. KOH; 2.

; 3. H3O+

1. LiAlH4; 2.

; 3. H3O+

1. LiAlH4; 2.

; 3. H3O+

1. KOH; 2.

; 3. H3O+

Answer: A Learning Objective: substitution reaction Difficulty: Hard 66.

22.5 Identify three methods for preparing an amine via a

What is the predicted product of the reaction sequence shown?

NH2

NH2 II

O Br NH2 O IV

III

O N O V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: substitution reaction Difficulty: Hard

22.5 Identify three methods for preparing an amine via a

67.

The ________ reaction is used to prepare primary amines by using potassium phthalimide. This reaction proceeds by a ________ mechanism.

A. B.

Azide, E1 Gabriel, SN2

C. D. E.

Gabriel, SN1 Hofmann, E2 Hofmann, SN1

Answer: B Learning Objective: substitution reaction Difficulty: Easy 68.

22.5 Identify three methods for preparing an amine via a

What is the predicted product of the reaction shown?

O NH2 , H 2SO4

A. B. C. D. E.

H N

III

I II III IV V

Answer: A Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Medium 69.

What is(are) the predicted product(s) of the reaction shown?

O 1.

NH2 , H2SO4

2. NaBH CN 3

A. B. C. D. E.

H N

HO III

I II III IV V

Answer: B Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Medium 70.

What is the predicted product of the reaction shown?

NH2 , H2SO4

A. B. C. D. E.

III

I II III IV V

Answer: A Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Medium 71.

What is the predicted product of the reaction shown?

NH2 , H2SO4

NaBH3CN

A. B. C. D. E.

III

I II III IV V

Answer: D Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Medium 72.

Provide the reagents necessary to carry out the following conversion.

H N

1. NaNO2; 2. HCl; 3. NH3 O

CH3CCl / AlCl3

; CH3CH2NH2, H2SO4, NaBH3CN

O CH3CCl / AlCl3

; CH3CH2NH2, H2SO4

; 2. NaBH3CN

; CH3CH2CH2NH2, H2SO4, NaBH3CN

Answer: B Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Hard 73. What are the structures of the products in each step of the reaction sequence shown?

1. BH 3 2. H2O2, NaOH/H2O A. B. C. D. E.

A is I, B is II, and C is III A is II, B is III, and C is IV A is II, B is I, and C is III A is II, B is IV, and C is III A is IV, B is I, and C is III

Answer: C

PCC

(CH3)2NH H2SO4, NaBH3CN

+ enantiomer O

+ enantiomer OH

III

N(CH3)2

+ enantiomer OH

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Hard

74. What are the structures of the products in each step of the reaction sequence shown?

H 3O+

PCC

H2SO4, NaBH3CN

O I

NH2 II

N III

OH IV

A. B. C. D. E.

A is I, B is II, and C is III A is II, B is III, and C is IV A is II, B is I, and C is III A is II, B is IV, and C is III A is IV, B is I, and C is III

Answer: E Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Hard 75.

What reagents are needed to carry out the conversion shown?

CN N

O A. B. C. D. E.

1. HOCH2CH2OH/TsOH; 2. H3O+ 1. HOCH2CH2OH/TsOH; 2. H2/Pt; 3. H3O+ 1. KOH; 2. LiAlH4 1. NH3; 2. NaBH3CN 1. NaNO2; 2. HCl

Answer: B Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents Difficulty: Hard 76.

What is the predicted product of the reaction sequence shown?

O Cl (CH3)2NH AlCl3

H2SO4, NaBH3CN

I A. B. C. D. E.

O II

III

N IV

I II III IV none of these

Answer: D Learning Objective: 22.8 Describe the reaction of amines with acyl halides, and explain why acylation of the amino group is a useful technique Difficulty: Hard 77.

What reagents are needed necessary to carry out the conversion shown?

Cl Cl

HN O O A,

1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. Fe/HCl; 4. CH3CH 2CCl

O B.

1.KOH; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. CH3CH 2CCl

O C.

1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. CH3CH 2CCl

O D.

1. Cl2/FeCl3; 2. NH3/H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. CH3CH 2CCl

O E.

1. HCl/FeCl3; 2. H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. CH3CH 2CCl

Answer: C Learning Objective: 22.8 Describe the reaction of amines with acyl halides, and explain why acylation of the amino group is a useful technique Difficulty: Hard 78.

What reagents are needed to carry out the conversion shown?

NO 2

NH 2

Br O A.

1. HBF4l; 2. CH3CCl ; 3. Br2/FeBr3; 4. Na2CO3 O

B. C. D. E.

1. Fe/HCl; 2. CH3CCl ; 3. Br2/FeBr3/ 4. H3O+; 5. dil. Na2CO3 1. HBr; 2. Br2/FeBr3; 3. H3O+; 4. dil. Na2CO3 1. Br2, hv; 2. H3O+; 3. dil. Na2CO3 1. NaNO2/HCl; 2. Br2/FeBr3; 3. H3O+

Answer: B Learning Objective: 22.8 Describe the reaction of amines with acyl halides, and explain why acylation of the amino group is a useful technique

Difficulty: Hard 79.

What is the predicted major product of the reaction shown?

NH 2

1. excess CH 3I 2. Ag2O, H2O heat

N(CH 3)2

A. B. C. D. E.

III

I II III IV V

Answer: B Learning Objective: 22.9 Predict the products of a Hofmann elimination Difficulty: Medium 80.

What is the predicted major product of the reaction shown?

NH 2

1. excess CH3I 2. Ag2O, H 2O heat

I A. B. C. D. E.

III

I II III IV I and III

Answer: A Learning Objective: 22.9 Predict the products of a Hofmann elimination Difficulty: Hard 81.

What is the predicted major product of the reaction shown?

1. excess CH3I 2. Ag2O, H 2O heat

N I A. B. C. D. E.

III

I II III IV V

Answer: E Learning Objective: 22.9 Predict the products of a Hofmann elimination Difficulty: Hard 82.

What is the predicted major product of the reaction shown?

1. excess CH 3I N

2. Ag2O, H 2O heat

N I

CH3

III

N IV

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 22.9 Predict the products of a Hofmann elimination Difficulty: Medium 83.

What is the predicted major product of the reaction shown?

NH 2

1. excess CH 3I 2. Ag2O, H 2O heat

A. B. C. D. E.

III

NH3

I II III IV V

Answer: C Learning Objective: 22.9 Predict the products of a Hofmann elimination Difficulty: Medium 84.

What reagents are needed to carry out the conversion shown?

NH 2 A

A. B. C. D. E.

1. KOH; 2. H2/Pt; 3. excess CH3I; 4. Ag2O, H2O; 5. mCPBA; 1. NH3; 2. H2/Pt; 3. excess CH3I; 4. Ag2O, H2O; 5. mCPBA 1. NH3; 2. H2/Pt; 3. Ag2O, H2O; 4. mCPBA; 5; NH3 1. NaOH; 2. excess CH3I; 3. mCPBA; 4; NH3 1. NH3; 2. H2/Pt; 3. excess CH3I; 4. Ag2O, H2O; 5. mCPBA; 6; NH3

Answer: E Learning Objective: 22.9 Predict the products of a Hofmann elimination

Difficulty: Hard 85.

What reagent(s) is(are) needed to carry out the conversion shown?

NO 2

NH 2

A. B. C. D. E.

1. NaNO2/HCl; <5°C; 2. CuCl CuCl 1. KOH; 2. CuCl; 3. H2O 1. H3PO2; 2. Cl2, hv 1. NaNO2/HCl; 2. Cl2

Answer: A Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Medium 86.

What is reagent A, which is needed to carry out the conversion shown?

Br NH 2

NaNO2/HCl < 5 0C

Br A. B. C. D. E.

H3PO2 HCN H2 O CH3OH, heat NaOCH3

Answer: D

OCH 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Medium 87.

What is reagent A, which is needed to carry out the conversion shown?

Br NH 2

Cl A. B. C. D. E.

NaNO2/HCl < 50C

A Cl

Br2/FeBr3 CuBr NaOH H3PO2 H3PO4

Answer: D Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Medium 88.

Which one of the following is the best synthesis for 3,5-dibromotoluene?

A. B.

toluene, Br2/FeBr3 excess 1. p-toluidine, Br2/ FeBr3; 2. NaNO2/HCl, < 5°C 3. H3PO2 1. Toluene, HNO3/H2SO4 2. NH3 3. NaNO2/HCl, < 5°C 4. CuBr m-dibromobenzene, CH3Cl/AlCl3 1. m-bromotoluene, HNO3, H2SO4 2. Fe/HCl 3. NaNO2/HCl, < 5°C 4. CuBr

D. E.

Answer: B Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

Difficulty: Medium 89.

What reagents are necessary to carry out the conversion shown?

OH Cl

F Answer: 1. CH3CH2Cl/AlCl3 2. HNO3/H2SO4 3. Cl2/FeCl3 4. Fe/HCl 5. NaNO2/HCl/ < 50C 6. HBF4 7. Na2Cr2O7/H2SO4/H2O Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 90.

What reagents are needed to carry out the conversion shown?

O A. B.

1. CH3CH 2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. CH3CH2OH/heat 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; H2SO4

O C. 1. CH3CH 2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat E. 1. H2SO4; 2. Cl2/hv3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat Answer: C Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 91.

Provide the reagents necessary to carry out the following conversion.

O A. B.

1. CH3CH 2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. CH3CH2OH/heat 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; H2SO4 O

C. 1. CH3CH 2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat E. 1. H2SO4; 2. Cl2/hv3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat Answer: D Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 92.

Provide the reagents necessary to carry out the following conversion.

NO 2 O A. 1. HNO3/H2SO4; 2. Fe/HCl; 3. CH3CH 2CCl / AlCl3 ; 4. HNO3/H2SO4; 5. H3O+; 6. NaNO2/HCl/< 5°C B. 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; H2SO4 O C. 1. CH3CH2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat E. 1. HNO3/H2SO4; 2. Fe/HCl; 3. NaNO2/HCl/< 5°C; 5. H2O/heat

; 4. HNO3/H2SO4; 5. H3O+; 6.

Answer: E Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 93.

What reagents are needed to carry out the conversion shown?

A. 1. HNO3/H2SO4; 2. Sn/HCl; 3. NaNO2/HCl/< 5°C; 4. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3; 6. H3O+/heat B. 1. HNO3/H2SO4; 2. NaNO2/HCl/< 5°C; 3. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3 O C. 1. CH3CH2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat ; 4. HNO3/H2SO4; 5. H3O+; 6.

E. 1. HNO3/H2SO4; 2. Fe/HCl; 3. NaNO2/HCl/< 5°C; 5. H2O/heat

Answer: A Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 94.

What reagents are needed to carry out the conversion shown?

A. 1. HNO3/H2SO4; 2. Sn/HCl; 3. NaNO2/HCl/< 5°C; 4. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3; 6. H3O+/heat

B. 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Na2Cr2O7/H2SO4/H2O; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 6. CuCN C. 1. Na2Cr2O7/H2SO4/H2O; 2. CH3CH2Cl/AlCl3; 3. HNO3/H2SO4; 5. Fe/HCl; 6. NaNO2/HCl/< 5°C; 6. CuCN D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat E. 1. HNO3/H2SO4; 2. Fe/HCl; 3. NaNO2/HCl/< 5°C; 5. H2O/heat

; 4. HNO3/H2SO4; 5. H3O+; 6.

Answer: B Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 95.

What reagents are needed to carry out the conversion shown?

NH 2

CH 3 Br

A. 1. HNO3/H2SO4; 2. Sn/HCl; 3. NaNO2/HCl/< 5°C; 4. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3; 6. H3O+/heat B. 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Na2Cr2O7/H2SO4/H2O; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 6. CuCN C. 1. HBr/heat; 2. NaNO2/HCl/< 5°C; 3. H2SO4; 4. KMnO4/NaOH/H2O; H3O+ D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat E. 1. Br2/FeBr3 excess; 2. NaNO2/HCl/< 5°C; 3. H3PO2; 4. KMnO4/NaOH/H2O; H3O+ Answer: E Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

Difficulty: Hard 96.

What is an appropriate stepwise synthesis to carry out the conversion shown?

NH 2

O HNO3/H2SO4

CH 3CH2CCl AlCl3 O

O A. 1. CH3CH2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CuCN; 6. Zn(Hg)/HCl; 7. LiAlH4; 8. H3O+ B. 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Na2Cr2O7/H2SO4/H2O; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 6. CuCN C. 1. HBr/heat; 2. NaNO2/HCl/< 5°C; 3. H2SO4; 4. KMnO4/NaOH/H2O; H3O+ D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat O E. 1. CH3CH2CCl / AlCl3 ; 2. Br2/AlBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CuCN; 6. Zn(Hg)/HCl; 7. LiAlH4; 8. H3O+ Answer: A Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 97.

What is an appropriate stepwise synthesis to carry out the conversion shown?

I Br

NH 2

NO2 HNO3/H2SO4

Sn/HCl

O A. 1. CH3CH2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CuCN; 6. Zn(Hg)/HCl; 7. LiAlH4; 8. H3O+ B. 1. HNO3/H2SO4; 2. Sn/HCl; 3. ; 4. fuming H2SO4; 5. Br2/FeBr3; 4. excess H3O+/heat; 5. NaNO2/HCl/< 5°C; 6. CuI C. 1. HBr/heat; 2. NaNO2/HCl/< 5°C; 3. H2SO4; 4. KMnO4/NaOH/H2O; H3O+ D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E. 1. HNO3/H2SO4; 2. ; 3. fuming H2SO4; 4. Br2/FeBr3; 5. excess + H3O /heat; 6. NaNO2/HCl/< 5°C; 7. H2SO4; 8. CuI Answer: B Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 98.

What reagents are needed to carry out the conversion shown?

NH2 Br

Br Br Br

NO2 O A. 1. CH3CH2CCl / AlCl3 ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CuCN; 6. Zn(Hg)/HCl; 7. LiAlH4; 8. H3O+ B. 1. HNO3/H2SO4; 2. Sn/HCl; 3. ; 4. fuming H2SO4; 5. Br2/FeBr3; 4. + excess H3O /heat; 5. NaNO2/HCl/< 5°C; 6. CuI C. 1. NaNO2/HCl/< 5°C; 2. CuBr; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. H3PO4 D. 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat E. 1. HNO3/H2SO4; 2. ; 3. fuming H2SO4; 4. Br2/FeBr3; 5. excess + H3O /heat; 6. NaNO2/HCl/< 5°C; 7. H2SO4; 8. CuI Answer: C Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 99.

What is the predicted major product of the reaction shown?

OCH2CH3 CH 3

NH2 2

NaNO2/HCl < 50 C

N OCH2CH3 CH3

N N

III

OCH2CH3

N N CH3

N N

OCH2CH3 CH3

N N H3C

A. B. C. D. E.

I II III IV V

OCH2CH3

Answer: D Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard

100. 2

What is the predicted major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C, followed by treatment with o-ethylphenol?

N OH

III

N N

B. C. D. E.

II III IV V

Answer: D Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Medium 101.

What is the predicted product of the reaction shown?

N(CH 3) 2

NH2

NaNO2/HCl < 50C N(CH3)2 N N I

N(CH3)2 O 2N

N(CH3)2 V

IV 2

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Medium 102.

What is the predicted major product of the reaction shown?

4-chloroaniline

NaNO2/HCl 4-ethylphenol <50C

N OH

III

Cl IV

Cl V

Cl A.

N OH

B. C. D. E.

II III IV V

Answer: A Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 103.

What is the predicted major product of the reaction shown?

CH 3 N(CH 3)2

N N

N(CH3)2

III

H3C

N N

H3C

N N(CH3)2

H3C

N N

A. B. C. D. E.

N(CH3)2

I II III IV V

Answer: E Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Medium 104.

What reagents are needed to carry out the conversion shown?

N Cl

OCH 3

OCH3

N Cl

OCH3

1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5.

1. HB4; 2. H2O; 3. H2SO4; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 5.

1. HNO3/H2SO4; 2. Fe/HCl; 3. NaNO2/HCl/< 5°C; 4.

1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E. 1. HNO3/H2SO4; 2. ; 3. fuming H2SO4; 4. Br2/FeBr3; 5. excess H3O+/heat; 6. NaNO2/HCl/< 5°C; 7. H2SO4; 8. CuI Answer: A Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling Difficulty: Hard 105.

What is the predicted major product of the reaction shown?

Br 2 0 0C

N H Br

N I Br A. B. C. D. E.

N H II

N H III

N H IV

N Br

I II III IV V

Answer: D Learning Objective: 23.12 Define heterocycle, and discuss the structure and reactions of pyrrole and pyridine and the structures of imidazole and pyrimidine Difficulty: Medium 106.

What is the predicted major product of the reaction shown?

Br2 N H

0 0C

N Br I A. B. C. D. E.

N H

III

N H IV

Br V

I II III IV V

Answer: D Learning Objective: 23.12 Define heterocycle, and discuss the structure and reactions of pyrrole and pyridine and the structures of imidazole and pyrimidine Difficulty: Medium 107.

What is the predicted major product when pyridine is treated with a mixture of nitric acid and sulfuric acid?

A. B. C. D. E.

3-nitropyridine 2-nitropyridine 4-nitropyridine 2,3-dinitropyridine 4-aminopyridine

Answer: A Learning Objective: 23.12 Define heterocycle, and discuss the structure and reactions of pyrrole and pyridine and the structures of imidazole and pyrimidine Difficulty: Medium 108.

A compound with molecular formula C8H10BrN exhibits a singlet at d 1.2 (2H), a triplet at d 2.8 (2H), a triplet at d 3.0 (2H), a doublet at d 7.1 (2H) and a doublet at

d 7.4 (2H) in its 1H NMR spectrum. Its IR spectrum shows two medium absorption bands near 3400 cm-1. What is the structure for this compound?

NH2

NH 2

Br NH2

II NH

A. B. C. D. E.

III Br

I II III IV V

Answer: A Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13 C NMR spectroscopy Difficulty: Medium 109.

A compound with molecular formula C8H19N exhibits a triplet at d 0.9 (6H), a singlet at d 1.1 (1H), a sextet at d 1.3 (4H), a quintet at d 1.4 (4H) and a triplet at d 2.6 (4H) in its 1H NMR spectrum. Its IR spectrum shows a medium absorption band near 3400 cm-1. Its 13C NMR spectrum showed peaks at d13.7, d 20.5, d 30.4 and d 49.2. What is the structure for this compound?

N H

H N

III

N H NH2

A. B. C. D. E.

H N

I II III IV V

Answer: B Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13 C NMR spectroscopy Difficulty: Medium 110.

A compound with molecular formula C4H11N exhibits a triplet at d 0.9 (3H), a doublet at d 1.1 (3H), a quintet at d 1.4 (2H), a singlet at d 1.7 (2H) and a sextet at d 2.8 (2H) in its 1H NMR spectrum. Its IR spectrum shows two medium absorption bands near 3400 cm-1. What is the structure for this compound?

H2N

NH2 NH2 I

III

H N

N H V

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13 C NMR spectroscopy Difficulty: Hard 111.

A compound with molecular formula C7H17N exhibits a triplet at d 1.0 (3H), a doublet at d 1.1 (I=6), a multiplet at d 2.0 (1H), a singlet at d 2.3 (3H), a doublet at d 2.3 (2H), and a quartet at d 2.4 (2H) in its 1H NMR spectrum. Its 13C NMR spectrum showed peaks at d 13.4, d 20, d 27.9, d 39.3, d 49.5 and d 65.2. What is the structure for this compound?

NH2

N IV

III

N V

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13 C NMR spectroscopy Difficulty: Medium 112.

A compound with molecular formula C6H15N displays the following IR, 1H NMR and 13C NMR spectra. What is a likely structure for this compound?

SDBS

H N I

H N

N H

H N

III

NH2 V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13 C NMR spectroscopy Difficulty: Medium

113.

A compound with molecular formula C8H11N displays the IR, 1H NMR and 13C NMR spectra shown. What is a possible structure for this compound?

140

SDBS

120

100

80 PPM

NH2

N IV

III

N V

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13 C NMR spectroscopy Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 23 1.

Which of the compounds shown has the most nucleophilic carbon atom?

A. B. C. D.

CH3Cl CH3Li (CH3)2Zn (CH3)2Cu

Answer: B Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Easy 2.

Which of the compounds shown has the most nucleophilic carbon atom?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Easy 3.

Which of the compounds shown has the least nucleophilic carbon atom?

A. B. C. D.

CH3CH2MgBr CH3CH2MgI (CH3CH2)2Zn (CH3CH2)2Cu

Answer: D Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Medium

Which of the compounds shown has the most ionic character in the C-M bond?

A. B. C. D.

HC≡CMgBr HC≡CK HC≡CNa HC≡CLi

Answer: B Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Easy 5.

Which of the choices has the most polar bond?

A. B. C. D.

C–B C–Pd C–Zn C–Pt

Answer: C Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Medium 6.

What functional group most typically results as a stable final product when a Grignard reagent reacts with an acid halide, after aqueous workup?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a ketone a nitrile

Answer: C Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Medium 7.

What functional group typically results when an organocopper compound (lithium organocuprate) reacts with an acid chloride?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a ketone a nitrile

Answer: D Learning Objective: 23.1 Describe the structural features of organometallic compounds, and how this results in reactivity Difficulty Level: Medium 8.

Which of the given statements is false regarding the preparation of organolithium compounds?

