TEST BANK for Organic Chemistry 11th Edition by Carey, Giuliano, Allison by ACADEMIAMILL

Organic Chemistry, 11e (Carey) Chapter 1 Structure Determines Properties 1) What is the ground state electron configuration of carbon? A) 1s22s22px1 B) 1s22s22px2 C) 1s22s22px12py1 D) 1s22s22px22py1 Answer: C Difficulty: 2 Medium Section: 01.01 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Periodic table trends 2) Which of the following has (have) the same electron configuration as Ne? Na− Mg2+ O2− Mg+ A) Na− and O2− B) Mg2+ and O2− C) Mg+ and O2− D) only Mg2+ Answer: B Difficulty: 2 Medium Section: 01.02 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Subtopic: Periodic table trends

3) What is the letter designation given to dumbbell shaped orbitals like the one depicted below?

A) s B) p C) d D) f Answer: B Difficulty: 1 Easy Section: 01.01 Topic: Molecular Shape Bloom's: 1. Remember Chapter: 01 Subtopic: Atomic orbitals 4) Predict which bond is the most polar in ethanol, CH3CH2OH. A) C-C B) C-H C) C-O D) O-H Answer: D Difficulty: 2 Medium Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Subtopic: Types of bonds; Bond properties 5) What can be said about the polarity of the C=O bond? A) C and O have the same electronegativity; the bond is nonpolar B) the C=O bond is polar; the O atom bears a partial negative charge C) the C=O bond is nonpolar; the C atom bears a partial positive charge D) the C=O bond is polar; the C atom bears a partial negative charge Answer: B Difficulty: 2 Medium Section: 01.04 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Types of bonds; Bond properties 2 Copyright © 2019

6) In which of the following compounds would you expect Cl to have a partial positive charge? A) HCl B) CCl4 C) NaCl D) HOCl Answer: D Difficulty: 2 Medium Section: 01.04 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Types of bonds; Bond properties 7) In which of the following does hydrogen have a partial negative charge based on electronegativity? A) BH3 B) CH4 C) NH3 D) H2O Answer: A Difficulty: 2 Medium Section: 01.04 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Types of bonds; Bond properties

8) What is the formal charge on the carbon atom?

A) +1 B) 0 C) −1 D) −2 Answer: C Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges 9) What is the formal charge on the oxygen atom in the structure below?

A) −1 B) 0 C) +1 D) +2 Answer: C Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges

10) What is the formal charge on the nitrogen atom in the structure below?

A) −1 B) 0 C) +1 D) +2 Answer: C Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges 11) The formal charges on the nitrogen and oxygen in the following structures are, respectively

A) +1, −1 B) 0, −1 C) +1, 0 D) 0, 0 Answer: A Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges

12) What are the formal charges of boron and nitrogen, respectively, in the following structure?

A) −1 and +1 B) −1 and 0 C) 0 and +1 D) 0 and 0 Answer: A Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges 13) Which of the following species have a zero formal charge on its carbon atom?

A) I and II B) II and IV C) III and IV D) I, II, and III Answer: B Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges

14) A Lewis structure of the azide ion, N3¯, is shown below. The formal charge on the middle nitrogen atom is

A) +2 B) +1 C) 0 D) −1 Answer: B Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges 15) What atom would have a formal charge in this structure?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Formal charges

16) Identify the condensed formula of the following structure

A) (CH3)2CHCHClCH(CH3)2 B) CH3CH(CH3)CHClCH(CH3)2 C) (CH3)2CHCHClC(CH3)3 D) (CH3)3CCHClCH(CH3)3 Answer: C Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 01 Subtopic: Skeletal/bond-line structures; Condensed formula 17) What is the chemical formula of the following carbon skeleton diagram?

A) C8H14 B) C8H16 C) C8H18 D) C8H20 Answer: C Difficulty: 1 Easy Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures

18) Give the molecular formula of the compound shown below

A) C8H16O B) C9H18O C) C10H18O D) C10H20O Answer: D Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures 19) How many hydrogen atoms are there on carbon atoms 1 and 2, respectively, in the structure below?

A) 4, 1 B) 4, 0 C) 3, 1 D) 3, 0 Answer: D Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures 9 Copyright © 2019

20) How many C3H8O constitutional isomers are possible? A) one B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 01 Subtopic: Constitutional isomers 21) Which of the following best describes the relationship between the two structures?

A) identical compounds B) resonance structures C) constitutional isomers D) different compounds with different constitutions Answer: A Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures

22) How many constitutional isomers of C4H9Br are possible? A) one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 01 Subtopic: Constitutional isomers 23) How many constitutional isomers of C3H6Cl2 are possible? A) three B) four C) five D) six Answer: B Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 01 Subtopic: Constitutional isomers 24) Which of the following describes the relationship between the following two structures?

A) identical structures B) resonance forms C) constitutional isomers D) different compounds with different compositions Answer: A Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures 11 Copyright © 2019

25) What is the molecular formula of aspirin?

A) C6H4O4 B) C8H8O4 C) C9H8O4 D) C9H10O4 Answer: C Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures 26) Which of the following is not identical to the others?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures

27) Which of the line-bond structures below cannot represent a stable molecule?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures 28) What would be the line-bond structure for (CH3)3CCH2CH(CH3)2?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 01.06 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 Subtopic: Skeletal/bond-line structures; Condensed formula

29) Which of the following describes the relationship between the following two ions?

A) identical structures B) resonance forms C) constitutional isomers D) different compounds with different compositions Answer: B Difficulty: 1 Easy Section: 01.07 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Resonance

30) The most stable resonance contributor of this would be:

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 01.07 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Subtopic: Resonance

31) Which of the electron-movement arrows below are NOT valid?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 01.07 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Resonance 32) The electron pair movement depicted below produces a second resonance form for the species. What is the formal charge on the nitrogen atom for this second resonance form?

A) −2 B) −1 C) 0 D) +1 Answer: B Difficulty: 3 Hard Section: 01.07 Topic: Structure and Bonding; Curved Arrows Bloom's: 3. Apply Chapter: 01 Subtopic: Formal charges; Resonance; Bond formation and bond breaking; Drawing and interpretation

33) Identify the resonance structure that results from the following "electron pair movements."

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 01.07 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Subtopic: Resonance 34) Which of the following atoms has vacant d orbitals that permit it to accommodate more than eight electrons in its valence shell? A) N B) C C) Ne D) S Answer: D Difficulty: 1 Easy Section: 01.08 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Subtopic: Octet rule exceptions 17 Copyright © 2019

35) Based on the VSEPR model, which of the following species has (have) a trigonal planar geometry? I. BCl3 II. NH3 III. NO3¯ A) only I B) I and II C) I and III D) I, II, and III Answer: C Difficulty: 3 Hard Section: 01.09 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Subtopic: VSEPR theory 36) Based on VSEPR theory, which of the following species has (have) a trigonal pyramidal geometry? I. CO32− II. NH3 A) only I B) only II C) I and II D) II and III

III. CH3+

Answer: B Difficulty: 3 Hard Section: 01.09 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Subtopic: VSEPR theory

37) Which of the following species has(have) a linear geometry? I. CO2 II. NO2 + III. NO2¯ A) only I B) only II C) I and II D) I, II, and III Answer: C Difficulty: 3 Hard Section: 01.09 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Subtopic: VSEPR theory 38) The H-C-H bond angles in ethylene, C2H4, are closest to A) 90°. B) 109.5°. C) 120°. D) 180°. Answer: C Difficulty: 2 Medium Section: 01.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Subtopic: Hybridization 39) The C-C-C bond angle in propane, C3H8, is closest to A) 90°. B) 109.5°. C) 120°. D) 180°. Answer: B Difficulty: 2 Medium Section: 01.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Subtopic: Hybridization

40) Which statement correctly describes the structures of BH3 and NH3? A) Both are trigonal and planar. B) Both are pyramidal. C) BH3 is trigonal planar and NH3 is trigonal pyramidal. D) BH3 is trigonal pyramidal and NH3 is trigonal planar. Answer: C Difficulty: 3 Hard Section: 01.09 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Subtopic: VSEPR theory 41) Which of the following molecules would you expect to have a dipole moment? I. CO2 II. HCN III. CHCl3 A) II and III B) only II C) only III D) I, II, and III Answer: A Difficulty: 3 Hard Section: 01.10 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 Subtopic: Dipole moments; Polarity of molecules 42) Which of the following molecules would you expect to have a dipole moment? I. CH2Cl2 II. CH3Cl III. CCl4 A) only I B) only II C) I and II D) I, II, and III Answer: C Difficulty: 3 Hard Section: 01.10 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 Subtopic: Dipole moments; Polarity of molecules 20 Copyright © 2019

43) Which one of the following is isoelectronic with CO2? A) NO2¯ B) NO2+ C) NO2 D) O3 Answer: B Difficulty: 3 Hard Section: 01.10 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 Subtopic: VSEPR theory; Dipole moments; Polarity of molecules 44) Which one of the following species is formed when diazomethane loses a nitrogen molecule?

diazomethane

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 01.11 Topic: Curved Arrows Bloom's: 3. Apply Chapter: 01 Subtopic: Bond formation and bond breaking; Drawing and interpretation

45) Which species is formed when the CH3N2+ cation loses a nitrogen molecule?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 01.11 Topic: Curved Arrows Bloom's: 3. Apply Chapter: 01 Subtopic: Bond formation and bond breaking; Drawing and interpretation

46) Which one of the following mechanistically depicts the protonation of methanol by hydrogen bromide?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 01.11 Topic: Curved Arrows Bloom's: 2. Understand Chapter: 01 Subtopic: Curved arrow notation

47) Identify the species that results from the following movement of electron pairs.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 01.11 Topic: Curved Arrows Bloom's: 3. Apply Chapter: 01 Subtopic: Bond formation and bond breaking; Drawing and interpretation; Curved arrow notation

48) What structure would result from these electron movement arrows?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 01.11 Topic: Curved Arrows Bloom's: 3. Apply Chapter: 01 Subtopic: Bond formation and bond breaking; Drawing and interpretation; Curved arrow notation 49) Which one of the following is the conjugate base of NH3? A) NH4+ B) H+ C) N3− D) NH2− Answer: D Difficulty: 2 Medium Section: 01.12 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 01 Subtopic: Acid/Base definitions

50) Which one of the following is the conjugate acid of ethanol? A) CH3CH2O− B) CH3CH2O+ C) CH3CH2OH2+ D) CH3CH2OH3+ Answer: C Difficulty: 2 Medium Section: 01.12 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 01 Subtopic: Acid/Base definitions 51) Which one of the following is the strongest base?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 01.13 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 01 Subtopic: Factors affecting acid strength

52) Which one of the following is the strongest acid? A) FCH2CO2H B) ClCH2CO2H C) BrCH2CO2H D) ICH2CO2H Answer: A Difficulty: 3 Hard Section: 01.13 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 01 Subtopic: Factors affecting acid strength 53) Which one of the following has the largest acid equilibrium constant, Ka? A) CH3CO2H B) CH2ClCO2H C) CHCl2CO2H D) CCl3CO2H Answer: D Difficulty: 3 Hard Section: 01.13 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 01 Subtopic: Factors affecting acid strength; pKa

54) In the equilibrium below, the strongest base is (pKa H2O = 15.7, pKa NH3 = 36).

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 01.14 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 01 Subtopic: Predicting acid/base reaction equilibrium 55) Rank the following in order of decreasing acidity. (more acidic > less acidic)

A) I > IV > III > II B) IV > I > II > III C) III > II > I > IV D) I > III > IV > II Answer: A Difficulty: 3 Hard Section: 01.13 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 01 Subtopic: Acid/Base definitions; Factors affecting acid strength 28 Copyright © 2019

56) Using resonance principles, what atom is acid first protonated in the molecule shown?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 01.13 Topic: Structure and Bonding; Acids and Bases Bloom's: 4. Analyze Chapter: 01 Subtopic: Acid/Base definitions; Resonance; Factors affecting acid strength

57) In the equilibrium below, which is the strongest acid?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 01.14 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 01 Subtopic: Predicting acid/base reaction equilibrium; Factors affecting acid strength

58) For which of the following does the equilibrium favor reactants?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 01.14 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 01 Subtopic: Predicting acid/base reaction equilibrium

Organic Chemistry, 11e (Carey) Chapter 2 Alkanes and Cycloalkanes: Introduction to Hydrocarbons 1) Which of the following statements is not true concerning hydrocarbons? A) Hydrocarbons are compounds that carbon, hydrogen, and oxygen atoms. B) Alkanes, alkenes, and alkynes are examples of aliphatic hydrocarbons. C) Aromatic hydrocarbons are also referred to as arenes. D) Hydrocarbons may contain sigma bonds and/or pi bonds. Answer: A Difficulty: 1 Easy Section: 02.01 Topic: Functional Groups Bloom's: 2. Understand Chapter: 02 Subtopic: Hydrocarbons; Alkanes; Alkenes; Alkynes; Arenes (Aromatics) 2) Alkanes are characterized by the general molecular formula: A) CnH2n−2 B) CnH2n C) CnH2n+2 D) CnH2n+4 Answer: C Difficulty: 1 Easy Section: 02.05 Topic: Functional Groups; Alkanes (Acyclic and Cyclic) Bloom's: 1. Remember Chapter: 02 Subtopic: Hydrocarbons; Alkanes; Acyclic vs cyclic 3) The carbon-carbon sigma bond in ethane is formed by overlap of which two orbitals? A) 2p-2p B) sp-sp C) sp2-sp2 D) sp3-sp3 Answer: D Difficulty: 2 Medium Section: 02.07 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization 1 Copyright © 2019

4) The sp3 orbitals of carbon in CH4 are formed from the A) three 2p orbitals. B) 2s and two of the 2p orbitals. C) 2s and one of the 2p orbitals. D) 2s and the three 2p orbitals. Answer: D Difficulty: 2 Medium Section: 02.06 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization 5) The geometry of sp3 hybrid orbitals can be described as pointing toward the corners of a A) triangle. B) square. C) tetrahedron. D) square pyramid. Answer: C Difficulty: 2 Medium Section: 02.06 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization 6) What is the Cl-C-Cl bond angle in CCl4? A) 60o B) 90o C) 109.5o D) 120o Answer: C Difficulty: 2 Medium Section: 02.06 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 02 Subtopic: Hybridization

7) What is the estimated C-C-C bond angle in the following model?

A) 90o B) 109.5o C) 120o D) 180o Answer: C Difficulty: 2 Medium Section: 02.08 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization 8) The hybridization of carbon atoms 1, 2, and 3 in the following are, respectively,

A) sp, sp, and sp2. B) sp, sp, and sp3. C) sp2, sp2, and sp3. D) sp2, sp3, and sp3. Answer: C Difficulty: 2 Medium Section: 02.08 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 02 Subtopic: Hybridization

9) The C-C sigma bond in acetylene is formed by the overlap of which two orbitals?

A) 2p-2p B) sp-sp C) sp2-sp2 D) sp3-sp3 Answer: B Difficulty: 2 Medium Section: 02.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization 10) What are the hybridizations of carbon atoms 2, 3, and 4 shown in the model below?

A) sp, sp2, sp2 B) sp, sp2, sp3 C) sp, sp, sp2 D) sp, sp, sp3 Answer: D Difficulty: 2 Medium Section: 02.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization

11) The shortest and longest carbon-carbon bonds, respectively, in this molecule are

A) II and III. B) IV and III. C) I and IV. D) IV and I. Answer: D Difficulty: 2 Medium Section: 02.09 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 02 Subtopic: Bond properties; Types of bonds 12) The C-C-C bond angle in propyne, shown below, is

A) 90°. B) 109.5°. C) 120°. D) 180°. Answer: D Difficulty: 2 Medium Section: 02.09 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 02 Subtopic: Hybridization

13) How many pi bonds are present in the following structure?

A) one B) two C) three D) four Answer: C Difficulty: 1 Easy Section: 02.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization 14) The carbon-carbon single bond in the following is formed by the overlap of which two orbitals?

A) sp-sp B) sp2-sp C) sp2-sp2 D) sp2-sp3 Answer: B Difficulty: 2 Medium Section: 02.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 02 Subtopic: Hybridization

15) How many isomers of C4H9Cl are possible? A) two B) three C) four D) five Answer: C Difficulty: 2 Medium Section: 02.12 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 02 Subtopic: Constitutional isomers 16) What is the relationship between the two structures below?

A) identical structures B) resonance forms C) constitutional isomers D) different compounds with different compositions Answer: C Difficulty: 2 Medium Section: 02.13 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 02 Subtopic: Constitutional isomers

17) What is the relationship between the following two structures?

A) identical structures B) resonance forms C) constitutional isomers D) different compounds with different compositions Answer: A Difficulty: 1 Easy Section: 02.13 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 02 Subtopic: Skeletal/bond-line structures 18) What is the total number of constitutional isomers with the formula C5H12? A) two B) three C) four D) five Answer: B Difficulty: 2 Medium Section: 02.14 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 02 Subtopic: Constitutional isomers

19) How many isomers of C6H14 are possible? A) four B) five C) six D) seven Answer: B Difficulty: 2 Medium Section: 02.16 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 02 Subtopic: Constitutional isomers 20) Which of the molecules below is NOT an isomer of formula C6H14?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 02.16 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 02 Subtopic: Constitutional isomers; Skeletal/bond-line structures

21) The common name of the following group is

A) n-butyl. B) sec-butyl. C) isobutyl. D) tert-butyl. Answer: B Difficulty: 2 Medium Section: 02.17 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 1. Remember Chapter: 02 Subtopic: Alkyl groups 22) The tert-butyl group can also be called A) 1,1-dimethylpropyl. B) 1,1-dimethylethyl. C) 2,2-dimethylpropyl. D) 2,2-dimethylethyl. Answer: B Difficulty: 2 Medium Section: 02.17 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: Alkyl groups 23) The 1,1-dimethylethyl group, -C(CH3)3, can also be called A) butyl. B) isobutyl. C) sec-butyl. D) tert-butyl. Answer: D Difficulty: 2 Medium Section: 02.17 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: Alkyl groups 10 Copyright © 2019

24) What is the IUPAC name of the following compound?

A) 4,4-dimethylpentane B) 1-tert-butylpropane C) 2,2-dimethylpentane D) 1,1,1-trimethylbutane Answer: C Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes 25) The correct IUPAC name of the following compound is

A) 2-ethyl-3,5-dimethylheptane. B) 6-ethyl-5,5-dimethylheptane. C) 3,4,4-trimethyloctane. D) 5,5,6-trimethyloctane. Answer: C Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes

26) Which one of the following is 2,2,5-trimethylhexane? A) (CH3)2CHCH2C(CH3)3 B) (CH3)2CHCH2CH2C(CH3)3 C) CH3CH2CH(CH3)C(CH3)3 D) (CH3)2CHCH2CH2CH2C(CH3)3 Answer: B Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes 27) The correct IUPAC name of the following is

A) 2,4,7-trimethylnonane. B) 7-ethyl-2,4-dimethyloctane. C) 3,6,8-trimethylnonane. D) 2-ethyl-5,7-dimethyloctane. Answer: A Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes

28) What is the IUPAC name of the following?

A) 5,6-diethylhexane B) 5-ethyl-6-methylheptane C) 2,3-diethylhexane D) 4-ethyl-3-methylheptane Answer: D Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes 29) Identify the isomer of C6H14 that only has primary and tertiary carbons. A) hexane B) 2,2-dimethylbutane C) 3-methylpentane D) 2,3-dimethylbutane Answer: D Difficulty: 3 Hard Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes

30) The systematic name of the following group is

A) 5-ethyl-2-methylpentyl. B) 1-ethyl-4-methylpentyl. C) 6-methyl-3-heptyl. D) 2-methyl-5-heptyl. Answer: B Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: Alkyl groups 31) What is the IUPAC name of the following?

A) 6-isopropyl-3-methylnonane B) 2-ethyl-5-isopropyloctane C) 6-propyl-3-methylnonane D) 2-ethyl-5-propyloctane Answer: A Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes

32) What is the IUPAC name of the following structure?

A) 3-propylpentane B) 3-ethylhexane C) 2-ethylheptane D) 4-ethylpentane Answer: B Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes 33) Which of the following are constitutional isomers? I. 2,3,3-dimethylhexane II. 2,2-diethylpentane III. 3-ethyl-2-methylheptane A) I and II B) I and III C) II and III D) They are all constitutional isomers. Answer: A Difficulty: 2 Medium Section: 02.18 Topic: Alkanes (Acyclic and Cyclic); Drawing Organic Molecules Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes; Constitutional isomers

34) Cycloalkanes are characterized by the general molecular formula A) CnH2n−2. B) CnH2n. C) CnH2n+2. D) CnH2n+4. Answer: B Difficulty: 1 Easy Section: 02.19 Topic: Functional Groups; Alkanes (Acyclic and Cyclic) Bloom's: 1. Remember Chapter: 02 Subtopic: Hydrocarbons; Alkanes; Acyclic vs cyclic 35) What is the IUPAC name of the following?

A) 1-ethyl-4.4-dimethylcyclopentane B) 1-ethyl-3,3-dimethylcyclopentane C) 3-ethyl-1,1-dimethylcyclopentane D) 4-ethyl-1,1-dimethylcyclopentane Answer: C Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of cycloalkanes

36) All the carbons in cyclopentane are A) primary carbons. B) secondary carbons. C) tertiary carbons. D) quaternary carbons. Answer: B Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: IUPAC Nomenclature of cycloalkanes 37) The correct name of the following compound is

A) (1-methylpropyl)cyclohexane. B) (2-methylpropyl)cyclohexane. C) (2,2-dimethylethyl)cyclohexane. D) (2,2-dimethylpropyl)cyclohexane. Answer: B Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of cycloalkanes

38) The correct IUPAC name of the following compound is

A) (1-methylhexyl)cyclopentane. B) (1-pentylethyl)cyclopentane. C) 2-cyclopentylheptane. D) 1-cyclopentyl-2-heptane. Answer: C Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 02 Subtopic: IUPAC Nomenclature of cycloalkanes 39) Cyclohexane is composed of A) methine groups. B) methylene groups. C) methyl groups. D) both methine and methylene groups. Answer: B Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: IUPAC Nomenclature of cycloalkanes

40) Carbon atoms 1, 2, and 3 in the following structure are classified, respectively, as

A) tertiary, primary, secondary. B) quaternary, secondary, secondary. C) quaternary, primary, tertiary. D) quaternary, secondary, tertiary. Answer: D Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: Alkyl groups 41) How many methine groups are there in isopropylcyclopentane? A) one B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 02.19 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: IUPAC Nomenclature of acyclic alkanes

42) Which of the following describes an atom or group of atoms that has similar chemical properties when it occurs in different compounds? A) hydrocarbon B) functional group C) paraffin D) isomer Answer: B Difficulty: 1 Easy Section: 02.20 Topic: Functional Groups Bloom's: 1. Remember Chapter: 02 Subtopic: Hydrocarbons; C-Z functional groups (Z = N, O, S, halogen) 43) The boiling point of isobutane (−10.2°C) is lower than n-butane (−0.4°C) because isobutane has A) weaker intermolecular van der Waals forces. B) stronger intermolecular van der Waals forces. C) weaker dipole-dipole attractive forces. D) stronger dipole-dipole attractive forces. Answer: A Difficulty: 2 Medium Section: 02.22 Topic: Functional Groups Bloom's: 2. Understand Chapter: 02 Subtopic: Intermolecular forces

44) Arrange the following hydrocarbons in order of increasing boiling point. I. pentane II. 2,2-dimethylpropane III. 2-methylbutane A) I < II < III B) I < III < II C) II < I < III D) II < III < I Answer: D Difficulty: 2 Medium Section: 02.22 Topic: Functional Groups Bloom's: 4. Analyze Chapter: 02 Subtopic: Intermolecular forces 45) Arrange the following isomeric alkanes in order of increasing boiling point. I. n-heptane II. 2,3-dimethylpentane III. 2,2,3-trimethylbutane A) I < II < III B) II < III < I C) III < I < II D) III < II < I Answer: D Difficulty: 2 Medium Section: 02.22 Topic: Functional Groups Bloom's: 4. Analyze Chapter: 02 Subtopic: Intermolecular forces

46) Which of the following has the lowest boiling point? A) pentane B) 2,2-dimethylpropane C) 2-methylbutane D) hexane Answer: B Difficulty: 2 Medium Section: 02.22 Topic: Functional Groups Bloom's: 2. Understand Chapter: 02 Subtopic: Intermolecular forces 47) The smallest straight-chain alkane that is liquid at room temperature and atmospheric pressure is A) propane. B) butane. C) pentane. D) hexane. Answer: C Difficulty: 2 Medium Section: 02.22 Topic: Functional Groups Bloom's: 2. Understand Chapter: 02 Subtopic: Intermolecular forces 48) The lowest-boiling isomer of C7H16 would be

49) Why can heats of combustion of constitutional isomers of hydrocarbons be used to measure their stabilities? I. Combustion of constitutional isomers gives different final states. II. Combustion of constitutional isomers gives the same final states. III. Constitutional isomers of hydrocarbons have the same potential energies. IV. Constitutional isomers of hydrocarbons have different potential energies. A) only I B) only II C) I and III D) II and IV Answer: D Difficulty: 2 Medium Section: 02.23 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: Reactions of alkanes 50) The heats of combustion (−∆H°) of heptane and 3,3-dimethypentane are 4,817 and 4,809 kJ/mol, respectively. Which statement is true? A) Heptane is 8 kJ/mol more stable then 3,3-dimethylpentane. B) 3,3-Dimethylpentane is 8 kJ/mol more stable than heptane. C) Stabilities cannot be compared since they are not isomers. D) Stabilities cannot be compared since they give different combustion products. Answer: B Difficulty: 2 Medium Section: 02.23 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: Reactions of alkanes

51) How many moles of O2 gas would be consumed in the complete combustion of 0.100 mole of C5H12? A) 0.100 mole O2 B) 0.400 mole O2 C) 0.800 mole O2 D) 1.60 mole O2 Answer: C Difficulty: 3 Hard Section: 02.23 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 02 Subtopic: Reactions of alkanes 52) Which of the following has(have) a higher oxidation state of carbon than the carbon in formaldehyde, H2C=O? I. CH3OH II. HCO2H III. H2CO3 A) I B) III C) II and III D) I, II, and III Answer: C Difficulty: 2 Medium Section: 02.24 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 02 Subtopic: Acyclic vs cyclic

53) The oxidation states of carbon range from A) 0 to +2. B) 0 to +4. C) −4 to 0. D) −4 to +4. Answer: D Difficulty: 1 Easy Section: 02.24 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 1. Remember Chapter: 02 Subtopic: Acyclic vs cyclic 54) The reaction of acetylene with hydrogen gas is shown below. Which statements are true concerning the reaction?

I. Acetylene is oxidized to ethane. II. Acetylene is reduced to ethane. III. Carbon changes oxidation state from −1 to −3. IV. Hydrogen (from H2) changes oxidation state from 0 to +1. A) I and III B) II and IV C) I, III, and IV D) II, III, and IV Answer: D Difficulty: 2 Medium Section: 02.24 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 02 Subtopic: Reactions of alkanes

55) How many constitutional isomers of C~6~H~14~ are possible? A) four B) five C) six D) seven Answer: B Difficulty: 2 Medium Section: 02.15 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 02 Subtopic: Constitutional isomers

Organic Chemistry, 11e (Carey) Chapter 3 Alkanes and Cycloalkanes: Conformations and cis-trans Stereoisomers 1) What is the dihedral (torsion) angle between the two bromine atoms in the following sawhorse drawing?

A) 0o B) 30o C) 60o D) 90o Answer: C Difficulty: 2 Medium Section: 03.01 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of acyclic alkanes; Projections of acyclic alkanes 2) What is the dihedral (torsion) angle between the two bromine atoms in the wedge-and-dash drawing below?

A) 60o B) 90o C) 120o D) 180o Answer: D Difficulty: 2 Medium Section: 03.01 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Projections of acyclic alkanes; Conformational analysis of acyclic alkanes 1 Copyright © 2019

3) Which of the following best describes the conformation of propane shown below?

A) C(1) - C(2) staggered and C(2) - C(3) staggered B) C(1) - C(2) staggered and C(2) - C(3) eclipsed C) C(1) - C(2) eclipsed and C(2) - C(3) staggered D) C(1) - C(2) eclipsed and C(2) - C(3) eclipsed Answer: C Difficulty: 2 Medium Section: 03.01 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Projections of acyclic alkanes; Conformational analysis of acyclic alkanes 4) Identify the conformation of butane shown below.

A) anti B) gauche C) skewed D) eclipsed Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of acyclic alkanes

5) What is the IUPAC name of the compound shown in the following Newman projection?

A) 1,1,2,2-tetramethylethane B) 2,2,3,3-tetramethylbutane C) 1,2-dimethylethane D) 2,3-dimethylbutane Answer: D Difficulty: 2 Medium Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of acyclic alkanes; IUPAC Nomenclature of acyclic alkanes 6) What is the IUPAC name of the compound shown below?

A) 1,2,3-trimethylbutane B) 2,3-dimethylpentane C) 2,3,4-trimethylpentane D) 2-isopropylbutane Answer: B Difficulty: 2 Medium Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of acyclic alkanes; IUPAC Nomenclature of acyclic alkanes

7) At room temperature, the various conformations of butane A) do not interconvert; only the anti form is present. B) do not interconvert, but all conformations are present. C) interconvert very slowly. D) interconvert very rapidly. Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 1. Remember Chapter: 03 Subtopic: Conformations of acyclic alkanes 8) Identify the relationship between the following two Newman projections.

A) identical B) stereoisomers C) different conformations of the same compound D) constitutional isomers Answer: C Difficulty: 2 Medium Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of acyclic alkanes

9) The sawhorse drawing of butane below is the

A) least stable staggered conformation. B) most stable staggered conformation. C) least stable eclipsed conformation. D) most stable eclipsed conformation. Answer: C Difficulty: 2 Medium Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Projections of acyclic alkanes; Conformational analysis of acyclic alkanes 10) What is the most specific name for the conformation shown?

A) anti B) staggered C) gauche D) eclipsed Answer: C Difficulty: 1 Easy Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of acyclic alkanes; Conformational analysis of acyclic alkanes 5 Copyright © 2019

11) The sawhorse drawing of butane below is

A) a gauche conformation. B) the anti conformation. C) the least stable eclipsed conformation. D) the most stable eclipsed conformation. Answer: A Difficulty: 2 Medium Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Projections of acyclic alkanes; Conformational analysis of acyclic alkanes

12) Which one of the following is the butane conformation shown below?

A) gauche B) anti C) skew D) eclipsed Answer: A Difficulty: 1 Easy Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Projections of acyclic alkanes; Conformational analysis of acyclic alkanes 13) Which of the staggered conformations of 2-methylbutane is most stable?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 03.02 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformations of acyclic alkanes; Conformational analysis of acyclic alkanes 7 Copyright © 2019

14) What would the C-C-C bond angles be in a planar cyclohexane? A) 60o B) 90o C) 109.5o D) 120o Answer: D Difficulty: 1 Easy Section: 03.04 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclohexane 15) The planar form of which ring would have bond angles close to the tetrahedral value but is destabilized by eclipsing interactions?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 03.04 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclic alkanes

16) Predict which of the following constitutional isomers of C5H10 would have the highest heat of combustion? A) methylcyclobutane B) cyclopentane C) cis-1,2-dimethylcyclopropane D) trans-1,2-dimethylcyclopropane Answer: C Difficulty: 2 Medium Section: 03.05 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformations of cyclic alkanes; Reactions of alkanes 17) The C-C-C bond angle in cyclopropane is A) 60o. B) 90o. C) 109.5o. D) 120o. Answer: A Difficulty: 1 Easy Section: 03.05 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 1. Remember Chapter: 03 Subtopic: Conformational analysis of cyclic alkanes

18) What is the IUPAC name of the compound shown below?

A) cis-1,2-diethylcyclobutane B) trans-1,2-diethylcyclobutane C) cis-1,3-diethylcyclobutane D) trans-1,3-diethylcyclobutane Answer: C Difficulty: 2 Medium Section: 03.05 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: IUPAC Nomenclature of cycloalkanes; Conformations of cyclic alkanes 19) Cyclohexane adopts the chair conformation rather than a planar structure because I. torsional strain is minimized. II. the C-C-C bond angles are close to 109.5o. III. there are no 1,3-diaxial interactions in a planar structure. A) only I B) only II C) I and II D) I, II, and III Answer: C Difficulty: 2 Medium Section: 03.07 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

20) The IUPAC name of the following compound is

A) cis-1,2-dimethylcyclohexane. B) 1,1-dimethylcyclohexane. C) trans-1,2-dimethylcyclohexane. D) cis-1,3-dimethylcyclohexane. Answer: A Difficulty: 2 Medium Section: 03.07 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of cyclohexane; IUPAC Nomenclature of cycloalkanes 21) The following structure is

A) cis-1,3-dimethylcyclohexane. B) cis-1,4-dimethylcyclohexane. C) trans-1,3-dimethylcyclohexane. D) trans-1,4-dimethylcyclohexane. Answer: C Difficulty: 2 Medium Section: 03.07 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of cyclohexane; IUPAC Nomenclature of cycloalkanes

22) Identify the spatial relationship of the two chlorine atoms.