A. B. C. D. E.

Organolithium compounds can be made from alkyl halides (R-X). Organolithium compounds can be made from aryl halides (Ar-X). Vinyl halides cannot be used to form vinyl lithium reagents. Lithium halides are byproducts of the reaction of lithium metal with alkyl halides. It is necessary to use two equivalents of lithium metal.

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 9.

Why is ethanol not a viable solvent in the synthesis of Grignard reagents?

A. B. C. D. E.

Ethanol will form hydrogen bonds, inhibiting the reaction. The –OH proton is too acidic. The –OH group is too unreactive. Grignard reagents do not dissolve in ethanol. The –OH proton is too basic.

Answer: B Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 10. A. B. C. D.

Explain why the solvent for a Grignard reaction must be free of water. Water will form hydrogen bonds, inhibiting the reaction. Water acts as a strong base in this context. Water consumes the Grignard reagent. Grignard reagents do not dissolve in water.

The reactant is more likely to react with water than with the Grignard reagent.

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 11.

Which of choices lists only good solvents that should be used in the preparation of organometallic reagents such as organolithiums and Grignard reagents?

A. B. C. D. E.

ethanol, water, and diethyl ether diethyl ether, tetrahydrofuran, and dioxane cyclohexanol, tetrahydrofuran, and water tetrahydrofuran, dioxane, and water dioxane, benzene, and water

Answer: B Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 12.

Diethyl ether is a good solvent to be used with Grignard reagents. Which of the given explanations for this fact is false?

It has a very high boiling point, so it can be heated to drive the Grignard formation to completion. B. It can serve as a Lewis base and stabilize the Grignard reagent, allowing time for the reaction to occur. C. It is polar enough to stabilize the Grignard reagent. D. It is aprotic and thus is not acidic enough to react with the Grignard reagent. Answer: A Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 13.

Which alkyl halide is most reactive with magnesium metal?

A. B. C. D.

CH3CH2CH2Br CH3CH2CH2F CH3CH2CH2I CH3CH2CH2Cl

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 14.

Which alkyl halide is least reactive with magnesium metal?

A. B. C. D.

CH3CH2CH2Br CH3CH2CH2F CH3CH2CH2I CH3CH2CH2Cl

Answer: B Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 15.

Which of the given functional groups does not afford an alcohol when treated with a Grignard reagent followed by a protic work-up.

A. B. C. D. E.

a ketone an aldehyde an ester an epoxide a nitrile

Answer: E Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 16.

What product is formed when formaldehyde reacts with one equivalent of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: A

Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 17.

What product is formed when butanal reacts with one equivalent of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: B Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 18.

What product is formed when 2-pentanone reacts with one equivalent of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 19.

What product is formed when ethylene oxide reacts with one equivalent of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: A

Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 20.

What product is formed when carbon dioxide reacts with one equivalent of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: D Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 21.

What product is formed when an ester reacts with two equivalents of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 22.

What product is formed when a nitrile reacts with one equivalent of a Grignard reagent?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: E

Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 23.

What product is formed when a nitrile reacts with two equivalent of a Grignard reagents?

A. B. C. D. E.

a primary alcohol a secondary alcohol a tertiary alcohol a carboxylic acid a ketone

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Easy 24.

What is the product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 25.

What is the final product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium

26.

What is the final product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium

27.

What is the final product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 28.

What is the final product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 29.

What is the product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 30.

What is the final of the sequence shown?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Hard 31.

What is the product of the sequence shown?

A. B. C. D. E.

I II III IV none of the them

Answer: E, A Grignard reagent cannot be prepared if OH is present in the compound. Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Hard 32.

What is the name of the product of the reaction sequence shown?

A. B. C. D. E.

3-methylbromobenzene 4-methylbenzoic acid p-bromobenzene p-methyl toluene 2-methylbenzoic acid

Answer: B Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Hard

33.

What is the product of the sequence shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Hard 34.

Which reactant would yield the product shown as the major isomeric product?

A. B. C. D. E.

I II III IV none of the above

Answer: A Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 35.

What is the starting material indicated by question marks in the reaction below?

A. B. C. D. E.

I II III IV The product cannot be formed directly from one of the reactants above.

Answer: D Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 36.

Starting from bromobenzene and any other reagents with two carbons or fewer, propose a synthesis of the compound shown.

A. B. C. D. E.

1. Mg, Et2O; 2. ethylene oxide; 3. H3O+; 4. PCC 1. Mg, Et2O; 2. CH3OH; 3. H3O+; 4. PCC 1. Mg, Et2O; 2. ethylene oxide; 3. PCC 1. Mg, Et2O; 2. ethylene oxide; 3. H2SO4 1. Mg, H2O; 2. ethylene oxide; 3. H3O+

Answer: A Learning Objective: 23.2 Discuss the preparation, properties, and reactivity of organolithium and organomagnesium compounds Difficulty Level: Medium 37.

Which of the given statements is(are) true regarding the preparation of Gilman reagents?

A. B. C. D. E.

Gilman reagents can be made from alkyl halides (R-X). Gilman reagents can be made from aryl halides (Ar-X). Gilman reagents can be made from organolithium reagents. Lithium halides are byproducts of the reaction to make Gilman reagents. all of the above

Answer: E Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react

Difficulty Level: Easy 38.

Which of the given reagents cannot be used in the synthesis of a Gilman reagent?

A. B. C. D. E. F.

lithium metal lithium halide alkyl halide aryl halide vinyl halide CuBr

Answer: B Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Easy 39.

Which of the choices lists only electrophiles that are commonly used with Gilman reagents to form C-C bonds?

A. B. C. D. E.

acid chlorides, α,β-unsaturated ketones, and alkyl halides α,β-unsaturated ketones, esters, and amides esters, amides, and alkyl halides alkyl halides, acid chlorides, and amides amides, acid chlorides, and esters

Answer: A Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Easy 40.

Which of the given electrophiles are commonly used with Gilman reagents to form C-C bonds?

A. B. C. D. E.

alkyl halides aryl halides vinyl halides acyl halides all the above

Answer: E Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react

Difficulty Level: Easy 41.

Which of the given statements is false regarding the reactivity of Gilman reagents?

A. B. C. D.

They react with acyl halides to give ketones. They react with α,β-unsaturated ketones to give alcohols. They react with alkyl halides or aryl halides in a coupling reaction. They are unreactive with tertiary halides.

Answer: B Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Easy 42.

The Corey-Posner/Whitesides-House reaction couples a lithium dialkyl cuprate with all but which of the given choices?

A. B. C. D. E.

primary alkyl halides tertiary alkyl halides aryl halides methyl halides vinyl halides

Answer: B Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Easy 43.

Which of the choices would react fastest in the Corey-Posner/Whitesides-House reaction?

A. B. C. D.

cyclohexyl chloride cyclohexyl iodide tert-butyl chloride tert-butyl iodide

Answer: B Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Easy

44.

What is the product of the reaction shown?

A. B. C. D. E.

(E)-1-phenyl-1-pentene (Z)-1-phenyl-1-pentene (E)-1-phenyl-2-pentene (Z)-1-phenyl-2-pentene 2-phenyl-1-pentene

Answer: A Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium 45.

What is the best reagent for the reaction below?

A. B. C. D.

I II III IV

Answer: B

Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium 46.

Which of the given Gilman reagents could be used with a vinyl halide to afford the (E,E)-diene shown below? Select all that apply.

A. B. C. D. E.

I II III IV II and III

Answer: E Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react

Difficulty Level: Medium 47.

Gillman reagents are intolerant to the presence of what functional group?

A. B. C. D.

ketone ester amide All of the functional groups above are compatible with Gilman reagents.

Answer: D Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Easy 48.

Starting from bromobenzene and ________ as the only source of carbon atoms, 1-phenylcyclohexene can be synthesized using a Corey-Posner/WhitesidesHouse coupling reaction.

A. B. C. D.

1-iodocyclohexene 3-iodocyclohexene iodocyclohexane (iodomethyl)cyclohexane

Answer: A Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium 49.

Starting from vinyl chloride and ________ as the only source of carbon atoms, 1heptene can be synthesized using a Corey-Posner/Whitesides-House coupling reaction.

A. B. C. D.

1-bromopropane 2-bromopentane 1-bromohexane 1-bromopentane

Answer: D Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium

50.

A total synthesis of ingenol utilized the Corey-Posner/Whitesides-House coupling reaction in a key C-C bond forming step (J. Am. Chem. Soc. 2002, 124, 9726). What reagent would be most appropriate to perform this transformation?

A. B. C. D. E.

CH3MgBr CH3CH2OH HOMgBr (CH3)2CuLi CH3CuLi

Answer: D Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium 51.

What is the product of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium 52.

The synthesis shown is not likely to work. Which of the given explanations is correct?

A. B.

Lithium cannot react with aryl halides to form organolithium compounds. CH3CH2Br does not do cross coupling in Corey-Posner/Whitesides-House reactions. The cuprate formed would react with the ketone. The organolithium formed would react with the ketone.

C. D.

Answer: D

Learning Objective: 23.3 Describe the preparation of Gilman reagents and how they react Difficulty Level: Medium 53.

Which of the choices is a Simmons-Smith cyclopropanation?

A. B. C. D.

R-X + Zn → R2C=CR2 + CH2I2 + Zn-Cu → CHCl3 + NaOH → R2C=CHI + (CH3)2CuLi →

Answer: B Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Easy 54.

The Simmons-Smith reaction involves the formation of _____?

A. B. C. D.

alkenes alkynes cyclopropanes cuprates

Answer: C Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Easy 55.

What are the conditions for the reaction shown?

A. B. C. D. E.

CH2I2 1. MgEt2O; 2. Bu3/SnCl CH2I2 / Zn-Cu Mg/EtO 9-BBN

Answer: C Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent

Difficulty Level: Medium 56.

What is the predicted product of reaction shown?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 57.

What are the product(s) of the reaction shown? Select all that apply.

A. B. C. D.

I II III IV

Answer: B and C Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 58.

What are the product(s) of the reaction shown? Select all that apply.

A. B. C. D. E.

I and II II and III I and IV II and IV I and III

Answer: C Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 59.

What are the product(s) of the reaction shown?

A. B. C. D. E.

I and II II and III III and IV I and IV II and IV

Answer: E Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 60.

Which of the given statements is false?

A. B. C. D. E.

Carbenes are generally long lived. Carbenes have a carbon with non-bonding electrons. Carbenes have a carbon missing an octet. Carbenes can be formed by α-elimination. Carbenes are electrophilic.

Answer: A Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Easy

61.

Treatment of chloroform (CHCl3) with strong bases results in _______, which is mechanistically described as a_______.

A. B. C. D.

α-elimination; loss of leaving group followed by deprotonation. α-elimination; deprotonation followed by a loss of leaving group. β-elimination; deprotonation followed by loss of leaving group. β-elimination; concerted deprotonation and loss of leaving group.

Answer: B Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 62.

A total synthesis of ingenol utilized a dibromocyclopropanation via a carbene intermediate (J. Am. Chem. Soc. 2002, 124, 9726). What key type of reagent is missing from the reaction conditions?

A. B. C. D.

Bronsted Acid Bronsted Base radical initiator Lewis Acid catalyst

Answer: B Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 63.

The reaction of a carbene with an alkene to make a cyclopropane commonly goes through which type of mechanism?

A. B. C. D.

proton transfer loss of leaving group cycloaddition α-elimination

Answer: C Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Easy 64.

What are the predicted products of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 65.

What are the predicted products of the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Medium 66.

A report on the synthesis of Aromatic Erythrina Alkaloids uses the given transformation (Org. Lett. 2006, 8, 2143). What are reaction conditions?

A. A. C. D. E.

CHCl3, t-BuOK CH2I2 CH2I2 / Zn-Cu Mg/EtO 9-BBN

Answer: A Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent Difficulty Level: Hard 67.

Elaboration of an advanced intermediate toward the synthesis of the pulmoside aglycon is shown below. What are the structures of intermediates A-C? (J. Am. Chem. Soc. 2013, 135, 2501.)

A. B. C. D. E.

I is A, II is B, and III is C I is A, II is C, and III is B II is A, I is B, and III ic C III is A, II is B, and I is C I is A, IV is B, and III is C

Answer: B Learning Objective: 23.4 Discuss the Simmons-Smith cyclopropanation reaction and the carbenoid reagent

Difficulty Level: Hard 68.

The Stille reaction involves coupling of which pair of reagents?

A. B. C. D.

organohalide and organotin organohalide and organoboron organotin and organozinc organoboron and organozinc

Answer: A Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 69.

Which catalysts are common in the Stille coupling reaction?

A. B. C. D.

Pd(PPh3)4 Pd (OAc)2 PdCl2(PPh3)2 All of the above

Answer: D Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 70.

The Stille reaction couples organotin reagents with all but one of the choices listed. Which of the choices is not a common coupling partner?

A. B. C. D. E.

–I –Br –Cl –F –OTf

Answer: D Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 71.

Which of the choices is not a mechanistic step in the generally accepted mechanism of the Stille coupling?

A. B. C. D.

transmetallation reductive elimination syn-elimination oxidative addition

Answer: C Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 72.

Which of the given R groups (R-SnBu3) would undergo the slowest transmetallation in a Stille coupling reaction?

A. B. C. D.

alkyl aryl vinyl benzyl

Answer: A Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 73.

Which of the given R groups (R-SnBu3) would undergo the fastest transmetallation in a Stille coupling reaction?

A. B. C. D.

alkyl aryl vinyl benzyl

Answer: C Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 74.

What is the predicted product of the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Hard 75.

In a total synthesis of the bisnortriterpenoid rubriflordilactone A, a key step involved the given transformation. Draw the product. (J. Am. Chem. Soc. 2014, 136, 16477).

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Hard 76.

What is the predicted product of the reaction shown?

A. B. C. D. E.

(2E,4Z)-4-methylhepta-2,4-diene (2Z,4E)-4-methylhepta-2,4-diene (3E,5Z)-4-methylhepta-3,5-diene (3Z,5Z)-4-methylhepta-3,5-diene (3E,5E)-4-methylhepta-3,5-diene

Answer: A Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Hard 77.

Biselyngbyolide A is a cytotoxic natural product that shows promise for the treatment of bone lytic diseases. Shown below is a recent synthesis of this molecule (Org. Lett. 2014, 16, 2858). Give the structure of intermediate 1 and Biselyngbyolide A. Hint: PPTS is a strong organic acid.

A. B. C. D. E.

Intermediate 1 is I and Biselyngbyolide A is II. Intermediate 1 is II and Biselyngbyolide A is III. Intermediate 1 is I and Biselyngbyolide A is II. Intermediate 1 is II and Biselyngbyolide A is I. Intermediate 1 is III and Biselyngbyolide A is II.

Answer: B Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Hard

78.

What is the product of the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 23.5 Describe the Stille coupling, the three stages involved in the mechanism, and chemistry of palladium and organostannanes Difficulty Level: Easy 79.

Which of the choices is a boronic ester?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Easy 80.

Which of the choices is a boronic acid?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Medium 81.

Which of the indicated bonds could be formed by a Suzuki coupling but not a Stille coupling?

a-b

B. C. D.

c-d d-e f-g

Answer: A Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Hard 82.

What is the product of the reaction shown?

A. B. C. D.

I II III IV

Answer: B

Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Medium 83.

Which of the given choices are advantages of the Suzuki coupling over the Stille coupling? Select all that apply.

A. B. C. D.

Organoboron compounds are less expensive than organotin compounds. Organoboron compounds are less toxic than organotin compounds. Formation of alkyl-aryl bonds is possible. The reaction requires a base.

Answer: A, B, C Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Medium 84.

What is the product of the reaction sequence shown?

A. B. C. D.

I II III IV

Answer: D Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Hard 85.

Macrocyle A was formed by a two- step process involving a hydroboration of an alkene in B followed by an intramolecular Suzuki coupling of a vinyl iodide in B to form the indicated bond below. What is the structure of B? (Org. Lett. 2002, 4, 2205).

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Hard 86.

Which two reagents can be coupled in a Suzuki reaction to form the product shown.

Answer: I and IV Learning Objective: 23.6 Describe the Suzuki coupling, its mechanism, and chemistry of organoboron compounds Difficulty Level: Hard 87.

Which of the organometallic species shown is not associated with the Negishi coupling reaction?

A. B. C. D.

organozinc organoaluminium organoboron organozirconium

Answer: C Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Easy 88.

Which of the organozinc compounds shown can be used in a Negishi coupling reaction?

A. B. C. D. E.

a vinyl organozinc an alkyl organozinc an aryl organozinc a benzyl organozinc all of the above

Answer: E Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Easy 89.

The reaction shown is an example of the __________.

A. B. C. D.

Stille coupling Suzuki coupling Negishi coupling Heck reaction

Answer: C Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Easy

90.

Which of the given methods is not a common/useful way to make an organozinc reagent?

A. B. C. D.

alkyl halide + Zn in ether alkyl halide + Mg followed by ZnBr2 organolithium +ZnBr2 organoborane + Zn

Answer: D Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Easy 91.

A synthesis of the taxadienone system involves the reaction shown (Org. Process. Res. Dev. 2015, 19, 284). What is the product?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Medium 92.

What is the major product of the following reaction?

B. C. D.

II III IV

Answer: B Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Medium 93.

The final steps of Sammakia’s total synthesis of caerulomycin C involved the reaction below (Org. Lett. 2002, 4, 2385). What is the structure of the product?

A. B. C. D. E.

I II III IV V

Answer: E Learning Objective: 23.7 Describe the Negishi coupling, its mechanism, and chemistry of organozinc compounds and their precursors Difficulty Level: Medium

94.

Which statement is true of the Heck reaction?

A. B. C. D. E.

Pd should not be used. It requires the presence of ethanol. It requires the presence of an acid. It is not a coupling reaction. It requires an alkane reactant.

Answer: C Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Easy 95.

Which of the alkenes shown is the most reactive in the Heck reaction?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 96.

Which of the alkenes shown is the most reactive in the Heck reaction?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 97.

Which of the dienes shown could not be formed as the major organic product in a Heck reaction with methyl vinyl ketone as the reactant alkene?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 98. Which of the choices is not a step in the Heck reaction catalytic cycle?

A. B. C. D. E.

transmetallation reductive elimination syn-elimination oxidative addition syn-addition

Answer: A Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Easy 99.

What is the major product for the Heck reaction shown?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 100.

What is the major product for the reaction shown?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 101.

Which alkene would be used in the Heck reaction below?

Answer: A Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 102.

Which of the choices shown are possible Heck reaction products?

A. B. C. D.

I II III all of the above

Answer: D

Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Hard 103.

Which statement is true of the reaction shown?

A. Compound I is the major product because it involves an intermolecular reaction. B. Compound II is the major product and is formed the most easily. C. Compound III is the major product. D. Compounds I and II are equally likely to be formed, but compound III is not formed. E. Compounds II and III are equally likely to be formed, but compound I is not formed. Answer: C Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Hard 104.

Heck reactions with allylic alcohols have a tendency to form carbonyl products. Considering the mechanism for the Heck reaction, how would the ketone product shown form?

A. Syn elimination would yield an enol that then tautomerizes to a ketone. B. Syn elimination would yield a ketone directly. C. Tautomerization would occur first. D. Anti elimination would yield a ketone directly. E. Anti elimination would yield a ketone after several steps.

Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 105.

What coupling partners can be used to prepare the given compound in a Heck reaction?

A. B. C. D. E.

Cyclohexene and p-bromobenzaldehyde Toluene and 2-bromocyclohexene Toluene and bromocyclohexane Cyclohexene and m-bromobenzaldehyde Cyclohexene and o-bromobenzaldehyde

Answer: D Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 106.

What coupling partners can be used to prepare the given compound in a Heck reaction?

A. B. C. D.

ethyl vinyl ketone and p-methylstyrene ethyl vinyl ketone and 4-iodotoluene p-methylstyrene and propionoyl chloride (E)-1-(2-bromovinyl)-4-methylbenzene and propionoyl chloride

Answer: B Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 107.

What coupling partners can be used to prepare the given compound in a Heck reaction?

A. B. C. D.

p-nitrostyrene and (E)-(2-bromovinyl)benzene p-nitrostyrene and (Z)-(2-bromovinyl)benzene (E)-1-(2-bromovinyl)-4-nitrobenzene and styrene (Z)-1-(2-bromovinyl)-4-nitrobenzene and styrene

Answer: B Learning Objective: 23.8 Describe the Heck reaction and its mechanism Difficulty Level: Medium 108.

Which of the choices can be used to make a C-C double bond?

A. B. C. D.

Simmons-Smith reaction Suzuki coupling Negishi coupling alkene metathesis

Answer: D

Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Easy 109.

Which of the metathesis reactions shown would not form ethylene gas?

A. B. C. D.

I II III IV

Answer: C Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Medium 110.

Each intermediate in alkene metathesis is formed by _____ cycloaddition

A. B. C. D. E.

[1 + 1] [1 + 2] [2 + 2] [2 + 3] [3 + 3]

Answer: C Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Easy 111.

Which of the choices is false regarding ring-opening metathesis?

A. B. C. D.

Cyclic alkenes react to form dienes. The Grubbs catalyst is commonly used. Ethylene is typically formed in the reaction. Ring opening metathesis can be performed in the presence of a variety of functional groups.

Answer: C Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Easy 112.

What is major the product for the reaction shown?

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Hard 113.

Which of the choices are products of the given reaction?

A. B. C. D. E.

I and II only I and III only II and III only I, II, and III only II, III, and IV only

Answer: I, II, and III Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Medium 114. In the given synthesis of a potent anti-cancer natural product, lasiodiplodin, which of the organometallic reactions shown are utilized? (J.Org. Chem. 2000, 65, 7990).

A. B. C. D. E.

Suzuki Coupling only Stille Coupling and ring-closing metathesis Negishi Coupling and ring-closing metathesis Heck reaction only ring-opening metathesis only

Answer: C and F Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Medium 115.

What is the product of treating styrene with the Grubbs Catalyst?

A. B. C. D.

E-stilbene only Z-stilbene only A mixture of E and Z stilbene No reaction because the alkene is terminal

Answer: C

Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Easy 116.

What diene is the reactant in the ring-closing metathesis reaction shown?

A. B. C. D. E.

I II III I or II II or III

Answer: C Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Medium 117.

What is the predicted major product of the reaction shown?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Hard 118.

What is the product of the given ring-opening/ring-closing metathesis reaction? (J. Am. Chem. Soc. 1996, 118, 6634.)

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Hard 119.

What is the product of the given ring-closing metathesis reaction?

A. B. C. D.

I II III IV

Answer: A Learning Objective: 23.9 Describe alkene metathesis, its mechanism, and applications Difficulty Level: Hard

Klein, Organic Chemistry 4e Chapter 24 1.

Plants convert carbon dioxide and water into glucose in the presence of sunlight via ________.

A. B. C. D. E.

hydrolysis retrosynthesis the Killiani synthesis photosynthesis none of these

Answer: D Learning Objective: 24.1 Describe the structural features of carbohydrates Difficulty: Easy 2.

Carbohydrates are _______.

A. B. C. D. E.

polyhydroxy esters polyhydroxy aldehydes polyhydroxy ketones polyhydroxy alkanes B and C

Answer: D Learning Objective: 24.1 Describe the structural features of carbohydrates Difficulty: Easy 3.

Simple sugars are called_______, a term that derives from the Latin word for sugar, saccharum.

A. B. C. D. E.

monosaccharides disaccharides polysaccharides saccharides all of these

Answer: A Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 4.

Polysaccharides are made by joining ________together.

A. B. C. D. E.

disaccharides trisaccharides polysaccharides monosaccharides all of these

Answer: D Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 5.

A monosaccharide with six carbon atoms and an aldehyde functional group is called a(n) _____.

A. B. C. D. E.

hexose ketohexose aldohexose ketoheptose ketose

Answer: C Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 6.

A monosaccharide with five carbon atoms and a ketone functional group is called a(n) _____.

A. B. C. D. E.

aldose ketohexose aldopentose ketopentose pentose

Answer: D Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 7.

Which of the choices is a ketohexose?

CH2OH

O O

CH 2OH

O H

OH HO

A. B. C. D. E.

CH2OH

CH 2OH

D-lyxose

D-fructose

D-ribose

D-glucose

D-xylulose

D-lyxose D-fructose D-ribose D-glucose D-xylulose

Answer: B Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 8.

Which of the choices is an aldohexose?

CH2OH

O O

CH 2OH

O H

OH HO

A. B. C. D. E.

CH2OH

CH 2OH

D-lyxose

D-fructose

D-ribose

D-glucose

D-xylulose

D-lyxose D-fructose D-ribose D-glucose D-xylulose

Answer: D Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 9.

Which of the choices is a ketopentose?

CH2OH

O O

CH 2OH

O H

OH HO

A. B. C. D. E.

CH2OH

CH 2OH

D-lyxose

D-fructose

D-ribose

D-glucose

D-xylulose

D-lyxose D-fructose D-ribose D-glucose D-xylulose

Answer: E Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 10.

Which of the choices is an aldopentose?

CH 2OH

O O

H HO

OH H

A. B. C. D. E.

CH2OH

OH HO

CH2OH

CH 2OH

CH2OH

D-galactose

D-fructose

D-ribose

D-glucose

D-xylulose

D-galactose D-fructose D-ribose D-glucose D-xylulose

Answer: C Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 11.

Which of the choices best describes L-galactose?

A. B. C. D. E.

aldopentose aldohexose ketopentose ketohexose aldotetrose

Answer: B Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Medium 12.

Which of the choices best describes the relationship between D-glucose and Dfructose?

A. B. C. D.

enantiomers epimers anomers constitutional isomers

diastereomers

Answer: D Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 13.

Which of the choices is an L-aldohexose?

CH 2OH

A. B. C. D. E.

OH HO

CH2OH

CH 2OH

CH2OH

CH 2OH

III

I II III IV V

Answer: D Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 14.

CH 2OH

Which of the choices is a D-aldopentose?

CH2OH

OH HO

O O

CH2OH

OH HO

CH2OH II

A. B. C. D. E.

CH2OH I

CH2OH

CH 2OH IV

III

OH V

I II III IV I and V

Answer: A Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 15.

Which of the choices is a L-ketopentose?

CH 2OH

OH HO

CH2OH

CH 2OH

CH2OH

III

I II III IV III and IV

Answer: B

CH2OH

A. B. C. D. E.

CH 2OH

CH2OH IV

CH 2OH V

Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 16.

Identify the compound that is found in nature.

A. B. C. D. E.

D-(+)-glyceraldehyde L-(+)-glyceraldehyde D-(-)-glyceraldehyde L-(-)-glyceraldehyde none of these

Answer: A Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 17.

Degradation of naturally occurring glucose produces _________ that is ________.

A. B. C. D. E.

D-glyceraldehyde, dextrorotatory D-glyceraldehyde, levorotatory L-glyceraldehyde, dextrorotatory L-glyceraldehyde, levorotatory none of these

Answer: A Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 18.

Degradation of synthetic glucose produces _________that is ________.

A. B. C. D.

glyceraldehyde, dextrorotatory glyceraldehyde, levorotatory glyceraldehyde, both dextrorotatory and levorotatory none of these

Answer: C Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 19.

Which of the choices give the characteristics of a D-sugar?

R configuration and dextrorotatory

B. C. D. E.

R configuration and levorotatory S configuration and dextrorotatory S configuration and levorotatory D and L have no correlation to configuration and rotation of plane-polarized light.

Answer: E Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 20.

All natural occurring sugars are ______.

A. B. C. D.

D sugars L sugars a combination of D and L sugars neither D nor L sugars

Answer: A Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Easy 21.

Which of the given aldohexoses is dextrorotatory?

A. B. C. D. E.

D-glucose D-galactose D-gulose D-mannose cannot predict

Answer: E Learning Objective: 24.2 Describe how monosaccharides are classified Difficulty: Medium 22.

In the Fischer projection of D-glyceraldehyde, the OH group connected to the chirality center farthest from the carbonyl group is pointing _______.

A. B. C. D. E.

to the left to the right up down all of these

Answer: B Learning Objective: 24.2 Describe how monosaccharides are classified

Difficulty: Medium 23.

Which of the given compounds represent a pair of enantiomers?

O H

OH HO

CH2OH I A. B. C. D. E.

CH 2OH

CH2OH

III

I and III II and IV III and V IV none of these

Answer: B Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 24.

Which choices gives the classification for D-erythrose?

A. B. C. D. E. F.

aldotetrose ketotetrose aldopentose ketopentose aldohexose ketohexose

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy

25.

Which choice gives the classification for D-threose?

A. B. C. D. E. F.

aldotetrose ketotetrose aldopentose ketopentose aldohexose ketohexose

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 26.

Which choice gives the classification for D-ribose?

A. B. C. D. E. F.

aldotetrose ketotetrose aldopentose ketopentose aldohexose ketohexose

Answer: C Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 27.

Which choice gives the classification for D-galactose?

A. B. C. D. E. F.

aldotetrose ketotetrose aldopentose ketopentose aldohexose ketohexose

Answer: C Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 28.

Of the possible stereoisomers for galactose, how many are L-isomers?

A. B. C. D. E.

8 6 10 3 4

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 29.

Of the possible stereoisomers for glucose, how many are D-isomers?

A. B. C. D. E.

8 6 10 3 4

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 30.

How many stereoisomers are possible for an aldohexose?

A. B. C. D. E.

8 16 10 12 4

Answer: B Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 31.

Which choice shows the Fisher projection for L-glucose?

CH2OH

III

A. B. C. D. E.

CH2OH

I II III IV V

Answer: C Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 32.

Which choice shows the Fisher projection for D-galactose?

A. B. C. D. E.

CH2OH

III

CH2OH

I II III IV V

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 33.

Which one of the choices is the correct Fischer projection for D-gulose?

H H

A. B. C. D. E.

CH 2OH

OH H

H HO

CH2OH

CH 2OH

III

I II III IV V

OH CH 2OH

CH2OH IV

Answer: E Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 34.

Which of the choices is a L-hexose?

H H

A. B. C. D.

CH 2OH

OH H

H HO

CH2OH

CH 2OH

III

I II III IV

CH2OH IV

OH CH2OH V

Answer: D Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 35.

O H HO H

Which of the choices is the correct stereochemical configuration for D-xylose?

C 2 3 4

H OH H OH

CH2OH A. B. C. D. E.

2S,3R,4S 2R,3S,4R 2R,3R,4S 2S,3S,4R 2S,3S,4S

Answer: B Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 36.

Which of the choices is the correct stereochemical configuration for D-mannose?

O HO HO H H

C 2 3 4 5

H H OH OH

CH 2OH A. B. C. D. E.

2S,3S,4R,5R 2R,3S,4R,5S 2R,3R,4S,5S 2S,3S,4R,5S 2S,3R,4S,5R

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 37.

What is the most common aldohexose?

A. B. C. D. E.

D-allose D-mannose D-galactose D-glucose D-altrose

Answer: D Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Easy 38.

Draw a Fisher projection for the enantiomer of D-glucose.

A. B. C. D. E.

CH2OH

III

CH2OH

I II III IV V

Answer: A Learning Objective: 24.3 Using the mnemonic device, provide names for all eight Daldohexoses Difficulty: Medium 39.

How many stereoisomers are possible for fructose?

A. B.

8 6

C. D. E.

10 3 4

Answer: A Learning Objective: 24.4 Provide names for the most common D-ketoses Difficulty: Medium 40.

Of the possible stereoisomers for fructose, how many are D-isomers?

A. B. C. D. E.

8 6 10 2 4

Answer: E Learning Objective: 24.4 Provide names for the most common D-ketoses Difficulty: Medium 41.

Draw a Fisher projection for D-fructose.

CH2OH

OH HO

H HO

OH HO

A. B. C. D. E.

CH2OH

III

I II III IV V

Answer: E

Learning Objective: 24.4 Provide names for the most common D-ketoses Difficulty: Medium 42.

Which of the choices is the correct structure for L-fructose?

H H

CH 2OH

CH2OH I A. B. C. D. E.

CH 2OH

CH 2OH II

CH 2OH III

CH2OH IV

I II III IV V

Answer: E Learning Objective: 24.4 Provide names for the most common D-ketoses Difficulty: Medium 43.

What is the most common naturally occurring ketose?

A. B. C. D. E.

D-xyulose D-fructose L-fructose L-xyulose D-ribulose

Answer: B Learning Objective: 24.4 Provide names for the most common D-ketoses Difficulty: Easy

CH 2OH V

44.

Which of the choices best describes the relationship between a-D-glucopyranose and b-D-glucopyranose?

A. B. C. D. E.

enantiomers anomers diastereomers constitutional isomers none of these

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 45.

What is the predicted major product of the reaction shown?

O HO O

A. B. C. D. E.

O OH

OH II

H 3O+

III

I II III IV none of these

Answer: A Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 46.

What is the predicted major product of the reaction shown?

O HO O

H 3O+ H O

O OH

O II

I A. B. C. D. E.

III

I II III IV none of these

Answer: D Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 47.

What is the reactant for the reaction shown?

H3O+

O OH

O H

O HO

H IV

III

O HO

H V

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 48.

Anomers of D-glucopyranose differ in stereochemistry at ____ carbon.

A. B. C. D. E.

C1 C2 C3 C4 C5

Answer: A Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation

Difficulty: Easy 49.

Which carbon in the given monosaccharide is the anomeric carbon?

V CH OH 2

IV OH OH III A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 50.

Six-membered cyclic hemiacetal carbohydrates are called ________.

A. B. C. D. E.

furanose pyranose ketopentose aldopentose none of these

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 51.

Five-membered cyclic hemiacetal carbohydrates are called ________.

A. B. C.

furanose pyranose ketohexose

D. E.

aldohexose none of these

Answer: A Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 52.

What is the correct Haworth projection for a-D-glucopyranose?

CH2OH

CH2OH O

O OH OH

OH OH

OH I

A. B. C.

I II III

OH II

D. E.

IV V

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 53.

What is the correct Haworth projection for b-D-allopyranose?

CH2OH

CH 2OH O

O OH OH

OH OH

A. B. C. D.

I II III IV

OH II

Answer: C Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 54.

What is the correct name for the compound shown?

CH2OH O

OH OH

OH OH A. B. C. D. E.

a-D-glucopyranose a-D-allopyranose b-D-glucopyranose a-D-galactopyranose b-D-gulopyranose

Answer: D Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 55.

What is the correct name for the compound shown?

CH2OH O OH OH OH A.

a-D-idopyranose

B. C. D. E.

b-D-altopyranose b-D-glucopyranose a-D-galactopyranose b-D-gulopyranose

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 56.

Pyranose forms of monosaccharides are_____.

A. B. C. D. E.

5-membered cyclic hemiacetals 6-membered cyclic acetals 5-membered cyclic acetals 6-membered cyclic hemiacetals none of these

Answer: D Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 57.

Furanose forms of monosaccharides are_____.

A. B. C. D. E.

5-membered cyclic hemiacetals 6-membered cyclic acetals 5-membered cyclic acetals 6-membered cyclic hemiacetals none of these

Answer: A Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 58.

Which of the compound(s) shown would undergo mutarotation in aqueous solution?

CH2OH O

CH2OH O OH

OH OH

A. B. C. D. E.

I II and III III and IV I, II, and III all of these

Answer: D Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 59.

Which of the compound(s) shown would NOT undergo mutarotation in aqueous solution?

CH2OH O

OCH3

OH OH OH I

OH II

A. B. C. D. E.

I II and IV III IV II, III and IV

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 60.

What is the correct name for the compound shown?

CH2OH

O OH

CH2OH OH A. B. C. D. E.

a-D-fructofuranose b-D-sorbofuranose a-D-glucopyranose b-D- fructofuranose b-D-gulopyranose

Answer: D Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 61.

Draw the Haworth projection for b-D-erythrofuranose.

OH OH

OH IV

III

O OH OH

OH V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Hard 62.

Which of the given structures represents b-D-glucopyranose?

OH H

OH OH O

H OH H H I

A. B. C. D. E.

H OH OH

HO HO H

O OH

OH II

I II III IV none of these

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 63.

Draw the chair conformation of a-D-galactopyranose.

O HO

O OH

OH OH

OH II

III

OH O

HO HO

OH OH IV

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 64.

Draw the Fischer projection for the open-chain form of the given cyclic monosaccharide.

OH O

HO HO

OH OH

OH HO

H HO

OH HO

OH H

OH HO

A. B. C. D. E.

CH2OH

III

I II III IV V

Answer: C Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 65.

Draw the alpha chair conformation for the monosaccharide shown.

OH CH2OH

OH OH

OH O

HO OH

OH IV

III

OH OHO

OH A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Medium 66.

Anomers of D-fructofuranose differ in stereochemistry at ____ carbon.

B. C. D. E.

C2 C3 C4 C5

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 67.

What reagents are necessary to carry out the conversion shown?

O OH

O O

OH O

O O

excess CH3I/Ag2O excess

O O

/ pyridine

D. E. Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium

68.

What is(are) the predicted product(s) when b-D-galactopyranose reacts with excess acetic anhydride in the presence of pyridine?

O OH

O O

O OH

OH II

O O

O IV

III

O H

O O O

H O

O H V

A. B. C.

I II III

O H

D. E.

IV V

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 69.

What reagents are needed to carry out the conversion shown?

OH HO HO

A. B. C. D. E.

O O OH OH

O O

excess CH3I/Ag2O excess CH2CH2I/Ag2O excess CH3I/pyridine excess CH3CH2I/pyridine excess CH3CH2I/Ag2O/pyridine

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 70.

All of the –OH groups on a monosaccharides can be converted to ethers via the Williamson ether synthesis with CH3I in the presence of ________.

A. B. C. D.

strong base weak base strong acid weak acid

Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 71.

Which of the compound(s) shown is a glycoside?

OCH3

OH O

HO HO

OH OH

OH II

A. B. C. D. E.

I II II and III III and IV II, III and IV

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 72.

What reagents are needed to carry out the conversion shown?

OH HO HO

O OH

A. B. C. D. E.

CH3I/Ag2O CH3OH/Ag2O CH3OH/pyridine CH3CH2OH/HCl CH3OH/HCl

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 73.

What are the predicted products of the reaction shown?

a-D-galactopyranose

CH3OH HCl

OH OH

OH OH O

OCH3

OH OCH3

III

H3CO

OCH3

H3CO

OH OCH3

OH OH

OCH3

O H3CO

OH OCH3

Answer: A

OH OCH3

I II III IV V

OH OCH3 II

A. B. C. D. E.

OH OH

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 74.

A glycoside is formed from D-glucopyranose by alkylated the –OH attached to _____.

A. B. C. D. E.

C-1 C-2 C-3 C-4 C-5

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 75.

What is(are) the predicted product(s) of the reaction shown?

OH OH H3O+

O HO

OH OCH3

OH OH

OH OH O

HO I

OH OH

O HO

OH II

A. B. C. D. E.

I I and II III and IV IV I, II and IV

Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 76.

Epimers are diastereomers that differ from each other in the configuration of ____ chiral center(s).

A. B. C. D. E.

no one two two or three three or four

Answer: B Learning Objective: 24.5 Describe the formation and structure of pyranose and furanose rings, alpha and beta anomers, and the process of mutarotation Difficulty: Easy 77.

Which of the compounds shown is(are) an epimer(s) of D-glucose?

A. B. C. D. E.

OH HO

CH 2OH

CH2OH

CH 2OH

III

I II I and III II and IV I and II

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 78.

Which of the choices best describes the relationship between D-glucose and Dgalactose?

A. B. C. D. E.

enantiomers anomers epimers constitutional isomers none of these

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 79.

D-glucose and D-galactose are ______ epimers of each other.

A. B. C. D.

C-1 C-2 C-3 C-4

C-5

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 80.

D-ribulose and D-xylulose are ______ epimers of each other.

A. B. C. D. E.

C-1 C-2 C-3 C-4 C-5

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 81.

When D-glucose is treated with aqueous NaOH, it undergoes_______.

A. B. C. D. E.

mutarotation oxidation glycoside formation epimerization none of these

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 82.

What is(are) the predicted product(s) of the reaction shown?

D-galactose NaBH 4 H2O

CH 3

CH 2OH

I A. B. C. D. E.

CH 2OH

CH2OH

III

I II III IV II and IV

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 83.

What is(are) the predicted product(s) of the reaction shown?

D-fructose NaBH 4 H2O CH2OH

CH2OH OH HO

OH HO

OH H

CH2OH

CH 2OH

CH2OH

CH 2OH

CH2OH

III

B. C. D. E.

II I and III IV I and V

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 84.

Which of the given D-aldoses will produce an optically inactive product when treated with NaBH4/H2O?

OH HO

A. B. C. D. E.

CH2OH

III

I II III IV none of these

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 85.

When D-threose is treated with NaBH4/H2O, it forms _______.

A. B. C. D. E.

a racemic mixture of alditols a meso alditol an optically active alditol an optically active aldonic acid none of these

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 86.

When D-erythrose is treated with NaBH4/H2O, it forms _______.

A. B. C. D. E.

a racemic mixture of alditols a meso alditol an optically active alditol an optically active aldonic acid none of these

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 87.

Which of the compound(s) shown would give a positive Tollens test?

OH OH

OCH3 O OH

HO I

A. B. C. D. E.

HO HO

O OH II OH

I II III IV I and II

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy

88.

Which one of the compounds shown is a non-reducing sugar?

OCH 3

OH OH O HO

A. B. C. D. E.

HO HO II

I II III IV none of these

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 89.

Which one of the compounds shown would give a positive test with Benedict’s solution?

OCH 3 OCH O H 3CO I

OCH3

OCH3 OCH3

HO HO

OH II

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 90.

What is(are) the predicted product(s) of the reaction shown?

OH CH2OH

Br2/H2O

OH HO

C I

A. B. C. D. E.

CH2OH

III

I II III IV V

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 91.

What is(are) the predicted product(s) of the reaction shown?

CH2OH C

OH CH2OH

Br2/H2O

A. B. C. D. E.

OH HO

CH2OH

III

I II III IV D-fructose is not oxidized by bromine water.

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 92.

What is the predicted product of the reaction shown?

OH CH2OH

Br2/H2O

A. B. C. D. E.

OH H

H HO

OH H

CH2OH

III

I II III IV V

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 93.

What is(are) the predicted product(s) of the reaction shown?

OH CH2OH

HNO 3

OH HO

C I

A. B. C. D. E.

OH HO

CH2OH

III

I II III IV V

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 94.

When D-ribose is treated with nitric acid, it forms

A. B. C. D. E.

a racemic mixture of aldonic acids a meso aldaric acid an optically active aldaric acid an optically active aldonic acid a meso aldonic acid

Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 95.

Which of the compounds shown would produce an optically active aldaric acid?

HO H HO

A. B. C. D. E.

OH HO H

OH HO

CH2OH

III

I II III IV V

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 96.

What is(are) the predicted product(s) of the reaction shown?