A) gauche B) anti C) eclipsed D) twist Answer: B Difficulty: 1 Easy Section: 03.08 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformational analysis of cyclohexane 23) Identify the two atoms anti to the bromine.

A) the equatorial H's on C-2 and C-6 B) C-2 and C-6 C) the axial H's on C-2 and C-6 D) C-3 and C-5 Answer: D Difficulty: 2 Medium Section: 03.08 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

24) Identify the relationship between the following two structures.

A) constitutional isomers B) stereoisomers C) different conformations of the same compound D) identical Answer: C Difficulty: 2 Medium Section: 03.09 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclohexane 25) Identify the relationship between the following two structures.

A) constitutional isomers B) stereoisomers C) different conformations of the same compound D) identical Answer: B Difficulty: 2 Medium Section: 03.09 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclohexane

26) Which statement below is true concerning the conversion of cis-1,4-dimethylcyclohexane to trans-1,4-dimethylcyclohexane? A) The conversion takes place by chair conformation ring-flipping. B) You cannot do the conversion without breaking covalent bonds. C) The conversion takes place by rotating the C(1)-C(2) bond by 180°. D) The conversion takes place through the skew boat conformations. Answer: B Difficulty: 2 Medium Section: 03.09 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclohexane 27) What is the IUPAC name of the compound shown below?

A) cis-1,3-dimethylcyclohexane B) trans-1,3-dimethylcyclohexane C) cis-1,4-dimethylcyclohexane D) trans-1,5-dimethylcyclohexane Answer: B Difficulty: 2 Medium Section: 03.10 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of cyclohexane; IUPAC Nomenclature of cycloalkanes

28) What is the IUPAC name of the following compound?

A) trans-1,4-dimethylcyclohexane B) trans-1,3-dimethylcyclohexane C) cis-1,4-dimethylcyclohexane D) cis-1,3-dimethylcyclohexane Answer: A Difficulty: 2 Medium Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of cyclohexane; IUPAC Nomenclature of cycloalkanes 29) Identify the relationship of the two compounds below.

A) identical B) constitutional isomers C) stereoisomers D) different conformations of the same compound Answer: A Difficulty: 2 Medium Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclic alkanes

30) Identify the relationship between the following two structures.

A) identical B) different conformations of the same compound C) stereoisomers D) constitutional isomers Answer: C Difficulty: 2 Medium Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclic alkanes 31) Which constitutional isomer of dimethylcyclohexane does not exhibit cis-trans isomerism? A) 1,1-dimethylcyclohexane B) 1,3-dimethylcyclohexane C) 1,2-dimethylcyclohexane D) 1,4-dimethylcyclohexane Answer: A Difficulty: 2 Medium Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclohexane

32) Which one of the following is a stereoisomer of trans-1,3-dimethylcyclopentane? A) 1,1-dimethylcyclopentane B) ethylcyclopentane C) cis-1,2-dimethylcyclopentane D) cis-1,3-dimethylcyclopentane Answer: D Difficulty: 2 Medium Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclic alkanes 33) β-D-Glucose is the six-carbon sugar with all nonhydrogen groups equatorial. Which structure is it?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

34) Which of the following can have cis-trans stereoisomers? A) 1,1-dimethylcyclobutane B) 1,3-dimethylcyclobutane C) 1,1,3-trimethylcyclobutane D) 1,1,3,3-tetramethylcylclobutane Answer: B Difficulty: 2 Medium Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformational analysis of cyclic alkanes 35) What is the relationship between the following two structures?

A) identical B) stereoisomers C) different conformations of the same compound D) constitutional isomers Answer: D Difficulty: 1 Easy Section: 03.11 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformations of cyclic alkanes

36) Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?

A) A is more stable. B) B is more stable. C) A and B are equal in stabilities. D) A and B are not equal in stability, but the preferred conformation cannot be determined by inspection. Answer: C Difficulty: 2 Medium Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

37) Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?

A) A is more stable. B) B is more stable. C) A and B are equal in stabilities. D) A and B are not equal in stability, but the preferred conformation cannot be determined by inspection. Answer: B Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane 38) The most stable conformation of the compound shown has

A) all methyl groups equatorial. B) equatorial methyl groups at C-1 and C-2, axial at C-4. C) equatorial methyl groups at C-1 and C-4, axial at C-2. D) equatorial methyl groups at C-2 and C-4, axial at C-1. Answer: D Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane 20 Copyright © 2019

39) The most stable chair conformation of cis-1-tert-butyl-3-methylcyclohexane has A) both groups equatorial. B) both groups axial. C) the tert-butyl group equatorial and the methyl group axial. D) the tert-butyl group axial and the methyl group equatorial. Answer: A Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

40) Identify the correct stereoisomer and the most stable conformation of the following compound.

A) A B) B C) C D) D

Answer: B Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

41) Which isomer of 1-tert-butyl-3-ethyl-5-methylcyclohexane below is thermodynamically the most stable?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

42) What is the estimated dihedral angle between the two methyl groups on the structure shown below?

A) 30o B) 60o C) 90o D) 120o Answer: B Difficulty: 2 Medium Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Conformational analysis of cyclohexane 43) What is the correct IUPAC name of the following compound?

A) cis-1-ethyl-2-methylcyclohexane B) trans-1-ethyl-2-methylcyclohexane C) cis-1-ethyl-6-methylcyclohexane D) trans-1-ethyl-6-methylcyclohexane Answer: B Difficulty: 2 Medium Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: Conformations of cyclohexane; IUPAC Nomenclature of cycloalkanes

44) The most stable conformation of cis-4-methyl-1-tert-butylcyclohexane is a chair conformation with A) both the -CH3 and -C(CH3)3 equatorial. B) both the -CH3 and -C(CH3)3 axial. C) the -CH3 equatorial and the -C(CH3)3 axial. D) the -CH3 axial and -C(CH3)3 equatorial. Answer: D Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane 45) Which is more stable, cis-1,3-dimethylcyclohexane or trans-1,3-dimethylcyclohexane? A) trans-1,3-dimethylcyclohexane B) cis-1,3-dimethylcyclohexane C) They are equally stable. D) Stabilities of cis, trans stereoisomers cannot be compared. Answer: B Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

46) How many alkyl groups would be equatorial in the most stable conformation of the cyclohexane below?

A) one B) two C) three D) four Answer: B Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane 47) Menthol is the most stable isomer of 2-isopropyl-5-methylcyclohexanol. Which compound is it?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane

48) Consider the lower energy chair conformation of each cyclohexane, which would be the least stable isomer of 1,2,3,4,5,6-hexamethylcyclohexane?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 03.12 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane 49) Identify the relationship of the two compounds below.

A) identical B) constitutional isomers C) stereoisomers D) different conformations of the same compound Answer: C Difficulty: 2 Medium Section: 03.14 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 2. Understand Chapter: 03 Subtopic: Polycyclic systems

50) What is the IUPAC name of the following compound?

A) bicyclo[2.2.2]octane B) bicyclo[3.3.3]octane C) bicyclo[2.2.2]hexane D) bicyclo[3.3.3]hexane Answer: A Difficulty: 3 Hard Section: 03.14 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: IUPAC Nomenclature of cycloalkanes; Polycyclic systems 51) What is the IUPAC name of the following bicycloalkane?

A) bicyclo[6.3.0]heptane B) bicyclo[4.2.1]hexane C) bicyclo[4.1.0]hexane D) bicyclo[4.1.0]heptane Answer: D Difficulty: 2 Medium Section: 03.14 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 3. Apply Chapter: 03 Subtopic: IUPAC Nomenclature of cycloalkanes; Polycyclic systems

52) Consider these two molecules. Which statement is true?

A) I is more stable than II. B) II is more stable than I. C) I and II are equally stable. D) There is no way to predict this. Answer: B Difficulty: 3 Hard Section: 03.14 Topic: Alkanes (Acyclic and Cyclic) Bloom's: 4. Analyze Chapter: 03 Subtopic: Conformational analysis of cyclohexane; Conformations of cyclohexane; Polycyclic systems

Organic Chemistry, 11e (Carey) Chapter 4 Chirality 1) Which object below is achiral? A) golf club (wood driver) B) baseball glove C) tennis shoe D) baseball bat Answer: D Difficulty: 1 Easy Section: 04.01 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Chiral vs achiral molecules 2) The most specific description of the relationship between the following two molecules is

A) identical. B) isomers. C) enantiomers. D) diastereomers. Answer: A Difficulty: 2 Medium Section: 04.01 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

3) Which of the molecules below are chiral?

A) only II B) only III C) I and III D) II and III Answer: D Difficulty: 1 Easy Section: 04.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules 4) Identify the chiral compound(s) below.

A) only II B) II and III C) III and IV D) I, II, and IV Answer: A Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules

5) Which of the following molecules are chiral?

A) only II B) only III C) II and III D) I, II, and III Answer: A Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules 6) How many chirality centers are there in the following molecule?

A) only 1 B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers

7) How many chirality centers are there in the following molecule?

A) only 1 B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules 8) Which of the following statements are true? I. If a molecule has a plane of symmetry it is achiral. II. If a molecule has a center of symmetry it is achiral. III. If a molecule has one chirality center it is chiral. A) I and II B) I and III C) II and III D) I, II, and III Answer: D Difficulty: 1 Easy Section: 04.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules

9) Which compound below has no stereoisomers? A) 1,2-dichlorobutane B) 2,3-dichlorobutane C) 1,3-dichlorobutane D) 1,4-dichlorobutane Answer: D Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso) 10) Which one of the isomeric C4H9Cl molecules is chiral? A) 1-chlorobutane B) 2-chlorobutane C) 1-chloro-2-methylpropane D) 2-chloro-2-methylpropane Answer: B Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules 11) Which of the following molecules is(are) chiral?

A) only I B) I and II C) II and III D) I, II, and III Answer: A Difficulty: 2 Medium Section: 04.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules 5 Copyright © 2019

12) How many chirality centers are present in histrionicotoxin?

A) 2 B) 3 C) 4 D) 5 Answer: C Difficulty: 3 Hard Section: 04.02 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers

13) How many chirality centers are in this molecule?

A) 2 B) 4 C) 5 D) 6 Answer: C Difficulty: 3 Hard Section: 04.02 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers 14) Which of the molecules below are chiral?

A) only I B) I and III C) II and III D) I, II, and III Answer: B Difficulty: 2 Medium Section: 04.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Chiral vs achiral molecules

15) A pure sample of (S)-phenylalanine has a specific rotation of +70°. A mixture of the two enantiomers of phenylalanine has a specific rotation of +7.0°. What are the percentages of the S and R enantiomers in the mixture? A) 95% S, 5% R B) 90% S, 10% R C) 55% S, 45% R D) 52.5% S, 47.5% R Answer: C Difficulty: 2 Medium Section: 04.04 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Optical activity 16) (+)-Tartaric acid has a specific rotation of +12.0°. What is the specific rotation of a mixture of 75% (+)-tartaric acid and 25% (−)-tartaric acid? A) +4.0° B) +6.0° C) +8.0° D) +9.0° Answer: B Difficulty: 2 Medium Section: 04.04 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Optical activity 17) Which of the following statements is false? A) Racemic mixtures are optically inactive. B) Enantiomers have specific rotations which are equal, but have opposite signs. C) Achiral molecules are optically inactive. D) Meso compounds contain equal amounts of enantiomers. Answer: D Difficulty: 1 Easy Section: 04.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso); Optical activity 8 Copyright © 2019

18) (−)-Fenchone can be purchased in 70% optical purity. What ratio of enantiomers is present?

A) 70% (−) : 30% (+) B) 85% (−) : 15% (+) C) 55% (−) : 45% (+) D) 60% (−) : 40% (+) Answer: B Difficulty: 2 Medium Section: 04.04 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Optical activity 19) Which one of the following isomeric dibromobutanes is shown below?

A) (2R, 3R)-2,3-dibromobutane B) (2S, 3S)-2,3-dibromobutane C) meso-2,3-dibromobutane D) (R)-1,2-dibromobutane Answer: C Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature 9 Copyright © 2019

20) Give the configurations, respectively, of the following two molecules.

A) R and R B) R and S C) S and S D) S and R Answer: B Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature 21) Give the configurations, respectively, of the following two molecules.

A) R and R B) R and S C) S and S D) S and R Answer: A Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature

22) Which one of the following groups has the highest rank as assigned by the Cahn-IngoldPrelog system for stereogenic carbons? A) -CH=CH2 B) -CH2OH C) -CH=O D) -CH2SH Answer: D Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: R and S nomenclature 23) Give the configurations of carbons 1 and 2, respectively, in the structure shown below.

A) R and R B) R and S C) S and S D) S and R Answer: B Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature

24) What is the IUPAC name of the following compound?

A) (2S, 3S)-2,3-dibromopentane B) (2R, 3S)-2,3-dibromopentane C) (2S, 3R)-2,3-dibromopentane D) (2R, 3R)-2,3-dibromopentane Answer: D Difficulty: 3 Hard Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature 25) What are the configurations of C(1) and C(2), respectively, for the stereoisomer of 2methylcyclopentanol shown below?

A) (1R, 2R) B) (1R, 2S) C) (1S, 2R) D) (1S, 2S) Answer: B Difficulty: 3 Hard Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature

26) Which of the following is the enantiomer of (2R,3R)-2,3-dibromopentane? A) (2S,3S)-2,3-dibromopentane B) (2R,3S)-2,3-dibromopentane C) (2S,3R)-2,3-dibromopentane D) (2R,4R)-2,4-dibromopentane Answer: A Difficulty: 1 Easy Section: 04.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 27) What is the IUPAC name of the following hydrocarbon?

A) (R)-4-ethylpentanane B) (S)-3-methylhexane C) (S)-2-ethylpentane D) (R)-3-methylhexane Answer: B Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature 13 Copyright © 2019

28) What are the R/S assignments in this molecule? (assume the carbons are numbered as shown)

A) 2S, 3R B) 2S, 3S C) 2R, 3S D) 2R, 3R Answer: B Difficulty: 2 Medium Section: 04.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature

29) Which of the following Fischer projections corresponds to the compound shown below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 04.07 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Dashes and wedges

30) What are the configurations of carbons 2 and 3 in the Fischer projection below?

A) 2R, 3R B) 2R, 3S C) 2S, 3R D) 2S, 3S Answer: D Difficulty: 3 Hard Section: 04.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: R and S nomenclature

31) Which sawhorse drawing below has the identical conformation as the following Fischer projection?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 04.07 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso); Dashes and wedges

32) What is the most important reason that chiral drugs are typically sold as single enantiomers? A) one enantiomer is typically a more effective drug B) one enantiomer is typically cheaper to make C) racemic mixtures have already been patented D) one enantiomer is typically easier to separate Answer: A Difficulty: 1 Easy Section: 04.09 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 33) What is the relationship between the following two molecules?

A) identical B) enantiomers C) diastereomers D) constitutional isomers Answer: A Difficulty: 2 Medium Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

34) What is the relationship between the following two compounds?

A) identical B) enantiomers C) diastereomers D) constitutional isomers Answer: D Difficulty: 2 Medium Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 35) What is the relationship between the following two compounds?

A) different conformations of the same compound B) enantiomers C) diastereomers D) constitutional isomers Answer: C Difficulty: 3 Hard Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

36) What is the relationship between the following two compounds?

A) identical B) enantiomers C) diastereomers D) constitutional isomers Answer: B Difficulty: 2 Medium Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 37) The four isomeric dimethylcyclopropanes are shown below. Identify two of the isomers that are related as diastereomers.

A) I and III B) I and IV C) II and III D) III and IV Answer: C Difficulty: 2 Medium Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

38) Which one of the following is a diastereomer of (R)-4-bromo-cis-2-hexene? A) (S)-4-bromo-cis-2-hexene B) (R)-5-bromo-cis-2-hexene C) (R)-4-bromo-trans-2-hexene D) (S)-5-bromo-trans-2-hexene Answer: C Difficulty: 2 Medium Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 39) Which one of the following is a diastereomer of (2R,3R)-2,3-dibromopentane? A) (2S,3S)-2,3-dibromopentane B) (2S,3R)-2,3-dibromopentane C) R-1,2-dibromopentane D) (2R,4R)-2,4-dibromopentane Answer: B Difficulty: 1 Easy Section: 04.10 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 40) Give the total number of stereoisomers of 2,3-dibromobutane. A) none, only a single structure B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 04.11 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso)

41) Which of the following has a meso stereoisomer? I. 2,4-dichloropentane II. 1,3-dimethylcyclopentane III. 2,3-dichloropentane A) only I B) only II C) I and III D) I and II Answer: D Difficulty: 2 Medium Section: 04.11 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 42) Which compound below has a meso form? A) 1,2-dichlorobutane B) 1,3-dichlorobutane C) 2,3-dichlorobutane D) 1,4-dichlorobutane Answer: C Difficulty: 2 Medium Section: 04.11 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso)

43) How many stereoisomers are there for the compound shown below?

A) two B) four C) six D) eight Answer: B Difficulty: 2 Medium Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso) 44) How many stereoisomers are there of D-fructose (including D-fructose), shown below?

A) four B) six C) eight D) twelve Answer: C Difficulty: 2 Medium Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso) 23 Copyright © 2019

45) How many stereoisomers are there of 1-isopropyl-4-methylcyclohexane? A) only one structure possible—no stereoisomers B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso) 46) How many stereoisomers of 2,3-pentanediol are possible?

A) 2 B) 3 C) 4 D) 6 Answer: C Difficulty: 2 Medium Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

47) How many stereoisomers are possible for this structure?

A) 1 B) 4 C) 8 D) 16 Answer: C Difficulty: 2 Medium Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 48) How many stereoisomers of 2,4-pentanediol are possible?

A) 2 B) 3 C) 4 D) 6 Answer: B Difficulty: 3 Hard Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

49) What is the total number of stereoisomers (including the one shown) for the following alcohol?

A) zero (none are possible) B) two C) three D) four Answer: B Difficulty: 3 Hard Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso)

50) Which of the following amines gives a pair of diastereomeric salts when reacted with (S)-(-)malic acid?

A) only I B) only II C) only III D) I and III Answer: D Difficulty: 3 Hard Section: 04.13 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso); Chiral resolution 51) The tartaric acid found in fruits, when isolated, exhibits [α] = +12°. Which configuration is NOT possible for this naturally occurring material?

52) Which of the following best describes a racemic mixture? A) A mixture containing equal amounts of two diastereomers. B) A mixture containing a meso stereoisomer. C) A mixture containing unequal amounts of enantiomers. D) A mixture containing equal amounts of enantiomers. Answer: D Difficulty: 1 Easy Section: 04.14 Topic: Stereochemistry Bloom's: 1. Remember Chapter: 04 Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 53) One stereoisomer of the structure below is a poison found in a certain mushroom. How many stereoisomers of this structure are possible?

A) 4 B) 8 C) 16 D) 32 Answer: B Difficulty: 2 Medium Section: 04.12 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 04 Subtopic: Stereogenic/chirality carbon centers; Stereoisomers (enantiomers, diastereomers, meso)

Organic Chemistry, 11e (Carey) Chapter 5 Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms Nucleophilic Substitution 1) The structure below is a generalized abbreviation for which class of compounds?

A) ketones B) aldehydes C) carboxylic acids D) esters Answer: B Difficulty: 1 Easy Section: 05.01 Topic: Functional Groups Bloom's: 1. Remember Chapter: 05 Subtopic: C=O containing functional groups 2) Identify the functional group in the boxed area.

A) ester B) ketone C) carboxylic acid D) ether Answer: A Difficulty: 2 Medium Section: 05.01 Topic: Functional Groups Bloom's: 2. Understand Chapter: 05 Subtopic: C=O containing functional groups

3) What is the IUPAC name of the compound below?

A) 8-chloro-4-isopropyl-4,7-dimethylnonane B) 2-chloro-6-isopropyl-3,6-dimethylnonane C) 2-chloro-3,6,7-trimethyl-6-propyloctane D) 6-sec-butyl-2-chloro-3,6-dimethyloctane Answer: B Difficulty: 2 Medium Section: 05.02 Topic: Alkyl Halides Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC nomenclature of alkyl halides 4) What is the IUPAC name of the compound below?

A) 5,5-dimethyl-2-hexanol B) 2,2-dimethyl-5-hexanol C) 5,5-dimethyl-2-pentanol D) 2,2-dimethyl-5-pentanol Answer: A Difficulty: 2 Medium Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols

5) What is the IUPAC name of the compound below?

A) 3-isobutyl-2-hexanol B) 2-methyl-5-(1-hydroxyethyl)octane C) 2-methyl-5-propyl-6-heptanol D) 6-methyl-3-propyl-2-heptanol Answer: D Difficulty: 2 Medium Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols 6) What is the IUPAC name of the following compound?

A) cis-3-methylcyclohexanol B) trans-3-methylcyclohexanol C) cis-5-methylcyclohexanol D) trans-5-methylcyclohexanol Answer: B Difficulty: 2 Medium Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols

7) What is the IUPAC name of the following compound?

A) 3-methyl-2-butanol B) 3-methyl-3-butanol C) 2-methyl-2-butanol D) 2,2-dimethyl-1-butanol Answer: C Difficulty: 2 Medium Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols

8) What is the name of the following compound?

A) cis-3-methylcyclohexanol B) cis-2-methylcyclopentanol C) trans-3-methylcyclohexanol D) trans-3-methylcyclopentanol Answer: C Difficulty: 3 Hard Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols 9) What is the IUPAC name of the following alcohol?

A) trans-4-methylcyclohexanol B) trans-3-methylcyclohexanol C) cis-4-methylcyclohexanol D) cis-3-methylcyclohexanol Answer: A Difficulty: 3 Hard Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols 5 Copyright © 2019

10) Which of the following is isobutyl alcohol? A) CH3CH2CH2CH2OH B) CH3CH2CH(OH)CH3 C) (CH3)2CHCH2OH D) (CH3)3COH Answer: C Difficulty: 2 Medium Section: 05.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols 11) Identify the tertiary alcohol(s).

A) only I B) only II C) only III D) both I and III Answer: C Difficulty: 1 Easy Section: 05.04 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: IUPAC Nomenclature of alcohols

12) Identify the tertiary halide(s).

A) I and II B) II and III C) III and IV D) only IV Answer: C Difficulty: 1 Easy Section: 05.04 Topic: Alkyl Halides Bloom's: 2. Understand Chapter: 05 Subtopic: Classify as primary, secondary, or tertiary alkyl halides 13) What is the hybridization of the oxygen atom in alcohols? A) sp B) sp2 C) sp3 Answer: C Difficulty: 2 Medium Section: 05.05 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Physical properties of alcohols

14) The C-O-H bond angle in alcohols is closest to A) 90o. B) 109.5o. C) 120o. D) 180o. Answer: B Difficulty: 1 Easy Section: 05.05 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Physical properties of alcohols 15) Which halogen forms the weakest bond to carbon? A) F B) Cl C) Br D) I Answer: D Difficulty: 2 Medium Section: 05.05 Topic: Alkyl Halides Bloom's: 1. Remember Chapter: 05 Subtopic: Reactions of alkyl halides 16) Which of these five-carbon alcohols would you expect to be most water soluble?

17) Rank the following three compounds in order of increasing boiling point. I. CH3CH2CH3 II. CH3CH2OH III. CH3OCH3 A) I < II < III B) I < III < II C) II < III < I D) II < I < III Answer: B Difficulty: 1 Easy Section: 05.06 Topic: Alcohols Bloom's: 4. Analyze Chapter: 05 Subtopic: Physical properties of alcohols 18) What are the products of the following reaction?

A) 1-bromobutane and water B) 1-bromobutane and hydrogen C) butane and HOBr D) CH3CH2CH2CH2OBr + hydrogen Answer: A Difficulty: 2 Medium Section: 05.07 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: Reactions of alcohols

19) Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 05.08 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols

20) What is the nucleophile in the following substitution reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 05.08 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols

21) Arrange the following carbocations in order of their decreasing stabilities (most stable first).

A) I > II > III B) III > II > I C) I > III > II D) II > III > I Answer: C Difficulty: 2 Medium Section: 05.09 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols 22) The central carbon of the tert-butyl carbocation, (CH3)3C+, is A) sp2 hybridized with a +1 formal charge. B) sp2 hybridized with a 0 formal charge. C) sp3 hybridized with a +1 formal charge. D) sp3 hybridized with a 0 formal charge. Answer: A Difficulty: 2 Medium Section: 05.09 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols

23) What are the C-C-C bond angles in the tert-butyl carbocation, (CH3)3C+? A) 60o B) 90o C) 109.5o D) 120o Answer: D Difficulty: 2 Medium Section: 05.09 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols 24) What occurs when an optically active alcohol reacts with HBr to give an alkyl halide? A) incomplete and varying inversion of configuration takes place at the chirality center B) complete inversion of configuration takes place at the chirality center C) the chirality center retains its configuration D) the molecule loses its optical activity Answer: A Difficulty: 2 Medium Section: 05.11 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols 25) Which of the following is most reactive with HBr? A) CH3OH B) CH3CH2OH C) (CH3)2CHOH D) (CH3)3COH Answer: D Difficulty: 2 Medium Section: 05.10 Topic: Alcohols Bloom's: 4. Analyze Chapter: 05 Subtopic: Reactions of alcohols

26) Arrange the following alcohols in order of their decreasing reactivity with HBr (most reactive first).

A) I > II > III B) I > III > II C) III > I > II D) II > III > I Answer: B Difficulty: 2 Medium Section: 05.10 Topic: Alcohols Bloom's: 4. Analyze Chapter: 05 Subtopic: Reactions of alcohols

27) If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of HCl, what major product would you expect?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 05.10 Topic: Alcohols Bloom's: 4. Analyze Chapter: 05 Subtopic: Reactions of alcohols 28) Rank the following alcohols in order of increasing reaction rate with HBr.

A) II < III < I B) III < II < I C) I < III < II D) I < II < III Answer: C Difficulty: 2 Medium Section: 05.10 Topic: Alcohols Bloom's: 4. Analyze Chapter: 05 Subtopic: Reactions of alcohols 15 Copyright © 2019

29) What is the driving force for a carbocation rearrangement to occur? A) the formation of a higher energy, less stable carbocation B) the formation of a higher energy, more stable carbocation C) the formation of a more stable, lower energy carbocation D) the transfer of the positive charge to a less substituted, less stable carbon atom Answer: C Difficulty: 2 Medium Section: 05.12 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols 30) Which of the following is not a good method to make bromocyclopentane? A) cyclopentanol plus HBr B) cyclopentanol plus NaBr C) cyclopentanol plus PBr3 D) cyclopentane plus Br2 with light Answer: B Difficulty: 2 Medium Section: 05.14 Topic: Alcohols Bloom's: 5. Evaluate Chapter: 05 Subtopic: Reactions of alcohols 31) What is the product of the following reaction? BrCH2CH2CH2CH2OH + SOCl2 → A) ClCH2CH2CH2CH2OH B) BrCH2CH2CH2CH2SH C) BrCH2CH2CH2CH2Cl D) ClCH2CH2CH2CH2SOCl Answer: C Difficulty: 2 Medium Section: 05.14 Topic: Alcohols Bloom's: 3. Apply Chapter: 05 Subtopic: Reactions of alcohols

32) Alkyl sulfonates undergo the same type of substitution reactions as alkyl halides and can also be prepared from alcohols. What advantage does the preparation of an alkyl sulfonate from an alcohol have over the preparation of an alkyl halide from an alcohol? A) the preparation of an alkyl sulfonate can be carried out at a much lower temperature and with less expensive reagents B) the configuration at the chirality center in the alcohol is retained in the alkyl sulfonate product and no rearrangements occur C) the alkyl sulfonate product is formed with complete inversion of configuration D) the alkyl sulfonate loses its optical activity and is therefore lower in energy Answer: B Difficulty: 2 Medium Section: 05.15 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols 33) Which of the following carbocation rearrangements is likely to occur? A) 2° → 2° B) 2° → 3° C) 3° → 2° D) 2° → 1° Answer: B Difficulty: 2 Medium Section: 05.15 Topic: Alcohols Bloom's: 2. Understand Chapter: 05 Subtopic: Reactions of alcohols

Organic Chemistry, 11e (Carey) Chapter 6 Nuclophilic Substitution 1) Identify the leaving group in the following reaction.

A) CH3CH2Br B) HS C) Br D) CH3OH Answer: C Difficulty: 1 Easy Section: 06.02 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Factors affecting substitution reactions 2) Which of the following undergoes a substitution reaction with sodium cyanide in DMSO at the fastest rate? A) CH3CH2F B) CH3CH2Cl C) CH3CH2Br D) CH3CH2I Answer: D Difficulty: 2 Medium Section: 06.02 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Factors affecting substitution reactions

3) 1-Chloro-4-fluorobutane is reacted with one equivalent of sodium iodide in acetone. During the reaction a precipitate forms. What is the precipitate? A) FCH2CH2CH2CH2I B) ClCH2CH2CH2CH2I C) NaCl D) NaF Answer: C Difficulty: 3 Hard Section: 06.02 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Factors affecting substitution reactions 4) Rank the following in decreasing order of leaving group ability.

A) I > III > IV > II B) I > III > II > IV C) III > II > I > IV D) II > I > III > IV Answer: B Difficulty: 2 Medium Section: 06.02 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Factors affecting substitution reactions

5) Which of the following undergoes SN1 solvolysis in ethanol/water at the fastest rate?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 06.02 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Factors affecting substitution reactions 6) The rate law for the following reaction is

A) rate = k[CH3CH2CH2Cl]. B) rate = k[CH3CH2CH2Cl][NaCN]. C) rate = k[CH3CH2CH2Cl][NaCN]2. D) rate = k[NaCN]. Answer: B Difficulty: 2 Medium Section: 06.03; 06.04 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

7) In the SN2 reaction, the "2" stands for A) two reactants in the reaction. B) two steps in the reaction. C) two intermediates in the reaction. D) bimolecular kinetics for the reaction. Answer: D Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 1. Remember Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 8) Identify the major product(s) in the reaction of (R)-2-bromopentane with sodium cyanide in DMSO. A) (R)-2-cyanopentane B) (S)-2-cyanopentane C) racemic mixture of 2-cyanopentane D) trans-2-pentene Answer: B Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 9) A pentacoordinate carbon is a transition state in the ________ mechanism. A) SN1 B) SN2 C) E1 D) E2 Answer: B Difficulty: 1 Easy Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

10) Which of the following does not correctly describe SN2 reactions of alkyl halides? A) Tertiary halides react faster than secondary halides. B) Rate of reaction depends on the concentrations of both the alkyl halide and the nucleophile. C) The mechanism consists of a single step with no intermediates. D) The transition state species has a pentavalent carbon atom. Answer: A Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions 11) The mechanism of the following reaction is

A) SN1. B) SN2. C) SN1/2. D) SN1−2. Answer: A Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

12) The species shown below represents the transition state for the

A) reaction of 1-propanol with HBr. B) reaction of 1-bromopropane with OH−. C) elimination of HBr from 1-bromopropane. D) addition of HBr to propene with peroxides. Answer: B Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

13) Which of the following is the double substitution product of the reaction below?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

14) Which of the following mechanistic steps is the most likely route for the formation of the cyclic ether shown?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions

15) Which one of the following correctly describes the reaction below?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

16) The major product(s) of this reaction would be

A) only (R). B) only (S). C) (R) and (S). D) achiral. Answer: B Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 17) The major product(s) of this reaction would be

A) only (R). B) only (S). C) (R) and (S). D) achiral. Answer: D Difficulty: 2 Medium Section: 06.03 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

18) Which of the following reacts the fastest by the SN2 mechanism? A) CH3Br B) CH3CH2Br C) (CH3)2CHBr D) (CH3)3CBr Answer: A Difficulty: 2 Medium Section: 06.04 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions 19) Give the product(s) of the following reaction.

A) A B) B C) C D) a mixture of A and B Answer: B Difficulty: 2 Medium Section: 06.04 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 11 Copyright © 2019

20) Which of the following reacts the slowest with sodium cyanide, NaCN?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 06.04 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Factors affecting substitution reactions 21) Identify the nucleophile in the following reaction.

A) CH3Br B) OH C) H2O D) Br Answer: B Difficulty: 1 Easy Section: 06.05 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Factors affecting substitution reactions 12 Copyright © 2019

22) Which of the following cannot act as a nucleophile? A) NH3 B) H2O C) I D) CH4 Answer: D Difficulty: 1 Easy Section: 06.05 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Factors affecting substitution reactions 23) Which of the following reacts fastest with methanol by the SN1 mechanism?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 06.06 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions

24) What is the leaving group in the following reaction?

A) OH− B) H2O C) CH3CH2+ D) C1− Answer: B Difficulty: 2 Medium Section: 06.06 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions 25) Which of the following is the rate law for the SN1 mechanism of an alkyl halide with a nucleophile? A) rate = k[alkyl halide] B) rate = k[nucleophile] C) rate = k[alkyl halide][nucleophile] D) rate = k[alkyl halide]2[nucleophile] Answer: A Difficulty: 1 Easy Section: 06.06 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions

26) What is the rate limiting step in the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 06.06 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 27) Which of the following conditions favor the SN1 mechanism as opposed to the SN2 mechanism? I. tertiary alkyl halide II. primary alkyl halide III. polar solvent A) only I B) only II C) I and III D) II and III Answer: C Difficulty: 1 Easy Section: 06.06 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions 15 Copyright © 2019

28) The species shown below represents the transition state for the

A) reaction of 1-propanol with HBr. B) reaction of 1-bromopropane with OH−. C) addition of HOBr to 1-propene. D) addition of HBr to propene with peroxides. Answer: A Difficulty: 2 Medium Section: 06.06 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 29) The major product of the following reaction is an alcohol. Which of the following best describes this reaction?

A) SN2 with inversion of configuration B) SN2 with racemization C) SN1 with complete inversion of configuration D) SN1 with partial racemization Answer: D Difficulty: 2 Medium Section: 06.07 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

30) Identify the substitution product(s) in the following reaction.

A) A B) B C) C D) a mixture of A and B Answer: D Difficulty: 2 Medium Section: 06.07 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

31) The major product(s) of this reaction would be

A) only (R). B) only (S). C) (R) and (S). D) achiral. Answer: C Difficulty: 2 Medium Section: 06.07 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 32) The major product expected from the reaction below would be

A) A. B) B. C) C. D) D. Answer: A Difficulty: 2 Medium Section: 06.07 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 18 Copyright © 2019

33) Which one of the following species forms the strongest ion-dipole attraction with 18-crown6?

A) F− B) K+ C) Cr2O72− D) Br2 Answer: B Difficulty: 1 Easy Section: 06.09 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Factors affecting substitution reactions 34) In which of the solvents below would the reaction shown take place at the fastest rate?

A) ethanol B) acetic acid C) dimethyl sulfoxide D) water Answer: C Difficulty: 2 Medium Section: 06.09 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Factors affecting substitution reactions

35) Which halide ion reacts the fastest with cyclopentyl p-toluenesulfonate in ethanol/water?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 06.10 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Factors affecting substitution reactions

36) How would you synthesize the following compound starting with optically pure (R) or (S)-2butanol?

A) (1) (R)-2-butanol + TsCl (2) NaCN/DMSO B) (1) (S)-2-butanol + TsCl (2) NaCN/DMSO C) (1) (S)-2-butanol + H2SO4 (heat) (2) HBr (3) NaCN/DMSO D) (R)-2-butanol + NaCN/DMSO Answer: A Difficulty: 3 Hard Section: 06.11 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2 37) Starting with optically pure (R) or (S)-2-butanol, which method below would give the best yield of the following ether?

A) (1) (R)-2-butanol + TsCl (2) CH3ONa B) (1) (S)-2-butanol + TsCl (2) CH3ONa C) (1) (R)-2-butanol + Na (2) CH3I D) (1) (S)-2-butanol + Na (2) CH3I Answer: D Difficulty: 3 Hard Section: 06.11 Topic: Substitution and Elimination Reactions Bloom's: 5. Evaluate Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

38) A limitation of substitution reactions with alkyl halides is that a competing elimination reaction often occurs. Consider the reaction below. One of the products results from the substitution reaction, and the other product results from the elimination reaction. What is being removed from the alkyl halide in the elimination reaction?

A) Br B) OCH3 C) Br and OCH3 D) Br and H Answer: D Difficulty: 2 Medium Section: 06.12 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 06 Subtopic: Substitution reaction mechanisms: SN1 and SN2

Organic Chemistry, 11e (Carey) Chapter 7 Stucture and Preparation of Alkenes: Elimination Reactions 1) What is the IUPAC name of the following compound?

A) 2,5-dimethyl-1-hexene B) 2,5-dimethyl-2-hexene C) 1,4-dimethyl-1-hexene D) 2,5-dimethyl-5-hexene Answer: A Difficulty: 2 Medium Section: 07.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 2) What is the IUPAC name of the following compound?

A) 2-methyl-3-propyl-2-pentene B) 2,3-dimethyl-2-hexene C) 4-ethyl-5-methyl-4-hexene D) 4-methyl-3-propyl-3-pentene Answer: B Difficulty: 2 Medium Section: 07.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 1 Copyright © 2019

3) What is the IUPAC name of the following compound?

A) 3-ethyl-8-methyl-3-nonene B) 1,1-diethyl-6-methyl-3-heptene C) 7-ethyl-2-methyl-6-nonene D) 3-ethyl-7-isopropyl-3-octene Answer: A Difficulty: 2 Medium Section: 07.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 4) What is the IUPAC name of the following compound?

A) 3-bromo-2-methylcyclohexene B) 1-bromo-2-methyl-2-cyclohexene C) 6-bromo-1-methylcyclohexene D) 2-bromo-1-methylcyclohexene Answer: C Difficulty: 2 Medium Section: 07.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes

5) What is the IUPAC name of the following compound?

A) 3-ethyl-propyl-1-heptene B) 4,6-diethyl-1-octene C) ethyl-3-vinyloctane D) 3,5-diethyl-1-octene Answer: D Difficulty: 2 Medium Section: 07.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 6) When a C=C is present in a molecule, what is the minimum number of atoms that must lie in a single plane? A) 2 B) 4 C) 6 D) 8 Answer: C Difficulty: 1 Easy Section: 07.02 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: Physical properties of alkenes

7) Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why? A) The double bond is much stronger and thus more difficult to rotate. B) Overlap of the two 2p orbitals of the π bond would be lost. C) The shorter bond length of the double bond makes it more difficult for the attached groups to pass each other. D) Overlap of the sp2 orbitals of the carbon-carbon σ bond would be lost. Answer: B Difficulty: 1 Easy Section: 07.03 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: Physical properties of alkenes 8) How many stereoisomers are possible for the following diene? CH3CH=CHCH2CH2CH=CHCH2CH2CH3 A) only one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 07.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 9) How many isomeric alkenes of formula C4H8, including stereoisomers, are possible? A) two B) three C) four D) five Answer: C Difficulty: 2 Medium Section: 07.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes

10) How many isomeric alkenes of formula C5H10, including stereoisomers, are possible? A) three B) four C) five D) six Answer: D Difficulty: 2 Medium Section: 07.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 11) Which of the following alkenes exhibit E-Z isomerism?

A) I and II B) I and III C) II and IV D) I, II, and III Answer: B Difficulty: 2 Medium Section: 07.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: Physical properties of alkenes; IUPAC Nomenclature of alkenes

12) Which of the following alkenes exhibit E-Z isomerism? I. 1-chloropropene II. 2-chloropropene III. 3-chloropropene A) only I B) I and II C) II and III D) I and III Answer: A Difficulty: 2 Medium Section: 07.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: Physical properties of alkenes; IUPAC Nomenclature of alkenes 13) What is the IUPAC name of the following compound?

A) (E)-3-bromo-1-fluoro-2-methylpropene B) (Z)-3-bromo-1-fluoro-2-methylpropene C) (E)-1-bromo-3-fluoro-2-methylpropene D) (Z)-1-bromo-3-fluoro-2-methylpropene Answer: A Difficulty: 3 Hard Section: 07.04 Topic: Alkenes Bloom's: 3. Apply Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes

14) Which of the alkenes below has the Z-configuration?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 07.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes 15) What would be the proper name of the molecule below?

A) (E)-2-ethyl-2-butene B) (Z)-3-methyl-3-pentene C) (E)-3-methyl-2-pentene D) (Z)-2-isohexene Answer: C Difficulty: 2 Medium Section: 07.04 Topic: Alkenes Bloom's: 4. Analyze Chapter: 07 Subtopic: IUPAC Nomenclature of alkenes

16) Which of the following C6H12 isomers has the highest heat of combustion? A) 1-hexene B) trans-3-hexene C) cis-3-hexene D) 2-methyl-2-pentene Answer: A Difficulty: 2 Medium Section: 07.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: Relative stability of alkenes 17) Which alkene of formula C5H10 gives off the least heat (per mol) when burned?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 07.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 07 Subtopic: Relative stabilities of alkenes

18) What is the first step in the mechanism of the dehydration reaction of a tertiary alcohol with sulfuric acid to form an alkene? A) the loss of OH− to form a carbocation B) the protonation of the hydroxyl group C) the loss of the proton from the hydroxyl group to give an alkoxide ion D) the removal of a β-hydrogen from the alcohol Answer: B Difficulty: 1 Easy Section: 07.09 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 19) Identify the major organic product expected from the acid-catalyzed dehydration of 2methyl-2-pentanol. A) 2-methyl-1-pentene B) 2-methyl-2-pentene C) 3-methyl-1-pentene D) cis-3-methyl-2-pentene Answer: B Difficulty: 2 Medium Section: 07.10 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 20) Zaitsev's rule can be used to predict the major product for which of the following reactions? A) 2-methylpentane + Br2(with light) B) 2-bromo-2-methylpentane + NaOCH2CH3 (in ethanol) C) 2-methyl-2-pentanol + PBr3 D) 2-methyl-2-pentanol + HCl Answer: B Difficulty: 1 Easy Section: 07.10 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

21) Which alcohol below would undergo acid-catalyzed dehydration most readily?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 07.12 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 22) What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-2propanol?

A) Protonation of the alcohol to form an oxonium ion. B) Loss of water from the oxonium ion to form a carbocation. C) Loss of a β-hydrogen from the carbocation to form an alkene. D) The simultaneous loss of a β-hydrogen and water from the oxonium ion. Answer: B Difficulty: 1 Easy Section: 07.12 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

23) Which of the following carbocations is(are) likely to undergo a rearrangement?

A) only I B) I and III C) II and III D) I, II, and III Answer: D Difficulty: 2 Medium Section: 07.13 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Carbocations 24) Predict the major product of the following reaction.

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 07.13 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 11 Copyright © 2019

25) Which of the following does not give 1,2-dimethylcyclohexene as one of the acid-catalyzed dehydration products?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 07.13 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 26) The acid-catalyzed dehydration of the alcohol shown below gives a major product, which results from a carbocation rearrangement. Identify this major product.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 07.13 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Substitution reactions SN1 and SN2; Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 12 Copyright © 2019

27) Which of the following would you predict to be the best method for doing the following conversion with the highest yield?

A) H2SO4, heat B) NaOCH2CH3 C) H3PO4 D) (1) PBr3 (2) KOC(CH3)3 Answer: D Difficulty: 3 Hard Section: 07.14 Topic: Substitution and Elimination Reactions Bloom's: 5. Evaluate Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 28) Which of the following will give 2-methyl-1-butene as the only alkene product on treatment with KOC(CH3)3 in dimethyl sulfoxide? A) 2-bromo-3-methylbutane B) 2-bromo-2-methylbutane C) 1-bromo-3-methylbutane D) 1-bromo-2-methylbutane Answer: D Difficulty: 2 Medium Section: 07.14 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

29) Which of the following expressions is the experimentally observed rate law for an E2 reaction of an alkyl halide? A) rate = k[RX] B) rate = k[RX][base] C) rate = k[RX]2 D) rate = k[base] Answer: B Difficulty: 1 Easy Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 30) Which of the following most readily undergoes an E2 reaction with sodium ethoxide (NaOCH2CH3)? A) (CH3)3CF B) (CH3)3CCl C) (CH3)3CBr D) (CH3)3CI Answer: D Difficulty: 2 Medium Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 31) When a strong base is used in the elimination reaction of an alkyl halide the mechanism, in general, is A) E1. B) E2. C) E1 for tertiary halides, E2 for primary and secondary halides. D) E2 for tertiary halides, E1 for primary and secondary halides. Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 14 Copyright © 2019

32) How many isomeric alkenes are possible, including stereoisomers, in the following reaction?

A) two B) three C) four D) five Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 33) Including E-Z isomers, how many E2 products are possible in the following reaction?

A) one B) two C) three D) four Answer: C Difficulty: 3 Hard Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

34) How many different E2 products are expected in the reaction of 3-bromo-1,1dimethylcyclohexane with NaOCH2CH3? A) only one B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 35) Based on Zaitsev's rule, which of the following is the major product of the reaction below?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

36) If you wanted to make compound III, starting with compound I or II, what would you do?

A) React I with H2SO4. B) React II with NaOEt. C) Either reacting I with H2SO4 or II with NaOEt would work. D) Neither reacting I with H2SO4 or II with NaOEt would work. Answer: B Difficulty: 3 Hard Section: 07.15 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 37) In the dehydrohalogenation of 2-bromobutane, which conformation below leads directly to the formation of cis-2-butene?

A) only I B) only II C) only III D) I and II Answer: A Difficulty: 2 Medium Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 17 Copyright © 2019

38) Which of the following cannot undergo an E2 reaction?

A) only I B) only II C) only III D) I and III Answer: A Difficulty: 2 Medium Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

39) Which of the following would have the fastest rate of reaction to form 4-tertbutylcyclohexene?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

40) Which of the following compounds gives a single E2 product on reaction with sodium ethoxide, NaOCH2CH3?

A) I and II B) I and III C) II and III D) I, II, and III Answer: B Difficulty: 2 Medium Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 41) If the following E2 reaction proceeds through an antiperiplanar transition state, what product or products are expected?

A) only 1-methylcyclohexene B) only 3-methylcyclohexene C) only 4-methylcyclohexene D) equal amounts of 1-methylcyclohexene and 3-methylcyclohexene Answer: B Difficulty: 3 Hard Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

42) Which of the following stereoisomers gives the exclusive E2 product shown?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

43) Which one of the following compounds cannot undergo an E2 reaction? A) 1-bromo-2,2-dimethylbutane B) 1-bromo-3,3-dimethylbutane C) 1-bromo-2,3-dimethylbutane D) 2-bromo-2,3-dimethylbutane Answer: A Difficulty: 2 Medium Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 44) Which of the following compounds gives 4,4-dimethylcyclohexene as the exclusive E2 product?

A) A B) B C) C D) both A and B Answer: A Difficulty: 2 Medium Section: 07.16 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

45) Considering E2 reactions involving the labeled deuterium atoms, which compound would have the slowest reaction rate?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 07.17 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand; 3. Apply; 4. Analyze Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 46) Which of the following sets of conditions most favors the E1 mechanism? A) when the alkyl halide is tertiary and the base is a weak base B) when the alkyl halide is tertiary and the base is a strong base C) when the alkyl halide is primary or secondary and the base is a weak base D) when the alkyl halide is primary or secondary and the base is a strong base Answer: A Difficulty: 2 Medium Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2

47) Considering the SN1, SN2, E1, and E2 mechanisms, the energy diagram shown below corresponds to

A) only the SN1 mechanism. B) both the SN1 and E1 mechanisms. C) only the SN2 mechanism. D) both the SN2 and E2 mechanisms. Answer: D Difficulty: 3 Hard Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Substitution reactions SN1 and SN2; Elimination reaction mechanisms: E1 and E2 48) Which of the following bases works best to maximize the E2 product in the reaction shown below?

A) KOCH2CH3 B) NaOCH2CH3 C) NaOC(CH3)3 D) NaOH Answer: C Difficulty: 2 Medium Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 24 Copyright © 2019

49) In the solvolysis of t-butyl chloride, a minor product is 2-methylpropene, which results from the:

A) E2 mechanism with OH− acting as the base. B) E2 mechanism with H2O acting as the base. C) E1 mechanism with OH− acting as the base. D) E1 mechanism with H2O acting as the base. Answer: D Difficulty: 2 Medium Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Factors affecting elimination reactions; Elimination reaction mechanisms: E1 and E2 50) Identify the mechanistic pathways, respectively, for the products in the following reaction.

A) E1, SN1 B) E1, SN2 C) E2, SN1 D) E2, SN2 Answer: D Difficulty: 2 Medium Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Elimination reaction mechanisms: E1 and E2

51) Identify the mechanistic pathways, respectively, for the products in the following reaction.

A) E1, SN1 B) E1, SN2 C) E2, SN1 D) E2, SN2 Answer: A Difficulty: 2 Medium Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 07 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Elimination reaction mechanisms: E1 and E2

52) What is the major product in the following reaction?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 07.19 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 07 Subtopic: Substitution reaction mechanisms: SN1 and SN2; Elimination reaction mechanisms: E1 and E2

Organic Chemistry, 11e (Carey) Chapter 8 Addition Reactions of Alkenes 1) Which one of the following is not a metal catalyst for the hydrogenation of an alkene? A) Pd B) Pt C) Na D) Ni Answer: C Difficulty: 1 Easy Section: 08.01 Topic: Alkenes Bloom's: 1. Remember Chapter: 08 Subtopic: Reactions of alkenes 2) A compound, C15H24, is reacted with excess hydrogen using a metal catalyst. One equivalent of the compound consumed three equivalents of hydrogen. How many rings did the original compound have? A) one only B) two only C) three only D) none Answer: A Difficulty: 2 Medium Section: 08.01 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes

3) A compound, C20H30, can be hydrogenated with platinum metal and hydrogen to give a compound C20H38. How many double bonds (DB) and rings (R) does the original compound have? (The original compound has no triple bonds.) A) 4 DB, 2 R B) 4 DB, 1 R C) 3 DB, 3 R D) 2 DB, 4 R Answer: A Difficulty: 3 Hard Section: 08.01 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes 4) Determine the SODAR (sum of double bonds and rings) for a compound with the formula of C6H9BrO. A) one B) two C) three D) four Answer: B Difficulty: 1 Easy Section: 08.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Physical properties of alkenes

5) Compound X, C5H10O, is optically active. The compound consumes one equivalent of hydrogen to give C5H12O. The hydrogenation product is also optically active. Which compound below matches the information?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 08.02 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Optical activity 6) What is(are) the product(s) in the Pd-catalyzed hydrogenation of 1,2-dimethylcyclopentene? A) trans-1,2-dimethylcyclopentane B) cis-1,2-dimethylcyclopentane C) a mixture of trans and cis-1,2-dimethylcyclopentane D) 1,1-dimethylcyclopentane Answer: B Difficulty: 2 Medium Section: 08.02 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes

7) The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via A) syn addition. B) Markovnikov addition. C) anti addition. D) anti-Markovnikov addition. Answer: A Difficulty: 1 Easy Section: 08.02 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes 8) The product(s) in the following reaction is(are)

A) only trans-1-4-dimethylcyclohexane. B) only cis-1-4-dimethylcyclohexane. C) both trans and cis-1-4-dimethylcyclohexane. D) methylcyclohexane. Answer: C Difficulty: 3 Hard Section: 08.02 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes

9) Compound X, C6H10, is optically active. Hydrogenation of the compound gives methylcyclopentane. Which compound below is compound X?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 08.02 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Optical activity; Chiral vs achiral molecules 10) Compound X (C7H12) is optically active. Hydrogenation of compound X gives two isomeric 1,2-dimethylcyclopentanes, one is optically active and the other is optically inactive. Of the following compounds, which is the only one that fits the data?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 08.02 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Optical activity

11) Which of the following alkenes is expected to have the highest heat of hydrogenation? A) 1-pentene B) trans-2-pentene C) cis-2-pentene D) 2-methyl-2-butene Answer: A Difficulty: 2 Medium Section: 08.03 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Relative stabilities of alkenes 12) Which alkene below is thermodynamically the most stable? A) 1-hexene B) trans-3-hexene C) cis-3-hexene D) 2-methyl-2-pentene Answer: D Difficulty: 1 Easy Section: 08.03 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Relative stabilities of alkenes

13) What is the major product of the following reaction?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 08.04 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

14) Which brief statement most accurately describes why alkenes react the way they do? A) C=C double bonds are weak. B) a π bond is lost but a stronger σ bond is gained. C) C=C double bonds are unstable. D) C=C π bonds are attacked by nucleophiles. Answer: B Difficulty: 1 Easy Section: 08.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

15) What is the intermediate in the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 08.04 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

16) Predict which of the following alkenes reacts the fastest with HCl. A) CH3CH2CH2CH2CH=CH2 B) trans-CH3CH2CH=CHCH2CH3 C) cis-CH3CH2CH=CHCH2CH3 D) (CH3)2C=CHCH2CH3 Answer: D Difficulty: 2 Medium Section: 08.04 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes 17) Which of the following correctly depicts the mechanistic first step in the addition of HBr to 2-methylpropene?

18) Which of the following is least likely to react with an alkene? A) H3O+ B) BrCl C) O3 D) NaOCH2CH3 Answer: D Difficulty: 2 Medium Section: 08.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes 19) Which point on the potential energy diagram corresponds to the species below for the reaction of 2-methylpropene with hydrogen chloride?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 08.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

20) Which of the following is not a possible reaction of a carbocation? A) addition of a nucleophile B) rearrangement to a more stable carbocation C) addition of a proton to form an alkane D) loss of a β-hydrogen to form an alkene Answer: C Difficulty: 2 Medium Section: 08.05 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 08 Subtopic: Carbocations 21) Addition of HCl to 3-methyl-1-pentene gives two products. One of these is 2-chloro-3methylpentane. What is the other product? A) 1-chloro-3-methylpentane B) 3-chloro-3-methylpentane C) 3-chloro-2-methylpentane D) 2-chloro-2-methylpentane Answer: B Difficulty: 3 Hard Section: 08.05 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene 22) The rearrangement which most likely occurs in the following reaction can be described as a

A) hydride shift from C-2 to C-1. B) hydride shift from C-3 to C-2. C) proton shift from C-2 to C-1. D) methyl group shift from C-3 to C-2. Answer: B Difficulty: 2 Medium Section: 08.05 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes 12 Copyright © 2019

23) Which of the following is the key intermediate in the Markovnikov addition of HBr to 1butene?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 08.04 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene 24) Identify the nucleophile in the following electrophilic addition reaction.

A) N3+ B) N3– C) I+ D) I– Answer: B Difficulty: 3 Hard Section: 08.04 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

25) The addition of HBr to 1-octene gives A) a racemic mixture of 2-bromooctane. B) a nonracemic mixture of 2-bromooctane. C) 1-bromooctane. D) a racemic mixture of 1,2-dibromooctane. Answer: A Difficulty: 2 Medium Section: 08.04 Topic: Alkenes; Stereochemistry Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Optical activity; Stereogenic/chirality carbon centers; Chiral vs achiral molecules 26) Which species below acts as the nucleophile in the acid-catalyzed addition of water to an alkene? A) H3O+ B) the carbocation C) OHD) H2O Answer: D Difficulty: 1 Easy Section: 08.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

27) Which of the following is the rate-determining step in the acid-catalyzed addition of water to 2-methylpropene?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 08.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

28) Which point on the potential energy diagram corresponds to the carbocation intermediate, (CH3)3C+, for the reaction shown below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 08.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

29) Identify the electrophilic species in the following reaction.

A) H2C=C(CH3)2 B) H2O C) H3O+ D) (CH3)3COH Answer: C Difficulty: 1 Easy Section: 08.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes 30) Which reagent(s) below would convert 2-methyl-2-pentene to 2-methyl-2-pentanol (shown below)?

A) (1) O3 (2) Zn, H2O B) Br2/H2O C) (1) BH3/THF (2) H2O2, NaOH D) H2O/H2SO4 (cat.) Answer: D Difficulty: 2 Medium Section: 08.06 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

31) What major product would you expect from this reaction?

A) 3,3-dimethyl-2-butanol B) 3,3-dimethyl-1-butanol C) 2,3-dimethyl-2-butanol D) 2,2-dimethyl-3-butanol Answer: C Difficulty: 3 Hard Section: 08.06 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene 32) Which reagent(s) below would work best in converting 2-methyl-2-hexene to 2-methyl-3hexanol? A) (1) H2SO4 (2) H2O B) 50% H2SO4/H2O C) (1) BH3/THF (2) H2O2, NaOH D) Br2/H2O Answer: C Difficulty: 2 Medium Section: 08.08 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

33) What is the major product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 08.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

34) What is(are) the product(s) of the following hydroboration-oxidation reaction?

A) 1-methylcyclobutanol B) trans-2-methylcyclobutanol C) cis-2-methylcyclobutanol D) equal amounts of B and C Answer: B Difficulty: 3 Hard Section: 08.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene 35) The hydroboration-oxidation reaction can be characterized as the ________ to an alkene. A) anti-Markovnikov syn addition of water B) anti-Markovnikov anti addition of water C) Markovnikov syn addition of water D) Markovnikov anti addition of water Answer: A Difficulty: 1 Easy Section: 08.08 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

36) What is the product in the following reaction?

A) (CH3CH2CH2)3B B) [(CH3)2CH]3B C) CH3CH2CH3 D) polypropylene Answer: A Difficulty: 2 Medium Section: 08.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene 37) Which of the alcohols below could NOT be prepared using hydroboration/oxidation of an alkene?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 08.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

38) Which of the following species is the intermediate in the bromination of propene?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 08.10 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

39) Which reaction proceeds by anti addition?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 08.10 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

40) Which of the following is the product of the reaction shown below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 08.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes

41) What is the major product of the following reaction?

A) 1,2-dibromo-2-methylhexane B) 2,2-dibromo-2-methylhexane C) 2,3-dibromo-2-methylhexane D) 2,4-dibromo-2-methylhexane Answer: C Difficulty: 2 Medium Section: 08.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes 42) Which of the following alkenes gives 1-bromo-2-methyl-2-pentanol upon reaction with Br2/H2O?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 08.10 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

43) Addition of hypobromous acid, HOBr, to 1-methylcyclohexene gives:

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 08.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

44) The reaction of 1-butene with bromine, Br2, in aqueous solution gives primarily 1-bromo-2butanol. Identify the nucleophilic species in the reaction. A) Br2 B) BrC) H2O D) HOBr Answer: C Difficulty: 2 Medium Section: 08.10 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes 45) What product results from this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 08.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

46) Rank the following in order of decreasing reactivity with bromine, Br2.

A) I > II > III B) II > III > I C) III > I > II D) III > II > I Answer: A Difficulty: 2 Medium Section: 08.10 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes 47) Which of the following species is the intermediate in the bromination of propene?

48) The addition of bromine, Br2, to trans-2-butene gives A) (2R,3R)-2,3-dibromobutane. B) (2S,3S)-2,3-dibromobutane. C) a racemic mixture of (2R,3R) and (2S,3S)-2,3-dibromobutane. D) meso-2,3-dibromobutane. Answer: D Difficulty: 3 Hard Section: 08.10 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; R and S nomenclature 49) Which of the following is the best method to make a racemic mixture of (+) and (-)-2,3dibromobutane? A) photochemical bromination of 2-bromobutane B) addition of HBr to racemic 3-bromo-2-butene C) addition of Br2 to cis-2-butene D) addition of Br2 to trans-2-butene Answer: C Difficulty: 3 Hard Section: 08.10 Topic: Alkenes; Stereochemistry Bloom's: 5. Evaluate Chapter: 08 Subtopic: Reactions of alkenes; Optical activity; Chiral vs achiral molecules

50) Which of the following reactions occurs by a one-step mechanism as opposed to a two-step mechanism?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 08.11 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

51) What product results from this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 08.11 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes

52) How many of these reagents cause only syn additions to alkenes?

A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 1 Easy Section: 08.11 Topic: Alkenes Bloom's: 2. Understand Chapter: 08 Subtopic: Reactions of alkenes

53) Which reaction below gives a pair of diastereomers?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 08.11 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Stereoisomers (enantiomers, diastereomers, meso) 54) Which of the following C6H10 cycloalkenes would give a pair of diastereomeric epoxides when reacted with peroxyacetic acid, CH3CO3H? A) 1-methylcyclopentene B) 3-methylcyclopentene C) 1,2-dimethylcyclobutene D) 3,3-dimethylcyclobutene Answer: B Difficulty: 3 Hard Section: 08.11 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Stereoisomers (enantiomers, diastereomers, meso) 33 Copyright © 2019

55) Which of the following compounds gives a pair of diastereomers upon epoxidation with peroxyacetic acid, CH3CO3H?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 08.11 Topic: Alkenes; Stereochemistry Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes; Stereoisomers (enantiomers, diastereomers, meso)

56) A compound is treated with ozone followed by zinc in water to give the following three products. Which structure below best fits the data?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 08.12 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes

57) Which of the following gives acetone, (CH3)2C=O, as one of the products of its ozonolysis?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 08.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes 58) What does it mean when a reaction is termed enantioselective? A) The reaction occurs with only one enantiomer of a chiral reactant. B) Both enantiomers of a chiral product are produced in equal amounts. C) Only one enantiomer of a chiral product is formed preferentially. D) The reaction starts with a chiral reactant, but loses chirality in the product. Answer: C Difficulty: 1 Easy Section: 08.13 Topic: Alkenes Bloom's: 1. Remember Chapter: 08 Subtopic: Reactions of alkenes

59) Which of the following series of reactions would convert cyclohexanol to 1,2epoxycyclohexane?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 08.14 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes

60) A compound, C7H13Cl, is reacted with sodium ethoxide and gives a single elimination product, C7H12. Treatment with ozone followed by zinc and water gives the compound below. Identify the original compound.

A) 2-chloro-1,1-dimethylcyclopentane B) 4-chloro-1,2-dimethylcyclopentane C) 1-chloro-1,2-dimethylcyclopentane D) 2-chloro-1,3-dimethylcyclopentane Answer: D Difficulty: 3 Hard Section: 08.12 Topic: Alkenes Bloom's: 4. Analyze Chapter: 08 Subtopic: Reactions of alkenes

61) What product results from this reaction?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 08.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 08 Subtopic: Reactions of alkenes 62) Which reaction sequence below would work best in converting 3-pentanol into 2,3dibromopentane? A) (1) H2SO4, heat; (2) 2 moles HBr B) (1) H2SO4, heat; (2) H2/Pt; (3) Br2 C) (1) HBr; (2) Br2/H2O D) (1) H2SO4, heat; (2) Br2 Answer: D Difficulty: 3 Hard Section: 08.14 Topic: Alkenes Bloom's: 5. Evaluate Chapter: 08 Subtopic: Reactions of alkenes 39 Copyright © 2019

Organic Chemistry, 11e (Carey) Chapter 9 Alkynes 1) What is the IUPAC name of the following compound?

A) 5-propyl-3-heptyne B) 5-isopropyl-3-heptyne C) 5-ethyl-3-octyne D) 4-ethyl-5-octyne Answer: C Difficulty: 2 Medium Section: 09.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: IUPAC Nomenclature of alkynes 2) What is the IUPAC name of the following compound?

A) 2-methyl-5-propyl-3-heptyne B) 1-isopropyl-3-propyl-1-pentyne C) 5-ethyl-2-methyl-3-octyne D) 4-ethyl-7-methyl-5-octyne Answer: C Difficulty: 2 Medium Section: 09.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: IUPAC Nomenclature of alkynes

3) Which of the following describes the orbital overlap of the C(1)-C(2) sigma bond of 1-butyne, shown below?

A) sp-sp B) sp2-sp2 C) sp3-sp3 D) 2p-2p Answer: A Difficulty: 1 Easy Section: 09.04 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Physical properties of alkynes 4) Which one of the following describes the C(2)-C(3) sigma bond in the structure below?

A) sp-sp B) sp2-sp2 C) sp3-sp3 D) 2p-2p Answer: A Difficulty: 1 Easy Section: 09.04 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Physical properties of alkynes

5) What would the name of this molecule be?

A) 2,3-dimethyl-4-hexyne B) 4,5,5-trimethyl-2-pentyne C) 3-isopropyl-2-butyne D) 4,5-dimethyl-2-hexyne Answer: D Difficulty: 2 Medium Section: 09.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: IUPAC Nomenclature of alkynes 6) Select the best base to quantitatively remove a proton from acetylene. A) NaNH2 B) NH3 C) NaOH D) NaOCH2CH3 Answer: A Difficulty: 1 Easy Section: 09.05 Topic: Alkynes Bloom's: 1. Remember Chapter: 09 Subtopic: Reactions of alkynes

7) Rank the following anions in order of increasing base strength.

A) I < II < III B) II < III < I C) III < II < I D) III < I < II Answer: C Difficulty: 1 Easy Section: 09.05 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes 8) What base is able to efficiently (completely) form alkynyl anions from terminal alkynes?