CH2OH C

OH CH2OH

HNO 3

C C

H OH

H HO

OH H

III

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 97.

What reagents are needed to carry out the conversion shown?

CH2OH A. B. C. D. E.

Br2/H2O NaOH/H2O HNO3 Ag+/NH3/H2O A and D

CH 2OH

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 98.

The sequence of reactions that results in a chain lengthening of the aldose chain is called the _______________ synthesis.

A. B. C. D. E.

Williamson Wohl Kiliani-Fischer Fischer Friedl-Crafts

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 99.

Which of the compounds shown would produce D-glucose and D-mannose when treated with HCN followed by H2/Pd/BaSO4/H2O?

HO H HO

OH HO

OH H

H CH2OH I

A. B. C. D. E.

CH2OH II

CH2OH

CH 2OH

III

CH 2OH V

I II III IV V

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium

100.

What are the predicted products of the Kiliani-Fischer synthesis shown?

1. HCN

2. H 2/Pd/BaSO 4/H2O

OH CH2OH

OH HO

A. B. C. D. E.

CH2OH

CH 2OH

CH2OH

CH 2OH

III

I and V II and IV I and III III and IV II and V

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 101.

Which aldose would produce D-ribose and D-arabinose when subjected to the Kiliani-Fischer synthesis?

A. B. C. D. E.

D-threose D-xylose D-erythrose D-allose D-lyxose

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 102.

What are the predicted products of the Kiliani-Fischer synthesis shown?

1. HCN 2. H2/Pd/BaSO4/H 2O

CH2OH D-lyxose A. B. C. D. E.

D-ribose and D-arabinose D-glucose and D-galactose D-altrose and D-mannose D-galactose and D-talose D-gulose and D-iodose

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 103.

What are the reagents needed to carry out the Kiliani-Fischer synthesis shown?

+ HO

CH 2OH

CH2OH

1. HCN 2. H2/Pd/BaSO4/H2O 1. NaBH4/H2O 2. CH3OH/HCl excess CH3I/Ag2O 1. NH2OH 2. acetic anhydride 3. NaOCH3 1. Br2/H2O 2. NaBH4/H2O

B. C. D. E.

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 104.

Which of the compounds shown would produce D-glucose and D-mannose when subjected to Kiliani-Fischer synthesis?

HO H HO

A. B. C. D. E.

OH HO

OH H

OH HO

H CH2OH

CH2OH

III

I II III IV V

Answer: E Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 105.

The sequence of reactions that results in a chain shortening of the aldose chain is called the _______________ degradation.

A. B. C. D. E.

Williamson Wohl Kiliani-Fischer Fischer Friedl-Crafts

Answer: B Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Easy 106.

What is the predicted products of the Wohl degradation shown?

NH2OH

NaOCH3

CH2OH

HO H HO

A. B. C. D. E.

I II III IV V

Answer: D

H HO

OH H

OH HO

CH2OH I

CH2OH

III

Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 107.

What is the predicted product for the Wohl degradation shown?

O NH 2OH

O NaOCH 3

CH2OH

H CH2OH I

H HO

OH HO

OH H

A. B. C. D. E.

H H

OH H

CH2OH

CH 2OH

CH2OH

III

I II III IV V

Answer: C Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 108.

What is(are) the predicted product(s) of the reaction shown?

O NH 2OH

O NaOCH3

CH2OH

CH2OH III

OH IV

I II III IV V

A. B. C. D. E.

O V

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 109.

Which of the given pairs of D-aldohexoses would both produce the same product when subjected to Wohl degradation?

A. B. C. D. E.

D-glucose and D-galactose D-mannose and D-galactose D-glucose and D-gulose D-allose and D-altrose D-glucose and D-allose

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 110.

D-mannose when subjected to Wohl degradation followed by Br2/H2O produces the same aldonic acid as does______ when treated with Br2/H2O.

A. B. C. D. E.

D-arabinose D-ribose D-xylose D-lyxose D-threose

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Medium 111.

An optically active D-aldohexose was treated with NaBH4/H2O and produced an optically inactive alditol. When the same D-aldohexose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. What is the structure of this D-aldohexose?

OH CH2OH

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Hard 112.

When an optically active D-aldopentose was subjected to Kiliani-Fischer synthesis, followed by NaBH4/H2O, it produced a mixture of an optically active and an optically inactive alditol. When the same D-aldopentose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. Provide the structure of this D-aldopentose.

OH HO

OH H

OH HO

OH H

H HO

CH2OH I

A. B.

I II

CH2OH II

CH2OH III

CH2OH IV

CH2OH V

C. D. E.

III IV V

Answer: D Learning Objective: 24.6 Predict the products for the reactions of monosaccharides Difficulty: Hard 113.

Which one of the choices is a correct structure for a-maltose?

HO OH

O HO

O OH HO I

A. B. C. D. E.

HO HO

OH OH

O OH

OH O HO

O OH OH

I II III IV none of these

Answer: B Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 114.

Which one of the choices is a correct structure for b-lactose?

OH OH

O OH HO

HO HO OH

OH O HO II

A. B. C. D. E.

OH O OH OH

I II III IV none of these

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 115.

Which one of the choices is a correct structure for sucrose?

OH OH

OH O O HO

HO OH I

O OH OH

HO HO

O OH O HO II

OH O OH

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 116.

Which one of the choices is a correct structure for b-cellobiose?

OH OH HO HO

OH O OH

O HO I

O OH

HO HO OH

O OH

O II HO

OH O OH OH

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 117.

Which of the disaccharides shown is a reducing sugar?

OH OH

O HO

O OH HO I

A. B. C. D. E.

HO HO

OH OH

OH O HO

OH O OH OCH3

I II III IV none of these

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium

118.

Which of the given statements best describe the main difference between maltose and cellobiose?

Maltose has a b-1-4 glycosidic linkage and cellobiose has an a-1-4 glycosidic linkage. Maltose is comprised of b-D-glucopyranose and cellobiose is comprised of a-Dglucopyranose. Maltose is comprised of a-D-glucopyranose and cellobiose is comprised of b-Dglucopyranose. Maltose has an a-1-4 glycosidic linkage and cellobiose has a b-1-4 glycosidic linkage. C and D

B. C. D. E.

Answer: E Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 119.

Which of the choices is a reducing sugar with a 1®4 a-glycosidic linkage?

A. B. C. D. E.

maltose cellobiose sucrose lactose B and D

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 120.

Which one or more of the given choices would reduce a Fehling solution?

A. B. C. D. E.

maltose cellobiose sucrose lactose A, B and D

Answer: E Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides

Difficulty: Medium 121.

What is(are) the predicted product(s) when lactose is treated with Br2/H2O?

A. B.

I II

C. D. E.

III IV V

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 122.

What is(are) the predicted product(s) when maltose is treated with NaBH4/H2O?

A. B. C.

I II III

D. E.

IV V

Answer: D Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 123.

What is(are) the predicted product(s) when maltose is treated with CH3OH/HCl?

A. B. C. D. E.

I II III A and B C and D

Answer: D Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium

124.

What is(are) the predicted product(s) when cellobiose is treated with excess acetic anhydride/pyridine?

A. B. C. D.

I II III IV

Answer: B Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 125.

What are the monosaccharide(s) in a-maltose?

A. B. C. D. E.

two b-D-glucopyranose b-D-galactopyranose and b-D-glucopyranose a-D-glucopyranose and b-D-fructofuranose two a-D-glucopyranose two b-D-fructofuranose

Answer: D Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 126.

What are the monosaccharide(s) in b-cellobiose?

A. B. C. D. E.

two b-D-glucopyranose b-D-galactopyranose and b-D-glucopyranose a-D-glucopyranose and b-D-fructofuranose two a-D-glucopyranose two b-D-fructofuranose

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 127.

What are the monosaccharide(s) in b-lactose?

A. B. C. D. E.

two b-D-glucopyranose b-D-galactopyranose and b-D-glucopyranose a-D-glucopyranose and b-D-fructofuranose two a-D-glucopyranose two b-D-fructofuranose

Answer: B Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 128.

Identify the monosaccharide(s) in sucrose.

A. B. C. D. E.

two b-D-glucopyranose b-D-galactopyranose and b-D-glucopyranose a-D-glucopyranose and b-D-fructofuranose two a-D-glucopyranose two b-D-fructofuranose

Answer: C Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 129.

Which of the given disaccharides is(are) a-glucoside(s)?

A. B. C. D. E.

sucrose maltose lactose cellobiose both A and B

Answer: E Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 130.

Which of the given disaccharides is(are) b-galactoside(s)?

A. B. C. D. E.

sucrose maltose lactose cellobiose both A and B

Answer: C

Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Easy 131.

Which of the given disaccharides is (are) not a reducing sugar(s)?

A. B. C. D. E.

sucrose maltose lactose cellobiose None of these

Answer: A Learning Objective: 24.7 Describe the structure of a disaccharide, and give three examples of disaccharides Difficulty: Medium 132.

What is the monomer in starch?

A. B. C. D. E.

a-D-glucose b-D-glucose a-D-galactose b-D-fructose maltose

Answer: A Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides Difficulty: Medium 133.

What is the monomer in cellulose?

A. B. C. D. E.

a-D-glucose b-D-glucose a-D-galactose b-D-fructose maltose

Answer: B Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides Difficulty: Easy

134.

What is the monomer in glycogen?

A. B. C. D. E.

a-D-glucose b-D-glucose a-D-galactose b-D-fructose maltose

Answer: A Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides Difficulty: Easy 135.

Raffinose is a trisaccharide found in whole grains. What is the correct description of the glycosidic linkage(s) in raffinose?

A. B. C. D. E.

1®6 a at galactose and glucose and 1®1 a at glucose and fructose 1®4 a at galactose and glucose and 1®1 a at glucose and fructose 1®6 a at galactose and glucose and 1®6 a at glucose and fructose 1®6 b at galactose and glucose and 1®1 b at glucose and fructose 1®4 b at galactose and glucose and 1®1 b at glucose and fructose

Answer: A Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides Difficulty: Medium

136.

Raffinose is a trisaccharide found in whole grains. Is raffinose a reducing sugar?

A. B.

yes no

Answer: B Learning Objective: 24.8 Describe the structure of a polysaccharide, and give three examples of polysaccharides Difficulty: Medium 137.

A polysaccharide that is a major component in the exoskeletons of insects and arthropods is called _______.

A. B. C. D. E.

cellulose chitin glycogen glycoasminoglycans peptidoglycan

Answer: B Learning Objective: 24.9 Describe the structure of an amino sugar Difficulty: Medium 138.

The main difference between cellulose and chitin is that:

A. B. C. D. E.

Cellulose has b-glycosidic linkages; chitin has a-glycosidic linkages. Cellulose has a-glycosidic linkages; chitin has b-glycosidic linkages. Cellulose is composed of D-glucose units; chitin is composed of an N-acetyl derivative of glucose, glucosamine. Cellulose has a linear structure; chitin has a helical structure. Cellulose has 1,6 branching; chitin has no branching.

Answer: C Learning Objective: 24.9 Describe the structure of an amino sugar Difficulty: Medium 139.

Which one of the given heterocyclic amines is not a base in DNA?

A. B. C. D. E.

uracil thymine cytosine adenine guanine

Answer: A Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA Difficulty: Easy 140.

Which one of the given heterocyclic amines is not a base in RNA?

A. B. C. D. E.

uracil thymine cytosine adenine guanine

Answer: B Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA Difficulty: Easy 141.

What is the difference between a nucleoside and a nucleotide?

A. B. C. D.

A nucleotide is a phosphorylated nucleoside. A nucleoside is a phosphorylated nucleotide. A nucleotide is a deoxynucleoside. A nucleoside is a deoxynucleotide.

none of these

Answer: A Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA Difficulty: Easy 142.

What is(are) the predicted product(s) when a-D-glucose is treated with methanamine in the presence of acid?

NH3 I

NH3 O

HO HO

OH II

HO HO

A. B. C.

I II III

NHCH3

+ HO HO OH OH

OH O

HO HO

OH NHCH3

+ HO HO OH NHCH3 OH

+ HO HO OH NHCH3

OH IV

NHCH3 III

+ HO HO OH OH

NHCH3

OH O + HO HO OH NH3

O OH

NH3

D. E.

IV V

Answer: B Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA Difficulty: Medium 143.

Provide the structure for cytidine.

NH2

HO O

H H

H OH

H H

O NH

NH O

HO O

H H

H OH

III

NH N HO H H

H H

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA Difficulty: Medium 144.

Provide the structure for uridine.

NH2

HO O

H H

H OH

H H

O NH

NH O

HO O

H H

H OH

III

NH N HO H H

H H

A. B. C. D. E.

I II III IV V

Answer: C Learning Objective: 24.10 Explain how N-glycosides are formed, and discuss the relationship of N-glycosides to DNA and RNA Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 25 1.

In a-amino acids, the amino and carboxylic acid groups are separated by ____,

A. B. C. D. E.

two carbon atoms one carbon atom peptide linkage amide linkage none of these

Answer: B Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 2.

Which one or more of the given statements is true about a-amino acids?

A. B.

the amino and carboxylic acid groups are separated by one carbon atom the amino group is connected to a carbon atom that is a to the carboxylic acid group the a carbon can be a chirality center all of these are true

C. D.

Answer: D Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 3.

Pairs of amino acids are connected together by____________.

A. B. C. D. E.

an ether linkage a peptide linkage an ester linkage an amide linkage both B and D

Answer: E Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 4.

When four amino acids are connected to each other, they form ____________.

A. B. C. D. E.

a tripeptide a protein a polypeptide a tetrapeptide a dipeptide

Answer: D Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 5.

When two amino acids are connected to each other, they form ____________.

A. B. C. D. E.

a tripeptide a protein a polypeptide a tetrapeptide a dipeptide

Answer: E Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 6.

When three amino acids are connected to each other, they form ____________.

A. B. C. D. E.

a tripeptide a protein a polypeptide a tetrapeptide a dipeptide

Answer: A Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 7.

When thirty amino acids are connected to each other, they form ____________.

A. B. C.

a tripeptide a protein a polypeptide

D. E.

a tetrapeptide none of these

Answer: C Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 8.

When more than fifty amino acids are connected to each other, they form _________.

A. B. C. D. E.

a tripeptide a protein a polypeptide a tetrapeptide none of these

Answer: B Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 9.

_______________ are certain proteins that serve as catalysts for most of the reactions in living cells.

Answer: Enzymes Learning Objective: 25.1 Describe the structures of amino acids, alpha amino acids, peptide bonds, peptides, and proteins Difficulty: Easy 10.

How many different amino acids are abundantly found in proteins?

A. B. C. D. E.

10 16 20 40 none of these

Answer: C Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy

11.

Proteins found in humans have all amino acids with ____configuration.

A. B. C. D. E.

D L meso A and B none of these

Answer: B Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 12.

Which of the given amino acids is achiral?

A. B. C. D. E.

alanine leucine glycine phenylalanine none of these

Answer: C Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 13.

Which of the choices is a correct structure for L-valine?

H 2N

NH 2

H 2N

CH(CH3)2 I

CH(CH 3)2 II

CH 2CH(CH3)2 III

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 14.

Which of the choices is a correct structure for D-leucine?

H 2N

NH 2

H 2N

CH(CH3)2 I

A. B. C. D. E.

I II III IV V

CH(CH 3)2 II

CH2CH(CH3)2 III

Answer: D Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 15.

Which one or more of the amino acids shown has have a basic side chain?

O H2N

CH C

H2N

CH C CH2

CH2

CH2 NH

NH2

A. B. C. D. E.

CH2

O OH

H2N

CH C

CH 2

NH2 I

III

I and II I, II and IV III and V I, II, III and IV all of these

Answer: A Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy

16.

Which of the amino acids shown have an acidic side chain?

O H 2N

CH C

A. B. C. D. E.

H 2N

CH C

H2N

CH C

CH2

CH 2

CH2

C I

OH II

III

I and III I, II and III IV and V II, IV and V all of these

Which one of the given amino acids has a hydroxyl side chain?

cysteine

B. C. D. E.

serine glutamine leucine proline

Which one of the given amino acids has a sulfur atom?

A. B. C. D. E.

cysteine serine glutamine leucine proline

Which one of the given amino acids has an amide side chain?

A. B. C. D. E.

cysteine serine glutamine leucine proline

Which of the given amino acids has a polar side chain?

A. B. C. D. E.

tyrosine proline leucine tryptophan glycine

Which of the given amino acids is the smallest?

A. B. C. D. E.

tyrosine proline leucine tryptophan glycine

Answer: E Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 22.

Which of the given amino acids is the largest amino acid with a nonpolar side chain?

A. B. C. D. E.

tyrosine proline leucine tryptophan glycine

Which one of the given amino acid does not have an L-isomer?

A. B. C. D. E.

valine alanine leucine glycine none of these

Answer: D

Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 24.

Which of the naturally occurring amino acids shown does not have the S configuration?

H 2N

H2N

H 2N

CH3 I A. B. C. D. E.

CH2SH II

CH 2OH III

CH(CH3)CH 2CH 3 IV

I II III IV none of these

Which of the given amino acids is not an essential amino acid?

A. B. C. D. E.

phenylalanine glycine isoleucine threonine valine

Which choice shows the Fischer projection for D-serine with the chirality center correctly identified as R or S.

NH2

H2N

NH2

CH2OH

H2N

A. B. C. D. E.

NH2

CH2OH

CH3

I II III IV V

Which choice shows the Fischer projection for L-cysteine with the chirality center correctly identified as R or S.

H2N

NH2

CH2SH

III

NH2 CH2SH V

A. B. C. D. E.

H2N

CH2OH V

I II III IV V

Which choice shows the Fischer projection for L-aspartic acid with the chirality center correctly identified as R or S.

H2N

NH2

CH2 O

NH2

H2N

CH2 O

OH IV

OH III

CH2

A. B. C. D. E.

CH2 O

SH V

I II III IV V

An amino acid can exist as a ________, which is a dipolar ion that carries both positive and negative charge.

A. B. C. D.

cation anion zwitterion none of these

Answer: C Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point

Difficulty: Easy 30.

Amino acids are considered amphoteric because _____________.

A. B. C. D. E.

they only react with acids they only react with bases they react with both acids and bases they do not react with acids or bases none of these

Which of the choices is a zwitterion for alanine?

O OH

A. B. C. D. E.

O O

O OH

NH3

NH 3

NH2

III

I II III IV both I and IV

Which of the choices is the predominant form of lysine at pH 14?

O H 3N I

A. B. C. D. E.

H3N

NH3

I II III IV V

Which of the choices is the predominant form of aspartic acid at pH 1?

O O

O OH

NH 2 I

O OH

NH 3 II

O O

NH2 III

A. B. C. D. E.

I II III IV V

Which of the choices is the predominant form of serine at physiological pH?

O HO

OH HO

NH2 I

A. B. C. D. E.

I II III IV V

Answer: C

NH3 II

O NH 3

III

Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 35.

Which of the choices is the predominant form of asparagine at physiological pH?

O O

OH NH2

NH 2 I

A. B. C. D. E.

O O

O OH

NH 2

NH3

O NH 2

NH2 III

I II III IV V

Which of the choices is the predominant form of arginine at pH 2?

NH H 3N

N H

OH I

A. B. C. D. E.

NH2

NH3

H 2N

N H

OH II

NH3

I II III IV V

What is the structure of the predominant form of alanine at a pH of 2?

OH O

NH2

NH3 I

NH3

III

A. B. C. D. E.

NH3

NH2

I II III IV V

What is the structure of the predominant form of valine at pH 10?

Answer:

O O

O OH

NH2

NH3

III

O O

A. B. C. D. E.

NH2

NH3

I II III IV V

Which of the given statements is true about the amino acids with isoelectric point around pH 10?

A. B. C. D. E.

The side chain must be acidic. The side chain must be basic. The side chain must be polar. The side chain must be non polar. none of these

Which of the given statements is true about the amino acids with isoelectric point around pH 3?

A. B. C. D. E.

The side chain must be acidic. The side chain must be basic. The side chain must be polar. The side chain must be non polar. none of these

The pH at which the concentration of the zwitterionic form of an amino acid is at a maximum value is called the _______.

A. B. C. D. E.

dipolar point electric point neutral point isoelectric point none of these

What is the pI of the amino acid shown?

O O

OH OH

A. B. C. D. E.

pK a1=1.88

pK a2=9.60 pK a3=3.65

NH 2

2.76 5.74 6.62 7.50 none of these

Answer: A Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point

Difficulty: Medium 43.

What is the pI of the amino acid shown?

O H 2N

pK a1=2.18 pK a2=8.95 pK a3=10.53

NH2 A. B. C. D. E.

5.56 6.35 9.74 10.53 none of these

What is the pI of the amino acid shown?

O OH

pK a1=2.32 pK a2=9.62

NH2 A. B. C. D. E.

1.16 4.81 5.97 9.62 none of these

Which of the amino acids shown has a pI around pH 10?

O H 2N

CH C

O OH

H2N

CH2 C NH2

A. B. C. D. E.

CH C

O OH

H2N

CH2 O

C II

CH C

CH 2 O

OH III

I II III IV V

Which of the amino acids shown has a pI around pH 3?

O H 2N

CH C

O OH

H2N

CH2 C

A. B. C. D. E.

H2N

CH2 O

NH2

CH C

C II

CH C

CH 2 O

OH III

I II III IV V

Which of the choices is used to detect the presence of amino acids using chromatography?

A. B. C. D. E.

2,4-DNP methyl orange phenolphthalein ninhydrin methyl red

Answer: D

Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 48.

Identify the compound that reacts with amino acids to form a fluorescent purple product.

A. B. C. D. E.

2,4-DNP ninhydrin methyl orange methyl red phenolphthalein

Separation of amino acids using electrophoresis is mainly based on ______.

A. B. C. D.

differences in the pI values concentration differences in pH values none of these

Which of the given amino acids will migrate towards the cathode at pH 7?

Glycine: pI = 6.0 Lysine: pI = 9.7 A. B. C. D. E.

Glycine Lysine Both glycine and lysine Neither glycine nor lysine It is impossible to determine without more information.

Answer: B

Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Easy 51.

Which of the given amino acids will migrate towards the anode at pH 7?

Glycine: pI = 6.0 Lysine: pI = 9.7 A. B. C. D. E.

Glycine Lysine Both glycine and lysine Neither glycine nor lysine It is impossible to determine without more information.

Which of the given amino acids will migrate towards the anode at pH 6?

Phenylalanine: pI = 5.5 Leucine: pI = 6 A. Phenylalanine B. Leucine C. Both phenylalanine and leucine D. Neither phenylalanine nor leucine E. It is impossible to determine without more information. Answer: A Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Medium 53.

Which of the given amino acids will not migrate towards the cathode/anode at pH 6?

Phenylalanine: pI = 5.5 Leucine: pI = 6 A. B.

Phenylalanine Leucine

C. D. E.

Both phenylalanine and leucine Neither phenylalanine nor leucine It is impossible to determine without more information.

Which of the given amino acids will move the farthest when subjected to electrophoresis at pH 7?

aspartic acid pI = 2.76 I A. B. C. D. E.

alanine pI = 6.01 II

histidine pI = 7.58 III

I II III II and III none of these

Which choice indicates the structure of the predominant form of each of the given amino acids at pH 6 and correctly predicts whether it will migrate toward the anode or cathode during electrophoresis?

phenylalanine pI = 5.5 I

leucine pI = 6.0 II

O O

NH3

O NH2

NH2 III

O OH NH2 V

A. Phenylalanine is I and will move toward the anode; leucine is II and will move toward the cathode. B. Phenylalanine is III and will move toward the anode; leucine is II and does not migrate C. Phenylalnine is V and will not move; leucine is IV and will move toward the cathode. D. Phenylalnine is I and will not move; leucine is II and will move toward the cathode. E. Phenylalanine is III and will move toward the cathode; leucine is II and does not migrate. Answer: B Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point Difficulty: Hard 56.

Which choice shows the structure of the predominant form of each of the given amino acids at pH 7 and correctly predicts it will migrate toward the anode or cathode during electrophoresis?

glycine pI = 6 I

lysine pI = 9.7 II

O H3N

NH2

NH3

O H3N

NH3

III

O H3N

O NH2 V

A. Glycine is I and will move toward the anode; lysine is II and will move toward the cathode. B. Glycine is III and will move toward the anode; lysine is II and does not migrate C. Glycine is V and will not move; lysine is IV and will move toward the cathode. D. Glycine is I and will not move; lysine is II and will move toward the cathode. E. Glycine is III and will move toward the cathode; lysine is II and does not migrate. Answer: B Learning Objective: 25.2 Discuss the acid-base properties of amino acids, including pKa values, zwitterions, the amphoteric nature of amino acids, and the isoelectric point

Difficulty: Hard 57.

Which amino acid is produced from the reaction sequence shown?

O 1. Br 2/PBr3 OH A. B. C. D. E.

excess NH3

2. H2O

alanine valine leucine isoleucine none of these

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 58.

Which amino acid is produced from the reaction sequence shown?

A. B. C. D. E.

1. Br 2/PBr3 excess NH3 OH 2. H2O

alanine valine leucine isoleucine none of these

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 59.

Which amino acid is produced from the reaction sequence shown?

4-methylpentanoic acid 1. Br2/PBr 3 2. H2O

excess NH3

A. B. C. D. E.

alanine valine leucine isoleucine none of these

Answer: C Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 60.

Which amino acid is produced from the reaction sequence shown?

3-methylpentanoic acid 1. Br 2/PBr3 2. H 2O A. B. C. D. E.

excess NH3

alanine valine leucine isoleucine none of these

Answer: D Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 61. How can you prepare phenylalanine using a Hell-Volhard-Zelinski reaction starting with the compound shown below?

O OH

A. B.

1. HBr; 2. H2O; 3. excess NH3 1. Na2Cr2O7/H2SO4/H2O; 2. Br2/PBr3; 3. H2O; 4. excess NH3

C. D. E.

1. Na2Cr2O7/H2SO4/H2O; 2. HBr; 3. excess NH3 1. Br2/PBr3; 2. H2O; 3. excess NH3 1. Na2Cr2O7/H2SO4/H2O; 2. NaOH; 3. excess NH3

Answer: D Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 62.

How can you prepare glycine staring with ethanol and using a Hell-VolhardZelinski reaction?

A. B. C. D. E.

1. HBr; 2. H2O; 3. excess NH3 1. Na2Cr2O7/H2SO4/H2O; 2. Br2/PBr3; 3. H2O; 4. excess NH3 1. Na2Cr2O7/H2SO4/H2O; 2. HBr; 3. excess NH3 1. Br2/PBr3; 2. H2O; 3. excess NH3 1. Na2Cr2O7/H2SO4/H2O; 2. NaOH; 3. excess NH3

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 63.

In the Hell-Volhard-Zelinski reaction, the ___- carbon of the carboxylic acid is halogenated.

A. B. C. D. E.

alpha beta gamma delta epsilon

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Easy 64.

Which amino acid is produced from the reaction sequence shown?

EtO

OEt HN

1. NaOEt 2.

H3O+ heat

Br O A. B. C. D. E.

alanine valine leucine isoleucine none of these

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 65.

Which amino acid is produced from the reaction sequence shown?

EtO

OEt

1. NaOEt 2. Cl

H 3O+ heat

O A. B. C. D. E.

alanine valine leucine isoleucine none of these

Answer: C Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard

66.

What is the structure of the amino acid produced from the reaction sequence shown?

EtO

H 3O+

1. NaOEt 2.

OEt

heat

HN O

O OH

NH2

O OH HN

NH3

O I

III

O OEt

EtO

OEt NH2

HN O IV

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 67.

What is the structure of the amino acid produced from the reaction sequence shown?

EtO

OEt HN O

1. NaOEt

H3O+

heat

O S

O OH

NH3

EtO

O OEt

OEt

NH2 O IV

III

OH HN O V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard

68.

What reagents are necessary to synthesize the given amino acid via the amidomalonate synthesis?

O OH NH 2

A. B. C. D. E.

1. NaOEt; 2. CH3CH2CH2Br; 3. H3O+ 1. NH4Cl/NaCN; 2. H3O+ 1. Br2/PBr3; 2. H2O; 3. excess NH3 1. HBr; 2. H2O; 3. excess NH3 1. NaOEt; 2. C(CH3)2CH2Br; 3. H3O+/heat

Answer: E Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 69.

What reagents are necessary to synthesize the given amino acid via the amidomalonate synthesis starting with the given compound?

O OH NH 2

Answer:

A. B. C.

1. NaOEt; 2. CH3CH2CH2Br; 3. H3O+ + 1. NH4Cl/NaCN; 2. H3O 1. Br2/PBr3; 2. H2O; 3. excess NH3

1. HBr; 2.

1. NaOEt; 2.

; 3. H2O; 4. excess NH3

; 3. H3O+/heat

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 70.

Which of the given aldehydes would produce isoleucine using a Strecker synthesis?

A. B. C. D. E.

3-methylbutanal 2-methylbutanal 2-methylpropanal propanal none of these

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 71.

Which of the given aldehydes would produce glycine using a Strecker synthesis?

A. B. C. D.

methanal ethanal propanal butanal

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 72.

Which amino acid is produced from the reaction shown?

O HS A. B. C. D. E.

1. NH4Cl, NaCN H

2. H 3O+

methionine serine cysteine lysine none of these

Answer: C Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 73.

Which amino acid is produced from the reaction shown?

O HO A. B. C. D. E.

1. NH4Cl, NaCN H

2. H 3O+

methionine serine cysteine lysine none of these

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 74.

Which choice shows how to prepare phenylalanine using a Strecker synthesis?

1. NH4Cl 2. H3O+ O

III

2. H3O+

1. NH4Cl, NaCN 2. H3O+ O

A. B. C. D. E.

1. NH4Cl, NaCN

1. NH4Cl

2. H2O

1. NH4Cl, NaCN 2. H3O+

I II III IV V

Answer: B Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 75.

Which choice shows how to prepare cysteine using a Strecker synthesis.

2. H3O+

H O

HS OH

A. B. C. D. E.

1. NH4Cl, NaCN 2. H3O+

H IV

1. NH4Cl 2. H2O

III

1. NH4Cl

1. NH4Cl, NaCN 2. H3O+

I II III IV V

Answer: D Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 76.

What is the structure of the amino acid produced from the reaction shown?

1. NH 4Cl, NaCN 2. H3O+

O OH

+ enantiomer NH3

O OH

+ enantiomer

CH3 OH

O OH

III

+ enantiomer

NH3 O OH

+ enantiomer

NH3 NH3 V

O OH + enantiomer

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 77.

What is the structure of the amino acid produced from the reaction shown?

O H

1. NH 4Cl, NaCN 2. H3O+

N H

H2N

H3N

+ enantiomer

N H

+ enantiomer

N H

OH NH3

N H

+ enantiomer

N H

III

H3N

N H V

A. B. C. D.

I II III IV

+ enantiomer

Answer: D Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 78.

Which of the given alkenes is used to prepare isoleucine using an asymmetric catalytic hydrogenation reaction?

H2/(R)-(-)Ru(BINAP)Cl2

1. NaOH/H 2O 2. H3O

L-isoleucine

OH I

A. B. C. D. E.

NHAc

I II III IV none of these

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Hard 79.

What is the structure of the amino acid produced from the reaction sequence shown?

O OH

H2/(R)-(-)Ru(BINAP)Cl2

1. NaOH/H 2O 2. H 3O+

NHAc

O OH

NH2 I

NH2

O OH

NH2

III

O OH

OH NH2

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 25.3 Identify the reagents necessary to prepare amino acids, either as a racemic mixture or enantioselectively Difficulty: Medium 80.

Which of the choices is a correct bond-line structure for the tripeptide Val-AspAla?

H N

H2N

O N H

OH I O

OH O

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 81.

Which of the choices is a correct bond-line structure for the tripeptide Ser-LysCys?

HO H N

H 2N O

O N H (CH 2)4NH2

SH OH O

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 82. Which choices shows an accurate bond-line structure for the tetrapeptide AlaSer-Cys-Phe?

H N

H3N O

III

H3N O

N H

O N H

N H OH

O SH

H N

O O

H N

H3N

N H OH

H N

H3N

H N O

O O

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 83.

Which choice shows an accurate bond-line structure for the tetrapeptide Ile-SerLeu-Gly?

Answer:

H N

H2N O

N H

H N

H N O

O N H

H N

III

N H OH

H N

H N O

O OH

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 84.

What is the correct sequence of amino acids for the given tripeptide?

HO H N

H 2N O A. B. C. D. E.

O N H S

OH O

Ser-Met-Ile Ser-Cys-Ile Thr-Met-Leu Thr-Cys-Leu Ile-Met-Thr

Answer: C Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 85.

What is the correct sequence of amino acids for the given tripeptide?

H N

H 2N

O N H

A. B. C. D. E.

OH O

Leu-Phe-Ala Val-Phe-Ala Ile-Tyr-Leu Leu-Tyr-Val Val-Ala-Phe

Answer: B Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 86.

What is the three letter abbreviation for the amino acid sequence of the given peptide?

H N

H 2N

N H

H N O

OH A. Ile-Phe-Ser-Val-Ala-Tyr B. Phe-Ala-Val-Ser-Tyr-Ile C. Gly-Phe-Val-Ser-Ala-Tyr D. Ile-Tyr-Ser-Val-Ala-Phe E. Leu-Ala-Ser-Tyr-Gly-Ala Answer: D

O N H

H N O

O OH

Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Medium 87.

Why is the s-trans conformation of a peptide bond more stable than the s-cis conformation?

A. B. C. D.

there is a restricted rotation around the peptide bond rotation is allowed around the peptide bond it has reduced steric hindrance none of these

Answer: C Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Easy 88.

How are disulfide bonds formed?

A. B. C. D.

oxidation of thiol groups joining cysteine residues within a peptide joining cysteine residues between two strands of a peptide all of these

Answer: D Learning Objective: 25.4 Describe the composition and structure of a peptide, including the N and C termini, s-trans and s-cis conformations, and disulfide bridges Difficulty: Easy

89.

Which of the given reagents is used to remove the N-terminus amino acid residue using Edman degradation?

N I

N S

C II

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 90.

Edman degradation removes one amino acid residue at a time from the _______ of the peptide.

A. B. C. D.

C-terminus N-terminus middle none of these

Answer: B Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Easy 91.

Which of the given peptides results after a single Edman degradation of the tetrapeptide Gly-Phe-Tyr-Ser?

A. B. C. D. E.

Gly-Phe-Tyr Tyr-Ser Phe-Tyr-Ser Gly-Phe Ser

Answer: C

Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 92.

Which of the given choices results after three steps of Edman degradation of the heptapeptide Lys-His-Gly-Phe-Tyr-Ser-Ala?

A. B. C. D. E.

Lys-His-Gly Phe-Tyr-Ser-Ala Tyr-Ser-Ala Lys-His-Gly-Phe Gly-Phe-Tyr-Ser-Ala

Answer: B Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 93.

Chymotrypsin, a digestive enzyme, catalyzes the hydrolysis of the peptide bond at the carboxyl end of which of the given amino acids?

O H 2N

CH C

O OH

CH2

phenyalanine

H 2N

CH C

CH 2

OH tyrosine

A. B. C. D. E.

phenylalanine tyrosine tryptophan histidine A, B and C

Answer: E Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 94

Trypsin, a digestive enzyme, catalyzes the hydrolysis of the peptide bond at the carboxyl end of which of the given amino acids?

O H 2N

CH C

O OH

H 2N

CH C

CH2

NH2

arginine

lysine

NH2

A. B. C. D. E.

arginine lysine histidine tryptophan A and B

Answer: E Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 95.

Which of the given tetrapeptides is not cleaved by trypsin?

A. B. C. D. E.

Gly-Lys-Cys-Phe Cys-Ala-Arg-Ser Gly-Ser-Ile-Lys Ala-Lys-Tyr-Arg Lys-Met-Pro-Ala

Answer: C Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 96.

Which of the given tetrapeptides is not cleaved by chymotrypsin?

A. B. C. D.

Gly-Lys-Cys-Trp Cys-Tyr-Arg-Phe Phe-Ser-Ile-Lys Ala-Trp-Tyr-Arg

Phe-Met-Pro-Arg

Answer: A Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 97.

Which of the given fragments are formed when the peptide shown is cleaved using chymotrypsin?

Gly-Lys-Cys-Phe-Ile-Val-Tyr-Ala-Ser A. B. C. D. E.

Gly-Lys-Cys, Phe-Ile-Val, Tyr-Ala-Ser Gly-Lys-Cys-Phe, Ile-Val-Tyr, Ala-Ser Gly-Lys-Cys-Phe, Ile-Val, Tyr-Ala-Ser Gly-Lys-Cys, Phe, Ile-Val-Tyr, Ala-Ser Gly-Lys, Cys-Phe, Ile-Val-Tyr-Ala-Ser

Answer: B Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 98.

Which of the given sets of fragments is formed when the given peptide is cleaved using trypsin?

Gly-Lys-Cys-Phe-Ile-Val-Tyr-Ala-Ser A. B. C. D. E.

Gly, Lys-Cys, Phe-Ile-Val, Tyr-Ala-Ser Gly-Lys, Cys-Phe-Ile-Val-Tyr-Ala-Ser Gly-Lys-Cys-Phe, Ile-Val-Tyr-Ala-Ser Gly-Lys, Cys, Phe-Ile-Val, Tyr-Ala-Ser Gly-Lys-Cys-Phe, Ile-Val-Tyr-Ala-Ser

Answer: B Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Medium 99.

A peptide with 12 amino acid residues produced the given fragments when treated with trypsin and chymotrypsin. Edman degradation of this peptide produced the phenylthiohydantoin derivative of glycine. What is the structure of this peptide?

Trypsin: Gly-Leu-Phe-Arg, Cys-Tyr-Ile-Gly, Val-Trp-Ser-Lys Chymotrypsin: Gly-Leu-Phe, Ser-Lys-Cys-Tyr, Ile-Gly, Arg-Val-Trp, A. Gly-Leu-Phe-Arg-Val-Trp-Ser-Lys-Cys-Tyr-Ile-Gly B. Gly-Leu-Phe-Arg-Cys-Tyr-Ile-Gly-Val-Trp-Ser-Lys C. Gly-Leu-Phe-Val-Trp-Ser-Lys-Cys-Tyr-Ile-Gly D. Val-Trp-Ser-Lys-Gly-Leu-Phe-Arg-Cys-Tyr-Ile-Gly E. Ser-Lys-Cys-Tyr-Gly-Leu-Phe-Arg-Val-Trp-Ile-Gly Answer: A Learning Objective: 25.5 Explain how the amino acid sequence of a peptide can determined via an Edman degradation or the use of peptidases Difficulty: Hard 100.

Which of the given reagents is used to protect the amino group in the selective synthesis of the dipeptide Ala-Val?

O Cl

A. B. C. D. E.

O O

I II III IV V

Answer: B Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Medium

101.

Which of the given dipeptides is formed when alanine and valine are reacted in the presence of dicyclohexylcarbodiimide (DCC)?

A. B. C. D. E.

Ala-Val Val-Ala Ala-Ala Val-Val all of these

Answer: E Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 102.

Which of the given dipeptides is formed when leucine is treated with (BoC)2O and glycine is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?

A. B. C. D. E.

Gly-Leu Gly-Gly Leu-Gly Leu-Leu all of these

Answer: C Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 103.

Which of the given dipeptides is formed when tyrosine is treated with (BoC)2O and proline is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?

A. B. C. D. E.

Tyr-Pro Pro-Tyr Pro-Pro Tyr-Tyr all of these

Answer: A Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis

Difficulty: Hard 104.

Which of the given tripeptides is formed when alanine is treated with (BoC)2O and proline is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with aqueous NaOH. The dipeptide is then reacted with the benzyl ester of leucine in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?

A. B. C. D. E.

Ala-Pro-Leu Pro-Ala-Leu Leu-Ala-Pro Pro-Leu-Ala all of these

Answer: A Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 105.

Which of the given tripeptides is formed when serine is treated with (BoC)2O and threonine is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with aqueous NaOH. The dipeptide is then reacted with the benzyl ester of isoleucine in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?

A. B. C. D. E.

Ser-Tyr-Ile Ser-Thr-Ile Ile-Ser-Thr Ile-Ser-Tyr none of these

Answer: B Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 106. Provide a stepwise synthesis for the dipeptide Ser-Phe beginning by adding the products of the two steps shown.

O H2N

CH C

O OH

H2N

CH 2

CH C

CH 2 OH

Ser

Phe

O H 2N

CH C

O OH

(Boc)2O

BocHN

CH C

CH2

CH 2

A. 1. DCC; 2. H2SO4; 3. NaOH/H2O B. 1. Br2/PBr3; 2. H2O; 3. excess NH3 C. 1. NaOEt; 2. CH3Br; 3. H3O+, heat D. 1. DCC; 2. NaOH/H2O; 3. excess NH3 E. 1. DCC; 2. CF3COOH; 3. NaOH/H2O

Answer: E Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 107.

The method developed by ______ is used to prepare larger peptides.

A. B. C. D.

Edman Strecker Merrifield Hell-Volhardt-Zelinski

Answer: C Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Easy 108.

Which of the given choices is the correct sequence of the tetrapeptide that is formed by the reaction sequence shown?

Boc Cl

polymer

H N

O O OH

O CF3COH

A. B. C. D. E.

Cys-Ala-Phe-Ser Cys-Phe-Ala-Ser Ser-Ala-Phe-Cys Ser-Phe-Ala-Cys none of these

Answer: A Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 109.

Provide the steps necessary to prepare the tetrapeptide Thr-Val-Ile-Met using the Merrifield synthesis beginning with a polymer bonded to CH2Cl.

H N

Boc

O (CH2)2SCH3

polymer

O CF3COH

O Boc-Ile

CF3COH

DCC

O Boc-Val

CF3COH

DCC O

Boc-Thr

CF3COH

DCC Sequence 1

A. Sequence 1 B. Sequence 2 C. Sequence 3 D. Sequence 4 E. Sequence 5 Answer: A Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 110.

Which of the given choices is the correct sequence for the pentapeptide that is formed by the reaction sequence shown?

Boc Cl

A. B. C. D. E.

H N

O (CH2)2SCH3

polymer

O CF3COH

Boc-Gly DCC

Leu-Lys-Ala-Gly-Met Met-Gly-Ala-Lys-Leu Cys- Gly-Ala-Lys-Leu Leu-Lys-Ala-Gly-Cys none of these

Answer: A Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 111.

Which of the given choices is the correct sequence for the pentapeptide that is formed by the reaction sequence shown?