A) KOtBu B) NaNH2 C) NaOH D) CH3ONa Answer: B Difficulty: 1 Easy Section: 09.05 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes

9) When a terminal alkyne is treated with sodium amide, NaNH2, in liquid ammonia, sodium amide acts as a A) Brønsted acid. B) Brønsted base. C) reducing agent. D) catalyst. Answer: B Difficulty: 1 Easy Section: 09.05 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes 10) The larger acid dissociation constant, Ka, of acetylene as compared to ethylene is primarily attributed to the A) greater electronegativity of an sp carbon as compared to an sp2 carbon. B) smaller electronegativity of an sp carbon as compared to an sp2 carbon. C) acetylide anion being resonance stabilized. D) the 4 π electrons of the acetylide anion stabilizing the negative charge. Answer: A Difficulty: 2 Medium Section: 09.05 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes 11) Why can't methanol, CH3OH, be used as a solvent for sodium amide, NaNH2? A) Sodium amide is nonpolar and methanol is polar. B) Sodium amide is polar and methanol is nonpolar. C) Sodium amide undergoes an acid-base reaction with methanol. D) There would be no ion-dipole attractive forces between the two compounds. Answer: C Difficulty: 2 Medium Section: 09.05 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes

12) Arrange the following in order of decreasing base strength (strongest base first).

A) IV > III > II > I B) I > II > IV > III C) II > III > I > IV D) II > III > IV > I Answer: D Difficulty: 3 Hard Section: 09.05 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes 13) Predict the major product(s) in the reactions below.

A) 1-nonyne B) 2-nonyne C) cis-2-nonene D) trans-2-nonene Answer: B Difficulty: 2 Medium Section: 09.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

14) Which sequence of reactions below works best in carrying out the following conversion?

A) (1) HBr (2) excess NaNH2 B) (1) Br2 (2) excess NaNH2 C) (1) Br2, H2O (2) excess NaNH2 D) (1) H2O, H2SO4(cat.) (2) excess NaNH2 Answer: B Difficulty: 2 Medium Section: 09.07 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes 15) Is the proposed synthesis of cyclohexanone below likely to work? If not, why not?

A) Yes, it would work. B) No, you would need to start with 1,2-dibromocyclohexane. C) No, cyclohexyne will not form. D) No, the enol of cyclohexanone cannot be formed from cyclohexyne. Answer: C Difficulty: 2 Medium Section: 09.07 Topic: Alkynes Bloom's: 5. Evaluate Chapter: 09 Subtopic: Reactions of alkynes

16) What is the product of the following reaction?

A) 3-methylhexane B) 2-bromo-3-methylhexane C) 3-methyl-1-hexyne D) 1-bromo-3-methylhexane Answer: C Difficulty: 3 Hard Section: 09.07 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes 17) Which of the following reagents would be used to convert 2-pentyne to cis-2-pentene? A) NaNH2, NH3 B) Na, NH3 C) H2, Lindlar Pd D) H2O, HgSO4/H2SO4 Answer: C Difficulty: 1 Easy Section: 09.09 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes

18) Select the best method to carry out the following conversion.

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 09.09 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes

19) What major product do you expect from this reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 09.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

20) Which sequence of reactions works best in synthesizing cis-3-nonene?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 09.09 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes 21) Identify compound Y.

A) 2-bromobutane B) meso-2,3-dibromobutane C) racemic (2R,3R) and (2S,3S)-2,3-dibromobutane D) 2,3-dibromo-2-butene Answer: C Difficulty: 2 Medium Section: 09.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

22) The product of this reaction would be

A) only (S) B) only (R) C) (R) + (S) D) achiral Answer: A Difficulty: 2 Medium Section: 09.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes 23) What is the product of the following reaction sequence?

A) 1-hexanol B) 2-hexanol C) 1,2-hexanediol D) 1-hexene Answer: A Difficulty: 3 Hard Section: 09.09 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes

24) What is the major product of the reaction shown below?

A) 1,1-dichlorobutane B) 1,2-dichlorobutane C) 2,2-dichlorobutane D) 1,1,2,2-tetrachlorobutane Answer: C Difficulty: 2 Medium Section: 09.10 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes 25) What is the relationship between the keto and enol forms of acetone?

A) resonance structure B) conformations C) diastereomers D) constitutional isomers Answer: D Difficulty: 1 Easy Section: 09.11 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes

26) What is the major product of the reaction shown below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 09.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

27) How many organic products do you expect from this reaction?

A) one B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 09.11 Topic: Alkynes Bloom's: 2. Understand Chapter: 09 Subtopic: Reactions of alkynes 28) Which of the following gives only one organic product on acid-catalyzed hydrolysis? A) 2-hexyne B) 3-hexyne C) 2-heptyne D) 3-heptyne Answer: B Difficulty: 2 Medium Section: 09.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

29) Hydration of an alkyne, C6H10, gave two ketones in approximately equal amounts. Which of the following alkynes would be expected to give these results? A) 1-hexyne B) 2-hexyne C) 3-hexyne D) 3,3-dimethyl-1-butyne Answer: B Difficulty: 2 Medium Section: 09.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes 30) Which one of the following alkynes gives a single ketone in the acid-catalyzed hydration of each? A) 2-decyne B) 3-decyne C) 4-decyne D) 5-decyne Answer: D Difficulty: 2 Medium Section: 09.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

31) Which of the following is the enol intermediate in the acid-catalyzed addition of water to propyne?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 09.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

32) Select the best reaction sequence to make the following ketone.

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 09.11 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes 33) Which of the following gives only one organic product on ozonolysis? A) 2-hexyne B) 3-hexyne C) 2-heptyne D) 3-heptyne Answer: B Difficulty: 1 Easy Section: 09.13 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes

34) What major product results from this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 09.13 Topic: Alkynes Bloom's: 3. Apply Chapter: 09 Subtopic: Reactions of alkynes 35) Ozonolysis of an alkyne gave the two compounds shown below. What is the IUPAC name of the original alkyne? CH3CH2CH2CO2H and (CH3)3CCO2H A) 2,2-dimethyl-3-octyne B) 3,3-dimethyl-4-octyne C) 2,2-dimethyl-3-heptyne D) 6,6-dimethyl-3-heptyne Answer: C Difficulty: 3 Hard Section: 09.13 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: IUPAC Nomenclature of alkynes; Reactions of alkynes 19 Copyright © 2019

36) Which of the following ketones cannot be made by the acid-catalyzed hydration of an alkyne?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 09.14 Topic: Alkynes Bloom's: 4. Analyze Chapter: 09 Subtopic: Reactions of alkynes

Organic Chemistry, 11e (Carey) Chapter 10 Introduction to Free Radicals 1) Which halogen forms the weakest bond to carbon? A) F B) Cl C) Br D) I Answer: A Difficulty: 1 Easy Section: 10.01 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Radical stability 2) Which of the following is the most stable radical?

3) Studies indicate that the methyl radical is trigonal planar. Based on this, which of the following best describes the methyl radical? A) The carbon is sp2 hybridized and the unpaired electron occupies an sp2 orbital. B) The carbon is sp2 hybridized and the unpaired electron occupies a 2p orbital. C) The carbon is sp3 hybridized and the unpaired electron occupies an sp3 orbital. D) The carbon is sp3 hybridized and the unpaired electron occupies a 2p orbital. Answer: B Difficulty: 2 Medium Section: 10.01 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Radical stability 4) Calculate ΔH° of reaction for the free radical bromination of cyclopentane to give bromocyclopentane.

A) −121 kJ/mol B) −63 kJ/mol C) +121 kJ/mol D) +63 kJ/mol Answer: B Difficulty: 2 Medium Section: 10.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes

5) The reaction shown below is what type?

A) addition B) termination C) propagation D) initiation Answer: C Difficulty: 1 Easy Section: 10.03 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Halogenation of alkanes 6) Which of the following are the chain propagating steps in the free radical chlorination of methane?

A) I and III B) II and VI C) III and IV D) III and V Answer: D Difficulty: 2 Medium Section: 10.03 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Halogenation of alkanes 3 Copyright © 2019

7) Which one of the following gives a single monochlorination product? A) 2,2-dimethylpropane B) 2,3-dimethylbutane C) 2,2-dimethylbutane D) 2-methylpropane Answer: A Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes 8) Which of the following hydrocarbons has the slowest reaction rate with Br2 and light? A) CH4 B) CH3CH2CH3 C) CH3CH2CH2CH3 D) (CH3)3CH Answer: A Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 10 Subtopic: Halogenation of alkanes; Radical stability 9) How many monochlorination products do you expect in the following reaction?

10) Which of the following is the key intermediate in the chlorination reaction below?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 10.04 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Halogenation of alkanes 11) How many C3H6Cl2 constitutional isomers do you expect in the dichlorination of propane? A) two B) three C) four D) five Answer: C Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes

12) Upon free-radical chlorination, the alkane shown would yield

A) a single monochloride. B) three isomeric monochlorides. C) two isomeric dichlorides. D) four isomeric monochlorides. Answer: D Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes 13) What is the major product in the monochlorination of pentane?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes

14) Which statement would be true of this reaction?

A) The organic product is achiral. B) The product is racemic. C) The product is more of one enantiomer than the other. D) There is no way to guess the stereochemistry. Answer: B Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions; Stereochemistry Bloom's: 2. Understand Chapter: 10 Subtopic: Halogenation of alkanes; Chiral vs achiral molecules; Stereoisomers (enantiomers, diastereomers, meso) 15) Where would this reaction occur fastest in this molecule?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 10 Subtopic: Halogenation of alkanes; Radical stability

16) Which constitutional isomer of C6H14 gives only two monochlorination products? A) 2-methylpentane B) 2,2-dimethylbutane C) 3-methylpentane D) 2,3-dimethylbutane Answer: D Difficulty: 2 Medium Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes 17) Consider the following reaction (X = Cl or Br).

Which statement(s) is(are) correct? I. Statistically the 1-halopropane should be the major isomer. II. The 2-halopropane to 1-halopropane ratio is largest when X=Br. III. The 2-halopropane to 1-halopropane ratio is the largest when X=Cl. A) only II B) only III C) I and II D) I and III Answer: C Difficulty: 3 Hard Section: 10.04 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Halogenation of alkanes

18) Chlorination of pentane gives a mixture of isomers having the molecular formula C5H11Cl. The percentage of 1-chloropentane is 22%. Assuming the secondary hydrogens in pentane are equally reactive to monochlorination, what is the percentage of 3-chloropentane in the mixture? A) 48% B) 26% C) 22% D) 14% Answer: B Difficulty: 3 Hard Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes

19) Dibromination of isopropylcyclopentane gives a product that can be isolated in good yields. Which of the following would you predict to be this product?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes

20) If you wanted to get the best yield of compound B from compound A, you would:

A) use chlorine + light rather than bromine + light B) use bromine + light rather than chlorine + light C) neither would give >50% yield D) either would give >50% yield Answer: A Difficulty: 3 Hard Section: 10.04 Topic: Radical Reactions Bloom's: 5. Evaluate Chapter: 10 Subtopic: Halogenation of alkanes 21) What is the major product of the reaction sequence shown below?

A) 2-methyl-1-butene B) 2-methyl-2-butene C) 3-methyl-1-butene D) 2-methylbutane Answer: B Difficulty: 3 Hard Section: 10.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Halogenation of alkanes

22) Which species below is the intermediate in the free radical addition of HBr to 1-butene?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 10.05 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Radical addition to alkenes and alkynes

23) Which reaction below gives a single enantiomer of a chiral product?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 10.05 Topic: Radical Reactions; Stereochemistry Bloom's: 4. Analyze Chapter: 10 Subtopic: Radical addition to alkenes and alkynes; Chiral vs achiral molecules; Stereoisomers (enantiomers, diastereomers, meso)

24) Which of the following does not give 1-bromo-1-methylcyclopentane as the major product?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 10.05 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Radical addition to alkenes and alkynes 25) Which reagent below would be used to convert 2-pentyne to trans-2-pentene? A) NaNH2, NH3 B) Na, NH3 C) H2, Lindlar Pd D) H2O, HgSO4/H2SO4 Answer: B Difficulty: 1 Easy Section: 10.06 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Radical addition to alkenes and alkynes

26) It is believed that the trans alkenyl radical, shown below, is an intermediate in the sodium metal reduction of an alkyne. Based on this information, the unpaired electron would be located in which of the following orbitals?

A) sp B) sp2 C) sp3 D) 2p Answer: B Difficulty: 2 Medium Section: 10.06 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Radical stability; Radical addition to alkenes and alkynes 27) Which of the following is the correct IUPAC name of the product for the reaction shown below?

A) cis-2-methyl-5-heptene B) cis-6-methyl-2-heptene C) trans-2-methyl-5-heptene D) trans-6-methyl-2-heptene Answer: D Difficulty: 2 Medium Section: 10.06 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 10 Subtopic: Radical addition to alkenes and alkynes

28) When alkynes are treated with sodium metal, Na, in liquid ammonia, sodium acts as a A) Brønsted acid. B) Brønsted base. C) reducing agent. D) catalyst. Answer: C Difficulty: 2 Medium Section: 10.06 Topic: Radical Reactions Bloom's: 2. Understand Chapter: 10 Subtopic: Radical addition to alkenes and alkynes 29) What reagents would be required to accomplish the conversion shown below?

A) NaOCH3, then Br2 and light. B) KOCH3, then HBr and peroxides. C) NaOCH3, then HBr. D) KOtBu, then Br2 and light. Answer: B Difficulty: 3 Hard Section: 10.07 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 10 Subtopic: Radical addition to alkenes and alkynes

30) How would you carry out the following conversion?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 10.07 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 10 Subtopic: Radical addition to alkenes and alkynes

Organic Chemistry, 11e (Carey) Chapter 11 Conjugation in Alkadienes and Allylic Systems 1) Identify the allylic halide(s).

A) only II B) I and II C) I and IV D) I, III, and IV Answer: C Difficulty: 1 Easy Section: 11.01 Topic: Alkyl Halides Bloom's: 2. Understand Chapter: 11 Subtopic: Classify as primary, secondary, or tertiary alkyl halides 2) How many allylic hydrogens are there in 1-ethylcyclohexene? A) one B) two C) four D) six Answer: D Difficulty: 2 Medium Section: 11.01 Topic: Alkenes Bloom's: 2. Understand Chapter: 11 Subtopic: IUPAC Nomenclature of alkenes

3) Which of the following carbocations is the most stable?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 11.02 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Carbocations 4) Which of the following compounds most readily undergoes solvolysis with methanol? A) (E)-1-bromo-1-butene B) 2-bromo-1-butene C) 3-bromo-1-butene D) 4-bromo-1-butene Answer: C Difficulty: 2 Medium Section: 11.02 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Carbocations; Factors affecting substitution reactions

5) Rank the following carbocations in decreasing order of stability.

A) I > II > III B) III > II > I C) II > I > III D) They are of equal stability. Answer: A Difficulty: 2 Medium Section: 11.02 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Carbocations 6) Give the total number of resonance forms of the carbocation, which results from the SN1 ionization of the compound shown below.

A) no resonance forms—a single Lewis structure B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 11.02 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Carbocations

7) Methanolysis of 4-bromo-2-methyl-2-pentene gives two isomeric substitution products, one of which is shown. What is the other substitution product?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 11.02 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Carbocations

8) Which reaction sequence below would work best (and with highest overall yield) in the following conversion?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 11.03 Topic: Radical Reactions Bloom's: 5. Evaluate Chapter: 11 Subtopic: Allylic and benzylic halogenation 9) Which one of the following gives only a single allylic bromide on heating with NBS in carbon tetrachloride?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 11.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Allylic and benzylic halogenation

10) Allylic bromination of methylenecyclohexane would be expected to give two isomeric monobromination products. Identify the other isomer.

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 11.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Allylic and benzylic halogenation

11) What is(are) the expected product(s) of the following reaction?

A) only II B) only III C) I and III D) II and IV Answer: C Difficulty: 2 Medium Section: 11.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Allylic and benzylic halogenation 12) Identify the weakest carbon-hydrogen bond in the following diene.

A) C-H on C(1) B) C-H on C(2) C) C-H on C(4) D) C-H on C(7) Answer: C Difficulty: 2 Medium Section: 11.03 Topic: Alkenes Bloom's: 4. Analyze Chapter: 11 Subtopic: Relative stabilities of alkenes

13) What is the product of the reaction sequence shown below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 11.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Allylic and benzylic halogenation

14) What is the IUPAC name of the following diene?

A) 3-chloro-2,5-dimethyl-2,6-heptadiene B) 3-chloro-2,5-dimethyl-1,5-heptadiene C) 5-chloro-3,5-dimethyl-1,6-heptadiene D) 5-chloro-3,6-dimethyl-1,5-heptadiene Answer: D Difficulty: 2 Medium Section: 11.05 Topic: Alkenes Bloom's: 3. Apply Chapter: 11 Subtopic: IUPAC Nomenclature of alkenes 15) Which of the following are conjugated dienes? I. 1,2-octadiene II. 1,3-octadiene III. 2,5-octadiene IV. 1,7-octadiene A) only I B) only II C) I and II D) II and III Answer: B Difficulty: 1 Easy Section: 11.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Properties of dienes

16) Chlorination of 14C-labeled propene (H214C=CHCH3) with Cl2 at high temperature would give which of the following chloropropenes?

A) only I B) only II C) I and II D) I and III Answer: C Difficulty: 3 Hard Section: 11.05 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Allylic and benzylic halogenation 17) Which of the following isomers of C10H12 has the greatest resonance energy (delocalization energy)?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 11.06 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Properties of dienes

18) Which compound below has the lowest heat of hydrogenation? A) 1,5-hexadiene B) 3,4-hexadiene C) (E)-1,4-hexadiene D) (E,E)-2,4-hexadiene Answer: D Difficulty: 2 Medium Section: 11.06 Topic: Alkenes Bloom's: 2. Understand Chapter: 11 Subtopic: Stability of alkenes 19) What is the relationship between the s-cis and s-trans forms of 1,3-butadiene?

A) constitutional isomers B) different conformations of the same compound C) diastereomers D) resonance forms Answer: B Difficulty: 1 Easy Section: 11.07 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Properties of Dienes

20) Which one of the following is the s-trans conformation of (E)-2-methyl-2,4-hexadiene?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 11.07 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Properties of dienes 21) What type or types of stereoisomers are possible for 3,4-heptadiene, shown below? CH3CH2CH=C=CHCH2CH3 A) a pair of enantiomers B) two diastereomers, E and Z C) three diastereomers, (E,E), (E,Z), and (Z,Z) D) no stereoisomers are possible Answer: A Difficulty: 2 Medium Section: 11.08 Topic: Alkenes Bloom's: 2. Understand Chapter: 11 Subtopic: Relative stabilities of alkenes

22) Addition of one equivalent of HBr to 1,3-cyclohexadiene gives A) bromocyclohexane. B) 3-bromocyclohexene. C) 4-bromocyclohexene. D) 3-bromocyclhexene and 4-bromocyclohexene. Answer: B Difficulty: 2 Medium Section: 11.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Electrophilic addition to dienes 23) What is the kinetically controlled product in the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 11.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Electrophilic addition to dienes

24) Which of the following is not true concerning the addition of HCl to 1,3-butadiene? A) The intermediate is an allylic carbocation. B) A carbocation rearrangement leads to the 1,4-addition product. C) The 1,4-addition product is the thermodynamically controlled product. D) The reaction mechanism has two steps. Answer: B Difficulty: 2 Medium Section: 11.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Electrophilic addition to dienes 25) The addition of HBr to 1,3-butadiene gives two products. One of the products is shown. Identify the second product.

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 11.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Electrophilic addition to dienes

26) Which of the following is the 1,4-addition product in the reaction shown below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 11.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Electrophilic addition to dienes 27) Which compound undergoes 1,4-addition with Br2?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 11.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Electrophilic addition to dienes

28) What product do you NOT expect from this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 11.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Electrophilic addition to dienes 29) Which of the following is the 1,4-addition product of Br2 to 1,3-cyclohexadiene?

30) Which of the following compounds cannot react as a diene in a Diels-Alder reaction?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Diels-Alder reactions 31) Which one of the following is not true concerning Diels-Alder reactions? A) The reaction is stereospecific. B) The reaction mechanism has only one step. C) The reaction mechanism involves a resonance stabilized carbocation. D) The diene must be a conjugated diene. Answer: C Difficulty: 1 Easy Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Diels-Alder reactions

32) Which would be the most reactive dienophile?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions 33) Which dienophile is most reactive with 1,3-butadiene?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions

34) Which of the following would react fastest with 1,3-cyclopentadiene?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions

35) What is the product of the reaction shown below?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Diels-Alder reactions

36) What is the product of the following Diels-Alder reaction?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Diels-Alder reactions; Pericyclic reaction rules

37) What product will result from this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 11.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Diels-Alder reactions; Pericyclic reaction rules

38) Which of the following is the product of the intramolecular Diels-Alder reaction shown below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 11.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 11 Subtopic: Diels-Alder reactions

39) Identify the diene and dienophile that would give the following product.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 11.14 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions

40) Identify the diene used in the reaction shown below.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 11.14 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions

41) Identify the diene and dienophile needed to make the following Diels-Alder adduct.

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 11.14 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions; Pericyclic reaction rules

42) Identify the diene needed for the following reaction.

A) 1,3-pentadiene B) 2-methyl-1,3-butadiene C) 1,4-pentadiene D) 1-methyl-1,3-cyclohexadiene Answer: A Difficulty: 3 Hard Section: 11.14 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 11 Subtopic: Diels-Alder reactions 43) Which of the following is NOT true about the reaction shown below?

A) It is a pericyclic reaction. B) It proceeds in a single step by means of a cyclic transition state. C) It converts one 1,5-diene unit to another. D) It is an example of a Diels-Alder reaction. Answer: D Difficulty: 2 Medium Section: 11.16 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 11 Subtopic: Pericyclic reaction rules

Organic Chemistry, 11e (Carey) Chapter 12 Arenes and Aromaticity 1) Which of the following is not true concerning the structure of benzene? A) All C-C-C bond angles are exactly 120o. B) The carbon-carbon bonds rapidly alternate between single and double bonds. C) The six hydrogens are equivalent. D) The π bonds are completely conjugated. Answer: B Difficulty: 1 Easy Section: 12.02 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Physical properties of aromatic compounds 2) In which of the following are carbon-carbon bond lengths arranged in the correct order?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 12.02 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Physical properties of aromatic compounds; Aromaticity, anti aromaticity, and non aromaticity

3) Which statement is true of the hydrogenation of benzene? A) The ΔHhydrogenation of benzene is greater than three times that of cyclohexene. B) The ΔHhydrogenation of benzene is equal to three times that of cyclohexene. C) The ΔHhydrogenation of benzene is less than three times that of cyclohexene. D) Benzene cannot be hydrogenated under any conditions. Answer: C Difficulty: 1 Easy Section: 12.03 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 4) Which of the following has the lowest heat of reaction on catalytic hydrogenation? (4 moles of H2 per mole of hydrocarbon)

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 12.03 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

5) Benzene has ________ π molecular orbitals (bonding and antibonding), and the lowest ________ molecular orbitals are filled with electrons in the ground state. A) three; three B) six; two C) six; three D) twelve; six Answer: C Difficulty: 2 Medium Section: 12.04 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 6) How many isomeric dichlorobenzenes are there? A) no isomers—only a single compound B) 2 C) 3 D) 4 Answer: C Difficulty: 1 Easy Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds

7) What is the IUPAC name of the following compound?

A) 6-phenylheptane B) 2-heptylbenzene C) 2-benzylheptane D) 2-phenylheptane Answer: D Difficulty: 1 Easy Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds 8) How many isomeric tetrachlorobenzenes are there? A) two B) three C) four D) five Answer: B Difficulty: 1 Easy Section: 12.05 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds

9) How many isomeric tribromobenzenes are possible? A) one B) two C) three D) four Answer: C Difficulty: 1 Easy Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds 10) What is the IUPAC name of the following compound?

A) ortho-ethyliodobenzene B) para-ethylphenyl iodide C) para-ethyliodobenzene D) 1-ethyl-4-iodo-1,3,5-cyclohexatriene Answer: C Difficulty: 2 Medium Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds

11) What is the IUPAC name of the following compound?

A) 4-tert-butyl-3-chlorophenol B) ortho-tert-butylchlorophenol C) 4-tert-butyl-5-chlorophenol D) 2-tert-butyl-meta-chlorophenol Answer: A Difficulty: 2 Medium Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds

12) Which of the following is 2-chloro-4-ethylphenol?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds

13) What is the correct IUPAC name of the following compound?

A) 1,4-dibromo-3-nitrobenzene B) 1,4-dibromo-2-nitrobenzene C) 2-nitro-1,4-dibromobenzene D) 1-nitro-2,5-dibromobenzene Answer: B Difficulty: 2 Medium Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds 14) What is the IUPAC name of the following compound?

A) 4,6-dichloro-2-benzoic acid B) 2,4-dichlorobenzoic acid C) 3,5-dichlorobenzoic acid D) meta-dichlorobenzoic acid Answer: C Difficulty: 2 Medium Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds

15) The name of the following compound is

A) meta-bromoanisole. B) meta-bromonitrobenzene. C) meta-bromoaniline. D) meta-bromophenol. Answer: C Difficulty: 2 Medium Section: 12.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: IUPAC nomenclature of aromatic compounds 16) When a ________ is on an atom directly attached to a benzene ring, the benzene ring will stabilize it by resonance. A) negative charge B) unpaired electron (a radical) C) positive charge D) All of the answers are correct. Answer: D Difficulty: 1 Easy Section: 12.08 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

17) The benzyl carbocation is shown below. In addition to the benzylic carbon, identify any other carbon atoms that carry a partial positive charge based on resonance theory.

A) ortho and para carbon atoms B) meta and para carbon atoms C) meta carbon atoms D) ortho and meta carbon atoms Answer: A Difficulty: 2 Medium Section: 12.08 Topic: Substitution and Elimination Reactions Bloom's: 2. Understand Chapter: 12 Subtopic: Carbocations 18) Which one of following is not a resonance form of the benzyl free radical?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 12.08 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

19) Which of the following has the fastest rate of SN1 hydrolysis in aqueous acetone?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 12.09 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 12 Subtopic: Factors affecting substitution reactions; Substitution reaction mechanisms: SN1 and SN2

20) Which one of the following compounds has the fastest SN1 reaction rate with H2O in acetone?

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 12.09 Topic: Substitution and Elimination Reactions Bloom's: 4. Analyze Chapter: 12 Subtopic: Factors affecting substitution reactions; Substitution reaction mechanisms: SN1 and SN2

21) Which hydrogen atom would be most easily extracted by a bromine atom?

A) 1 B) 2 C) 3 D) 4 Answer: A Difficulty: 2 Medium Section: 12.10 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 12 Subtopic: Allylic and benzylic halogenation

22) What is the product of the reaction shown below?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 12.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 12 Subtopic: Allylic and benzylic halogenation 23) Which of the following reacts at the fastest rate when heated with N-bromosuccinimide (NBS) and benzoyl peroxide in carbon tetrachloride at 80oC? A) toluene B) ethylbenzene C) isopropylbenzene (cumene) D) tert-butylbenzene Answer: C Difficulty: 3 Hard Section: 12.10 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 12 Subtopic: Allylic and benzylic halogenation

24) Where would this reaction occur fastest in this molecule?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 12.10 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 12 Subtopic: Allylic and benzylic halogenation 25) Side chain oxidations of alkylbenzenes with Na2Cr2O7 and H2SO4/H2O will not work if the alkyl side chain has A) only one carbon. B) benzylic hydrogens. C) four or more carbons. D) no benzylic hydrogens. Answer: D Difficulty: 1 Easy Section: 12.12 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Oxidation of substituted aromatic compounds

26) A compound X, C8H10, is oxidized to benzoic acid with potassium dichromate, K2Cr2O7, in sulfuric acid. What is compound X? A) para-xylene B) propylbenzene C) styrene D) ethylbenzene Answer: D Difficulty: 3 Hard Section: 12.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 12 Subtopic: Oxidation of substituted aromatic compounds 27) Acid-catalyzed dehydration of cis-2-phenylcyclopentanol gives A) 1-phenylcyclopentene. B) 4-phenylcyclopentene. C) phenylcyclopentane. D) 1-phenylcyclopentanol. Answer: A Difficulty: 2 Medium Section: 12.13 Topic: Substitution and Elimination Reactions Bloom's: 3. Apply Chapter: 12 Subtopic: Factors affecting elimination reactions

28) Predict the major organic product in the following reaction.

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 12.13 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 Subtopic: Reactions of alkenes 29) Select the best method to convert styrene, C6H5CH=CH2, to 2-phenylethanol with minimal by-product formation. A) H2O, H2SO4 B) (1) BH3-THF (2) H2O2, NaOH C) (1) HBr (2) KOH, H2O D) (1) HBr, peroxides (2) NaOH, H2O Answer: B Difficulty: 3 Hard Section: 12.13 Topic: Alkenes Bloom's: 5. Evaluate Chapter: 12 Subtopic: Reactions of alkenes; Regioselectivity of electrophilic addition to an alkene

30) Propylbenzene is subjected to the sequence of reactions below. What is the final product?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 12.13 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 12 Subtopic: Allylic and benzylic halogenation

31) Which of the following is the product from the reaction sequence shown below?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 12.13 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 12 Subtopic: Allylic and benzylic halogenation

32) Which species is oxidized in the Birch reduction shown below?

A) benzene B) Na C) CH3OH D) NH3 Answer: B Difficulty: 1 Easy Section: 12.15 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity; Reduction of substituted aromatic compounds 33) The Birch reduction of benzene with sodium in NH3/CH3OH goes by a four-step mechanism. The first step is the A) transfer of a proton from CH3OH to benzene. B) transfer of an electron from Na to benzene. C) transfer of an electron from benzene to NH3. D) transfer of a hydride ion, H¯, from NH3 to benzene. Answer: B Difficulty: 2 Medium Section: 12.15 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity; Reduction of substituted aromatic compounds

34) Starting with toluene, which sequence of reactions below works best to prepare the following cyclohexadiene compound?

A) A B) B C) C D) All of these choices would be good syntheses. Answer: B Difficulty: 3 Hard Section: 12.15 Topic: Aromatic Compounds Bloom's: 5. Evaluate Chapter: 12 Subtopic: Reduction of substituted aromatic compounds

35) Which of the following are consistent with the requirements for aromaticity? I. A system with delocalized π electrons in a ring. II. 4n π electrons in the ring. III. All the ring atoms must be carbons. IV. (4n + 2) p electrons in the ring. A) I and II B) I and IV C) I, II, and III D) I, III, and IV Answer: B Difficulty: 1 Easy Section: 12.18 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 36) Which of the following would be a correct number of π electrons for a planar, monocyclic, completely conjugated polyene to be aromatic? A) 3 B) 8 C) 18 D) 24 Answer: C Difficulty: 1 Easy Section: 12.18 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

37) How many π electrons are there in the following model polycyclic aromatic hydrocarbon?

A) 6 B) 8 C) 10 D) 14 Answer: C Difficulty: 1 Easy Section: 12.18 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 38) Which of the following is an aromatic hydrocarbon?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 12.18 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

39) Which statement concerning the following compounds is correct?

A) both compounds are aromatic B) the compound on the right is aromatic C) the compound on the left is antiaromatic D) both compounds are nonaromatic Answer: C Difficulty: 2 Medium Section: 12.18 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 40) What is the value of n from Huckel's rule for the following aromatic compound?

A) n = 3 B) n = 4 C) n = 8 D) n = 9 Answer: B Difficulty: 2 Medium Section: 12.19 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

41) 1,3-cyclopentadiene is known for A) its unusually high acidity (pKa ~ 16). B) slowly dimerizing at room temperature. C) being a good Diels-Alder diene. D) All of the answers are correct. Answer: D Difficulty: 2 Medium Section: 12.20 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 42) Cyclopentadiene is unusually acidic for a hydrocarbon. Why? A) Cyclopentadiene is aromatic. B) The conjugate base of cyclopentadiene is aromatic. C) Cyclopentadiene is an unstable diradical. D) The conjugate base of cyclopentadiene is an unstable diradical. Answer: B Difficulty: 2 Medium Section: 12.20 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

43) Which of the following ions has a ground state that is predicted to be a diradical by simple molecular orbital theory?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 12.20 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 44) Which of the following would most readily react with a strong base, such as NaNH2, to form a carbanion?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 12.20 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

45) Considering aromaticity, which of these would be the least acidic?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 12.21 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 46) Which of the following ions are aromatic species?

A) I and III B) II and III C) II and IV D) III and IV Answer: B Difficulty: 2 Medium Section: 12.20 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

47) The total number of resonance forms of the cyclopentadienide anion, C5H5¯, is A) two. B) three. C) four. D) five. Answer: D Difficulty: 2 Medium Section: 12.20 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 48) Identify the site of protonation when one equivalent of HCl is added to the compound below.

A) N-1 B) N-2 C) both N-1 and N-2 (about 50% each) D) neither N-1 or N-2, the compound is not basic Answer: A Difficulty: 2 Medium Section: 12.22 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

49) What is the hybridization of the nitrogen atom in pyrrole?

A) sp B) sp2 C) sp3 D) 2p Answer: B Difficulty: 2 Medium Section: 12.22 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 50) Identify the aromatic compounds.

A) I and II B) III and IV C) I, II, and IV D) All of the answers are correct. Answer: C Difficulty: 3 Hard Section: 12.22 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

51) Which of these would be most reactive with pure methanol?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 12.22 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

52) When treated with acid, pyrrole forms what?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 12.22 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 12 Subtopic: Aromaticity, anti aromaticity, and non aromaticity

Organic Chemistry, 11e (Carey) Chapter 13 Electrophilic and Nucleophilic Aromatic Substitution 1) Which of the following is NOT a common electrophile in electrophilic aromatic substitution reactions? A) +SO3H B) +Br C) +CN D) +NO2 Answer: C Difficulty: 1 Easy Section: 13.02 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 2) Which one of the following is the electrophile in the reaction shown below?

A) benzene B) NO3¯ C) NO2+ D) H2SO4 Answer: C Difficulty: 1 Easy Section: 13.03 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

3) Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic nitration of benzene with HNO3/H2SO4?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 13.03 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 4) Which species below best depicts the electrophile in the FeBr3-catalyzed bromination of benzene? A) Br2 B) FeBr4− C) D) FeBr3 Answer: C Difficulty: 1 Easy Section: 13.05 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

5) Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic bromination of benzene with Br2/FeBr3?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 13.05 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

6) Which one of the following is not a resonance form of the cyclohexadienyl cation intermediate in the bromination of benzene?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 13.05 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 7) What is the electrophile in the Friedel-Crafts alkylation reaction below?

A) AlCl3 B) Cl¯ C) benzene D) (CH3)3C+ Answer: D Difficulty: 1 Easy Section: 13.06 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 4 Copyright © 2019

8) Which one of the following reactions does not give tert-butylbenzene? A) benzene + (CH3)3CCl/AlCl3 B) benzene + (CH3)2C=CH2/H2SO4 C) benzene + (CH3)3CH/AlCl3 D) benzene + (CH3)3COH/H2SO4 Answer: C Difficulty: 2 Medium Section: 13.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 9) Based on resonance theory, what is the approximate charge on the indicated carbon?

A) +1 B) +0.50 C) +0.33 D) +0.20 Answer: C Difficulty: 2 Medium Section: 13.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

10) Which one of the common electrophilic aromatic substitution reactions puts an electron donating group on a benzene ring? A) Br2, FeBr3 B) SO3 + H2SO4 C) RCOCl + AlCl3 D) RCl + AlCl3 Answer: D Difficulty: 2 Medium Section: 13.06 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 11) What major product(s) would you expect from this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 13.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

12) What is(are) the product(s) of the following reaction?

A) C6H5CH2CH2CH3 B) C6H5CH(CH3)2 C) C6H5CH2CH2CH2C1 D) a mixture of C6H5CH2CH2CH3 and C6H5CH(CH3)2 Answer: D Difficulty: 3 Hard Section: 13.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 13) What is the product of the following reaction?

A) isobutylbenzene B) sec-butylbenzene C) 2-methyl-1-phenylpropene D) tert-butylbenzene Answer: D Difficulty: 3 Hard Section: 13.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

14) What is the major product of the Friedel-Crafts alkylation of benzene with (CH3)2CHCH2Cl and AlCl3? A) isobutylbenzene B) tert-butylbenzene C) sec-butylbenzene D) butylbenzene Answer: B Difficulty: 3 Hard Section: 13.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 15) In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant by-product. Which of the following is the primary reason for this difference? A) Alkyl groups activate the ring to further substitution, acyl groups deactivate it. B) Alkyl groups are less sterically hindered than acyl groups. C) Acyl cations are more difficult to make with Lewis acids. D) Unlike acyl cations, carbocations can undergo rearrangements. Answer: A Difficulty: 1 Easy Section: 13.07 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

16) Which of the following is the best method to make n-butylbenzene?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 13.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

17) Based on directing effects in electrophilic aromatic substitution reactions, predict the major addition product of the following reaction.

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 13.11 Topic: Alkenes Bloom's: 3. Apply Chapter: 13 Subtopic: Reactions of alkenes 18) Which of the following groups are ortho/para directors? I. -NO2 II. -OCH3 III. -CO2CH3 IV. -CH3 A) I and III B) II and III C) II and IV D) III and IV Answer: C Difficulty: 1 Easy Section: 13.12 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

19) Which of the following aromatic compounds reacts faster than benzene in electrophilic aromatic bromination?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 20) Rank the following compounds in order of decreasing reactivity to aromatic electrophilic bromination. I. benzene II. toluene A) IV > II > I > III B) II > I > IV > III C) IV > III > II > I D) II > III > IV > I

III. benzoic acid

IV. phenol

Answer: A Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

21) Arrange the following compounds in order of increasing reaction rate with HNO3/H2SO4. I. C6H5CH=O II. C6H5OCH3 III. C6H5Br IV. C6H5CH3 A) I < III < IV < II B) III < I < II < IV C) I < IV < III < II D) III < I < IV < II Answer: A Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 22) Identify the preferred site(s) of electrophilic attack on the following compound.

A) ortho/para positions on ring 1 B) meta position on ring 1 C) ortho/para positions on ring 2 D) meta position on ring 2 Answer: C Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

23) Which one of the following compounds undergoes electrophilic aromatic sulfonation at the fastest rate?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

24) Consider the partial rate factors for electrophilic aromatic substitution at the indicated position of anisole and nitrobenzene. Which of the following correlates to these partial rate factors?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

25) Which of the following is not a valid resonance form of the intermediate species in the reaction shown below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

26) Ranked in order of decreasing reactivity in electrophilic aromatic substitution reactions, the order would be (more reactive > less reactive) A) chlorobenzene > toluene > acetophenone B) chlorobenzene > acetophenone > toluene C) toluene > chlorobenzene > acetophenone D) toluene > acetophenone > chlorobenzene Answer: C Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 27) Which statement is true in electrophilic aromatic substitution? A) no meta directors have a nitrogen atom directly attached to the ring B) all ortho/para directors make the ring more reactive than benzene C) no meta directors have nonbonding electrons on the atom directly attached to the ring D) all ortho/para directors have nonbonding electrons on the atom directly attached to the ring Answer: C Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

28) How many TOTAL resonance structures can be drawn for this intermediate? (incl. this one)

A) one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 29) Of the choices given, where would an aromatic substitution occur on this molecule?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 13.12 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 17 Copyright © 2019

30) Identify the major product(s) of the reaction sequence shown below.

A) ortho and para-chloroacetophenone B) meta-chloroacetophenone C) ortho and para-chlorobenzaldehyde D) meta-chlorobenzaldehyde Answer: B Difficulty: 3 Hard Section: 13.12 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 31) The major product(s) in the nitration of benzoic acid is(are) A) mixture of ortho and para-nitrobenzoic acid. B) nitrobenzene. C) meta-nitrobenzoic acid. D) nitrobenzene and para-nitrobenzoic acid. Answer: C Difficulty: 2 Medium Section: 13.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

32) Nitration of benzoic acid has a reaction rate which is ________ than the nitration rate of benzene and gives primarily the ________ product(s). A) slower; meta B) faster; ortho, para C) slower; ortho, para D) faster; meta Answer: A Difficulty: 2 Medium Section: 13.13 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 33) Predict the effect the substituent attached to the benzene ring below would have on electrophilic aromatic substitution reactions.

A) ortho/para director, activator B) meta director, activator C) ortho/para director, deactivator D) meta director, deactivator Answer: D Difficulty: 2 Medium Section: 13.13 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

34) Nitration of chlorobenzene has a reaction rate that is ________ than the nitration rate of benzene and gives primarily the ________ product(s). A) faster; ortho/para B) faster; meta C) slower; ortho/para D) slower; meta Answer: C Difficulty: 1 Easy Section: 13.14 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 35) Which one of the following substituents is deactivating and ortho-para directing in electrophilic aromatic substitution reactions? A) -Cl B) -N(CH3)2 C) -CO2H D) -CH=CH2 Answer: A Difficulty: 1 Easy Section: 13.14 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

36) What major product do you expect?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 13.14 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 37) Which isomer of dichlorobenzene gives a single mononitration product? A) ortho B) meta C) para D) None of the answers is correct. Answer: C Difficulty: 1 Easy Section: 13.15 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 21 Copyright © 2019

38) Where would the compound shown below undergo bromination with Br2/FeBr3?

A) ortho/para position on ring 1 B) ortho/para position on ring 2 C) meta position on ring 1 D) meta position on ring 2 Answer: A Difficulty: 2 Medium Section: 13.15 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 39) Where would the compound shown below undergo bromination with NBS and benzoyl peroxide?

A) ortho/para position on ring 1 B) C(2) position on ring 2 C) meta position on ring 1 D) methyl group on ring 2 Answer: D Difficulty: 2 Medium Section: 13.15 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

40) What is the major product of the following reaction?

A) 4-ethyl-2-nitrophenol B) 1-ethyl-4-nitrobenzene C) 4-ethyl-3-nitrophenol D) 4-nitrophenol Answer: A Difficulty: 3 Hard Section: 13.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

41) Salicylic acid reacts with two equivalents of ICl to give one of the products below. Which one is it? (Hint: Cl is more electronegative than I.)

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 13.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

42) What is the product of the following series of reactions?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 13.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

43) Starting with toluene, which of the following is the best synthesis of meta-bromobenzoic acid?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 13.16 Topic: Aromatic Compounds Bloom's: 5. Evaluate Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 44) What would be the most efficient way to make meta-nitrobromobenzene?

A) bromobenzene + HNO3/H2SO4 B) nitrobenzene + Br2/FeBr3 C) either of these approaches would work D) neither of these approaches would work Answer: B Difficulty: 2 Medium Section: 13.16 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

45) How would you best accomplish this?

A) 1. SO3, H2SO4, heat; 2. K2Cr2O7, H2SO4 B) 1. K2Cr2O7, H2SO4, heat; 2. SO3, H2SO4 C) either of these would work D) neither of these would work Answer: B Difficulty: 2 Medium Section: 13.16 Topic: Aromatic Compounds Bloom's: 5. Evaluate Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 46) Which of the following is the best method to make meta-bromoethylbenzene from benzene?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 13.16 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions

47) How many mononitration products are possible in the nitration of naphthalene, shown below?

A) only one B) two C) three D) four Answer: B Difficulty: 1 Easy Section: 13.17 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 48) Predict which position of the naphthalene compound below is the most reactive with electrophiles in electrophilic aromatic substitution.

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 13.17 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 28 Copyright © 2019

49) How many mononitration products are possible in the nitration of the compound shown below?

A) only one B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 13.17 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Electrophilic aromatic substitution (EAS) reactions 50) In nucleophilic aromatic substitution, the aromatic ring acts as which of the following? A) a nucleophile B) an electrophile C) a carbocation D) a reducing agent Answer: B Difficulty: 1 Easy Section: 13.19 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

51) Which of the following reacts at the fastest rate with potassium methoxide (KOCH3) in methanol? A) fluorobenzene B) 2,4-dinitrofluorobenzene C) 4-nitrofluorobenzene D) 2,4,6-trinitrofluorobenzene Answer: D Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

52) What is the product of the following reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

53) Which of the following reacts at the fastest rate with potassium methoxide (KOCH3) in methanol? A) fluorobenzene B) p-nitrofluorobenzene C) p-fluorotoluene D) p-bromofluorobenzene Answer: B Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 54) Which chlorine is most susceptible to nucleophilic substitution with NaOCH3 in methanol?

A) #1 B) #2 C) #1 and #2 are equally susceptible. D) No substitution is possible. Answer: B Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

55) Which one of the following has the fastest rate of reaction with sodium ethoxide, NaOCH2CH3, at 25°C? A) para-fluoronitrobenzene B) para-bromonitrobenzene C) para-chloronitrobenzene D) para-iodonitrobenzene Answer: A Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 56) Arrange the following compounds in order of increasing reactivity with sodium methoxide, NaOCH3.

A) I < II < III B) I < III < II C) II < I < III D) III < II < I Answer: B Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

57) Identify the likely mechanism in the reaction shown below.

A) SN2 B) electrophilic addition-elimination C) SN1 D) nucleophilic addition-elimination Answer: D Difficulty: 2 Medium Section: 13.19 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

58) Which of the following would work best for the synthesis of the ether shown below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 13.19 Topic: Aromatic Compounds Bloom's: 5. Evaluate Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

59) Which of the following is the product from the reaction sequence shown below?

60) Which of the following is the kinetic rate equation for the addition-elimination mechanism of nucleophilic aromatic substitution? A) rate = k[aryl halide] B) rate = k[nucleophile] C) rate = k[aryl halide][nucleophile] D) rate = k[aryl halide][nucleophile]2 Answer: C Difficulty: 2 Medium Section: 13.20 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 61) Which of the following is not a resonance form of the intermediate in the nucleophilic addition of hydroxide ion to para-fluoronitrobenzene?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 13.20 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

62) Which of the following is(are) true concerning the intermediate in the addition-elimination mechanism of the reaction below?

I. The intermediate is aromatic. II. The intermediate is a resonance stabilized anion. III. Electron withdrawing groups on the benzene ring stabilize the intermediate. A) only I B) only II C) I and III D) II and III Answer: D Difficulty: 2 Medium Section: 13.20 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

63) Which position on the potential energy diagram corresponds to the species shown for the reaction of para-fluoro (trifluoromethyl) benzene with sodium methoxide?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 13.20 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 64) What is the product of the following reaction?

A) benzene B) ortho-chloroaniline C) meta-chloroaniline D) aniline Answer: D Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 39 Copyright © 2019

65) Which compound in each of the following pairs is the most reactive to the conditions indicated?

A) I and III B) I and IV C) II and III D) II and IV Answer: A Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 66) Which one of the reagents readily reacts with bromobenzene without heating? A) NaOCH2CH3 B) NaCN/DMSO C) NaNH2/NH3 D) (CH3)2NH Answer: C Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

67) Identify the product(s) of the following reaction.

A) only ortho-methylaniline B) ortho-methylaniline and meta-methylaniline C) meta-methylaniline and para-methylaniline D) ortho-methylaniline and para-methylaniline Answer: B Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

68) Which of the following is a key intermediate in the reaction shown below?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

69) Assume that the following reaction goes by the elimination-addition mechanism for nucleophilic aromatic substitution. Based on that, how many isomeric naphthylamines are expected in the following reaction?

A) only a single product B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions 70) Which of the following is(are) true concerning the intermediate benzyne? I. Benzyne is aromatic. II. All the hydrogens of benzyne are equivalent and indistinguishable. III. The benzyne molecule has strain energy. A) only I B) only III C) I and III D) II and III Answer: C Difficulty: 2 Medium Section: 13.23 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

71) Carbon-14 labeled chlorobenzene is reacted with sodium amide in ammonia as shown below. Which of the following depicts the carbon-14 labeled in the product(s)?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 13.23 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

72) Which of the following best estimates the percentages of the three isomeric methylanilines from the reaction shown below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 13.23 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

73) Identify the diene required for the synthesis shown below.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 13.23 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

74) Which of the following best estimates the percentages of the three isomeric deuterated anilines from the reaction shown below?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 13.23 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 13 Subtopic: Nucleophilic aromatic substitution reactions

Organic Chemistry, 11e (Carey) Chapter 14 Spectroscopy 1) What region of the electromagnetic spectrum is used in nuclear magnetic resonance spectroscopy? A) radio wave B) X-ray C) ultraviolet D) microwave Answer: A Difficulty: 1 Easy Section: 14.03 Topic: Analytical/Spectroscopy Bloom's: 1. Remember Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 2) Which of the following gives the furthest downfield shift from TMS in its proton NMR spectrum? A) (CH3)4C B) (CH3)3N C) (CH3)2O D) CH3F Answer: D Difficulty: 2 Medium Section: 14.05 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

3) Which of the following gives the furthest downfield shift from TMS in its proton NMR spectrum? A) CCl4 B) CHCl3 C) CH2Cl2 D) CH3Cl Answer: B Difficulty: 2 Medium Section: 14.05 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 4) How many different sets of equivalent protons are there for para-xylene (1,4dimethylbenzene)? A) only 1 B) two C) three D) four Answer: B Difficulty: 1 Easy Section: 14.06 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 5) What are the approximate intensities of the four lines in the quartet from the proton NMR of diethyl ether, (CH3CH2)2O? (Assume distortion of the quartet is minimal.) A) 1:1:1:1 B) 1:2:2:1 C) 2:3:3:2 D) 1:3:3:1 Answer: D Difficulty: 1 Easy Section: 14.06 Topic: Analytical/Spectroscopy Bloom's: 1. Remember Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 2 Copyright © 2019

6) How many different sets of equivalent protons are there in the following compound?

A) three B) four C) five D) six Answer: A Difficulty: 2 Medium Section: 14.06 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 7) Which of the following isomeric dibromopropanes has only a single peak in its proton NMR spectrum? A) 1,1-dibromopropane B) 1,2-dibromopropane C) 1,3-dibromopropane D) 2,2-dibromopropane Answer: D Difficulty: 2 Medium Section: 14.06 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

8) How many different types(sets) of hydrogens are there in 2,2-dimethylpentane? A) two B) three C) four D) five Answer: C Difficulty: 2 Medium Section: 14.06 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 9) Which of the following has only a single peak in its proton NMR spectrum?

A) only I B) only II C) I and II D) I, II, and III Answer: C Difficulty: 2 Medium Section: 14.06 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

10) What compound of formula C8H10 would exhibit the following 1H NMR: d 1.2 (t, 3H), d 2.6 (q, 2H), d 7.1 (br. s, 5H)?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 11) What is the multiplicity of the methylene hydrogens indicated in the proton NMR of the following compound?

A) doublet B) triplet C) quartet D) pentet Answer: D Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 5 Copyright © 2019

12) What is the multiplicity of the methylene hydrogens indicated in the proton NMR of the following compound?

A) singlet B) doublet C) triplet D) quartet Answer: A Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 13) The proton NMR of 1,1-dibromoethane would appear as a A) downfield doublet and upfield quartet. B) downfield quartet and upfield doublet. C) downfield doublet and upfield triplet. D) downfield triplet and upfield doublet. Answer: B Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

14) The proton NMR spectrum of a compound, C3H6Cl2, has a pentet at δ 2.19 and a triplet at δ 3.72 in a 1:2 ratio, respectively. Which compound below best matches the data?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

15) Identify the C4H9Cl isomer given the following proton NMR data: doublet δ 1.04 (6H) multiplet δ 1.95 (1H) doublet δ 3.35 (2H)

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

16) Which of the following C5H8 compounds best fits the proton NMR spectrum shown below? (The numbers above the peaks are integration values.)

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

17) Which compound C4H9Cl would give the 1H NMR shown below?

A) 1-chlorobutane B) 1-chloro-2-methylpropane C) 2-chlorobutane D) 2-chloro-2-methylpropane Answer: C Difficulty: 2 Medium Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

18) Which compound below fits the following proton NMR data? triplet δ 1.22 (3H) singlet δ 1.98 (3H) quartet δ 4.07 (2H)

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

19) The proton NMR spectrum of a compound gives singlets at δ 2.10 and δ 2.56 in a ratio of 3:2, respectively. Which compound below is the best match for the spectrum?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

20) The proton NMR of a compound, C8H9ClO, has the following peaks. Which compound below best fits the data? broad singlet δ 2.41 (1H) triplet δ 2.41 (2H) triplet δ 3.69 (2H) doublet δ 7.02 (2H) doublet δ 7.50 (2H)

A) I B) II C) III D) IV Answer: C Difficulty: 3 Hard Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

21) Which of the following compounds fits the proton NMR shown below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

22) Which of the following C4H7OCl compounds best fits the proton NMR spectrum shown below? (The numbers above the peaks are integration values.)

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 14.07 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

23) A triplet and quartet pattern in 1H NMR often indicates the presence of a(n) A) ethyl group. B) propyl group. C) isopropyl group. D) phenyl group. Answer: A Difficulty: 1 Easy Section: 14.08 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 24) A large doublet and a small septet pattern in 1H NMR is usually indicative of a(n) A) ethyl group. B) propyl group. C) isopropyl group. D) phenyl group. Answer: C Difficulty: 1 Easy Section: 14.09 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

25) Which compound would you expect to give the 1H NMR pattern shown?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 14.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR)

26) Which of the following describes the spin-spin splitting of the indicated H in the 1H NMR of the compound shown below?

A) singlet B) doublet of doublets C) triplet D) doublet of triplets Answer: B Difficulty: 2 Medium Section: 14.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Proton nuclear magnetic resonance (1H NMR) 27) Which of the methods below would be most useful in distinguishing between the following two compounds?

A) UV spectroscopy B) IR spectroscopy C) C-13 NMR D) mass spectrometry Answer: B Difficulty: 1 Easy Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

28) Which one of the following compounds fits the C-13 NMR spectrum shown below?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

29) Which of the compounds below would exhibit the FEWEST peaks in the 13C NMR spectrum?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

30) Which of the compounds below fit the following C-13 NMR?

A) para-dichlorobenzene B) meta-dichlorobenzene C) ortho-dichlorobenzene D) chlorobenzene Answer: C Difficulty: 2 Medium Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

31) Identify which one of the following isomers of C6H14 has the C-13 NMR below.

A) CH3CH2CH2CH2CH2CH3 B) (CH3)2CHCH(CH3)2 C) CH3CH2CH2CH(CH3)2 D) CH3CH2C(CH3)3 Answer: D Difficulty: 2 Medium Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

32) Which one of the following isomers of C8H18 has only two peaks in its 13C NMR?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR) 33) Which one of the following isomeric C8H18 compounds has five peaks in its 13C NMR spectrum? A) octane B) 2-methylheptane C) 3-methylheptane D) 4-methylheptane Answer: D Difficulty: 2 Medium Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

34) A C-13 NMR spectrum of a compound, C10H14, has five peaks. Two peaks are in the 10-30 ppm region and the other three are in the 120–140 ppm area. Which of the following compounds fits the data?

A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR) 35) In proton NMR, 1H-1H spin-spin splitting is common. Why is there no comparable 13C-13C spin-spin splitting in C-13 NMR? A) C-13 has a nuclear spin of zero. B) The probability of two C-13 nuclei being next to each other in a compound is very low. C) The coupling constant is very small—too small to be observed. D) There is 13C-13C spin-spin splitting but because of the complex splitting patterns decoupling techniques are used to suppress it. Answer: B Difficulty: 1 Easy Section: 14.17 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

36) What is the multiplicity of the indicated carbon in an off-resonance decoupled C-13 NMR spectrum? (In off-resonance decoupled spectra, direct 13C-1H coupling is observed.)

A) singlet B) doublet C) quartet D) multiplet Answer: B Difficulty: 2 Medium Section: 14.17 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

37) The IR spectrum below reveals what functional group, if any?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 14.22 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Infrared (IR) spectroscopy

38) Which structure is most consistent with the 13C NMR shown?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 14.15 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Carbon nuclear magnetic resonance (13C NMR)

39) In infrared spectroscopy, absorption of electromagnetic radiation results in transitions between ________ energy levels. A) vibrational B) electronic C) rotational D) nuclear Answer: A Difficulty: 1 Easy Section: 14.21 Topic: Analytical/Spectroscopy Bloom's: 1. Remember Chapter: 14 Subtopic: Infrared (IR) spectroscopy

40) The IR spectrum shown below is most consistent with which structure?

41) Which one of the following has a λmax in its UV-visible spectrum with the longest wavelength?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 14.23 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Ultraviolet/visible spectroscopy (UV Vis)

42) Match each steroid below with its λmax in its UV-visible spectrum.

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 14.23 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Ultraviolet/visible spectroscopy (UV Vis) 43) A compound is either cyclononane or cyclodecane. Which of the following is the most useful technique in identifying the compound? A) IR spectroscopy B) mass spectrometry C) proton NMR D) C-13 NMR Answer: B Difficulty: 1 Easy Section: 14.24 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: 14 Subtopic: Mass spectrometry (MS) 31 Copyright © 2019

44) Which C-C bond would most likely break and give fragments in the mass spectrum of butyl benzene?

A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 2 Medium Section: 14.24 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: 14 Subtopic: Mass spectrometry (MS)

45) The reaction shown below gave two products in a ratio of approximately 1:2. The mass spectrum of the major product has a base peak at m/z 119. The minor product gave a base peak at m/z 133. Based on the reaction given and the information on the mass spectra, which of the following is the major product?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 14.24 Topic: Analytical/Spectroscopy Bloom's: 4. Analyze Chapter: 14 Subtopic: Mass spectrometry (MS)

Organic Chemistry, 11e (Carey) Chapter 15 Organometallic Compounds 1) Which one of the following would not be a suitable solvent for Grignard reagents? A) CH3CH2OCH2CH3, diethyl ether B) CH3CH2OH, ethanol C)

tetrahydrofuran (THF) D) They would all be suitable solvents. Answer: B Difficulty: 1 Easy Section: 15.03 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Grignard reactions 2) What are the products of the following sequence of reactions?

A) 2-butanol and Mg(OH)Br B) 2-butanol and MgHBr C) butane and Mg(OH)Br D) butane and MgHBr Answer: C Difficulty: 2 Medium Section: 15.03 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions

3) What organic product would result from this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 15.04 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Organolithium reactions 4) The reaction of a Grignard reagent with a solvent such as water or an alcohol produces which of the following? A) primary alcohol B) tertiary alcohol C) secondary alcohol D) alkane Answer: D Difficulty: 1 Easy Section: 15.04 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Grignard reactions

5) Which of the following has the largest acid dissociation constant, Ka? A) CH3CH3 B) H2C=CH2 C) HCºCH D) CH3CH2OH Answer: D Difficulty: 2 Medium Section: 15.04 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 15 Subtopic: Factors affecting acid strength 6) Arrange the following in order of decreasing basicity (most basic first). I. CH3CH2MgBr II. HCºCMgBr III. CH3CH2OMgBr A) I > II > III B) I > III > II C) III > II > I D) II > I > III Answer: A Difficulty: 2 Medium Section: 15.04 Topic: Organometallics (C-C bond transformations) Bloom's: 4. Analyze Chapter: 15 Subtopic: Grignard reactions 7) Select the strongest base in the following. A) NaNH2 B) CH3Li C) NaOCH2CH3 D) HCºCNa Answer: B Difficulty: 2 Medium Section: 15.04 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Organolithium reactions 3 Copyright © 2019

8) The reaction of a Grignard reagent with a ketone followed by dilute acid gives a(n) A) primary alcohol. B) secondary alcohol. C) tertiary alcohol. D) ester. Answer: C Difficulty: 1 Easy Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Grignard reactions 9) The reaction of a Grignard reagent with an aldehyde followed by dilute acid gives a(n) A) primary alcohol. B) secondary alcohol. C) tertiary alcohol. D) ester. Answer: B Difficulty: 1 Easy Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Grignard reactions 10) The reaction of 4-methylcyclohexanone with CH3MgBr followed by neutralization gives two alcohols. These two alcohols are A) constitutional isomers. B) enantiomers formed in equal amounts. C) enantiomers formed in unequal amounts. D) diastereomers. Answer: D Difficulty: 2 Medium Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Grignard reactions

11) The reaction of phenylmagnesium bromide (C6H5MgBr) with propanal (CH3CH2CH=O), followed by hydrolysis yields A) 2-phenyl-1-propanol. B) 1-phenyl-1-propanol. C) 2-phenyl-2-propanol. D) 3-phenyl-1-propanol. Answer: B Difficulty: 2 Medium Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions 12) What is the product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Organolithium reactions

13) How many stereoisomers are formed in this reaction?

A) just one B) two C) three D) four Answer: B Difficulty: 2 Medium Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions 14) What is the product of the following reaction sequence?

A) 2-heptanol B) 2-methyl-3-hexanol C) 3-methyl-3-hexanol D) 3-ethyl-2-pentanol Answer: C Difficulty: 3 Hard Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions

15) Which of the following reaction sequences would convert 2-butanol into the deuterated compound below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions

16) What is the major product of the following reaction?

A) 2-ethyl-1-pentanol B) 2-ethyl-1-butanol C) 3-pentanol D) 3-methyl-1-pentanol Answer: B Difficulty: 3 Hard Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions 17) What is the product of the following reaction sequence?

A) 3-chloro-4-heptanol B) 3-chloroheptane C) 3-heptene D) 4-chloroheptane Answer: D Difficulty: 3 Hard Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions

18) What is the product of the reaction sequence below?

A) 2-methyl-1-hexanol B) 2-methyl-2-hexanol C) 1-heptanol D) 2-heptanol Answer: D Difficulty: 3 Hard Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions

19) Consider the two syntheses of the compound shown below. Which method would work best with minimal by-products?

A) Method I B) Method II C) Both methods would work. D) Neither method would work. Answer: B Difficulty: 3 Hard Section: 15.05 Topic: Organometallics (C-C bond transformations) Bloom's: 5. Evaluate Chapter: 15 Subtopic: Grignard reactions

20) Which of the following is the major organic product in the reaction sequence below?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 15.06 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions

21) How many different combinations of a ketone and an organolithium would give the molecule shown?

A) just one B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 15.07 Topic: Organometallics (C-C bond transformations) Bloom's: 4. Analyze Chapter: 15 Subtopic: Organolithium reactions

22) Which of the following pairs of reagents would you use to prepare 4-methyl-2-pentanol?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 15.07 Topic: Organometallics (C-C bond transformations) Bloom's: 4. Analyze Chapter: 15 Subtopic: Organolithium reactions 23) Which metal is associated with the synthesis of cyclopropanes? A) Li B) Mg C) Cu D) Zn Answer: D Difficulty: 1 Easy Section: 15.08 Topic: Organometallics (C-C bond transformations) Bloom's: 1. Remember Chapter: 15 Subtopic: Organocuprate reactions

24) The reaction of cis-2-butene with CH2I2 and Zn(Cu) to give cis-1,2-dimethylcyclopropane is a(n) A) enantiospecific reaction. B) diastereoselective reaction. C) stereospecific reaction. D) regioselective reaction. Answer: C Difficulty: 1 Easy Section: 15.08 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 15 Subtopic: Grignard reactions 25) What is the product of the following sequence of reactions?

A) 1,1-diethylcyclopropane B) trans-1,2-diethylcyclopropane C) cis-1,2-diethylcyclopropane D) cis and trans-1,1-diiodo-2,3-diethylcyclopropane Answer: C Difficulty: 3 Hard Section: 15.08 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Grignard reactions; Carbene reactions

26) What is the product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 15.08 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Carbene reactions 27) What is the product of the reaction shown below?

A) 4-nonene B) nonane C) 4-bromononane D) 5-bromononane Answer: B Difficulty: 3 Hard Section: 15.11 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 15 Subtopic: Organolithium reactions; Organocuprate reactions

28) 1-Phenylnaphthalene, shown below, can be prepared in over 80% yield by one of the reactions below. Which one?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 15.11 Topic: Organometallics (C-C bond transformations) Bloom's: 4. Analyze Chapter: 15 Subtopic: Organocuprate reactions 29) A Ziegler-Natta catalyst, such as TiCl4/Al(CH2CH3)3, is used for the preparation of A) polyethylene. B) cyclopropanes. C) alcohols. D) carbenes or carbenoids. Answer: A Difficulty: 1 Easy Section: 15.15 Topic: Organometallics (C-C bond transformations) Bloom's: 1. Remember Chapter: 15 Subtopic: Olefin metathesis (Grubs, RCM) 16 Copyright © 2019

30) Which one of the following best describes the polymer chain shown below?

A) atactic polypropylene B) isotactic polypropylene C) syndiotactic polypropylene D) cross-linked polypropylene Answer: B Difficulty: 1 Easy Section: 15.15 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 15 Subtopic: Classes of synthetic polymers 31) Which one of the following best describes the polymer chain shown below?