Boc Cl

polymer

H N

O O CH 2OH

O CF3COH

Boc-Thr DCC

A. B. C. D. E.

Ser-Thr-Pro-Lys-Leu Leu-Lys-Pro-Thr-Ser Thr-Thr- Pro-Lys-Leu Leu-Lys-Pro-Thr-Thr none of these

Answer: B Learning Objective: 25.6 Describe the reagents and reaction sequence necessary for peptide synthesis, including the Merrifield synthesis Difficulty: Hard 112.

The ______ of amino acids in a protein is referred to as its primary structure.

A. B. C. D. E.

twisting sequence folding bonding reacting

Answer: B Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 113.

The ______ structure of a protein is most important because the ______of the amino acids determines its overall shape, function and properties.

A. B. C. D. E.

primary, twisting primary, sequence secondary, twisting secondary, folding tertiary, folding

Answer: B Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 114.

The secondary structure of a protein is due to ________ between amino acid residues.

A. B. C. D. E.

hydrophobic interactions hydrogen bonding salt bridges disulfide linkage covalent bonding

Answer: B Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 115.

The hydrogen bonding between the carbonyl group of an amino acid with the amino group of the fourth amino acid farther along the chain leads to ______.

A. B. C. D. E.

parallel b-pleated sheets antiparallel b-pleated sheets a-helix b-helix none of these

Answer: C Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 116.

Hydrogen bonding between the carbonyl group of an amino acid on one strand with the amino group of the neighboring strand leads to ______.

A. B. C. D. E.

parallel b-pleated sheets antiparallel b-pleated sheets an a-helix a b-helix either A or B

Answer: E Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 117.

Which of the choices is a secondary structure of fibroin found in spider web and silk?

A. B. C. D. E.

b-pleated sheets a-pleated sheets a-helix b-helix none of these

Answer: A Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 118.

Which of the choices is a major component of the secondary structure of keratin found in hair?

A. B. C. D. E.

b-pleated sheets a-pleated sheets a-helix b-helix cylinder

Answer: C Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Medium 119.

Which of the given side chain interactions results in the tertiary structure of a protein?

A. B. C. D. E.

hydrogen bonding salt bridges disulfide linkages hydrophobic interactions all of these

Answer: E

Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 120.

Heating of proteins results in loss of activity and the process is referred to as _______.

A. B. C. D. E.

hydrolysis denaturation sequencing hydrophobic interactions covalent bonding

Answer: B Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 121.

Denaturation of proteins results in loss of ________structure.

A. B. C. D. E.

primary secondary tertiary B and C A, B and C

Answer: D Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 122.

Denaturation is ______.

A. B. C. D. E.

irreversible reversible with heat reversible with a catalyst reversible with UV reversible under the same conditions

Answer: A Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy

123.

Cooking an egg is an example of ________________, and is irreversible.

Answer: denaturation Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 124.

The quaternary structure of a protein is due to _______.

A. B. C. D.

hydrogen bonding within the peptide aggregation of two or more polypeptides disulfide linkages within the peptide covalent bonding between peptides

Answer: B Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 125.

In a quaternary structure, the nonpolar groups are attracted to each other with _________________.

A. B. C. D. E.

hydrogen bonding van der Waals interactions ion-dipole interactions dipole-dipole interactions covalent bonding

Answer: B Learning Objective: 25.7 Describe the primary, secondary, tertiary, and quaternary structures of proteins, and the structures of the alpha helix and beta pleated sheet Difficulty: Easy 126.

Proteins that consist of linear polypeptide chains bundled together are classified as________.

A. B. C. D. E.

globular proteins fibrous proteins lipoproteins tetrapeptides pleated sheets

Answer: B Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy 127.

Proteins that are chains that are coiled into compact shapes are classified as________.

A. B. C. D. E.

globular proteins fibrous proteins lipoproteins tetrapeptides pleated sheets

Answer: A Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy 128.

a-Keratin found in hair, nails, and feathers is classified as ______.

A. B. C. D. E.

globular protein fibrous protein structural protein B and C none of these

Answer: D Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy 129.

a-Keratin found in nails has more strength than a-keratin found in hair due to the presence of more ___________.

A. B. C. D. E.

hydrophobic interactions salt bridges a-helix disulfide bridges pleated sheets

Answer: D

Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Medium 130.

Proteins that catalyze biochemical reactions are called ______.

A. B. C. D. E.

apoproteins peptides enzymes transport proteins cellular proteins

Answer: C Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy 131.

Hemoglobin, found in blood, is classified as a ______ protein.

A. B. C. D. E.

structural regulatory transport fibrous globular

Answer: C Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy 132.

The heme group present in hemoglobin is called a _______.

A. B. C. D. E.

prosthetic group substrate cofactor byfactor enzyme

Answer: A Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy

133.

_______________ is a condition where the hemoglobin is distorted.

A. Malaria B. Sickle cell anemia C. Spina bifida D. Thalassemia E. Scabies Answer: B Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy 134.

How do enzymes speed up a reaction?

A. By changing the free energy of the reaction B. By increasing the amount of energy released C. By making reactions exergonic D. By lowering the activation energy required E. By adding heat to the reactants Answer: D Learning Objective: 25.8 Discuss the structures and functions of fibrous, globular, structural, and transport proteins and enzymes Difficulty: Easy

Klein, Organic Chemistry 4e Chapter 26 1.

Which of the given statements is (are) true about lipids?

A. B. C. D. E.

Lipids are soluble in nonpolar organic solvents Lipids include waxes, steroids, and triacylglycerides Lipids have little in common except their solubility Many lipids have biological roles all of these

Answer: E Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 2.

Which of the choices is a class of complex lipids?

A. B. C. D. E.

steroids terpenes waxes prostaglandins furans

Answer: C Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 3.

Which one of the choices is a class of simple lipids?

A. B. C. D. E.

steroids triglycerides phoshpholipids waxes furans

Answer: A Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 4.

Which of the choices is not a class of complex lipids?

A. B.

waxes prostaglandins

C. D.

triglycerides phospholipids

Answer: B Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 5.

Which of the choices is not a class of simple lipids?

A. B. C. D.

phospholipids prostaglandins terpenes steroids

Answer: A Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 6.

Which one of the choices is a complex lipid?

A. B. C. D. E.

cortisone vitamin A prostaglandins progestin tripalmitin

Answer: E Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Medium 7.

Which of the choices is a simple lipid?

O CH 2OC(CH2)16CH 3 O

CH 2OC(CH2)14CH 3 O

CHOC(CH 2)16CH3 O

CHOC(CH 2)14CH3

CH2OPOCH 2CH 2N(CH 3) 3

CH 2OC(CH2)14CH3 O

O lecithin

A. B. C. D. E.

tripalmitin

lecithin tripalmitin sodium lauryl sulfate androsterone carbohydrates

Answer: D Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Medium 8.

______lipids do not undergo hydrolysis in the presence of aqueous acid or base.

A. B. C. D. E.

simple complex heterogeneous acidified any

Answer: A Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy

______lipids undergo hydrolysis in the presence of aqueous acid or base.

A. B. C. D. E.

simple complex heterogeneous acidified any

Answer: B Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 10.

Complex lipids contain the _____________ functional group and are __________ in organic solvents.

A. B. C. D. E.

ester, not soluble ketone, not soluble alcohol, soluble ester, soluble ether, soluble

Answer: D Learning Objective: 26.1 Define the terms lipids, simple lipids, and complex lipids Difficulty: Easy 11.

Which of the choices is a correct description of waxes?

A. B. C. D. E.

long chain esters long chain ethers long chain anhydrides long chain fatty acids long chain alcohols

Answer: A Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Easy

12.

Which of the choices is a structure of a wax?

CH3(CH 2)14COCH2(CH 2)28CH3

CH3(CH2)20COCH2CH2CH 3

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Easy 13.

What are the predicted products when spermaceti is treated with aqueous NaOH?

O CH3(CH2)14COCH2(CH2)14CH3

NaOH/H2O

O CH3(CH 2)14CONa + CH 3(CH2)14CH 2OH I

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Medium 14.

What are the predicted products when triacontyl hexadecanoate, a major component of beeswax, is treated with aqueous NaOH?

O CH3(CH2)14COCH2(CH2)28CH3

NaOH/H2O

O CH3(CH 2)14COH + CH3(CH2)28CH2ONa I

A. B. C. D. E.

I II III IV none of these

Answer: D Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Medium 15.

The exoskeleton of all insects is covered by _____________.

A. B. C. D. E.

a protective coating of wax a lubricating layer of oils a barrier of hairs a complex system of scales a cholesterol-rich layer of membrane

Answer: A Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Easy

16.

Birds have a layer of wax on their ______________, making them water repellant.

A. B. C. D. E.

legs feathers ears skin eyes

Answer: B Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Easy 17.

Sheep have ___________________ on their wool.

A. B. C. D. E.

oil lanolin spermaceti carnauba wax beeswax

Answer: B Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Easy 18.

______________ is produced by the Brazilian palm tree and is commonly used in polish formulations for boats and cars.

A. B. C. D. E.

Oil Lanolin Spermaceti Carnauba wax Beeswax

Answer: D Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Easy 19. What compound produces the products showing when treated with aqueous NaOH?

O CH3(CH 2)14CONa

CH 3(CH 2)14CH2OH

A. lanolin B. beeswax C. spermaceti D. cholesterol E. lecithin Learning Objective: 26.2 Describe the structure and physical properties of a wax Difficulty: Medium 20.

The compound shown is best classified as a(n) _________.

O CH2OCCH2(CH 2)16CH3 O CHOCCH2(CH 2)16CH3 CH2OCCH2(CH 2)16CH3 O A. B. C. D. E.

simple lipid fat cephalin wax oil

Answer: B Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 21.

The compound shown is best classified as a(n) _________.

O CH2OC(CH 2) 6CH=CH(CH2)6CH 3 O CHOC(CH 2)6CH=CH(CH2)6CH 3 CH2OC(CH 2) 6CH=CH(CH2)6CH 3 O A. B. C. D. E.

simple lipid fat cephalin wax oil

Answer: E Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 22.

The compound shown is best classified as a(n) _________.

O CH3(CH 2)14CH=CH(CH2)6COH A. B. C. D. E.

simple lipid unsaturated triglyceride unsaturated fatty acid fat wax

Answer: C Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 23.

The compound shown is best classified as an _________.

O CH3(CH 2)14COH A. B. C. D. E.

simple lipid saturated triglyceride saturated fatty acid fat wax

Answer: C Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 24.

Which of the given fatty acids is not likely to occur in a natural source?

A. B. C. D. E.

octadecanoic acid hexadecanoic acid (Z)-9-hexadecenoic acid pentadecanoic acid (Z)-11-tetradecenoic acid

Answer: D Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Medium 25.

Which of the given fatty acids are most likely to occur in natural sources?

O OH I

A. B. C. D. E.

I and III I, III and IV II and V IV and V I, III, IV and V

Answer: D Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 26.

Arrange the given compounds in decreasing order of melting point.

CH3(CH 2)14COH

CH3(CH 2)10COH

A. B. C. D. E.

II > I > IV > III III > IV > I > II IV > I > II > III III > II > IV > I I > II > IV > III

Answer: B Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Medium 27.

Which one of the given fatty acids has the highest melting point?

A. B. C. D. E.

stearic acid palmitic acid lauric acid arachidic acid oleic acid

Answer: D Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 28.

Which one of the given fatty acids has the lowest melting point?

A. B. C. D. E.

stearic acid palmitic acid lauric acid arachidic acid myristic acid

Answer: C Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 29.

Which one of the given fatty acids has the highest melting point?

A. B. C.

oleic acid linoleic acid palmitoleic acid

D. E.

arachidonic acid arachidic acid

Answer: E Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 30.

Which one of the given fatty acids has the lowest melting point?

A. B. C. D. E.

oleic acid linoleic acid palmitoleic acid arachidonic acid arachidic acid

Answer: D Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 31.

Which one of the choices has the highest melting point?

O CH2OC(CH2)7CH=CH(CH 2)7CH3 O CHOC(CH2)7CH=CH(CH2)7CH 3 CH 2OC(CH2)7CH=CH(CH 2)7CH3 O triolein

O CH2OC(CH 2)12CH3 O CHOC(CH 2)12CH3 CH2OC(CH 2) 12CH3 O trimyrsitin A. B. C. D.

triolein trilinolein tripalmitolein trimyrisitin

Answer: D Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 32.

Which one of the choices has the lowest melting point?

O CH2OC(CH 2) 10CH3 O

O CH 2OC(CH 2)16CH3 O

CHOC(CH 2)10CH3

CHOC(CH 2)16CH3

CH2OC(CH 2) 10CH3

CH 2OC(CH 2)16CH3

O trilaurin

O tristearin

O CH2OC(CH 2) 7CH=CH(CH2)5CH 3 O CHOC(CH 2)7CH=CH(CH2)5CH3 CH2OC(CH 2) 7CH=CH(CH2)5CH 3 O tripalmitolein A. B. C. D.

trilaurin tristearin trilinolein tripalmitolein

Answer: C Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 33.

Which one of the choices is classified as a fat?

A. B. C. D.

triolein trilinolein tripalmitolein triarchadin

Answer: D Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 34.

Which one of the choices is classified as an oil?

A. B. C. D.

trilaurin trilinolein tripalmitin triarchadin

Answer: B

Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 35.

Which of the given fatty acids is not likely to be present in natural fats and oils?

A. B. C. D. E.

octadecanoic acid heptadecanoic acid hexadecanoic acid octadeca-9,12-dienoic acid none of these

Answer: B Learning Objective: 26.3 Discuss the composition of triglycerides and the various factors that affect their melting points Difficulty: Easy 36.

Which of the given reagent(s) would convert palmitoleic acid to palmitic acid?

A. B. C. D. E.

NaBH4/CH3OH 1. LiAlH4, 2. H2O NaOH/H2O heat H2/Ni A and B

Answer: D Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 37.

Which of the given fatty acids is produced when oleic acid is hydrogenated?

O CH3(CH2)7CH=CH(CH2)7COH A. B. C. D. E.

palmitic acid lauric acid myrsitic acid arachidic acid stearic acid

Answer: E

hydrogenation

Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Medium 38.

What is the predicted product of the reaction shown?

O CH2OC(CH 2) 7CH=CH(CH2)7CH 3 O CHOC(CH 2)7CH=CH(CH2)5CH3 CH2OC(CH 2) 7CH=CH(CH2)7CH 3 O

H 2/Ni pressure

CH2OC(CH2)16CH3

CH2OC(CH2)7CH=CH(CH2)7CH3

CHOC(CH2)14CH3

CHOC(CH2)7CH=CH(CH2)5CH3

CH2OC(CH2)16CH3

CH2OCH2(CH2)7CH=CH(CH2)7CH3

O I

O CH2OC(CH2)16CH3

CH2OCH2(CH2)7CH=CH(CH2)7CH3

O CHOC(CH2)14CH3

CHOCH2(CH2)7CH=CH(CH2)5CH3

CH3

CH2OCH2(CH2)7CH=CH(CH2)7CH3 III

O CH2OC(CH2)7CH2CH2(CH2)7CH3 O CHOC(CH2)7CH=CH(CH2)5CH3 CH2OC(CH2)7CH2CH2(CH2)7CH3 O V

A. B.

I II

C. D. E.

III IV V

Answer: A Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Medium 39.

What is(are) the predicted product(s) of the reaction shown?

O CH2OC(CH 2) 7CH=CH(CH2)3CH=CH(CH 2)2CH3 O CHOC(CH2)7CH=CH(CH 2)5CH3 CH2OC(CH2)7CH=CH(CH 2)3CH=CH(CH2)2CH 3 O Answer:

excess H2/Ni pressure

O CH2OC(CH2)7CH=CH(CH2)3CH2CH2(CH2)2CH3 O I

CHOC(CH2)7CH=CH(CH2)5CH3 CH2OC(CH2)7CH=CH(CH2)3CH2CH2(CH2)2CH3 O O CH2OC(CH2)7CH=CH(CH2)3CH=CH2 O

CHOC(CH2)7CH=CH(CH2)5CH3 CH2OCH2(CH2)7CH=CH(CH2)3CH=CH2 O CH2OC(CH2)16CH3 O

III

CHOC(CH2)14CH3 CH2OC(CH2)16CH3 O CH3 O CHOC(CH2)7CH=CH(CH2)5CH3

CH2OCH2(CH2)7CH=CH(CH2)3CH=CH(CH2)2CH3 A. B.

I II

C. D. E.

III IV A or B

Answer: C Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Medium 40.

How many different structures (including stereoisomers) are possible for a triglyceride that contains two palmitic acid residues and one stearic acid residue?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Medium 41.

How many different structures (including stereoisomers) are possible for a triglyceride that contains one palmitic acid residue, one arachidic acid residue and one stearic acid residue?

A. B. C. D. E.

3 6 9 12 15

Answer: B Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Medium 42.

In the presence of molecular oxygen, autooxidation to yield hydroperoxides.

A. B.

true false

saturated

triglycerides

undergo

Answer: B Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 43.

Unsaturated triglycerides undergo autooxidation at the ___________ position of the fatty acid residue.

A. B. C. D. E.

vinylic allylic gamma delta next to carbonyl

Answer: B Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 44.

The rancid smell from unsaturated oils is due to ______________.

A. B. C. D. E.

the reduction of the ester group the oxidation of the ester group the oxidation of the alkene the reduction of the alkene autooxidation

Answer: E Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 45.

The interior of a micelle is ______, whereas the exterior is _______.

A. B. C. D.

hydrophilic, hydrophobic hydrophilic, hydrophilic hydrophobic, hydrophobic hydrophobic, hydrophilic

Answer: D Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides

Difficulty: Easy 46.

The reaction of triglycerides with a base is a(n) ________ reaction.

A. B. C. D. E.

esterification transesterification saponification autooxidation oxidation

Answer: C Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 47.

What is(are) the predicted product(s of the reaction shown?

O CH2OC(CH 2) 14CH3 O CHOC(CH 2)16CH3 CH2OC(CH 2) 14CH3 O Answer:

NaOH excess D

OH I

HOCH2CHCH2OH O

2 CH3(CH2)14CONa O

III

CH3(CH2)16CONa OH CH2OCH(CH2)14CH3

OH CHOCH(CH2)16CH3 CH2OCH(CH2)14CH3 OH

A. B. C. D. E.

I II III IV A, B, and C

Answer: E Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Medium 48.

What is(are) the predicted product(s of the reaction shown?

O CH2OC(CH2)14CH3 O CHOC(CH2)16CH3

H3O+ excess H

CH2OC(CH2)14CH3 O

O I

CH3(CH2)16COH O

CH3(CH2)14COH OH

III

HOCH2CHCH2OH OH

HOCH2CHCH2OH

A. B. C. D. E.

I II III A and B A and C

O CH3(CH2)16COH

O 2 CH3(CH2)14COH O CH3(CH2)16COH

Answer: E Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Hard

49.

An optically active triglyceride produced two palmitic acid residues and one oleic acid residue, when heated in the presence of an acid. What is the structure(s) of the triglyceride(s) produced?

CH2OC(CH2)14CH3 O

CHOC(CH2)14CH3

CHOC(CH2)16CH3

CH2OC(CH2)7CH=CH(CH2)7CH3

CH2OC(CH2)14CH3

A. B. C. D. E.

CH2OC(CH2)14CH3

I II III IV B and C

Answer: A Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides

Difficulty: Hard 50.

An optically inactive triglyceride produced two palmitic acid residues and one oleic acid residue, when heated in the presence of an acid. What is the structure(s) of the triglyceride(s) produced?

CH2OC(CH2)14CH3 O

CHOC(CH2)16CH3

CH2OC(CH2)7CH=CH(CH2)7CH3

CH2OC(CH2)14CH3

I II III IV B and C

Answer: C

CHOC(CH2)14CH3

A. B. C. D. E.

CH2OC(CH2)14CH3

Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Hard 51.

When heated in the presence of an acid, a triglyceride produced a linoleic acid residue, a palmitoleic acid residue, and an oleic acid residue. What is possible structures for this triglyceride?

O CH2OC(CH2)7CH=CHCH2CH=CH(CH2)4CH3 O I

CHOC(CH2)7CH=CH(CH2)5CH3 CH2OC(CH2)7CH=CH(CH2)7CH3 O O CH2OC(CH2)7CH=CHCH2(CH2)6CH3 O

CHOC(CH2)7CH=CH(CH2)5CH3 CH2OC(CH2)7CH=CH(CH2)7CH3 O O CH2OC(CH2)7CH=CHCH2CH=CH(CH2)4CH3 O

III

CHOC(CH2)7CH=CH(CH2)5CH3 CH2OC(CH2)7CH2(CH2)5CH3 O

A. B. C. D. E.

I II III A and B B and C

Answer: A Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Hard 52.

An optically active triglyceride that produced two myristic acid residues and an oleic acid residue when heated in the presence of an acid. What is the structure of this triglyceride?

CH2OC(CH2)10CH3

CH2OC(CH2)12CH3

CHOC(CH2)12CH3

CH2OC(CH2)7CH=CH(CH2)2CH3

CH2OC(CH2)7CH=CH(CH2)7CH3

CH2OC(CH2)11 CH3

CH2OC(CH2)11 CH=CHCH3

CHOC(CH2)12CH3

CH2OC(CH2)7CH3

O IV

III

O CH2OC(CH2)12CH=CHCH3 O CHOC(CH2)12CH3 CH2OC(CH2)7CH=CH(CH2)7CH3 O V

A. B. C.

I II III

D. E.

IV V

Answer: B Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Hard 53.

What is(are) the predicted product(s of the reaction shown?