A) atactic polypropylene B) isotactic polypropylene C) syndiotactic polypropylene D) cross-linked polypropylene Answer: C Difficulty: 1 Easy Section: 15.15 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 15 Subtopic: Classes of synthetic polymers

32) Which one of the following initiators is used to make isotactic polypropylene? A) benzoyl peroxide B) CH3CH2CH2CH2Li C) BF3 D) Al(CH2CH3)3, TiCl4 Answer: D Difficulty: 2 Medium Section: 15.15 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 15 Subtopic: Polymerization methods (mechanisms)

Organic Chemistry, 11e (Carey) Chapter 16 Alcohols, Diols, and Thiols 1) Which of the following methods will NOT produce an alcohol as the product? A) acid-catalyzed hydration of an alkene B) hydroboration-oxidation of an alkene C) reaction of a Grignard reagent with an aldehyde D) oxidation of an aldehyde Answer: D Difficulty: 1 Easy Section: 16.01 Topic: Alcohols Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of alcohols 2) Consider the structure of the AlH4¯ ion. The formal charge of Al is A) −1. B) 0. C) +1. D) +3. Answer: A Difficulty: 1 Easy Section: 16.02 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

3) The alcohol product(s) of the reduction of 2-methyl-3-pentanone with LiAlH4 is(are)

A) a single enantiomer. B) a racemic mixture. C) two diastereomers. D) two constitutional isomers. Answer: B Difficulty: 2 Medium Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 4) In general, the reduction of a ketone to an alcohol can be accomplished by all of the following except one. Which one will not reduce a ketone? A) H2/Pt B) HIO4 C) LiAlH4 D) NaBH4 Answer: B Difficulty: 1 Easy Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 1. Remember Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

5) As a reducing agent, NaBH4 donates a ________ to a ketone or aldehyde. A) proton B) hydrogen atom C) hydride ion D) hydrogen molecule Answer: C Difficulty: 1 Easy Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 6) What is the product of the following reaction?

A) cyclohexanol B) cyclohexane C) cyclohexene D) 1,2-cyclohexanediol Answer: A Difficulty: 2 Medium Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

7) What is the product of the following reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 8) What is the product of the following reactions?

A) CH3CH2CH2CH2CH2CO2H B) CH3CH2CH2CH2CH2CH2OH C) CH3CH2CH2CH2CH=CH2 D) CH3CH2CH2CH2CH2CH3 Answer: B Difficulty: 2 Medium Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

9) What is the product of the reaction shown below?

A) hexane B) 1-hexene C) 1-hexanol D) 2-hexanol Answer: D Difficulty: 2 Medium Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 10) What is the product of the following reaction sequence?

A) cyclopentene oxide B) cyclopentene C) cyclopentane D) cis-1,2-cyclopentanediol Answer: B Difficulty: 2 Medium Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

11) Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH4 in methanol? A) 1-butanol B) 2-butanol C) 2-methyl-1-propanol D) 2-methyl-2-propanol Answer: D Difficulty: 3 Hard Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

12) Give the product of the following reaction.

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 16.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

13) Which of the following reagents would be used to carry out the transformation shown below?

A) NaBH4 B) LiAlH4 C) H2/Pt D) PCC/CH2Cl2 Answer: B Difficulty: 1 Easy Section: 16.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 14) The reaction of a Grignard reagent with ethylene oxide followed by dilute acid gives A) a primary alcohol. B) a tertiary alcohol. C) a secondary alcohol. D) methanol. Answer: A Difficulty: 2 Medium Section: 16.04 Topic: Epoxides; Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of epoxides; Grignard reactions

15) Which of the following syntheses gives 3-methyl-1-hexanol?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 16.04 Topic: Epoxides; Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of epoxides; Grignard reactions 16) Which of the following reagents will convert cyclohexene into cis-1,2-cyclohexanediol? A) OsO4, (CH3)3COOH, (CH3)3COH, OH¯ B) HIO4 C) O3 followed by Zn/H2O D) CH3CO3H (peroxyacetic acid) Answer: A Difficulty: 2 Medium Section: 16.05 Topic: Alkenes Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of alkenes 9 Copyright © 2019

17) What is the product of the following reaction?

A) CH3CH=O B) meso-2,3-butanediol C) racemic (2R,3R) and (2S,3S)-2,3-butanediol D) cis-2,3-epoxybutane Answer: B Difficulty: 2 Medium Section: 16.05 Topic: Alkenes Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alkenes 18) What is the result of this reaction?

19) What is the product of the reaction below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 16.08 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

20) Which of the following reagents would react with a primary alcohol to produce an aldehyde as the final product? A) H2SO4 B) CH3MgBr, followed by HCl C) PCC D) H2CrO4 Answer: C Difficulty: 1 Easy Section: 16.09 Topic: Alcohols Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of alcohols 21) Consider the conversion of 1-butanol to each of the compounds shown below. In which conversion is an oxidizing agent needed? A) CH3CH2CH=CH2 B) (CH3CH2CH2CH2)2O C) CH3CH2CH2CH2Br D) CH3CH2CH2CH=O Answer: D Difficulty: 1 Easy Section: 16.09 Topic: Alcohols Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of alcohols

22) Identify the reagent needed to carry out the following conversion.

A) K2Cr2O7, H2SO4/H2O B) PCC/CH2Cl2 C) HIO4 D) OsO4, (CH3)3COOH, (CH3)3COH, OH− Answer: B Difficulty: 1 Easy Section: 16.09 Topic: Alcohols Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of alcohols 23) Which one of the following is not readily oxidized by K2Cr2O7 in H2SO4/H2O? A) n-butyl alcohol B) isobutyl alcohol C) sec-butyl alcohol D) tert-butyl alcohol Answer: D Difficulty: 2 Medium Section: 16.09 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

24) Which one of the following reaction steps work best to carry out the transformation shown below?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 16.09 Topic: Alcohols Bloom's: 4. Analyze Chapter: 16 Subtopic: Reactions of alcohols

25) What is the product of the synthetic sequence below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 16.09 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols 26) What is the final product of the following reactions?

A) 2,3-dimethyl-3-pentanol B) 2,4-dimethyl-3-pentanol C) 2,3-dimethyl-2-pentanol D) 2,2-dimethyl-3-pentanol Answer: A Difficulty: 3 Hard Section: 16.09 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

27) Predict the major product of this reaction sequence

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 16.09 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

28) Which of the following best describes the role of the coenzyme NAD+ (nicotinamide adenine dinucleotide) in biological chemistry? A) It reduces other species. B) It oxidizes other species. C) It catalyzes oxidation-reduction reactions. D) It inhibits oxidation-reduction reactions. Answer: B Difficulty: 1 Easy Section: 16.10 Topic: Alcohols Bloom's: 1. Remember Chapter: 16 Subtopic: Reactions of alcohols 29) In which of the following forms does nicotinamide adenine dinucleotide have an aromatic pyridine ring? A) NADH B) NAD+ C) both NADH and NAD+ D) neither NADH or NAD+ Answer: B Difficulty: 2 Medium Section: 16.10 Topic: Aromatic Compounds Bloom's: 1. Remember Chapter: 16 Subtopic: Aromaticity, anti aromaticity, and non aromaticity 30) Which one of the following diols would cleave into two fragments with HIO4? A) 1,3-hexanediol B) 2,4-hexanediol C) 3,4-hexanediol D) 1,6-hexanediol Answer: C Difficulty: 2 Medium Section: 16.11 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

31) Which of the synthetic procedures below would carry out the following transformation?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 16.11 Topic: Alcohols Bloom's: 3. Apply Chapter: 16 Subtopic: Reactions of alcohols

32) To which side, if any, would the reaction below lie?

A) to the right B) equally to both sides C) to the left D) this reaction cannot occur Answer: A Difficulty: 2 Medium Section: 16.12 Topic: Thiols Bloom's: 2. Understand Chapter: 16 Subtopic: Reactions of thiols 33) Thiols (RSH) are A) more acidic than alcohols. B) lower-boiling than alcohols. C) less water soluble than alcohols. D) All of the answers are correct. Answer: D Difficulty: 1 Easy Section: 16.12 Topic: Thiols Bloom's: 2. Understand Chapter: 16 Subtopic: Physical properties of thiols

Organic Chemistry, 11e (Carey) Chapter 17 Ethers, Epoxides, and Sulfides 1) How many constitutionally isomeric ethers are there with a formula of C4H10O? A) only one B) two C) three D) four Answer: C Difficulty: 1 Easy Section: 17.01 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: IUPAC Nomenclature of ethers 2) Which of the following is the correct name of the compound below?

A) benzyl ethyl ether B) ethylbenzene ether C) ethyl phenyl ether D) ethoxy phenoxy ether Answer: C Difficulty: 1 Easy Section: 17.01 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: IUPAC Nomenclature of ethers

3) The name of the following compound is

A) cis-2-methoxycyclohexanol. B) trans-2-methoxycyclohexanol. C) cis-2-methyl-1,2-cyclohexanediol. D) trans-1-hydroxy-2-methoxycyclohexane. Answer: A Difficulty: 2 Medium Section: 17.01 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: IUPAC Nomenclature of ethers 4) The name of the following ether is

A) butyl isopropyl ether. B) isobutyl propyl ether. C) sec-butyl isopropyl ether. D) butyl propyl ether. Answer: A Difficulty: 2 Medium Section: 17.01 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: IUPAC Nomenclature of ethers

5) The IUPAC name of the following epoxide is

A) cis-2-ethyl-3-methyloxirane. B) trans-2-ethyl-3-methyloxirane. C) trans-1-ethyl-2-methyloxycyclopropane. D) trans-1-ethyl-2-methylethane epoxide. Answer: B Difficulty: 2 Medium Section: 17.01 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: IUPAC Nomenclature of epoxides 6) Which of the following compounds is the most soluble in water? A) CH3CH2CH2CH2CH2Cl B) CH3CH2CH2CH2CH2OH C) CH3CH2OCH2CH2CH3 D) CH3CH2CH2CH2OCH3 Answer: B Difficulty: 1 Easy Section: 17.03 Topic: Ethers Bloom's: 2. Understand Chapter: 17 Subtopic: Physical properties of ethers

7) The C-O-C bond angle in dimethyl ether is closest to A) 90o. B) 109o. C) 120o. D) 180o. Answer: B Difficulty: 1 Easy Section: 17.03 Topic: Ethers Bloom's: 1. Remember Chapter: 17 Subtopic: Physical properties of ethers 8) Consider the three compounds below. I. CH3CH2OCH2CH3 II. CH3CH2CH2CH2CH3 III. CH3CH2CH2CH2OH The two most similar in boiling point are ________ and the two most similar in solubility in water are ________. A) I and III; II and III B) II and III; I and II C) I and II; I and III D) I and III; I and III Answer: B Difficulty: 1 Easy Section: 17.03 Topic: Ethers Bloom's: 2. Understand Chapter: 17 Subtopic: Physical properties of ethers

9) In general, ethers have a much lower boiling point than their isomeric alcohols. Why? A) The carbon-oxygen bond in ethers is nonpolar. B) Unlike alcohols, ethers cannot act as Lewis bases. C) Ethers are less reactive than alcohols. D) Unlike alcohols, ethers cannot hydrogen bond with each other. Answer: D Difficulty: 1 Easy Section: 17.03 Topic: Ethers Bloom's: 2. Understand Chapter: 17 Subtopic: Reactions of ethers 10) Match the boiling points with the following three isomers of C4H10O2.

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 17.03 Topic: Ethers Bloom's: 2. Understand Chapter: 17 Subtopic: Physical properties of ethers

11) The role of 18-crown-6 in the reaction shown below is to

A) complex F¯ by ion-dipole attraction and make it more nucleophilic. B) remove Br¯ by ion-dipole attraction and shift the equilibrium to the products. C) complex K+ by ion-dipole attraction increasing the solubility of KF and the nucleophilicity of F¯. D) stabilize the carbocation in the substitution reaction. Answer: C Difficulty: 2 Medium Section: 17.04 Topic: Ethers Bloom's: 2. Understand Chapter: 17 Subtopic: Physical properties of ethers

12) Which of the following is not an intermediate in the reaction below?

A) A B) B C) C D) they are all intermediates Answer: C Difficulty: 2 Medium Section: 17.05 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of ethers

13) Ethylene glycol reacts in acid to form a cyclic compound with the formula of C4H8O2. Which one of the following is this cyclic compound?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 17.05 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of ethers

14) Which one of the following reactions makes the cyclic ether shown below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 17.05 Topic: Ethers Bloom's: 4. Analyze Chapter: 17 Subtopic: Reactions of ethers

15) Which of the following ethers could NOT be made efficiently using the Williamson ether synthesis?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 17.06 Topic: Ethers Bloom's: 4. Analyze Chapter: 17 Subtopic: Reactions of ethers 16) Of the following, which yields isopropyl methyl ether as the major product with little or no by-products?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 17.06 Topic: Ethers Bloom's: 4. Analyze Chapter: 17 Subtopic: Reactions of ethers

17) Which of the following is not a good method to make tert-butyl methyl ether?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 17.06 Topic: Ethers Bloom's: 5. Evaluate Chapter: 17 Subtopic: Reactions of ethers

18) What is the major product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 17.06 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of ethers 19) The hazard(s) of working with diethyl ether is (are) A) it is poisonous. B) it is highly flammable. C) it slowly forms explosive peroxides. D) more than one of these. Answer: D Difficulty: 1 Easy Section: 17.07 Topic: Ethers Bloom's: 2. Understand Chapter: 17 Subtopic: Physical properties of ethers

20) What is the product of the following reaction?

A) 1,2-dibromobutane B) 1,3-dibromopropane C) 1,4-dibromobutane D) 1,2-dibromopropane Answer: B Difficulty: 2 Medium Section: 17.08 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of ethers

21) What is the product of the following reaction?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 17.08 Topic: Ethers Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of ethers

22) What are the products of the reaction below?

23) Which of the following is the preferred conformation for epoxide ring formation? (Assume a base is provided.)

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 17.10 Topic: Epoxides Bloom's: 2. Understand Chapter: 17 Subtopic: Reactions of epoxides

24) What is the product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 17.09 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

25) Which of the following is compound X of the synthesis shown below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 17.10 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

26) The reaction shown below can be described as an:

A) acid-base reaction followed by an intramolecular Williamson ether synthesis. B) acid-base reaction followed by an intramolecular SN1 reaction. C) E2 reaction followed by an addition reaction to a double bond. D) SN2 reaction followed by an intramolecular Williamson ether synthesis. Answer: A Difficulty: 2 Medium Section: 17.10 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides 27) Which of the following yields an epoxide on treatment with NaOH? A) cis-2-bromocyclohexanol B) trans-2-bromocyclohexanol C) cis-1,2-cyclohexanediol D) 3-bromocyclohexene Answer: B Difficulty: 2 Medium Section: 17.10 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

28) What is the product of the following sequence of reactions?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 17.10 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

29) Which of the following epoxides is formed when KOH is added to the optically active halohydrin shown below?

A) trans-(2S,3S)-2,3-dimethyloxirane B) trans-(2R,3R)-2,3-dimethyloxirane C) 2,2-dimethyloxirane D) meso-2,3-dimethyloxirane Answer: D Difficulty: 3 Hard Section: 17.10 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides 30) Which of the following reacts the fastest with NaOH, H2O? A) ethylene oxide (oxirane) B) cis-2,3-dimethyloxirane C) trans-2,3-dimethyloxirane D) 2,2,3,3-tetramethyloxirane Answer: A Difficulty: 2 Medium Section: 17.11 Topic: Epoxides Bloom's: 4. Analyze Chapter: 17 Subtopic: Reactions of epoxides

31) Which reagent(s) below converts cyclohexene to trans-1,2-cyclohexanediol?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

32) What is the major product of the following nucleophilic ring-opening reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

33) What is the product of the reaction shown below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

34) What is the product of the following reaction?

A) 1-pentanol B) 2-pentanol C) 2-methyl-1-butanol D) 2-methyl-2-butanol Answer: A Difficulty: 2 Medium Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

35) Which synthetic pathway below gives a racemic mixture of the following deuterated compound with little or no isomeric impurities?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 17.11 Topic: Epoxides Bloom's: 4. Analyze Chapter: 17 Subtopic: Reactions of epoxides

36) What reagents and/or reaction sequence below would convert trans-3-hexene to meso-3,4hexanediol? A) OsO4, (CH3)3COOH, (CH3)3COH, NaOH B) B2H6/diglyme followed by H2O2/NaOH C) O3 followed by Zn/H2O D) CH3CO3H followed by NaOH/H2O Answer: D Difficulty: 3 Hard Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides 37) What reagents and/or reaction sequence below would convert cis-3-hexene to meso-3,4hexanediol? A) OsO4, (CH3)3COOH, (CH3)3COH, NaOH B) B2H6/diglyme followed by H2O2/NaOH C) O3 followed by Zn/H2O D) CH3CO3H followed by NaOH/H2O Answer: A Difficulty: 3 Hard Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

38) What is the product of the following reaction?

A) (S)-1,2-propanediol B) (R)-1,2-propanediol C) racemic mixture of 1,2-propanediol D) 1,3-propanediol Answer: A Difficulty: 3 Hard Section: 17.11 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides 39) What is the final product of the following sequence of reactions?

40) Which one of the following reagent(s) converts ethylene oxide into the compound shown below?

A) CH3CH2MgBr followed by H2O B) HOCH2CH2OH, H+ C) CH3CH2Br, H+ D) CH3CH2OH, H+ Answer: D Difficulty: 2 Medium Section: 17.12 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides 41) Which of the followings reagents would be used to carry out the reaction shown below?

A) CH3OH, CH3O−Na+ B) CH3OH, H2SO4 C) CH3MgBr/ether followed by H3O+ D) H2O/H2SO4 followed by CH3OH Answer: B Difficulty: 2 Medium Section: 17.12 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

42) What is the product of the reactions below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 17.12 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

43) What product would result from

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 17.12 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides

44) Benzene reacts with 2-methyloxirane in the presence of AlCl3 to give a product with a formula of C9H12O. Identify the product.

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 17.12 Topic: Epoxides Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of epoxides 45) What is the general formula for a sulfide? A) RSH B) ROSH C) RSSH D) RSR' Answer: D Difficulty: 1 Easy Section: 17.14 Topic: Sulfides (Thioethers) Bloom's: 1. Remember Chapter: 17 Subtopic: Physical properties of sulfides

46) What results when dimethylsulfide is treated with sodium periodate?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 17.15 Topic: Sulfides (Thioethers) Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of sulfides

47) What results when dimethylsulfide is treated with methyl iodide?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 17.16 Topic: Sulfides (Thioethers) Bloom's: 3. Apply Chapter: 17 Subtopic: Reactions of sulfides

Organic Chemistry, 11e (Carey) Chapter 18 Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group 1) Which of the following is 3-ethyl-2-hexanone?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 18.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: IUPAC nomenclature of aldehydes and ketones

2) Which of the following is an acceptable name for the compound shown below?

A) ortho-methoxybenzaldehyde B) ortho-methoxyacetophenone C) ortho-formylanisole D) ortho-methylacetophenone Answer: A Difficulty: 2 Medium Section: 18.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: IUPAC nomenclature of aldehydes and ketones 3) What is the name of the following compound?

A) 3-tert-butylheptanal B) 2-isopropylheptanal C) 3-isopropylheptanal D) 3-butyl-4-methylpentanal Answer: C Difficulty: 2 Medium Section: 18.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: IUPAC nomenclature of aldehydes and ketones

4) What is the IUPAC name of the following compound?

A) 3-methyl-5-heptanone B) 5-ethyl-3-hexanone C) 5-methyl-3-heptanone D) 2-ethyl-4-hexanone Answer: C Difficulty: 2 Medium Section: 18.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: IUPAC nomenclature of aldehydes and ketones 5) Which of the following is an acceptable IUPAC name for the compound below?

A) o-bromo-m-chlorobenzaldehyde B) 6-bromo-3-chlorobenzaldehyde C) 2-bromo-5-chlorobenzaldehyde D) 1-bromo-4-chlorobenzaldehyde Answer: C Difficulty: 2 Medium Section: 18.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: IUPAC nomenclature of aldehydes and ketones

6) Identify the correct IUPAC name of the compound below.

A) 4-benzyl-5-methylhexanal B) 5-isopropyl-5-phenylbutanal C) 2-methyl-3-phenylhexanal D) 5-methyl-4-phenylhexanal Answer: D Difficulty: 3 Hard Section: 18.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: IUPAC nomenclature of aldehydes and ketones 7) What is the hybridization of the carbon atom in a carbonyl group? A) 2p B) sp C) sp2 D) sp3 Answer: C Difficulty: 1 Easy Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Physical properties of aldehydes and ketones

8) The carbon-oxygen p bond of an aldehyde is formed by overlap of which two orbitals? A) sp-sp B) sp2-sp2 C) sp2-2p D) 2p-2p Answer: D Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Physical properties of aldehydes and ketones 9) Which of the reagents below will oxidize a secondary alcohol to a ketone? A) LiAlH4 B) HIO4 C) K2Cr2O7, H2SO4/H2O D) HgSO4, H2SO4/H2O Answer: C Difficulty: 1 Easy Section: 18.04 Topic: Aldehydes and Ketones Bloom's: 1. Remember Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 10) Identify the reagents needed to carry out the following conversion.

A) H2/Lindlar Pd followed by H2SO4/H2O B) O3 followed by H2O C) H2O, HgSO4/H2SO4 D) LiA1H4 followed by H2O Answer: C Difficulty: 2 Medium Section: 18.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 5 Copyright © 2019

11) Which one of the following works best as the reaction steps to carry out the conversion below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 18.04 Topic: Aldehydes and Ketones Bloom's: 5. Evaluate Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 12) What is the product of the following reaction?

A) 3-methylpentane B) 3-methyl-2-pentanol C) 3-methyl-2-pentene D) 3-methyl-1-pentyne Answer: A Difficulty: 2 Medium Section: 18.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 6 Copyright © 2019

13) Which of the following reagents would carry out the isotopic substitution reaction shown below?

A) 18O2/Ni (cat.) B) H218O/HCl (cat.) C) Cr18O3/pyridine D) 18O3 Answer: B Difficulty: 2 Medium Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 14) Which of the following reacts with methylamine at the fastest rate? A) 1-pentene B) pentanal C) 2-pentanone D) 3-pentanone Answer: B Difficulty: 1 Easy Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

15) Which of the following has the largest Keq for the formation of the hydrate (as shown below)?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Physical properties of aldehydes and ketones; Reactions of aldehydes and ketones acting as electrophiles; Physical properties of aldehydes and ketones

16) Which of the following gives the greatest percentage of hydrate (gem-diol) when dissolved in water? A) butanal B) 2,2-dichlorobutanal C) 3,3-dichlorobutanal D) 4,4-dichlorobutanal Answer: B Difficulty: 2 Medium Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 17) What is the product of the reaction below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 18.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

18) What is the product of the reaction shown below?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 18.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 19) The acid-catalyzed reaction of propanal with two equivalents of methanol forms an acetal. This can mechanistically be thought of as A) an addition reaction followed by a substitution reaction. B) a substitution reaction followed by an addition reaction. C) an elimination reaction followed by a substitution reaction. D) an addition reaction followed by an elimination reaction. Answer: A Difficulty: 1 Easy Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

20) Acid-catalyzed hydrolysis of the cyclic acetal below gives

A) ethanal and 2-chlorocyclohexanol. B) 1,2-ethanediol and 2-chlorocyclohexanol. C) ethanol and 2-chlorocyclohexanol. D) 1,2-ethanediol and 2-chlorocyclohexanone. Answer: D Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 21) Which of the following is a hemiacetal?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 11 Copyright © 2019

22) Which of the following is an acetal?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 23) The compound shown below is the hemiacetal formed between

A) propanal and 2-propanol. B) 2-methylpropanal and ethanol. C) acetone and 1-propanol. D) ethanal and 2-methyl-1-propanol. Answer: A Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

24) What is the product of the reaction of butanal with excess methanol and catalytic sulfuric acid?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

25) Identify the products of the hydrolysis of the following compound.

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

26) Which one of the following is not an intermediate in the acid-catalyzed reaction of benzaldehyde with two equivalents of methanol to give benzaldehyde dimethyl acetal?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

27) In what major form would this diol-aldehyde exist?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 5. Evaluate Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

28) The compound shown below is the cyclic hemiacetal of

A) 5-hydroxyheptanal. B) 5-hydroxy-2-heptanone C) 6-hydroxy-3-heptanone. D) 6-hydroxyheptanal. Answer: B Difficulty: 3 Hard Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

29) What is the product of the reaction shown?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

30) What are the products of the following reaction?

A) cyclohexanone and ethanol B) cyclohexanone and ethanal C) 1,2-cyclohexanediol and ethanal D) 1,2-cyclohexanediol and ethanol Answer: C Difficulty: 3 Hard Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

31) Which one of the following gives ethanal, CH3CH=O, (as one of two products) when added to an aqueous solution of HCl?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

32) Domiodol, shown below, is used medicinally as a mucolytic agent. What are the acidcatalyzed hydrolysis products of Domiodol?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

33) Which synthetic method below correctly does the following conversion?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

34) Which of the following is the product of the reaction between acetone, CH3COCH3, and methylamine, CH3NH2?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

35) Identify the missing reagent for the reaction below.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

36) What product would be expected in this reaction?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

37) Which of the following reacts with (CH3CH2)2NH to give the compound shown below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 18.11 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

38) What is the product of the reaction below?

A) 2-methyl-1-pentene B) 2-methyl-2-propyloxirane C) 4-methyl-1-pentene D) 1-pentene Answer: A Difficulty: 2 Medium Section: 18.12 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 39) What is the product of the following reaction sequence?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 18.12 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 27 Copyright © 2019

40) Which of the following methods can be used to synthesize 2-methyl-1-hexene, shown below, with no formation of isomeric by-products?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 18.12 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

41) Which of the following is the best method to synthesize 2-methyl-2-pentene, shown below, with little or no by-product formation?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 18.12 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

42) What is the product of the reaction sequence below?

A) 2-methyl-1-hexene B) 2,3-dimethyl-2-pentene C) 2-methyl-2-hexene D) 3-methyl-1-hexene Answer: D Difficulty: 3 Hard Section: 18.12 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 43) At about what IR frequency is the C=O group typically found? A) 1640 cm−1 B) 1720 cm−1 C) 2240 cm−1 D) 3400 cm−1 Answer: B Difficulty: 1 Easy Section: 18.15 Topic: Aldehydes and Ketones Bloom's: 1. Remember Chapter: 18 Subtopic: Physical properties of aldehydes and ketones

44) Which structure is consistent with this 1H NMR spectrum?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 18.15 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 18 Subtopic: Physical properties of aldehydes and ketones 45) Baeyer-Villiger oxidation reactions use peroxycarboxylic acids to convert ketones to A) carboxylic acids. B) esters. C) epoxides. D) a-hydroxy ketones. Answer: B Difficulty: 1 Easy Section: 18.17 Topic: Aldehydes and Ketones Bloom's: 1. Remember Chapter: 18 Subtopic: Oxidation of aldehydes and ketones 31 Copyright © 2019

46) What is the product of the following Baeyer-Villiger oxidation reaction?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 18.17 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Subtopic: Oxidation of aldehydes and ketones

47) What reagent would you use to accomplish this?

A) H2O2, NaOH B) cat. OsO4, tBuOOH C) CH3CO3H D) air does this slowly Answer: C Difficulty: 2 Medium Section: 18.17 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Subtopic: Oxidation of aldehydes and ketones

Organic Chemistry, 11e (Carey) Chapter 19 Carboxylic Acids 1) What is the name of the following carboxylic acid?

A) 3-propylbutanoic acid B) 3-methyl-3-propylpropanoic acid C) 3-methylpentanoic acid D) 3-methylhexanoic acid Answer: D Difficulty: 1 Easy Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives; Reactions of carboxylic acids and carboxylic acid derivatives; Physical properties of carboxylic acids and carboxylic acid derivatives 2) What is the IUPAC name of the following compound?

A) 4-hydroxy-3-methylbutanoic acid B) 3-hydroxy-2-methylbutanoic acid C) 1-hydroxy-2-methylbutanoic acid D) 3-(hydroxymethyl)butanoic acid Answer: A Difficulty: 2 Medium Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives

3) What is the systematic IUPAC name of the compound below?

A) 6-bromo-4-ethylbenzenecarboxylic acid B) 2-bromo-4-ethylbenzenecarboxylic acid C) ortho-bromo-para-ethylbenzoic acid D) 1-bromo-3-ethylbenzoic acid Answer: B Difficulty: 2 Medium Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives 4) What is the name of the compound below?

A) trans-3-bromocyclohexanecarboxylic acid B) cis-3-bromocyclohexanecarboxylic acid C) trans-5-bromocyclohexanecarboxylic acid D) cis-5-bromocyclohexanecarboxylic acid Answer: B Difficulty: 2 Medium Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives

5) You would expect benzoic acid to be quite

A) soluble in water. B) soluble in aqueous base. C) soluble in aqueous acid. D) insoluble in any aqueous solution. Answer: B Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives 6) Which of the following would you expect to have the highest boiling point?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives 3 Copyright © 2019

7) Which of the following is the conjugate base of 5-hydroxypentanoic acid?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 19.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 8) Rank the following compounds in decreasing order of acidity.

A) II > I > III B) II > III > I C) III > II > I D) III > I > II Answer: B Difficulty: 2 Medium Section: 19.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

9) Which of the following is the strongest acid? A) FCH2CO2H B) ClCH2CO2H C) BrCH2CO2H D) ICH2CO2H Answer: A Difficulty: 2 Medium Section: 19.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 10) Chloroacetic acid, ClCH2CO2H, is a stronger acid than acetic acid. Which one of the following best explains this? A) ClCH2CO2¯ is more stable than CH3CO2¯ because of the electron-withdrawing Cl. B) ClCH2CO2¯ is more soluble in water than CH3CO2¯ because of the Cl. C) ClCH2CO2¯ is more stable than CH3CO2¯ because of an additional resonance form. D) ClCH2CO2¯ is more stable than CH3CO2¯ because of hydrogen bonding. Answer: A Difficulty: 2 Medium Section: 19.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 11) Rank the following three carboxylic acids in order of increasing acidity. I. 4-chlorobutanoic acid A) I < II < III B) I < III < II C) III < I < II D) III < II < I

II. 3-chlorobutanoic acid

III. 2-chlorobutanoic acid

Answer: A Difficulty: 2 Medium Section: 19.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 5 Copyright © 2019

12) Which of the following has the largest acid equilibrium constant, Ka? A) CH3CO2H B) CH2ClCO2H C) CHCl2CO2H D) CCl3CO2H Answer: D Difficulty: 3 Hard Section: 19.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 13) Which of the following would be the strongest acid?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 19.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

14) Which of the following has the largest acid equilibrium constant, Ka? A) benzoic acid B) ortho-nitrobenzoic acid C) para-methylbenzoic acid (para-toluic acid) D) para-methoxybenzoic acid Answer: B Difficulty: 3 Hard Section: 19.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 15) The cleansing action of soaps is due to the formation of A) water-insoluble micelles with lipophilic interiors. B) water-soluble micelles with lipophilic interiors. C) water-insoluble micelles with hydrophilic interiors. D) water-soluble micelles with hydrophilic interiors. Answer: B Difficulty: 1 Easy Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives

16) What is the product of the reaction shown below?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 17) Which one of the following has the best soap cleansing properties? A) CH3(CH2)16CO2H B) CH3CH2CO2H C) CH3(CH2)16CO2Na D) CH3CH2CO2Na Answer: C Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives

18) What product(s) would you expect from the following reaction?

19) A mixture of 1-hexanol and hexanoic acid in diethyl ether is shaken with an aqueous sodium bicarbonate solution. Which line below correctly describes the major organic species in the two resulting immiscible solutions?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives 20) Rank the following in order of decreasing acidity.

A) I > II > III B) III > I > II C) II > I > III D) I > III > II Answer: C Difficulty: 2 Medium Section: 19.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 10 Copyright © 2019

21) Which of the following methods does not work to synthesize benzoic acid?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 19.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

22) Only one of the reaction sequences below can carry out the following transformation. Identify which reaction sequence it is.

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 19.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

23) Which of the following is the product of the reaction sequence below?

A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 19.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

24) To convert a nitrile to a carboxylic acid, as shown below, you need to

A) hydrolyze with aqueous acid (H2O, H+). B) reduce with H2. C) reduce with LiAlH4. D) oxidize with Ag+. Answer: A Difficulty: 1 Easy Section: 19.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

25) What is the product of the reaction shown below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 19.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

26) Two possible methods to synthesize carboxylic acids are shown below.

For the synthesis of cyclopentanecarboxylic acid from bromocyclopentane, which of the following statements is true?

A) Neither method I or II would work. B) Only method I would work. C) Only method II would work. D) Both method I and II would work. Answer: D Difficulty: 2 Medium Section: 19.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 5. Evaluate Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

27) What is the product of the reaction sequence below?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 19.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 28) What is the product of the following sequence of reactions?