O CH2OC(CH 2) 14CH3 O CHOC(CH 2)16CH3 CH 2OC(CH2)14CH 3

excess CH3CH 2OH H2SO 4

CH3(CH2)16COCH2CH3 HOCH2CHCH2OH 2 CH3(CH2)14COCH2CH3 I

A. B. C. D. E.

III

I II III I and II I, II, and III

Answer: E Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Hard 54.

What is(are) the predicted product(s of the reaction shown?

O CH2OC(CH 2) 14CH3 excess (CH3)2CHOH

O CHOC(CH 2)14CH3

H 2SO4

CH 2OC(CH2)14CH 3 O

OH I

3 CH3(CH2)14CHOCH(CH3)2

OH II

HOCH2CHCH2OH O

III

3 CH3(CH2)14COCH(CH3)2

A. B. C. D. E.

I II III I and II II and III

Answer: E Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Hard 55.

What fuel is produced when vegetable oil undergoes transesterification?

A. B.

gasoline diesel

C. D. E.

biodiesel kerosene natural gas

Answer: C Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 56.

What substance can be made from heating animal fat with wood ashes, which contain alkaline substances?

A. B. C. D. E.

detergent soap cooking oil kerosene biodiesel

Answer: B Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 57.

Which of the substance shown has a hydrophobic group and a hydrophilic group, but does not generate a precipitate through the ion exchange reaction?

A. B. C. D. E.

detergent soap cooking oil kerosene biodiesel

Answer: A Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 58.

What are the ions that are typically in soap scum?

A. B. C. D.

sodium and potassium lithium and potassium hydroxide and nitrate calcium and magnesium

silver and tin

Answer: D Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 59.

Which of the compounds shown is used as a detergent?

O CH3(CH 2)14CONa I

A. B. C. D. E.

CH3(CH 2)15OSONa CH3(CH2)14CO Ca 2 O III II

I II III IV V

Answer: B Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 60.

Which of the given compounds is used as a soap?

O CH3(CH 2)14CONa I

CH3(CH 2)15OSONa CH3(CH2)14CO Ca 2 O III II

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 26.4 Discuss the hydrogenation, oxidation, saponification, and transesterification of triglycerides Difficulty: Easy 61.

Phosphoglycerides differ from triglycerides in that one of the three fatty acid residues is replaced by a(n) ______ group.

A. B. C. D. E.

thioester phosphoester thiol alcohol ester

Answer: B Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 62.

Phosphoglycerides that contain ethanolamine are called_____.

A. B. C. D. E.

lecithins phosphatidyl serines plasmalogens cephalins biodiesel

Answer: D Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy

63.

Phosphoglycerides that contain choline are called_____.

A. B. C. D. E.

lecithins phosphatidyl serines plasmalogens cephalins biodiesel

Answer: A Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 64.

Which of the choices is a phosphatidic acid?

A. B. C. D.

phosphoric acid phosphoric acid monoester phosphoric acid diester phosphoric acid trimester

Answer: B Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 65.

Which of the given compounds is a phosphatidic acid?

CH2OC(CH 2) 14CH3 O

CH 2OC(CH2)14CH 3 O

CHOC(CH 2)16CH3

CHOC(CH2)16CH 3

CH2OP(OH)2

CH 2OC(CH2)14CH 3

O I

O II

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 66.

Which of the given lipids would produce two fatty acid residues along with ethanolamine on hydrolysis?

A. B. C. D. E.

cephalins phosphatidyl serines triolein lecithins phospholipid

Answer: A Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 67.

Which of the given lipids would produce two fatty acid residues along with choline on hydrolysis?

A. B. C. D. E.

cephalins phosphatidyl serines triolein lecithins phospholipid

Answer: D Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 68.

What are the components of lechithins and cephalins?

A. B. C. D.

three polar head groups two polar head groups and one nonpolar hydrophobic tail one polar head group and two nonpolar hydrophobic tails three nonpolar hydrophobic tails

Answer: C Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 69.

Which of the choices is the structure of a cephalin that would produce one equivalent of oleic acid and one equivalent of stearic acid residues on hydrolysis?

CH2OC(CH 2) 7CH=CH(CH2)7CH 3 O

CH2OC(CH 2)7CH=CH(CH2)7CH 3 O

CHOC(CH 2)16CH3

CH2OPOCH 2CH 2NH3 O

CH2OPOCH 2CH2N(CH 3) 3 O

O CH2OC(CH 2) 16CH3

O CHOC(CH 2)7CH=CH(CH2)7CH 3

CHOC(CH 2)7CH=CH(CH 2)7CH3 O

O CH 2OPOCH 2CH2NH3 O

CH2OPOCH2CH 2N(CH 3)3 O

III A. B. C. D. E.

CH2OC(CH2)16CH3

I II III I and III II and IV

Answer: D Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Hard 70.

Which choice(s) show(s) the structure of a cephalin that would produce two oleic acid residues on hydrolysis?

CH2OC(CH2)7CH=CH(CH2)7CH3 O

CHOC(CH2)7CH=CH(CH2)7CH3

CH2OPOCH2CH2NH3

CH2OCCH2CH2NH3

O II

O CH2OC(CH2)7CH=CH(CH2)7CH3 O

CH2OC(CH2)7CH=CH(CH2)7CH3 O

CHOC(CH2)7CH=CH(CH2)7CH3

CHOC(CH2)7CH=CH(CH2)7CH3 O

O CH2OPOCH2CH2CH3

CH2OCOCH2CH2CH3

O III

A. B. C. D. E.

I II III IV A and B

Answer: A Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Hard 71.

Which choice(s) show(s) the structure of a lecithin that would produce two stearic acid residues on hydrolysis?

O CH2OC(CH2)10CH3 O

CH2OC(CH2)16CH3 O

CHOC(CH2)16CH3

CHOC(CH2)16CH3 O

O CH2OPOCH2CH2N(CH3)3

CH2OPOCH2CH2N(CH3)3 O

CH2OC(CH2)12CH3 O

CH2OC(CH2)14CH3 O

CHOC(CH2)14CH3

CHOC(CH2)10CH3

CH2OPOCH2CH2N(CH3)3 O

O III

A. B. C. D. E.

CH2OPOCH2CH2N(CH3)3 IV

I II III IV A and B

Answer: B Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Medium 72.

A lipid bilayer is formed by the self assembly of _________.

A. B.

triglycerides saturated fatty acids

C. D. E.

phosphoglycerides unsaturated fatty acids alcohols

Answer: C Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 73.

Explain why fatty acids cannot form a bilayer.

Answer: Fatty acids have a polar head group and a nonpolar tail, but their geometry prevents them from forming a bilayer because the assembly of a bilayer would leave empty space between each fatty acid. Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Medium 74.

Why is decanol more efficient at crossing the cell membrane than hexanol?

Answer: Decanol has a longer hydrophobic tail than hexanol, therefore it is more efficient in crossing the nonpolar cell membrane. Learning Objective: 26.5 Compare the structures of phospholipids and triglycerides and of cephalins and lecithins, and describe the formation of a lipid bilayer Difficulty: Easy 75.

Which of the choices is a correct description of the compound shown?

H HO A. B. C.

H triglyceride steroid phospholipid

D. E.

prostaglandin terpene

Answer: B Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 76.

In naturally occurring steroids mostly the B-C ring fusion is ______and the C-D ring fusion is ______.

A. B. C. D. E.

cis, trans cis, cis trans, cis trans, trans both cis and trans, both cis and trans

Answer: D Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 77.

In androsterone the A-B ring fusion is ______and the B-C ring fusion is ______.

C A HO

A. B. C. D. E.

Androsterone

cis, trans cis, cis trans, cis trans, trans both cis and trans, both cis and trans

Answer: D

Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 78.

In estrone the B-C ring fusion is ______and the C-D ring fusion is ______.

O C H A

H B

HO A. B. C. D. E.

D H

Estrone cis, trans cis, cis trans, cis trans, trans both cis and trans, both cis and trans

Answer: D Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Medium 79.

Which of thechoices correctly shows the numbering of the steroid nucleus?

12 11 1 2 3 4

10 5 I

11 15

9 17 16 8 7 6

13 14 1 2 3 4

6 5

13 17 16

7 8 14 15 9 10 II

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 80.

What is the predicted product when cholesterol is treated with acetyl chloride in presence of pyridine?

H H acetyl chloride

pyridine H HO

H H H H

H H H

H H

O OH

H H

III

HO A. B. C. D. E.

I II III A or B B or C

Answer: B Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Medium

81. What is the predicted major product when cholesterol is treated with peroxy acetic acid?

H H peroxy acetic acid

H H HO

H H H I

HO H H H II

H HO

OH OH

H H H

III

H HO

A. B. C. D. E.

I II III A and B B and C

Answer: C Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Medium

82.

What is the predicted major product when cholesterol is treated with hydrogen in the presence of a palladium catalyst?

H H H 2/Pd

H H HO

H H H H

H H

H H H

III

HO OH A. B. C. D. E.

I II III A and B A and C

Answer: B Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Medium

83.

Which of the choices is a male sex hormone?

A. B. C. D. E.

estrone androsterone cortisone lanosterol progesterone

Answer: B Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 84.

Which of the choices is a female sex hormone?

A. B. C. D. E.

estrone androsterone cortisone lanosterol nandrolone

Answer: A Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 85.

Male sex hormones are called ______ and female sex hormones are called ____.

A. B. C. D. E.

progestins; estrogens and androgens testosterone; androgens corticosteroids; estradiols progestins; estrogens androgens; estrogens and progestins

Answer: Dandrogens, estrogens and progestins Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 86.

Which of the given hormones is (are) female sex hormones?

A. B.

estrone androsterone

C. D. E.

cortisone estradiol both A and D

Answer: E Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 87.

Which of the given hormones is (are) especially important in the development of male characteristics?

A. B. C. D. E.

testosterone androsterone cortisone estradiol both A and B

Answer: E Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Medium 88.

Which one of the choices is used to treat the inflammatory condition caused by arthritis?

A. B. C. D. E.

norethindrone androsterone cortisone lanosterol stanozolol

Answer: C Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 89.

Which of the given steroid hormones is secreted by the adrenal cortex?

A. B. C. D.

cortisone androsterone esrone lanosterol

estradiol

Answer: A Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 90.

Which of the choices is an anabolic steroid?

A. B. C. D. E.

cortisone androsterone esrone nandrolone progesterone

Answer: D Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Easy 91.

What is the predicted product when testosterone is treated with PCC?

OH H

H H

OH H

H H

III

O H H

O V

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Hard

92.

What is the predicted product when estradiol is treated with excess NaH followed by excess bromopropane?

OH excess 1. NaH 2. bromopropane

H H HO

O H I

H HO

O H

H O

OH H

III

H HO

OH H IV

H HO

A. B. C. D. E.

I II III IV C and D

Answer: B Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Hard 93.

Which of the choices isa chair conformation for the compound shown?

O H H HO

H O

HO H

H II

HO H

H O

H III

HO O H O

H H

H O

OH A. B. C. D. E.

I II III IV V

Answer: A

Learning Objective: 26.6 Discuss the structures and functions of naturally occurring steroids Difficulty: Medium 94.

Prostaglandins are made up of ___ carbon atoms.

A. B. C. D. E.

14 16 18 20 22

Answer: D Learning Objective: prostaglandins Difficulty: Easy

26.7

Discuss

the

structure,

synthesis,

95.

Which of the choices is not a characteristic of prostaglandins?

A. B. C. D. E.

five-membered cyclic ring carbonyl group two side chains hydroxyl group six-membered monocyclic ring

Answer: E Learning Objective: prostaglandins Difficulty: Easy

26.7

Discuss

the

structure,

synthesis,

96.

Which of thechoices can be characteristics of prostaglandins?

A. B. C. D. E.

five-membered cyclic ring carbonyl group two side chains hydroxyl group all of these

Answer: E Learning Objective: prostaglandins Difficulty: Medium

26.7

Discuss

the

structure,

synthesis,

and

functions

and

functions

and

functions

97.

Which of the choices is a common characteristic of prostaglandins PGA, PGB and PGC?

A. B. C. D. E.

They all have a hydroxyl group in the five-membered ring They all have a carbonyl group in the five-membered ring They all have a C double bonded to C in the five-membered ring A and B B and C

Answer: E Learning Objective: prostaglandins Difficulty: Medium

26.7

Discuss

the

structure,

synthesis,

and

functions

98.

Which of the choices is a common characteristic of prostaglandins PGD and PGE?

A. B. C. D. E.

They are both diols. They both are α-hydroxyketones. They both are b-hydroxyketones. They are both aldehydes. They are both aromatic.

Answer: C Learning Objective: prostaglandins Difficulty: Medium 99.

26.7

Discuss

the

structure,

synthesis,

functions

Which one of the choices is a correct representation of PGBs?

O R

R' I I II III

III

OH R

R HO

A. B. C.

and

O V

D. E.

IV V

Answer: C Learning Objective: prostaglandins Difficulty: Easy 100.

26.7

Discuss

the

structure,

synthesis,

and

O R

OH R

R HO

III

I II III IV V

Answer: B Learning Objective: prostaglandins Difficulty: Easy 101.

26.7

Discuss

the

structure,

synthesis,

and

functions

Which one of the choices is a correct representation of PGAs?

O R

R' I A.

Which one of the choices is a correct representation of PGCs?

A. B. C. D. E.

functions

O R

III

B. C. D. E.

II III IV V

Answer: A Learning Objective: prostaglandins Difficulty: Easy 102.

26.7

Discuss

the

structure,

O R

HO I

functions

III

R V

I II III IV V

Answer: D Learning Objective: prostaglandins Difficulty: Easy 103.

and

Which one of the choices is a correct representation of PGFs?

A. B. C. D. E.

synthesis,

26.7

Discuss

the

structure,

synthesis,

and

functions

Which one of the choices is a correct representation of PGDs?

O R

HO I

III

R V

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: prostaglandins Difficulty: Easy 104.

26.7

Discuss

the

structure,

O R

HO I

functions

III

R V

I II III IV V

Answer: D Learning Objective: prostaglandins Difficulty: Easy 105.

and

Which one of the choices is a correct representation of PGEs?

A. B. C. D. E.

synthesis,

26.7

Discuss

the

structure,

synthesis,

and

functions

Which one of the choices is an accurate classification of the compound shown?

O O OH HO HO A. B. C. D. E.

steroid prostaglandin triglyceride terpene lecithin

Answer: B Learning Objective: prostaglandins Difficulty: Medium

26.7

Discuss

the

structure,

synthesis,

106.

Which one of the choices is not classified as an eicosanoid?

A. B. C. D. E.

leukotrienes prostaglandins thromboxanes prostacyclins cortisone

Answer: E Learning Objective: prostaglandins Difficulty: Medium

26.7

Discuss

the

structure,

synthesis,

and

functions

and

functions

107.

Aspirin blocks the biosynthesis of which of the given eicosanoids?

A. B. C. D. E.

leukotrienes prostaglandins thromboxanes prostacyclins C and D

Answer: B

Learning Objective: prostaglandins Difficulty: Medium 108.

26.7

Discuss

the

structure,

synthesis,

and

functions

The structure for PGF2bis shown. What structural feature is represented by 2b In the name of this compound?

HO O OH HO HO A. B. C. D. E.

2 represents the number of double bonds b represents the trans relationship between the two OH groups b represents the trans relationship between the side chains A and C A and B

Answer: E Learning Objective: prostaglandins Difficulty: Medium

26.7

Discuss

the

structure,

synthesis,

and

109.

Which of the choices is(are) synthesized from arachidonic acid?

A. B. C. D. E.

leukotrienes prostaglandins thromboxanes prostacyclins all of these

Answer: E Learning Objective: prostaglandins Difficulty: Easy

26.7

Discuss

the

structure,

synthesis,

and

functions

110.

Which of the choices is a precursor for the synthesis of prostaglandins?

A. B. C. D. E.

arachidonic acid linoleic acid cholesterol linolenic acid biodiesel

Answer: A Learning Objective: prostaglandins Difficulty: Easy

26.7

Discuss

the

structure,

synthesis,

and

functions

111.

Compounds containing repeated isoprene units are called ________.

A. B. C. D. E.

cephalins terpenes eicosanoids steroids diterpene

Answer: B Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Easy 112.

Which one of the compounds shown is classified as a sesquiterpene?

O H I A. B. C. D.

I II III IV

III

all of these

Answer: A Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 113.

How many carbons are in a tetraterpene?

A. B. C. D. E.

10 15 20 30 40

Answer: E Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Easy 114.

Citral is best classified as a ___________.

O H Citral A. B. C. D. E.

monoterpene diterpene sesquiterpene triterpene tetraterpene

Answer: A Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 115.

The structure of capsanthin, found in capsicum, is shown. Which of the choices is an accurate classification of capsanthin?

O HO A. B. C. D. E.

monoterpene diterpene sesquiterpene triterpene tetraterpene

Answer: E Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 116.

How many isoprene units does the given compound have?

OH O A. B. C. D. E.

1 2 3 4 5

Answer: D Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium

117.

Farnesol, isolated from lily of the valley flowers, has the structure shown. How many isoprene units does farnesol have?

A. B. C. D. E.

1 2 3 4 5

Answer: C Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 118.

The structure of zingiberene, found in ginger, is shown below. How many isoprene units are present in zingiberene?

A. B. C. D. E.

1 2 3 4 5

Answer: C

Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 119.

How many isoprene units are present in partheniol?

A. B. C. D. E.

1 2 3 4 5

Answer: C

Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 120.

How many isoprene units are present in manool?

A. B. C. D. E.

1 2 3 4 5

Answer: D

Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 121.

How many isoprene units are present in cedrol, which is found in cedar?

OH A. B. C. D. E.

1 2 3 4 5

Answer: C

Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 122.

How many isoprene units are present in squalene?

A. B. C. D. E.

3 4 5 6 9

Answer: D

Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium 123.

Which of the choices represent building blocks of terpenes?

OPP I A. B. C. D. E.

OPP

OPP II

III

OPP

I and III II and III I and IV II and V II and IV

Answer: A Learning Objective: 26.8 Describe the structural unit for all terpenes, and name two naturally occurring terpenes Difficulty: Medium

Klein, Organic Chemistry 4e Chapter 27 1.

Polymers are comprised of repeating units that are formed by joining _______.

A. B. C. D. E.

tetramers monomers dimers trimers none of these

Answer: B Learning Objective: 27.1 Describe the general structure of a polymer, and compare synthetic polymers and biopolymers Difficulty: Easy 2.

Which one of the choices is (are) a biopolymer?

A. B. C. D. E.

RNA DNA polysaccharides proteins all of these

Answer: E Learning Objective: 27.1 Describe the general structure of a polymer, and compare synthetic polymers and biopolymers Difficulty: Easy 3.

Which one of the choices is not a biopolymer?

A. B. C. D. E.

amylopectin DNA glycogen chitin none of these

Answer: E Learning Objective: 27.1 Describe the general structure of a polymer, and compare synthetic polymers and biopolymers Difficulty: Easy 4.

Which one of the given monomers will produce polyisobutylene?

CH2CH 3 H C

A. B. C. D. E.

C H

CH3

C CH3

CH 3

H3C

C H

III

CH2CH 3

C IV H

I II III IV none of these

Answer: B Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 5.

Which one of the given monomers will produce poly(vinyl chloride)?

Cl C

H A. B. C. D. E.

C I

CH2Cl C

C II

CH3 C

C III Cl

CH3 C

C IV H

I II III IV none of these

Answer: A Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 6.

Which one of the given monomers will produce polyisoprene?

III

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 7.

Which one of the given monomers will produce polytetrafluoroethylene?

F C

H A. B. C. D. E.

C I

CH2F C

C F

FH 2C

C F

III

CH2F

C IV F

I II III IV none of these

Answer: C Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 8.

A. B. C. D. E.

Which one of the choices is the correct structure for polystyrene?

CH 3

CH3 H n I

H n

CH 3 n

I II III IV none of these

III

Answer: C Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 9.

Which one of the choices is the correct structure for poly(vinylidene fluoride)?

F n

H n

F n

I A. B. C. D. E.

III

I II III IV none of these

Answer: D Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 10.

Which one of the choices is the correct structure for poly(vinyl acetate)?

H 3C

H3C

CCH3

CCH 3

H n

I A. B. C. D. E.

I II III IV none of these

CH3H III

CH 3H n IV

Answer: A Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 11.

Which one of the choices is the correct structure for poly(methyl acyanoacrylate?

H 3C

H 3CO O H C

CN H n

I A. B. C. D. E.

H 3C

CCH 3

CN n

CN H

CN n

III

I II III IV none of these

Answer: B Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 12.

Identify the polymer used in nonstick frying pans.

A. B. C. D. E.

polytetrafluoroethylene polystyrene polypropylene polyethylene poly(vinyl chloride)

Answer: A Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 13.

Identify the polymer used in plumbing.

polytetrafluoroethylene

B. C. D. E.

polystyrene polypropylene polyethylene poly(vinyl chloride)

Answer: E Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 14.

Identify the polymer used in disposable cups.

A. B. C. D. E.

polytetrafluoroethylene polystyrene polypropylene polyethylene poly(vinyl chloride)

Answer: B Learning Objective: 27.2 Assign a name to a polymer using IUPAC rules Difficulty: Easy 15.

A homopolymer is a polymer constructed from ______.

A. B. C. D. E.

a single type of monomer two different types of monomers many different types of monomers a dimer a trimer

Answer: A Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 16.

A copolymer is a polymer constructed from ______.

A. B. C. D. E.

a single type of monomer two or more different types of monomers monosaccharides a dimer a trimer

Answer: B

Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 17.

Which one of the choices is classified as a homopolymer?