A) (CH3)2CHCH2CH2NH2 B) (CH3)2C=CHCO2H C) (CH3)2CHCHBrCO2H D) (CH3)2CHCH2CO2H Answer: D Difficulty: 3 Hard Section: 19.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 17 Copyright © 2019

29) Which of the following is not a good method to make 2,2-dimethylpropanoic acid?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 19.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

30) Which of the following is the tetrahedral intermediate in the acid-catalyzed Fischer esterification reaction of acetic acid, CH3CO2H, and ethanol, CH3CH2OH?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 19.14 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 31) Which of the following is true of the Fischer esterification reaction? A) it requires an acid catalyst B) the reaction is an equilibrium C) excess alcohol helps drive it near completion D) All of the answers are correct. Answer: D Difficulty: 2 Medium Section: 19.14 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

32) Reaction of acetic acid, CH3CO2H, with isotopically labeled CH318OH and catalytic sulfuric acid gives:

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 19.14 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

33) Acetic acid is mixed with isotopically labeled water, H218O, and a small amount of hydrochloric acid. Which of the following results of 18O labeling would be expected?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 19.14 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

34) Identify the lactone formed by the following hydroxy carboxylic acid.

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 19.15 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

35) Which structure below is the hydroxy acid, which corresponds to the following lactone?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 19.15 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

36) Which of the following undergo decarboxylation upon heating?

A) I and IV B) I and III C) II and III D) III and IV Answer: A Difficulty: 2 Medium Section: 19.16 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 37) What is the product of the thermal decarboxylation of dimethylpropanedioic acid? A) propanoic acid B) 2-methylpropanoic acid C) 2,2-dimethylpropanoic acid D) acetic acid Answer: B Difficulty: 2 Medium Section: 19.16 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

38) Which one of the following compounds undergoes decarboxylation upon heating?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 19.16 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

39) Which of the following is the enol intermediate in the thermal decarboxylation of methylpropanedioic acid, CH3CH(CO2H)2?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 19.16 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

Organic Chemistry, 11e (Carey) Chapter 20 Carboxylic Acid Derivatives: Nucleophilic Substitution 1) The compound shown below is classified as a(n)

A) lactone. B) β-ketoester. C) diketone. D) carboxylic acid anhydride. Answer: D Difficulty: 1 Easy Section: 20.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives 2) What is the name of the following ester?

A) propyl ethanoate B) ethyl propanoate C) ethoxy butanoate D) ethyl butanoate Answer: D Difficulty: 2 Medium Section: 20.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives 1 Copyright © 2019

3) Which of the following is isopropyl benzoate? A) C6H5CO2CH(CH3)2 B) C6H5CH2CO2CH(CH3)2 C) (CH3)2CHCO2C6H5 D) (CH3)2CHCO2CH2C6H5 Answer: A Difficulty: 2 Medium Section: 20.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives 4) What is the name of the following compound?

A) 2-chlorohexyl ethanoate B) 1-chlorohexyl ethanoate C) ethyl 2-chlorohexanoate D) ethyl 1-chlorohexanoate Answer: C Difficulty: 2 Medium Section: 20.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives

5) What is the name of the compound shown below?

A) 2-bromo-N-methylpentanamide B) 2-bromo(methylamino)pentanamide C) methylamino 2-bromopentanamide D) methyl 2-bromopentanamide Answer: A Difficulty: 2 Medium Section: 20.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives 6) Which of the following has the fastest rate of hydrolysis to give acetic acid?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 20.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

7) Which of the following compounds, on reaction with aqueous sodium hydroxide, yields sodium butanoate, CH3CH2CH2CO2Na, at the slowest rate?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 20.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

8) Rank the following in order of decreasing rate of hydrolysis. I. acetyl chloride II. acetic anhydride III. ethyl acetate IV. acetamide A) I > II > III > IV B) I > III > II > IV C) IV > III > II > I D) II > III > IV > I Answer: A Difficulty: 2 Medium Section: 20.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 9) What is the characteristic reaction of carboxylic acid derivatives? A) electrophilic addition B) nucleophilic elimination C) nucleophilic acyl substitution D) oxidation Answer: C Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 10) How are reactions between aldehydes and nucleophiles fundamentally different than reactions between acyl chlorides and nucleophiles? A) Aldehydes are readily oxidized by nucleophiles to carboxylic acids. B) Acyl chlorides have a leaving group, Cl¯, whereas aldehydes do not. C) Aldehydes do not form tetrahedral intermediates with nucleophiles. D) Acyl chlorides readily form enol tautomers. Answer: B Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 5 Copyright © 2019

11) Which one of the following does not give butanoic acid when hydrolyzed with aqueous hydrochloric acid?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 12) Which one of the following reagents converts a carboxylic acid to an acyl chloride as shown below?

A) HCl B) NaCl, H2O C) SOCl2 D) Cl2 Answer: C Difficulty: 1 Easy Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

13) The following tetrahedral intermediate breaks down to

A) propanoyl chloride and CH3OH. B) propanoic acid and CH3Cl. C) propanal and HCl. D) methyl propanoate and HCl. Answer: D Difficulty: 2 Medium Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 14) What is(are) the major organic product(s) of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

15) Which of the following is the product of the reaction shown below?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

16) Which one of the following tetrahedral intermediates dissociates to an ester?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 20.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 17) Identify the product obtained in the hydrolysis of the following cyclic acid anhydride.

A) HOCH2CH2CH2CH2CH2OH B) HOCH2CH2CH2CH2CO2H C) HO2CCH2CH2CH2CO2H D) HOCH2CH2CH2CH2CH=O Answer: C Difficulty: 2 Medium Section: 20.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

18) What is the product of the following reaction?

A) butanal B) butyl acetate C) 2-hexanone D) ethyl butanoate Answer: B Difficulty: 2 Medium Section: 20.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 19) What major product is expected from this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 20.05 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

20) The compounds shown below have similar molecular weights but significantly different boiling points. Match the compound with its boiling point. Boiling points (oC): 28, 57, 100, 141

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives 21) Which one of the following is not a good way to make ethyl acetate? A) CH3CO2H and CH3CH2OH with H2SO4 as a catalyst B) CH3CO2H and CH3CH2OH with NaOH C) CH3COCl and CH3CH2OH with pyridine D) (CH3CO)2O and CH3CH2OH with H2SO4 as a catalyst Answer: B Difficulty: 2 Medium Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 5. Evaluate Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

22) Which one of the following would not give butyl acetate when reacted with 1-butanol?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 23) Which of the following would work best in preparing tert-butyl benzoate? A) C6H5CO2H plus (CH3)3COH with H2SO4 catalyst and heat B) C6H5CO2Na plus (CH3)3CBr and heat C) C6H5CONH2 plus (CH3)3COH and heat D) C6H5CO2H plus SOCl2 followed by (CH3)3COH with pyridine Answer: D Difficulty: 3 Hard Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 5. Evaluate Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

24) Saponification and neutralization of 18O labeled ethyl acetate, as shown below, yields which of the following isotopically labeled products?

A) A B) B C) C D) approximately equal amounts of A and B Answer: C Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

25) What are the products of the following reaction?

A) trans-2-methylcyclohexanol and sodium acetate B) cis-2-methylcyclohexanol and sodium acetate C)

Answer: B Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

26) With the stereochemistry of the starting material shown, identify the stereochemistry of 2butanol in the following reaction sequence.

A) (S)-2-butanol B) (R)-2-butanol C) racemic 2-butanol D) meso-2-butanol Answer: A Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

27) Identify the stereochemistries of sec-butyl benzoate and 2-butanol in the following reaction sequence. (Assume that the reaction sequence shown follows the customary mechanisms for bimolecular nucleophilic substitution and nucleophilic acyl substitution.)

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

28) Treatment of cocaine with hot aqueous NaOH would yield which of the following?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

29) What major product is formed in the reaction shown?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

30) What is the product of the following reactions?

31) Which of the following is the product of the reaction below?

A) (C6H5)3COH B) (C6H5)2CHOH C) C6H5CH2OH D) (C6H5)3CH Answer: B Difficulty: 2 Medium Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 32) Which of the following are intermediates in the reaction of excess methylmagnesium bromide with ethyl benzoate (shown below) to make 2-phenyl-2-propanol?

A) I and II B) I and III C) II and III D) I, II, and III (they are all intermediates) Answer: D Difficulty: 2 Medium Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

33) What is being made in this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

34) Which compound below is the product expected from the following reaction?

35) The lithium aluminum hydride reduction of this ester would yield which of the following?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 36) What is the product of the following reaction sequence?

37) Reaction of excess Grignard reagent with diethyl carbonate, shown below, gives a(n)

A) ketone. B) tertiary alcohol. C) secondary alcohol. D) ester. Answer: B Difficulty: 3 Hard Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 38) Which of the reaction schemes below gives 1,4-pentadien-3-ol, H2C=CHCH(OH)CH=CH2 as the major organic product and with minimal by-product formation?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 4. Analyze Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 24 Copyright © 2019

39) What is the product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 20.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

40) Which one of the following does not react with benzoyl chloride, C6H5COCl? A) NH3 B) CH3NH2 C) (CH3)2NH D) (CH3)3N Answer: D Difficulty: 1 Easy Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 41) What is the product of the following reaction sequence?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

42) The major product from this reaction would be

A) an acid chloride. B) an anhydride. C) an amide. D) an ester. Answer: C Difficulty: 2 Medium Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 43) What is the relationship between the following two structures?

A) resonance forms B) stereoisomers C) constitutional isomers D) tautomers Answer: A Difficulty: 1 Easy Section: 20.13 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

44) Each of the following gives methylammonium chloride, CH3NH3+ Cl¯, when hydrolyzed in aqueous acid solution except one. Which one?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 20.13 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

45) What are the hydrolysis products of the following reaction?

A) ortho-chloroaniline and CH3CH=O B)

C) ortho-chloroaniline and CH3CO2Na D) chlorobenzene and CH3CO2Na Answer: C Difficulty: 3 Hard Section: 20.13 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

46) Identify the product obtained in the hydrolysis of the following cyclic acid anhydride.

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 20.13 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

47) Which carboxylic acid derivative can be made from another carboxylic acid derivative by a dehydration reaction? A) ester B) nitrile C) acid chloride D) amide Answer: B Difficulty: 1 Easy Section: 20.15 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

48) Which of the following best represents a mechanistic step in the acid-catalyzed hydrolysis of acetonitrile?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 20.16 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 32 Copyright © 2019

49) What is the product of the following reaction sequence?

A) 2-methyl-1-pentanol B) 2-bromo-3-methylpentanoic acid C) 2-methylpentanoic acid D) 4-hydroxyhexanoic acid Answer: C Difficulty: 3 Hard Section: 20.16 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives 50) What major product is formed in the reaction shown?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 20.17 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

51) Carboxylic acid derivatives all contain the carbonyl group. However, the stretching frequency of the carbonyl group differs based on what atoms are attached. Which carboxylic acid derivative has the highest stretching frequency for its carbonyl group in an IR spectrum? A) amide B) ester C) acid chloride D) anhydride Answer: C Difficulty: 1 Easy Section: 20.18 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Subtopic: Physical properties of carboxylic acids and carboxylic acid derivatives

52) Which of the following is the tetrahedral intermediate formed in the reaction of a thioester with ammonia?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 20.20 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives

Organic Chemistry, 11e (Carey) Chapter 21 Enols and Enolates 1) Which one of the following cannot form an enolate anion? A) 2,2-dimethylbutanal B) 2-ethylbutanal C) 2,3-dimethylbutanal D) 3,3-dimethylbutanal Answer: A Difficulty: 2 Medium Section: 21.01 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: IUPAC nomenclature of aldehydes and ketones; Physical properties of aldehydes and ketones; Reactions of aldehydes and ketones acting as nucleophiles 2) Rank the following compounds in order of decreasing acidity.

A) II > III > I B) III > I > II C) III > II > I D) I > III > II Answer: B Difficulty: 2 Medium Section: 21.01 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Factors affecting acid strength; Acid strength of functional groups

3) Which of the following works best as a base to quantitatively convert ethyl acetate, CH3CO2CH2CH3, to its enolate? A) NaOH B) KOC(CH3)3 C) CH3Li D) [(CH3)2CH]2NLi Answer: D Difficulty: 2 Medium Section: 21.01 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 4) Identify the most acidic hydrogen on the following molecule.

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 21.01 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Factors affecting acid strength; Acid strength of functional groups

5) When the keto ester shown is treated with NaOCH3, how many singly-charged resonance structures can be drawn for the product?

A) one B) two C) three D) four Answer: C Difficulty: 2 Medium Section: 21.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 6) Rank the compounds below in order of decreasing basicity.

A) II > III > I B) II > I > III C) III > I > II D) I > III > II Answer: B Difficulty: 3 Hard Section: 21.01 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Factors affecting acid strength; Acid strength of functional groups

7) The b-hydroxy carbonyl compounds formed in aldol reactions undergo dehydration to a,bunsaturated carbonyl compounds A) if new C=C will be conjugated to an aromatic ring. B) when treated with acid. C) when heated. D) All of the answers are correct. Answer: D Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 8) Identify the most acidic hydrogen in the following compound.

A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 2 Medium Section: 21.02 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Factors affecting acid strength; Acid strength of functional groups

9) Arrange the following compounds in order of decreasing acidity.

A) I > II > III B) II > III > I C) III > II > I D) III > I > II Answer: D Difficulty: 2 Medium Section: 21.02 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Factors affecting acid strength; Acid strength of functional groups 10) What is the aldol addition product of propanal?

A) 2-hydroxy-2-methylpentanal B) 3-hydroxy-2-methylpentanal C) 3-hydroxyhexanal D) 4-hydroxyhexanal Answer: B Difficulty: 2 Medium Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

11) Which of the following is the aldol addition product of butanal?

A) 2-ethyl-3-hydroxyhexanal B) 2-methyl-2-hydroxyheptanal C) 3-ethyl-2-hydroxyhexanal D) 2-ethyl-2-hydroxyhexanal Answer: A Difficulty: 2 Medium Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 12) What is the product of the following intramolecular aldol condensation reaction?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

13) Arrange the following anions in order of decreasing basicity.

A) I > II > III B) I > III > II C) II > I > III D) II > III > I E) III > I > II Answer: A Difficulty: 3 Hard Section: 21.02 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Acid strength of functional groups 14) How many different aldol addition products can be formed in the reaction of equal amounts of propanal and butanal with aqueous sodium hydroxide at 0°C? (Consider only constitutional isomer—not stereoisomers.) A) only one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

15) Which of the following is the mixed aldol condensation product of the reaction shown below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

16) Which of the following is the product in the reaction shown below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

17) Benzalacetone is the crossed aldol condensation product formed between benzaldehyde and acetone. Which of the following is the structure of benzalacetone?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

18) The compound shown below undergoes a retro (reverse) aldol reaction under these conditions. What product(s) result(s)?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

19) Identify the starting reagent needed to make the following cyclic ketone by an intramolecular aldol condensation reaction.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

20) Identify the starting reagents needed to make the following compound by a mixed aldol condensation.

A) benzaldehyde (C6H5CH=O) and 3-pentanone B) benzaldehyde (C6H5CH=O) and 2-pentanone C) acetophenone (methyl phenyl ketone) and 2-butanone D) acetophenone (methyl phenyl ketone) and butanal Answer: A Difficulty: 3 Hard Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

21) What product would result from this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 22) Which one of the following esters cannot form an enolate ion? A) phenyl acetate B) tert-butyl acetate C) ethyl 2-methylbutanoate D) ethyl benzoate Answer: D Difficulty: 1 Easy Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

23) Which one of the following cannot give a Claisen condensation product? A) (CH3)3CCO2Et B) C6H5CH2CO2Et C) H2C=CHCH2CH2CO2Et D) (CH3)2CHCH2CO2Et Answer: A Difficulty: 1 Easy Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

24) What is the product of the following reaction?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

25) Which of the following is the conjugate base of ethyl butanoate?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

26) Which of the following is the Claisen condensation product of ethyl propanoate, CH3CH2CO2Et?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 27) Which one of the following would not give an appreciable yield of Claisen condensation product? A) ethyl hexanoate B) ethyl 2-methylhexanoate C) ethyl 3-methylhexanoate D) ethyl 4-methylhexanoate Answer: B Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 18 Copyright © 2019

28) How many different Claisen condensation products are possible in the reaction of equal amounts of ethyl acetate (CH3CO2Et) and ethyl propanoate (CH3CH2CO2Et)? A) only one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 29) Identify the missing reagent in the reaction shown below.

A) ethyl formate, HCO2Et B) diethyl carbonate, (EtO)2C=O C) diethyl oxalate, EtO2CCO2Et D) ethyl acetate, CH3CO2Et Answer: B Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

30) Which one of the following esters gives the Claisen condensation product shown below?

A) ethyl 2-methylpentanoate B) ethyl 4-methylpentanoate C) ethyl 3,3-dimethylbutanoate D) ethyl 5-methylhexanoate Answer: B Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

31) Which one of the following would not be expected to give a significant yield in a Dieckmann condensation?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

32) The following compound can be synthesized by a mixed Claisen condensation. Identify the two compounds that give this condensation product.

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

33) How many products do you expect from this reaction?

A) just one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 34) What is the product of the reaction shown below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 23 Copyright © 2019

35) What product would you expect to result from this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

36) What product would result from this reaction?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

37) What is the product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 38) Heating butylmalonic acid, CH3CH2CH2CH2CH(CO2H)2, to 140oC yields A) hexanoic acid. B) pentanoic acid. C) 2-methylpentanoic acid. D) 2-hexenoic acid. Answer: A Difficulty: 2 Medium Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

39) Which one of the following is not a resonance form of the enolate ion formed from ethyl acetoacetate?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 40) Consider the following synthetic scheme below. Which one of the following best explains why the synthesis does not work?

A) Using NaOEt gives Claisen condensation instead of alkylation. B) The alkyl halide used will lead to elimination rather than alkylation. C) The keto-acid formed does not decarboxylate in the last step. D) The base-promoted hydrolysis step does not work on the b-keto ester intermediate. Answer: B Difficulty: 2 Medium Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

41) What is the product of this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 42) Identify the keto form of the following enol.

A) 1-penten-3-one B) (E)-3-penten-2-one C) 2-pentanone D) (E)-3-pentenal Answer: B Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 28 Copyright © 2019

43) Which of the following is the product of the reaction sequence shown below?

A) 4-methyl-3-hexanone B) 4-heptanone C) 2-propylbutanoic acid D) 2-ethylpentanoic acid Answer: B Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 44) What is the product of the following reactions?

A) 2,2-dimethylpropanedioic acid B) 2-methylpropanoic acid C) 2-methyl-1-propanol D) 2,2-dimethyl-1,3-propanediol Answer: D Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

45) Which of the following could be used as the missing reagent to carry out the following transformation?

A) CH3CH=O B) CH3CH2CH2OH C) CH3CH2CH2Br D) CH3CH2CH2CH2I Answer: C Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 46) What is the missing reagent in the synthesis shown below?

A) bromocyclopentane B) 1,4-dibromobutane C) 1,5-dibromopentane D) 1,1-dibromocyclopentane Answer: B Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

47) The acetoacetic ester synthesis, shown below, can be used to prepare 5-methyl-2-hexanone. Which one of the following alkyl bromides would be used in the synthesis?

A) (CH3)2CHBr B) (CH3)2CHCH2Br C) (CH3)2CHCH2CH2Br D) CH3CH2CHBrCH3 Answer: B Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

48) What is the product of the following reaction sequence?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

49) Which of the following would you predict to be the major product of the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 50) How many alpha hydrogens are there on 2,4-dimethyl-3-pentanone? A) two B) three C) four D) six Answer: A Difficulty: 1 Easy Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: IUPAC nomenclature of aldehydes and ketones; Physical properties of aldehydes and ketones; Reactions of aldehydes and ketones acting as nucleophiles

51) What is the relationship between keto and enol tautomers? A) resonance forms B) stereoisomers C) constitutional isomers D) different conformations of the same compound Answer: C Difficulty: 1 Easy Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 52) Which of the following is the enol of cyclohexanone?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

53) How many α-hydrogens does 2-hexanone have? A) 3 B) 4 C) 5 D) 6 Answer: C Difficulty: 1 Easy Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: IUPAC nomenclature of aldehydes and ketones; Physical properties of aldehydes and ketones; Reactions of aldehydes and ketones acting as nucleophiles 54) Which of the following has the largest acid dissociation constant, Ka?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 21.06 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 21 Subtopic: Factors affecting acid strength; Acid strength of functional groups

55) Identify the keto form of the following enol structure.

A) 2-methylcyclopentanone B) 3-methylcyclopentanone C) 1-methylcyclopentanol D) 2-methylcyclopentanol Answer: A Difficulty: 2 Medium Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 56) Which of the following have an enol form? I. benzaldehyde, C6H5CHO II. 2,2-dimethylpropanal, (CH3)3CCHO III. 2-chloropropanal, CH3CHClCHO A) only I B) only II C) only III D) All of the answers are correct. Answer: C Difficulty: 2 Medium Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Physical properties of aldehydes and ketones; Reactions of aldehydes and ketones acting as nucleophiles

57) Which one of the following has two different enol forms? A) cyclohexanone B) 2,2-dimethylcyclohexanone C) 3,3-dimethylcyclohexanone D) 4,4-dimethylcyclohexanone Answer: C Difficulty: 2 Medium Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: IUPAC nomenclature of aldehydes and ketones; Physical properties of aldehydes and ketones; Reactions of aldehydes and ketones acting as nucleophiles 58) What is the product of the reaction below?

A) 2,3-dibromobutanoic acid B) 3-chlorobutanoic acid C) 2-bromobutanoic acid D) 2-chlorobutanoic acid Answer: C Difficulty: 2 Medium Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

59) What is the expected product from this reaction?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 60) Which of the following has the highest percentage of enol in a keto-enol equilibrium? A) hexanal B) 2-hexanone C) 2,4-hexanedione D) 2,5-hexanedione Answer: C Difficulty: 3 Hard Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

61) What is the product of the reaction below?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

62) Which one of the following optically active compounds racemizes in dilute KOH/CH3OH solution?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

63) Identify the deuterated compound resulting from the following reaction.

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

64) What would result from treating (-)-menthone with basic D2O?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 21.08 Topic: Aldehydes and Ketones; Acids and Bases Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles; Acid strength of functional groups

65) What would result from the process shown below?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

66) Which of the following is not a resonance form of the enolate ion formed in the following acid-base equilibrium?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

67) The Robinson annulation reaction is shown below. Identify the missing reagent in the first step.

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

68) Which carbon atoms are most susceptible to nucleophilic attack?

A) I and II B) II and III C) II and IV D) I and IV Answer: C Difficulty: 2 Medium Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as electrophiles 69) Which one of the following reagents adds a methyl group by conjugate (1,4-addition) addition to an α,β-unsaturated ketone or aldehyde? A) LiCu(CH3)2 B) CH3MgBr C) Hg(O2CCH3)2 D) CH3Li Answer: A Difficulty: 2 Medium Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as electrophiles

70) What is the product of the following reaction sequence?

A) 2,3-dimethyl-1-pentanol B) 3,3-dimethyl-1-pentanol C) 3-ethyl-2-methyl-1-hexanol D) 2-ethyl-3-methyl-1-hexanol Answer: D Difficulty: 3 Hard Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles 71) Heating a mixture of 1,3-diphenylacetone and acrolein in trimethylamine gives a product, C18H16O, in 53% yield. The mechanism for product formation is a Michael addition followed by an intramolecular aldol condensation. Which of the following is the product of this reaction?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

72) Which of the following is the Michael addition product of the reaction below?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Subtopic: Reactions of aldehydes and ketones acting as nucleophiles

Organic Chemistry, 11e (Carey) Chapter 22 Amines 1) Which of the following is a tertiary amine? A) CH3CH2CH2NH2 B) CH3CH2NHCH3 C) (CH3)2CHNH2 D) (CH3)3N Answer: D Difficulty: 1 Easy Section: 22.01 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: IUPAC Nomenclature of amines 2) The following compound is classified as a(n)

A) amide. B) primary amine. C) secondary amine. D) tertiary amine. Answer: D Difficulty: 1 Easy Section: 22.01 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: IUPAC Nomenclature of amines

3) What is an acceptable name of the following compound? CH3CH2CH2CH2NHCH3 A) N-methylbutylamine B) N-butylmethylamine C) 1-methyl-1-butylamine D) 2-pentylamine Answer: A Difficulty: 2 Medium Section: 22.01 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: IUPAC Nomenclature of amines 4) What is the IUPAC name of the following compound?

A) 2-methyl-4-hexanamine B) 2-methyl-4-aminohexane C) 5-methyl-3-hexanamine D) 5-methyl-3-aminohexane Answer: C Difficulty: 2 Medium Section: 22.01 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: IUPAC Nomenclature of amines

5) In the following two-phase reaction, the catalyst works by

A) transferring CN¯ from the aqueous phase to the organic phase containing C6H5CH2Br. B) transferring C6H5CH2Br from the organic phase to the aqueous phase containing CN¯. C) removing Br¯ from the organic phase to the aqueous phase. D) removing K+ from the organic phase to make cyanide ion more nucleophilic. Answer: A Difficulty: 2 Medium Section: 22.01 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Reactions of amines 6) Which of the following is the correct IUPAC name of the compound shown below?

A) 1,2-dichloro-4-(N,N-dimethyl)aniline B) dimethyl-(3,4-dichlorophenyl)amine C) 3,4-dichloro-N,N-dimethylaniline D) N,N-dimethylamino-3,4-dichlorobenzene Answer: C Difficulty: 3 Hard Section: 22.01 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: IUPAC Nomenclature of amines

7) Which one of the following is ethyl 4-(dimethylamino) butanoate?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 22.01 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: IUPAC Nomenclature of amines 8) Among the isomeric C4H11N amines below, choose the one with the lowest boiling point. A) CH3CH2CH2CH2NH2 B) (CH3)2CHNHCH3 C) (CH3CH2)2NH D) (CH3)2NCH2CH3 Answer: D Difficulty: 2 Medium Section: 22.03 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Physical properties of amines

9) Which one of the isomeric C3H9N amines would you expect to have the lowest boiling point? A) CH3CH2CH2NH2 B) CH3CH2NHCH3 C) (CH3)3N D) (CH3)2CHNH2 Answer: C Difficulty: 2 Medium Section: 22.03 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Physical properties of amines 10) You would expect cocaine to be quite soluble in

A) water. B) aqueous base. C) aqueous acid. D) All of the answers are correct. Answer: C Difficulty: 1 Easy Section: 22.04 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Amines as bases

11) Arrange the following three amines in order of decreasing basicity. I. aniline II. diphenylamine III. triphenylamine A) I > II > III B) I > III > II C) II > III > I D) III > II > I Answer: A Difficulty: 2 Medium Section: 22.04 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: IUPAC Nomenclature of amines; Amines as bases 12) Which nitrogen is most basic?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 22.04 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Amines as bases

13) Which one of the following is most soluble in aqueous HCl?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 22.04 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Physical properties of amines; Amines as bases

14) Rank the following three compounds in order of decreasing basicity.

A) I > II > III B) II > I > III C) III > II > I D) III > I > II Answer: D Difficulty: 2 Medium Section: 22.04 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Amines as bases 15) Rank the following three compounds in decreasing order of basicity.

16) Rank the following three compounds in order of decreasing acidity.

A) II > III > I B) II > I > III C) III > I > II D) III > II > I Answer: B Difficulty: 3 Hard Section: 22.04 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Amines as bases; Reactions of amines

17) Which one of the following is not a resonance form of para-aminobenzaldehyde?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 22.04 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Physical properties of amines; Amines as bases; Reactions of amines

18) Which one of the following is the strongest base?

19) What is the product of the following reaction?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 22.07 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

20) What would result from this reaction?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 22.07 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

21) Which of the following is the product of the reaction shown below?

A) (CH3)2CHCH2CH2NHNH2 B) (CH3)2CHCH2CH2NH2 C) [(CH3)2CHCH2CH2]2NH D) (CH3)2CHCH2CH2CONH2 Answer: B Difficulty: 2 Medium Section: 22.08 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

22) Which one of the following does not give N-ethylcyclopentylamine as the major product?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 22.09 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines 23) To convert a nitrile to a primary amine you must A) hydrolyze it with water. B) oxidize it with chromic acid. C) reduce it with hydrogen or lithium aluminum hydride. D) substitute it with an alkyl halide. Answer: C Difficulty: 2 Medium Section: 22.09 Topic: Amines Bloom's: 1. Remember Chapter: 22 Subtopic: Reactions of amines

24) What is the product of the following reaction?

A) 1-amino-2-methylpropane B) isopropylamine C) 2-amino-2-methylpropane D) tert-butylamine Answer: A Difficulty: 2 Medium Section: 22.09 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines 25) What is the product of the following reaction sequence?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 22.09 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

26) Which of the following is(are) the product(s) of the reaction sequence shown below?

A) 1,3-dichlorobenzene B) meta-chloroaniline C) mixture of ortho and para-chloroaniline D) meta-chloronitrobenzene Answer: B Difficulty: 3 Hard Section: 22.09 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

27) Which one of the following synthetic routes gives the best yield of meta-bromoaniline starting with benzene?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 22.09 Topic: Amines Bloom's: 5. Evaluate Chapter: 22 Subtopic: Reactions of amines

28) The amine below can be prepared from the ketone shown and what reagents?

A) 1. NaCN 2. LiAlH4 3. H2O B) 1. NaN3 2. LiAlH4 3. H2O C) NH3, H2, Ni, CH3OH D) CH3NH2, H2, Ni, CH3OH Answer: D Difficulty: 3 Hard Section: 22.10 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Reactions of amines 29) Which pair of reagents would be used to make the following amine by reductive amination?

A) methylamine and 2-methylbutanoic acid B) methylamine and 2-methylbutanal C) ammonia and 3-methyl-2-pentanone D) dimethylamine and 2-butanone Answer: B Difficulty: 3 Hard Section: 22.10 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Reactions of amines

30) Which of the following reagents can convert cyclohexanone to N-ethylcyclohexylamine as shown below?

A) CH3CH2NH2 and H2/Pt B) LiAlH4 followed by H2O and then CH3CH2Br C) CH3CH2Br and NH3 D) CH3CH=O and NH3 Answer: A Difficulty: 2 Medium Section: 22.10 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Reactions of amines

31) What is the major product of the reaction sequence below?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 22.13 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

32) Which one of the following compounds gives propylamine, CH3CH2CH2NH2, upon hydrolysis?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 22.14 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines 33) Which one of the following forms a diazonium ion on being treated with NaNO2 in aqueous HCl? A) para-nitrotoluene B) ethylamine C) N,N-dimethylaniline D) triethylamine Answer: B Difficulty: 2 Medium Section: 22.15 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Reactions of amines

34) Which one of the following amines gives an N-nitrosoamine on treatment with nitrous acid, HNO2? A) 2,4-dimethylaniline B) 3,5-dimethyaniline C) N,4-dimethylaniline D) N,N-dimethylaniline Answer: C Difficulty: 2 Medium Section: 22.15 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines 35) The N2+ group in an aryldiazonium salt CANNOT be replaced with which group? A) OH B) F C) I D) All of these can replace the N2+ group. Answer: D Difficulty: 1 Easy Section: 22.16 Topic: Amines Bloom's: 1. Remember Chapter: 22 Subtopic: Reactions of amines

36) What is the product of the following reaction?

A) 3,5-dimethyl-4-nitrophenol B) meta-xylene (meta-dimethylbenzene) C) 1,3-dimethyl-5-nitrobenzene D) 3,5-dimethylphenol Answer: D Difficulty: 2 Medium Section: 22.16 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Reactions of amines 37) Reaction of an N,N-dialkylaniline with nitrous acid yields A) a diazonium salt. B) a para-nitroso compound. C) an N-nitroso compound. D) an azo compound. Answer: B Difficulty: 2 Medium Section: 22.16 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Reactions of amines

38) What is the product of the reaction series shown below?

A) I B) II C) III D) IV Answer: C Difficulty: 3 Hard Section: 22.16 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

39) Which of the following is the product of the reaction sequence shown below?

A) meta-bromochlorobenzene B) 1,3,5-tribromobenzene C) 1,3-dibromo-5-chlorobenzene D) mixture of ortho and para-bromochlorobenzene Answer: A Difficulty: 3 Hard Section: 22.16 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

40) Which of the following would be the starting reagents needed to make the azo compound shown below?

A) A B) B C) p-ethylaniline + phenol D) aniline + p-ethylphenol Answer: C Difficulty: 2 Medium Section: 22.18 Topic: Amines Bloom's: 4. Analyze Chapter: 22 Subtopic: Reactions of amines

41) What is the mechanism of the following reaction?

A) SN1 B) SN2 C) free radical D) electrophilic aromatic substitution Answer: D Difficulty: 2 Medium Section: 22.18 Topic: Amines Bloom's: 2. Understand Chapter: 22 Subtopic: Reactions of amines

42) What product is expected from this reaction?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 22.18 Topic: Amines Bloom's: 3. Apply Chapter: 22 Subtopic: Reactions of amines

Organic Chemistry, 11e (Carey) Chapter 23 Carbohydrates 1) The Fischer projection of (+)-glyceraldehyde is shown below. Which of the following describes this structure?