A. B. C. D. E.

saran viton poly(vinyl bromide) SAN ABS

Answer: C Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 18.

Which one of the choices is classified as a copolymer?

A. B. C. D. E.

saran polyacrylonitrile poly(vinyl bromide) polystyrene polyethylene

Answer: A Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium 19.

Polymers constructed from a single type of monomer are called_______, whereas those constructed from two or more different types of monomers are called________.

A. B. C. D. E.

copolymers, homopolymers homopolymers, copolymers block polymers, homopolymers homopolymers, block polymers copolymers, block polymers

Answer: B Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers

Difficulty: Easy 20.

Identify the polymer used in food packaging.

A. B. C. D. E.

SAN ABS butyl rubber viton saran

Answer: E Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 21.

The given polymer is classified as a(n) ________.

A B A B A B A B A. B. C. D. E.

homopolymer block copolymer graft copolymer alternating copolymer random copolymer

Answer: D Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 22.

The given polymer is classified as a(n) ________.

A A A B A B B B A. B. C. D. E.

homopolymer block copolymer graft copolymer alternating copolymer random copolymer

Answer: E

Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 23.

The given polymer is classified as a(n) ________.

A A A A B B B B A. B. C. D. E.

homopolymer block copolymer graft copolymer alternating copolymer random copolymer

Answer: B Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 24.

A A

A. B. C. D. E.

The given polymer is classified as a(n) ________.

A A

homopolymer block copolymer graft copolymer alternating copolymer random copolymer

Answer: C Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 25.

Which of the choices is a region of a block copolymer constructed from isobutylene and vinyl fluoride?

CH3 H

CH 3H

CH3 H

CH 3H

A. B. C. D. E.

I II III IV none of these

Answer: B Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 26.

Which of the choices is a region of an alternate copolymer constructed from isobutylene and vinyl fluoride?

CH3 H

CH 3H

CH3 H

CH 3H

A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy

27.

Which of the choices is a region of a random copolymer constructed from isobutylene and vinyl fluoride?

CH3 H

CH 3H

CH3 H

CH 3H

A. B. C. D. E.

I II III IV none of these

Answer: C Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium

28.

III

A. B. C. D. E.

Which choice shows the structure of a region of a block copolymer constructed from isobutylene and vinyl fluoride? H

CH3H

CH3

CH3H

CH3

CH3H

CH3

CH3H

I II III IV V

Answer: B Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium

29.

Which choice shows the structure of a region of an alternating copolymer constructed from propylene and acrylonitrile?

III

A. B. C. D. E.

CH3H

CN H

CH3H

CN H

CH3H

CN H

CH3H

CN H

CH3H

CH3

CH3H

CN H

I II III IV V

Answer: A Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers

Difficulty: Medium 30.

Which choice shows the structure of a region of a random copolymer constructed from ethylene and styrene?

III

A. B. C. D. E.

Ph H

Ph Ph Ph Ph Ph Ph Ph

Ph Ph Ph Ph Ph Ph H

I II III IV V

Answer: A

Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium 31.

PET, used to make soft-drink bottles, is classified as a(n) __________.

A. B. C. D. E.

homopolymer block copolymer graft copolymer alternating copolymer random copolymer

Answer: D Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 32.

Polyesters are classified as __________.

A. B. C. D. E.

homopolymers block copolymers graft copolymers alternating copolymers random copolymers

Answer: D Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Easy 33.

A. B. C. D. E.

Which of the given monomers is required to make the polymer below?

CH3 H

CH3

CH3 H

propene isobutylene isoprene styrene none of these

CH3 H

CH3

Answer: B Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium 34.

Which of the given monomer pairs is required to make the polymer shown?

CH3 H

A. B. C. D. E.

propene and acrylonitrile isoprene and acrylonitrile ethylene and acrylonitrile isobutylene and acrylonitrile none of these

Answer: D Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium 35.

A. B. C. D. E.

Which of the given monomer pairs is required to make the polymer below?

CH3 H

CH=CH 2

CH3 H

CH3

propene and isobutylene isoprene and propene ethylene and butene isobutylene and isoprene none of these

Answer: D

Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium 36.

A. B. C. D. E.

Which of the given monomer pairs is required to make the polymer below?

Ph H

styrene and acrylonitrile styrene and propylnitrile phenylpropene and acrylonitrile phenylpropene and propylnitrile none of these

Answer: A Learning Objective: 27.3 Compare and contrast homopolymers and copolymers, alternating and random copolymers, and block and graft copolymers Difficulty: Medium 37.

Which of the choices is used as an initiator in radical polymerization?

A. B. C. D. E.

BF3, H2O CH3CH2CH2CH2Li ROOR NaOH H2 O

Answer: C Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 38.

Which of the choices is used as an initiator in cationic polymerization?

A. B. C. D.

BF3, H2O CH3CH2CH2CH2Li ROOR NaOH

none of these

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 39.

Which of the choices is used as an initiator in anionic polymerization?

A. B. C. D. E.

BF3, H2O CH3CH2CH2CH2Li ROOR H2SO4 none of these

Answer: B Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 40.

Which of the given monomers would be most reactive towards cationic polymerization?

OCH 3 I A. B. C. D. E.

CN II

III

O IV

CF3

NO2

I II III IV V

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 41.

Which of the given monomers would be most reactive towards anionic polymerization?

O OCH 3 II

I A. B. C. D. E.

NH2

O V

III

I II III IV V

Answer: B Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 42.

Arrange the given monomers in decreasing order of reactivity towards cationic polymerization.

O C I A. B. C. D. E.

NH 2 II

III

I > III > II II > I > III III > II > I II > III > I III > I > II

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 43.

Arrange the given monomers in decreasing order of reactivity towards anionic polymerization.

OCH 3

CF3

I A. B. C. D. E.

III

I > III > II II > III > I III > II > I II > I > III III > I > II

Answer: B Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 44.

Arrange the given monomers in decreasing order of reactivity towards anionic polymerization.

O NH2 I A. B. C. D. E.

C II

III

I > III > II II > I > III III > II > I II > III > I III > I > II

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 45.

Which of the given monomer(s) would undergo cationic polymerization?

A. B. C. D. E.

vinylidene fluoride acrylonitrile isobutylene vinyl acetate all of these

Answer: C and D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 46.

Which of the given monomer(s) would undergo anionic polymerization?

A. B. C. D. E.

vinyl acetate acrylonitrile isobutylene vinylidene chloride all of these

Answer: B and D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 47.

Which of the given monomer(s) would undergo both radical and cationic polymerization?

A. B. C. D. E.

methyl methacrylate acrylonitrile isobutylene vinylidene chloride all of these

Answer: C Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 48.

Which of the given polymers would be best prepared using cationic polymerization?

O H3C

NO2

CCH3

H n

F n

CH3H

III

I A. B. C. D. E.

I II III IV none of these

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 49.

Which of the given polymers would be best prepared using anionic polymerization?

H 3C

CCH 3

CH 3

H n

I A. B. C. D. E.

CH3H III

I II III IV none of these

Answer: C Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers

Difficulty: Medium 50.

_________ polymerization usually forms living polymers if the process is not terminated by an electrophile.

A. B. C. D. E.

anionic cationic radical condensation elimination

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Easy 51.

Identify the type of addition that is used to form Superglue.

A. B. C. D. E.

anionic cationic radical condensation elimination

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Easy 52.

Which of the choices is (are) condensation polymer(s)?

A. B. C. D. E.

nylon 6,6 polyisobutylene poly(vinyl chloride) polycarbonate A and D

Answer: E Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium

53.

Which of the given monomers would produce the condensation polymer shown?

C OCH 2CH2CH2O C

OCH2CH 2CH 2O

HOCH2CH2OH

HOCH2CH2CH2OH

H IV

III

A. B. C. D. E.

I and II I and III II and III II and IV I and IV

Answer: C Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Hard 54.

What is the structure of a region of the polymer that is produced when the given monomers react?

O + HOCH2CH 2CH2CH2OH

H 3CO

OCH3

III

A. B. C. D. E.

H2 C

H2 C OCH2CH2CH2CH2O

H2 C

H2 C OCH2CH2CH2CH2O

OCH2CH2CH2O

CH2CH2CH2CH2

OCH2CH2CH2CH2O

OCH2CH2CH2O

CH2CH2CH2

OCH2CH2CH2CH2O

I II III IV V

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Hard

55.

Which of the given monomers would produce the condensation polymer shown?

O N H

H N O

O N H

H N O

A. B. C. D. E.

III

NH2

I II III IV C and D

Answer: C Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Hard 56.

Which of the given monomers would produce the condensation polymer shown?

O O

O I A. B. C. D. E.

III

OH IV

I II III IV C and D

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers

Difficulty: Hard 57.

Nomex is a synthetic polymer with the structure shown. What is the structure(s) of the monomer(s) that would produce Nomex?

O N H

N H

O N H

N H

HO H2N

NH2

OH O

O II

NH2NH2 O III

A. B. C. D. E.

O IV

I and II I and III II and III II and IV I and IV

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium

58.

What is the structure of the monomer(s) that would produce the condensation polymer shown?

O O

OH H3C

A. B. C. D. E.

O CH3

III

Cl IV

I and II I and III II and III II and IV I and IV

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 59.

What is the structure of the monomer(s) that would produce the condensation polymer shown?

O O

O O Cl

A. B. C. D. E.

Cl II

III

I and II I and III II and III II and IV I and IV

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 60.

Provide the structure of a region of the polymer that is produced when phosgene is treated with 3,3-dimethyl-1,5-pentanediol.

III

O O V

O O

A. B. C. D. E.

I II III IV V

Answer: B Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 61.

Provide the structure of a region of the polymer that is produced when the given monomers are treated in the presence of dilute NaOH.

O + H2N(CH2)4NH 2

ClCO(CH2)6OCCl

O O

H O N O

H N O

III

O O OH O O O

O N O H O

H N

N H

O O

O O H O N OH

O OH N O H O

O O

H O N O

N O H

O N O H O N H O

O O

N O H

H O N OH

OH N O H O

O O

N O H

A. B. C. D. E.

I II III IV V

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 62.

What monomers form PET?

A. B. C. D. E,

terephthalic acid and ethylene glycol phosgene and ethylene glycol terephthalic acid and propylene glycol urethane and carbamate terephthalic acid and carbamate

Answer: A Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 63.

What monomers form Nylon 6,6?

A. B. C. D. E,

adipic acid and ethylene glycol phosgene and 1,6-hexandiamine terephthalic acid and 1,6-hexandiamine adipic acid and 1,6-hexandiamine terephthalic acid and carbamate

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 64.

What monomers form Lexan?

A. B. C. D.

adipic acid and Bisphenol-A phosgene and 1,6-hexandiamine terephthalic acid and 1,6-hexandiamine adipic acid and 1,6-hexandiamine

phosgene and Bisphenol-A

Answer: E Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 65.

Identify the type of compound used to make safety goggles.

A. B. C. D. E.

polyester polyamide polyether polyalcohol polycarbonate

Answer: E Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 66.

What is not an example of a small molecule that is released in a condensation reaction?

A. B. C. D.

water carbon dioxide nitrogen gas benzene

Answer: D Learning Objective: 27.4 Discuss the reaction types that can be used in the synthesis of addition and condensation polymers Difficulty: Medium 67.

Which of the choices are examples of chain growth polymerization?

A. B. C. D. E.

radical polymerization cationic polymerization anionic polymerization condensation polymerization A, B and C

Answer: E

Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Easy 68.

Which of the choices are examples of step growth polymerization?

A. B. C. D. E.

radical polymerization cationic polymerization anionic polymerization condensation polymerization none of these

Answer: D Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Easy 69.

Which of the given polymerization processes best describes the formation of polycarbonates?

A. B. C. D. E.

step growth addition chain growth addition step growth condensation chain growth condensation none of these

Answer: C Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium 70.

Which of the given polymerization processes best describes the formation of polyurethanes?

A. B. C. D. E.

step growth addition chain growth addition step growth condensation chain growth condensation none of these

Answer: A Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers

Difficulty: Medium 71.

Which of the given polymerization processes best describes the formation of polyisobutylene?

A. B. C. D. E.

step growth addition chain growth addition step growth condensation chain growth condensation none of these

Answer: B Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium 72.

What are the monomers in a polyurethane?

A. B. C. D. E.

isocyanate and alcohol diisocyanate and diol ester and amine carboxylic acid and amine amide and alcohol

Answer: B Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium 73.

_______ polymers are formed under conditions in which the individual monomers react with each other to form oligomers, which are then joined to form polymers.

A. B. C. D. E.

Step growth Chain growth Branched Graft none of these

Answer: A Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium

74.

What is the classification of the polymer shown?

HN A. B. C. D. E.

O O

O H N

H N

polyester polyamide polyurethane polycarbonate none of these

Answer: C Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium 75.

What monomer(s) would produce the polymer shown?

O O

O H N

A. B. C. D. E.

I and II I and III II and III II and IV I and IV

H N

OH II

N III

C IV

Answer: A Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium 76.

Provide the structure of a region of the polymer that is produced when isocyanate, shown below, is treated with 1,4-butanediol.

N(CH2)4N

H N

N H

1,4-butanediol

H N

N H

O O

O N H

H N

N H

O O

O N H

N H

O O

III

H N

O O

O N H

O O

N H

H N

O O

N H

O O

H N

O O

N H

A. B. C. D. E. Answer: C Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Medium

77.

What is the polymer that is used in bullet-proof vests?

A. B. C. D. E.

Nylon 6 Teflon Kevlar Lexan Nylon 6,6

Answer: C Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Easy 78.

What polymer is used in bicycle helmets?

A. B. C. D. E.

Nylon 6 Teflon Kevlar Lexan Nylon 6,6

Answer: D Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Easy 79.

What polymer is used in rope?

A. B. C. D. E.

Nylon 6 Teflon Kevlar Lexan Nylon 6,6

Answer: A Learning Objective: 27.5 Compare the processes involved in the formation of chaingrowth and step-growth polymers Difficulty: Easy 80.

Which of the given statements is(are) true about linear polymers?

they are highly branched

B. C. D. E.

they may be slightly branched they can have no branching A and B B and C

Answer: E Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Easy 81.

Which of the choices best describes the polymer shown?

A. B. C. D. E.

atactic isotactic syndiotactic antidiotactic none of these

Answer: B Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Easy 82.

Which of the choices best describes the polymer shown?

A. B. C. D. E.

atactic isotactic syndiotactic antidiotactic none of these

Answer: C

Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Easy 83.

Which of the choices best describes the polymer shown?

A. B. C. D. E.

atactic isotactic syndiotactic antidiotactic none of these

Answer: A Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Easy 84.

An isotactic polymer has a _______ configuration.

A. B. C. D. E.

random alternating same block graft

Answer: C Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Easy 85.

An atactic polymer has a _______ configuration.

A. B. C.

random alternating same

D. E.

block graft

A syndiotactic polymer has a _______ configuration.

A. B. C. D. E.

random alternating same block graft

Draw a possible segment of atactic polyacrylonitrile.

III

A. B. C. D. E.

I II III IV V

Draw a possible segment of isotactic polyacrylonitrile.

Answer:

III

A. B. C. D. E.

I II III IV V

89.

Draw a possible segment of syndiotactic polyacrylonitrile.

Answer:

III

A. B. C. D. E.

I II III IV V

Answer: E

Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Medium 90.

Draw a possible segment of syndiotactic poly(vinyl fluoride).

III

A. B. C. D. E.

I II III IV V

Answer: D Learning Objective: 27.6 Compare branched, linear, and cross-linked polymers, isotactic, syndiotactic, and atactic polymers, and compare crystalline and amorphous polymers Difficulty: Medium 91.

Draw a possible segment of isotactic poly(vinyl acetate).

OAc

III

A. B. C. D.

I II III IV

Polymerization of ethylene in the presence of a Ziegler-Natta catalyst results in _______.

A. B. C. D. E.

LDPE MDPE HDPE B and C none of these

Free radical polymerization of ethylene results in _______.

A. B. C. D. E.

LDPE MDPE HDPE B and C none of these

Answer: A Learning Objective: Polymer classification by structure Section: 27.6 Difficulty: Medium 94.

Which of the given types of polyethylene is used to make trash bags?

A. B. C. D. E.

HDPE LDPE MDPE A and C none of these

Which of the given types of polyethylene is used to make Tupperware?

A. B. C. D. E.

HDPE LDPE MDPE A and C none of these

Vulcanization of rubber results in _______ between the neighboring chains of the polymer.

A. B. C. D. E.

hydrogen bonding salt bridges phosphide bridges disulfide bridges none of these

Which of the given elements is used during the vulcanization of rubber?

A. B. C. D. E.

silicon aluminum sulfur phosphorous aluminum

Neoprene, which is used in gaskets, electrical insulation, and other products, has the structure shown. What is the structure of the monomer?

III

A. B. C. D. E.

II III IV V

SBR (styrene-butadiene rubber) is used in the manufacturing of automobile tires. What is the structure of a region of this polymer?

III

A. B.

I II

C. D. E.

III IV V

Which of the choices best describes crystallites?

A. B. C. D. E.

crossed linked chains with disulfide bridges linearly arranged chains held together by van der Waals forces crossed linked chains held together by van der Waals forces linearly arranged chains with disulfide bridges hydrogen bonding between chains

________ regions in polymers make the polymer hard and durable.

A. B. C. D. E.

amorphous cross linked crystalline A and B B and C

________ regions in polymers make the polymer flexible.

A. B. C.

amorphous cross linked crystalline

D. E.

B and C none of these

The glass transition temperature (Tg), is the temperature at which the ________regions of the polymers become ________.

A. B. C. D. E.

crystalline, amorphous amorphous, hard crystalline, hard amorphous, soft none of these

The melt transition temperature (Tm), is the temperature at which the ________ regions of the polymers become ________.

A. B. C. D. E.

crystalline, amorphous amorphous, hard crystalline, hard non-crystalline, soft none of these

Which of the given polymers are hard at room temperature and soft at high temperature?

fibers

B. C. D. E.

elastomers plasticizers thermoplastics thermosetting resins

Answer: D Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Easy 106.

Which of the given polymers is(are) classified as thermoplastics?

A. B. C. D. E.

PVC PET LDPE HDPE all of these

Answer: E Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 107.

Addition of _____ to thermoplastics increases flexibility of the polymer.

A. B. C. D. E.

PVC plasticizers resins LDPE elastomers

Answer: B Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 108.

Which one of the choices is the best classification of an amorphous polymer that is flexible?

A. B. C. D.

fibers elastomers plasticizers thermoplastics

thermosetting resins

Answer: B Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 109.

Which of the given polymers is(are) classified as elastomers?

A. B. C. D. E.

spandex natural rubber HDPE A and B all of these

Answer: D Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 110.

Which of the choices best describe elastomers?

A. B. C. D. E.

polymers that are hard at room temperature polymers that return to original shape after being stretched small molecules that are added to polymers to increase flexibility polymers that can form fibers none of these

Answer: B Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 111.

Which of the choices is the best classification of crystalline polymers with high tensile strength?

A. B. C. D. E.

fibers elastomers plasticizers thermoplastics thermosetting resins

Answer: A

Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 112.

Which of the choices is the best classification of chewing gum?

A. B. C. D. E.

fibers elastomers plasticizers thermoplastics thermosetting resins

Answer: B Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Easy 113.

Which of the choices is the best classification of Nylon?

A. B. C. D. E.

fibers elastomers plasticizers thermoplastics thermosetting resins

Answer: A Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Easy 114.

Which of the choices is the best classification of the polymer Bakelite?

A. B. C. D. E.

fibers elastomers plasticizers thermoplastics thermosetting resins

Answer: E Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium

115.

The strength of the thermosetting polymers like Bakelite is due to ____________.

A. B. C. D. E.

cross linking elastomers plasticizers thermoplastics thermosetting resins

Answer: A Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 116.

Which of the given monomer(s) are used to prepare the polymer Bakelite?

A. B. C. D. E.

phenol and acetaldehyde phenol and formaldehyde phenol and methanol thermoplastics none of these

Answer: B Learning Objective: 27.7 Describe thermoplastic polymers, elastomers, fibers, and thermosetting resins Difficulty: Medium 117.

Which of the given functional groups are common in biodegradable polymers?

A. B. C. D. E.

esters amides anhydrides A and B A and C

Answer: D Learning Objective: 27.8 Discuss the limitations on recycling polymers, and the potential benefits of biodegradable polymers Difficulty: Medium 118.

Which of the given processes is(are) used in the recycling of soft drink bottles made of PET?

A. B. C. D. E.

esterification acid hydrolysis melting B and C none of these

Answer: B Learning Objective: 27.8 Discuss the limitations on recycling polymers, and the potential benefits of biodegradable polymers Difficulty: Medium 119.

Which of the given descriptions is(are) consistent with biodegradable polymers?

A. B. C. D. E.

polymers that can be broken down by enzymes produced by microorganisms polymers with ester moieties polymers with amide moieties polymers known as polyhydroxyalkanoates all of these

Answer: E Learning Objective: 27.8 Discuss the limitations on recycling polymers, and the potential benefits of biodegradable polymers Difficulty: Medium 120.

Which choice best defines biogradable polymers?

A. Polymers made of natural substances. B. Polymers that can be broken down by enzymes produced by soil microorganisms. C. Polymers that can be recycled using standard means. D. Polymers that contain only organic materials. E. Polymers that are not harmful to the environment even if they persist in the environment for an extended time. Answer: B Learning Objective: 27.8 Discuss the limitations on recycling polymers, and the potential benefits of biodegradable polymers Difficulty: Medium