A) D-aldotriose with the R configuration B) L-aldotriose with the R configuration C) D-aldotriose with the S configuration D) L-aldotriose with the S configuration Answer: A Difficulty: 2 Medium Section: 23.02 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Aldoses and ketoses; D and L nomenclature 2) What are the configurations of carbon atoms 2 and 3, respectively, of D-threose, shown below?

3) What was used as a stereochemical reference compound, whose absolute configuration was only assumed, not proven, until the 1950s? A) glucose B) glyceraldehyde C) glucitol D) ribose Answer: B Difficulty: 1 Easy Section: 23.02 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: D and L nomenclature 4) Which statement is not true of the D and L stereoisomers of any given sugar? A) they have equal but opposite optical rotations B) they both form cyclic hemiacetals in solution C) they both undergo the same enzymatic digestion process D) they can both undergo the α- and β-anomer equilibration process Answer: C Difficulty: 2 Medium Section: 23.02 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: D and L nomenclature

5) The following carbohydrate is a

A) D-aldotetrose. B) L-aldotetrose. C) D-ketotetrose. D) L-aldopentose. Answer: B Difficulty: 2 Medium Section: 23.03 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Aldoses and ketoses; D and L nomenclature 6) How many stereoisomeric D-aldopentoses are there? A) four B) six C) eight D) sixteen Answer: A Difficulty: 1 Easy Section: 23.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 23 Subtopic: Aldoses and ketoses; Physical properties of monosaccharides

7) What is the relationship between D-xylose and L-xylose? A) identical structures B) enantiomers C) constitutional isomers D) epimers Answer: B Difficulty: 1 Easy Section: 23.04 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: D and L nomenclature 8) How many stereoisomeric aldopentoses are there? (count D and L separately) A) four B) six C) eight D) sixteen Answer: C Difficulty: 1 Easy Section: 23.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 23 Subtopic: Aldoses and ketoses; Physical properties of monosaccharides 9) How many stereoisomeric aldohexoses are there? A) four B) eight C) sixteen D) eighteen Answer: C Difficulty: 1 Easy Section: 23.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 23 Subtopic: Aldoses and ketoses; Physical properties of monosaccharides

10) What is the relationship between the open-chain forms of D-glucose and D-altrose? A) enantiomers B) diastereomers C) constitutional isomers D) different conformations of the same compound Answer: B Difficulty: 2 Medium Section: 23.04 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides 11) The Fischer projection of (+)-glucose is shown below. Which of the following describes this structure?

A) D-aldopentose B) L-aldopentose C) D-aldohexose D) L-aldohexose Answer: C Difficulty: 2 Medium Section: 23.04 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Aldoses and ketoses; D and L nomenclature

12) Which one of the following describes the furanose forms of carbohydrates? A) a six-membered ring consisting of all carbons B) a six-membered ring consisting of five carbons and one oxygen C) a five-membered ring consisting of all carbons D) a five-membered ring consisting of four carbons and one oxygen Answer: D Difficulty: 1 Easy Section: 23.06 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides 13) Which one of the following is β-D-ribofuranose?

14) Identify the anomeric carbon in the following.

A) C-1 B) C-2 C) C-3 D) C-4 Answer: A Difficulty: 2 Medium Section: 23.06 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides 15) Which one of the following is not true concerning D-glucose? A) Its enantiomer is L-glucose. B) It readily forms cyclic hemiacetals. C) It is optically active. D) It is classified as a ketose. Answer: D Difficulty: 2 Medium Section: 23.07 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Aldoses and ketoses; Physical properties of monosaccharides; Reactions of carbohydrates

16) The α and β forms of D-glucopyranose can be described as A) constitutional isomers. B) enantiomers. C) different conformations of the same compound. D) anomers. Answer: D Difficulty: 1 Easy Section: 23.07 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides 17) The α- and β-pyranose forms of D-glucose can be described as A) cyclic acetals formed between the aldehyde and the hydroxy group on carbon-5. B) cyclic hemiacetals formed between the aldehyde and the hydroxy group on carbon-5. C) cyclic acetals formed between the aldehyde and the hydroxy group on carbon-6. D) cyclic hemiacetals formed between the aldehyde and the hydroxy group on carbon-6. Answer: B Difficulty: 1 Easy Section: 23.07 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides; Reactions of carbohydrates

18) Identify the β-pyranose form of D-glucose.

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 23.07 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides

19) Which of the following is the open-chain form of the pyranose structure shown below?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 23.07 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides 20) The major form of D-glucose in aqueous solution is A) the open-chain form. B) α-D-glucopyranose. C) β-D-glucopyranose. D) α-D-glucofuranose. Answer: C Difficulty: 1 Easy Section: 23.08 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Physical properties of monosaccharides 10 Copyright © 2019

21) The α- and β-pyranose forms of D-glucose interconvert by A) "ring-flipping" between the two chair conformations. B) ring-opening and ring-closing through the open-chain aldehyde form. C) epimerization through the enol tautomer. D) SN2 inversion with nucleophilic hydroxide ion. Answer: B Difficulty: 2 Medium Section: 23.08 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides 22) Which of the following statements is(are) true concerning the equilibrium between the α- and β-pyranose forms of D-glucose? I. The interconversion is acid-catalyzed. II. Both anomers are equally stable. III. Both anomers are optically active. A) only III B) II and III C) I and III D) I, II, and III Answer: C Difficulty: 2 Medium Section: 23.08 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides

23) Identify the anomeric carbon in the following carbohydrate.

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 23.10 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Physical properties of monosaccharides

24) What results from the reaction shown?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 23.14 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 23 Subtopic: Reactions of carbohydrates

25) The following series of reactions was done on a monosaccharide. What information does this give about the monosaccharide?

A) The monosaccharide was in the open-chain form. B) The monosaccharide was in the furanose form. C) The monosaccharide was in the pyranose form. D) The monosaccharide was the α anomer. Answer: B Difficulty: 3 Hard Section: 23.14 Topic: Carbohydrates Bloom's: 4. Analyze Chapter: 23 Subtopic: Physical properties of monosaccharides; Reactions of carbohydrates 26) Sucrose is a nonreducing sugar, meaning it is not able to be oxidized. This means A) C-1 of glucose is linked to C-1 of fructose. B) C-1 of glucose is linked to C-2 of fructose. C) C-4 of glucose is linked to C-1 of fructose. D) C-6 of glucose is linked to C-2 of fructose. Answer: A Difficulty: 1 Easy Section: 23.15 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Disaccharides

27) Which one of the generally-digestible disaccharides has a β-(1→ 4) linkage? A) maltose B) lactose C) cellobiose D) sucrose Answer: B Difficulty: 1 Easy Section: 23.15 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Disaccharides 28) How would the glycosidic linkage indicated by the arrow be described for the following disaccharide?

A) α-(1→ 5) B) α-(1→ 6) C) α-(2→ 6) D) β-(1→ 6) Answer: B Difficulty: 2 Medium Section: 23.15 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Disaccharides

29) Which of the following is not true about the disaccharide, lactose, shown below?

A) It is a reducing sugar. B) It undergoes mutarotation. C) It has a β-(1→ 4) glycosidic linkage. D) It consists of two (D)-glucose units. Answer: D Difficulty: 2 Medium Section: 23.15 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Disaccharides 30) Which one of the following is not true concerning sucrose? A) Sucrose is a disaccharide. B) Sucrose is also known as table sugar. C) Acid-catalyzed hydrolysis of sucrose gives D-glucose and D-fructose. D) Sucrose undergoes mutarotation between its α and β forms. Answer: D Difficulty: 2 Medium Section: 23.15 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Disaccharides

31) Which one of the following disaccharides does not undergo mutarotation? A) sucrose B) maltose C) lactose D) cellobiose Answer: A Difficulty: 1 Easy Section: 23.15 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Disaccharides 32) Which one of the following disaccharides is obtained from the partial hydrolysis of starch? A) sucrose B) maltose C) lactose D) cellobiose Answer: B Difficulty: 1 Easy Section: 23.15 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Reactions of carbohydrates; Disaccharides 33) An unknown disaccharide is does not undergo mutarotation. Acid-catalyzed hydrolysis of the disaccharide gives only D-glucose. What information does this tell you about how the two glucose units are linked in the disaccharide? A) Each of the two glucose units is linked C-1 to C-1. B) One of the glucose units uses C-1 and it links to the other unit which uses either C-2, C-3, C4, or C-6. C) Each of the two glucose units is linked via any carbons except for C-1. D) The two units must both have β linkages. Answer: A Difficulty: 3 Hard Section: 23.15 Topic: Carbohydrates Bloom's: 4. Analyze Chapter: 23 Subtopic: Reactions of carbohydrates; Disaccharides

34) Which one of the following polysaccharides has all β-(1→ 4) glycosidic linkages? A) amylose B) glycogen C) cellulose D) amylopectin Answer: C Difficulty: 1 Easy Section: 23.16 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Polysaccharides 35) Which one of the following is most similar to glycogen in terms of how glucose units are linked? A) amylose B) amylopectin C) cellulose D) cellobiose Answer: B Difficulty: 1 Easy Section: 23.16 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Polysaccharides 36) The most abundant polysaccharide in plants is nearly always A) starch. B) glycogen. C) cellulose. D) amylopectin. Answer: A Difficulty: 1 Easy Section: 23.16 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Polysaccharides

37) Which of the following polysaccharides has all β-(1→ 4) glycosidic linkages? A) amylose B) glycogen C) cellulose D) amylopectin Answer: C Difficulty: 1 Easy Section: 23.16 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 23 Subtopic: Polysaccharides 38) The principal difference between amylose (from starch) and cellulose is A) amylose has exclusively α-(1→ 4)-linked glucose and cellulose has exclusively β-(1→ 4)linked glucose. B) amylose has exclusively α-(1→ 6)-linked glucose and cellulose has exclusively β-(1→ 4)linked glucose. C) amylose has α-(1→ 4)-linked glucose with α-(1→ 6) branches and cellulose has exclusively β-(1→ 4)-linked glucose. D) amylose has exclusively α-(1→ 4)-linked glucose and cellulose has β-(1→ 4)-linked glucose with α-(1→ 6) branches. Answer: A Difficulty: 2 Medium Section: 23.16 Topic: Carbohydrates Bloom's: 2. Understand Chapter: 23 Subtopic: Polysaccharides

39) Which of the following give an optically inactive compound when reacted with sodium borohydride, NaBH4?

A) I and II B) II and III C) III and IV D) I and IV Answer: D Difficulty: 3 Hard Section: 23.17 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 23 Subtopic: Physical properties of monosaccharides; Reactions of carbohydrates 40) How many of the six-carbon D-sugars give achiral alditols upon reduction with sodium borohydride? A) just one B) two C) three D) four Answer: B Difficulty: 3 Hard Section: 23.17 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 23 Subtopic: Reactions of carbohydrates

Organic Chemistry, 11e (Carey) Chapter 24 Lipids 1) Lipids, by definition, are A) fats. B) nonpolymeric biomolecules. C) biomolecules that form micelles. D) biomolecules that are water-insoluble and extractable (soluble) with nonpolar solvents. Answer: D Difficulty: 1 Easy Section: 24.01 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Triacylglycerols 2) Lipids are all ultimately derived (biosynthesized) from A) amino acids. B) fatty acids. C) glucose. D) terpenes. Answer: C Difficulty: 1 Easy Section: 24.01 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Biosynthesis 3) Which of the following fatty acids is most reactive to free radical oxidations with O2 or •OH? A) CH3(CH2)16CO2H B) CH3(CH2)7CH=CH(CH2)7CO2H C) CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H D) All have approximately the same reactivities with O2 and •OH Answer: C Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 4. Analyze Chapter: 24 Subtopic: Triacylglycerols 1 Copyright © 2019

4) Triglycerides are esters of fatty acids and

A) A. B) B. C) C. D) D. Answer: D Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols 5) Unsaturated fatty acids have primarily A) cis double bonds. B) terminal double bonds. C) trans double bonds. D) triple bonds. Answer: A Difficulty: 1 Easy Section: 24.02 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Triacylglycerols

6) Which of the following reagents can be used for the saponification of a fat or oil? A) H2, Ni B) LiAlH4 followed by H2O C) H2O, NaOH D) H2O, HCl Answer: C Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols 7) Saponification of a triglyceride with aqueous sodium hydroxide gives A) glycerol and the sodium salts of long-chained fatty acids. B) glycerol and long-chained alcohols. C) sodium acetate and long-chained alcohols. D) sodium acetate and long-chained fatty acids. Answer: A Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 3. Apply Chapter: 24 Subtopic: Triacylglycerols

8) Which of the following has the highest melting point?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 4. Analyze Chapter: 24 Subtopic: Triacylglycerols 9) Which of the following is a product in the saponification of a fat or oil?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols

10) Which structure below is a triacylglycerol (triglyceride)?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols

11) Which of the following fatty acids is least reactive to free radical oxidations with O2 or •OH?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 4. Analyze Chapter: 24 Subtopic: Triacylglycerols 12) Which of the following reactions isomerizes cis double bonds to trans double bonds in fats and oils? A) saponification with H2O, NaOH B) hydrogenation with H2/Ni C) ozonolysis with O3 D) reduction with LiAlH4 Answer: B Difficulty: 1 Easy Section: 24.02 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Triacylglycerols

13) Which one of the following reagents is used for the "hardening" of a vegetable oil to a vegetable solid? A) H2, Ni B) LiAlH4 followed by H2O C) H2O, NaOH D) H2O, HCl Answer: A Difficulty: 1 Easy Section: 24.02 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Triacylglycerols 14) Why are vegetable oils often subjected to catalytic hydrogenation? A) to increase the amount of trans carbon-carbon double bonds B) to increase the melting point C) to prevent air oxidation and prolong shelf life D) More than one of these is true. Answer: D Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols 15) Triacylglycerols (triglycerides) A) cannot be chiral. B) are always chiral. C) are sometimes chiral. D) exist as diastereomers. Answer: C Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols

16) Hydrogenation of triacylglycerols (triglycerides) can be accompanied by A) isomerization of cis double bonds to trans. B) migration of carbon-carbon double bonds. C) formation of carbon-carbon triple bonds. D) More than one of these. Answer: D Difficulty: 2 Medium Section: 24.02 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Triacylglycerols 17) Fatty acids are biosynthesized from A) isopentyl pyrophosphate. B) acetic acid derivatives. C) glycerol. D) terpenes. Answer: B Difficulty: 2 Medium Section: 24.03 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Triacylglycerols 18) In the synthesis of fatty acids, what is the next step in the reaction of S-acetoacetyl acyl carrier protein?

A) reduction with NADPH B) alkylation at C-2 C) oxidation with NADP+ D) condensation with CH3CO-S-ACP Answer: A Difficulty: 2 Medium Section: 24.03 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Triacylglycerols 8 Copyright © 2019

19) The in vivo conversion below used in fatty acid synthesis requires three steps. Which of the following in vitro reaction sequences most closely mimics the in vivo process?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 24.03 Topic: Lipids Bloom's: 3. Apply Chapter: 24 Subtopic: Triacylglycerols 20) Waxes are A) esters of unbranched long-chained fatty acids and unbranched long-chained alcohols. B) esters of steroids. C) polymers of isoprene units. D) esters of unbranched long-chained fatty acids and glycerol. Answer: A Difficulty: 1 Easy Section: 24.05 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Waxes

21) Prostaglandins are biosynthesized from A) terpenes. B) steroids. C) fatty acids. D) carbohydrates. Answer: C Difficulty: 1 Easy Section: 24.06 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Biosynthesis 22) How many C5 units are there in a diterpene? A) one B) two C) three D) four Answer: D Difficulty: 2 Medium Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes

23) Terpenes are formed from "isoprene units." What is the structure of isoprene?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 24.07 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Terpenes

24) Which one of the following is classified as a terpene?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes

25) Farnesol, shown below, is biosynthesized from three isoprene units. Identify where the isoprene units are connected.

A) C-3 to C-4 and C-7 to C-8 B) C-4 to C-5 and C-8 to C-9 C) C-4 to C-5 and C-9 to C-10 D) C-5 to C-6 and C-9 to C-10 Answer: B Difficulty: 2 Medium Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes; Biosynthesis 26) The structure of menthone is shown below. Menthone is a

27) How is the isoprene linkage between C-12 and C-13 of squalene described?

A) head-to-head B) head-to-tail C) tail-to-tail D) tail-to-head Answer: C Difficulty: 2 Medium Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes 28) α-Selinene is a sesquiterpene with all head-to-tail linkages. The structure of α-selinene is shown below except for one missing methyl group. Based on this information, where is the missing methyl group located?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes

29) The structure of the terpene phytol is shown below. Which one of the carbon-carbon bonds indicated is a head-to-tail linkage?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes 30) The terpenecitral cleaves into two fragments, as shown below, when heated in aqueous base. Which of the following best describes the mechanism of this reaction?

A) retro-aldol B) retro Diels-Alder C) ozonolysis D) hydrolysis Answer: A Difficulty: 3 Hard Section: 24.07 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes

31) Which one of the following is an important function of the pyrophosphate group in isoprenoid biosynthesis? A) to be an acid catalyst for terpene synthesis B) to provide a good leaving group for terpene synthesis C) to act as a nucleophile for terpene synthesis D) to provide resonance stability for terpene synthesis Answer: B Difficulty: 2 Medium Section: 24.08 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Terpenes 32) The following transformation occurs through two carbocations, X and Y.

Which of the following carbocations, respectively, are X and Y?

33) Which of the following is the most abundant steroid in the human body? A) squalene B) β-carotene C) cholesterol D) estrogen Answer: C Difficulty: 1 Easy Section: 24.11 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Steroids 34) Aromatic rings are more likely to occur in A) fatty acids. B) waxes. C) terpenes. D) steroids. Answer: D Difficulty: 1 Easy Section: 24.11 Topic: Lipids Bloom's: 2. Understand Chapter: 24 Subtopic: Steroids 35) Lanosterol (the precursor of steroids) is biosynthesized from the triterpene A) β-carotene. B) caryophyllene. C) α-farnesene. D) squalene. Answer: D Difficulty: 2 Medium Section: 24.11 Topic: Lipids Bloom's: 1. Remember Chapter: 24 Subtopic: Terpenes; Biosynthesis

36) The conversion below was reported in the chemical literature for the synthesis of progesterone. Which one of the following reaction sequences will carry out this conversion?

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 24.11 Topic: Lipids Bloom's: 3. Apply Chapter: 24 Subtopic: Steroids

Organic Chemistry, 11e (Carey) Chapter 25 Amino Acids, Peptides, and Proteins 1) How many of the 20 common amino acids contain sulfur? A) none B) one C) two D) three Answer: C Difficulty: 1 Easy Section: 25.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Classification and stereochemistry of amino acids 2) How many of the 20 common amino acids are primary amines? A) 20 B) 19 C) 18 D) 17 Answer: B Difficulty: 1 Easy Section: 25.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids 3) The amino groups in amino acids are A) stronger bases than primary amines. B) weaker bases than primary amines. C) same basicity of primary amines. D) stronger bases than secondary amines. Answer: B Difficulty: 2 Medium Section: 25.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Synthesis and reactions of amino acids

4) How many of the 20 common amino acids contain acidic side chains? A) none B) one C) two D) three Answer: C Difficulty: 2 Medium Section: 25.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids 5) Which one of the following amino acids has a side chain that is likely to be on the surface of a globular protein? A) alanine B) phenylalanine C) leucine D) glutamic acid Answer: D Difficulty: 2 Medium Section: 25.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids; Proteins and Protein structures 6) How many of the 20 common amino acids are achiral? A) none B) one C) two D) three Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids

7) The Fischer projection shown below denotes a ________ amino acid, which has the ________ configuration.

A) D; S B) D; R C) L; S D) L; R Answer: C Difficulty: 2 Medium Section: 25.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Classification and stereochemistry of amino acids 8) How many of the 20 common amino acids contain more than one chiral center? A) none B) one C) two D) three Answer: C Difficulty: 2 Medium Section: 25.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids

9) Which of the following is the zwitterion form of alanine?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids; Physical properties of amino acids; Synthesis and reactions of amino acids 10) Which one of the following best defines the isoelectric point, pI? A) The charge on the amino acid when the pH is 7.0. B) The charge on the amino acid when the pH equals the pKa of the carboxylic acid group. C) The pH at which the charge on the amino acid is 0. D) The pH at which the charge on the amino acid is +1. Answer: C Difficulty: 1 Easy Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Physical properties of amino acids; Synthesis and reactions of amino acids

11) What is the pI of valine, shown below? (the pKa's are shown)

A) 2.32 B) 4.81 C) 5.97 D) 9.62 Answer: C Difficulty: 1 Easy Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Physical properties of amino acids; Synthesis and reactions of amino acids 12) What is the purpose of electrophoresis? A) to neutralize amino acids B) to separate amino acids or proteins C) to analyze the amino acid sequence in a protein D) to synthesize amino acids or proteins Answer: B Difficulty: 1 Easy Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Synthesis and reactions of amino acids

13) Which of the following is the major product of the reaction shown below? (the pKa's are

shown)

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 4. Analyze Chapter: 25 Subtopic: Synthesis and reactions of amino acids 14) What is the net charge on lysine at pH of 1.0? A) +1 B) +2 C) +3 D) +4 Answer: B Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Synthesis and reactions of amino acids

15) The pKa's of the acidic hydrogens of lysine are shown below. What is the isoelectric point of lysine?

A) 2.18 B) 5.56 C) 6.36 D) 9.74 Answer: D Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Physical properties of amino acids; Synthesis and reactions of amino acids 16) What is the net charge on L-aspartic acid (R = −CH2CO2H) at a pH of 11.0? A) +1 B) +2 C) −1 D) −2 Answer: D Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Synthesis and reactions of amino acids

17) In the following table, which column has the isoelectric points (pI) correctly matched with the amino acids on the left? (Note: The side chains are given for each.)

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 4. Analyze Chapter: 25 Subtopic: Physical properties of amino acids; Synthesis and reactions of amino acids 18) In strongly acidic solution L-lysine is primarily a dication as shown below. As the pH is raised, which proton is lost to form the monocation?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 4. Analyze Chapter: 25 Subtopic: Synthesis and reactions of amino acids

19) The pKa's of the acidic hydrogens for aspartic acid are shown below. What is the isoelectric point of aspartic acid?

A) 2.77 B) 3.65 C) 5.74 D) 6.62 Answer: A Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Physical properties of amino acids; Synthesis and reactions of amino acids 20) The pKa's of the -CO2H groups of amino acids are usually between 2 and 3. Why are these so much lower than the pKa of acetic acid, which is 4.7? A) The amino group in amino acids can hydrogen bond with water. B) Amino acids are more soluble in water than acetic acid. C) Amino acids are amphoteric. D) The electron-withdrawing effect of the amino group increases the acidity of the acid group. Answer: D Difficulty: 2 Medium Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Classification and stereochemistry of amino acids; Physical properties of amino acids; Synthesis and reactions of amino acids

21) What is the net charge on the dipeptide lys-asp at a pH of 1.0? aspartic acid (R = −CH2CO2H) lysine (R = CH2CH2CH2CH2NH2) A) +1 B) +2 C) +3 D) +4 Answer: B Difficulty: 3 Hard Section: 25.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Synthesis and reactions of amino acids; Peptides and peptide bonds

22) Which one of the following is the final product of the reaction sequence shown below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 25.04 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Synthesis and reactions of amino acids

23) Identify the missing starting reagent needed in the Strecker synthesis of isoleucine. (Assume you will get all the stereoisomers of isoleucine.)

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 25.04 Topic: Amino Acids, Peptides, and Proteins Bloom's: 4. Analyze Chapter: 25 Subtopic: Synthesis and reactions of amino acids

24) In aqueous solution, the artificial sweetener aspartame slowly converts to the cyclic compound shown below. Which of the following best describes this reaction?

A) nucleophilic acyl substitution B) ester hydrolysis C) Dieckmann condensation D) SN2 reaction Answer: A Difficulty: 3 Hard Section: 25.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Synthesis and reactions of amino acids; Peptides and peptide bonds 25) What is the relationship between the following two structures?

A) resonance forms B) enantiomers C) diastereomers D) keto-enol forms Answer: A Difficulty: 1 Easy Section: 25.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Peptides and peptide bonds

26) The peptide linkage in proteins and peptides is planar and has restricted rotation about the carbon-nitrogen bond because A) the peptide bond has partial double bond character. B) hydrogen bonding requires a planar arrangement and restricts bond rotation. C) the steric hindrance of the large side chains. D) the carbonyl is predominately in the enol form. Answer: A Difficulty: 2 Medium Section: 25.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Peptides and peptide bonds 27) Which of the following is the abbreviated formula of the tetrapeptide shown below? (Hint: remember to start at the N-terminal end.)

A) lys-ser-asp-ala B) ser-lys-ala-asp C) asp-ala-ser-lys D) asp-ser-ala-lys Answer: C Difficulty: 2 Medium Section: 25.08 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Peptides and peptide bonds

28) Sanger's reagent (1-fluoro-2,4-dinitrobenzene) reacts with the N-terminal amino acids and the side chain of ________ in peptides and proteins. A) lysine B) cysteine C) glutamic acid D) phenylalanine Answer: A Difficulty: 1 Easy Section: 25.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Synthesis and reactions of amino acids 29) Which of the following is the mechanism by which Sanger's reagent reacts with N-terminal amino acids? A) electrophilic aromatic substitution B) nucleophilic aromatic substitution (addition-elimination mechanism) C) nucleophilic aromatic substitution (elimination-addition mechanism) D) bimolecular nucleophilic substitution (SN2) Answer: B Difficulty: 2 Medium Section: 25.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Synthesis and reactions of amino acids

30) Which of the following is the DNP derivative obtained from the reaction sequence shown below?

A) DNP-ala B) DNP-phe C) DNP-ser D) DNP-ala-phe-ser Answer: A Difficulty: 2 Medium Section: 25.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Synthesis and reactions of amino acids; Peptides and peptide bonds 31) A pentapeptide was found to contain the amino acids ala, gly, met, phe, and ser. Partial hydrolysis of the pentapeptide gave the dipeptides gly-ser, met-phe, ala-gly, and ser-met. What is the sequence of the pentapeptide? A) gly-ser-met-phe-ala B) ala-gly-ser-phe-met C) gly-ser-met-ala-phe D) ala-gly-ser-met-phe Answer: D Difficulty: 3 Hard Section: 25.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 4. Analyze Chapter: 25 Subtopic: Peptides and peptide bonds; Proteins and Protein structures

32) Which of the following is the DNP derivative obtained from the reaction sequence shown below?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 25.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Synthesis and reactions of amino acids; Peptides and peptide bonds; Proteins and Protein structures

33) Complete hydrolysis of a nonapeptide gave 3 ala, 2 phe, 2 asp, gly, and ser. Reaction of the nonapeptide with Sanger's reagent (1-fluoro-2,4-dinitrobenzene) followed by hydrolysis gave N(2,4-dinitrophenyl) alanine. Partial hydrolysis of the nonapeptide gave the following fragments: gly-ala-phe ala-asp-gly-ala phe-ser-ala ser-ala-phe-asp Which one of the following is the nonapeptide's primary structure? A) ala-asp-gly-ala-asp-ala-phe-ser-phe B) ala-phe-asp-gly-ala-asp-ser-phe-ala C) ala-asp-gly-ala-phe-ser-ala-phe-asp D) gly-ala-phe-ser-ala-phe-asp-asp-ala Answer: C Difficulty: 3 Hard Section: 25.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 4. Analyze Chapter: 25 Subtopic: Peptides and peptide bonds; Proteins and Protein structures 34) Which of the following is used for N-terminal analysis of peptides and proteins? A) hydrogenolysis B) Edman degradation C) Merrifield method D) Pauling method Answer: B Difficulty: 1 Easy Section: 25.11 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Peptides and peptide bonds; Proteins and Protein structures

35) Which of the following analyses for the N-terminal amino acid of a peptide does not require hydrolysis of the peptide chain? A) Edman degradation B) Both require hydrolysis C) Sanger's reagent D) Neither requires hydrolysis Answer: A Difficulty: 2 Medium Section: 25.11 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Peptides and peptide bonds; Proteins and Protein structures 36) What is the total number of different acyclic tripeptides that can result from three different Lamino acids? A) three B) four C) six D) nine Answer: C Difficulty: 2 Medium Section: 25.13 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Peptides and peptide bonds 37) What is the total number of different tripeptides that can result from two L-alanines and one L-serine amino acids? A) two B) three C) four D) six Answer: B Difficulty: 2 Medium Section: 25.13 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 25 Subtopic: Peptides and peptide bonds

38) Linus Pauling is credited with describing the α-helix structure of a polypeptide. The α-helix is an example of a polypeptide's A) primary structure. B) secondary structure. C) tertiary structure. D) quaternary structure. Answer: B Difficulty: 1 Easy Section: 25.17 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Proteins and Protein structures 39) Adjacent polypeptide chains in the β-pleated sheet structure of a protein are held together by A) peptide bonds. B) disulfide bridges. C) hydrogen bonds. D) ionic bonds. Answer: C Difficulty: 1 Easy Section: 25.17 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Proteins and Protein structures 40) Which of the following best describes the interactions between the side chain groups of valine and phenylalanine? A) hydrogen bonding B) disulfide bonds C) salt bridges D) Van der Waals Answer: D Difficulty: 2 Medium Section: 25.18 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 25 Subtopic: Proteins and Protein structures

41) Two cysteine side chains of a polypeptide are often connected to each other by a(n) A) ionic bond. B) hydrogen bond. C) disulfide bond. D) peptide bond. Answer: C Difficulty: 1 Easy Section: 25.18 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 25 Subtopic: Synthesis and reactions of amino acids; Proteins and Protein structures

Organic Chemistry, 11e (Carey) Chapter 26 Nucleosides, Nucleotides, and Nucleic Acids 1) Which of the following are purines? I. adenine A) I and II B) I and III C) II and III D) II and IV

II. cytosine

III. guanine

IV. thymine

Answer: B Difficulty: 1 Easy Section: 26.01 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids; Nucleosides and nucleotides 2) Which one of the following is in DNA but not in RNA? A) adenine B) uracil C) guanine D) thymine Answer: D Difficulty: 1 Easy Section: 26.02 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids 3) Which one of the following does not include phosphate as part of its structure? A) nucleosides B) nucleotides C) nucleic acids D) RNA Answer: A Difficulty: 1 Easy Section: 26.02 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Nucleosides and nucleotides 1 Copyright © 2019

4) Which of the following is the "enol" form of guanine?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 26.01 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Nucleosides and nucleotides 5) Identify the carbohydrate present in DNA. A) 2-deoxyribose B) 3-deoxyribose C) 4-deoxyribose D) 5-deoxyribose Answer: A Difficulty: 1 Easy Section: 26.02 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication) 2 Copyright © 2019

6) The carbohydrate in RNA is in the A) open-chain form. B) furanose form. C) pyranose form. D) ketose form. Answer: B Difficulty: 2 Medium Section: 26.02 Topic: Nucleic Acids Bloom's: 2. Understand Chapter: 26 Subtopic: Composition of nucleic acids; RNA (includes transcription) 7) Which of the following is the sugar found in DNA?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 26.02 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication)

8) How is the following structure classified?

A) DNA base B) nucleoside C) nucleotide D) nucleic acid Answer: C Difficulty: 1 Easy Section: 26.03 Topic: Nucleic Acids Bloom's: 2. Understand Chapter: 26 Subtopic: Nucleosides and nucleotides 9) What is the name of the following nucleotide?

A) 2'-deoxythymidine-3'-monophosphate B) 2'-deoxythymidine-5'-monophosphate C) 2'-deoxycytosine-3'-monophosphate D) 3'-deoxycytosine-5'-monophosphate Answer: B Difficulty: 2 Medium Section: 26.03 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Nucleosides and nucleotides 4 Copyright © 2019

10) Which of the following is the abbreviated name for the structure shown below?

A) dAMP B) dADP C) AMP D) ADP Answer: D Difficulty: 2 Medium Section: 26.03 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Nucleosides and nucleotides 11) Which carbon(s) on the sugar is(are) in DNA is used to make the phosphate ester linkages? A) 3' to 2' B) 4' to 3' C) 5' to 2' D) 5' to 3' Answer: D Difficulty: 1 Easy Section: 26.06 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication)

12) Nucleic acids can be thought of as a biopolymer. What is the repeating unit for this biopolymer? A) 2-deoxyribose B) nucleosides C) purine and pyrimidine bases D) nucleotides Answer: D Difficulty: 1 Easy Section: 26.06 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids; Nucleosides and nucleotides 13) Which of the following is not part of the structure of DNA? A) 2-deoxyribose B) phosphate C) acetate D) purine and pyrimidine bases Answer: C Difficulty: 1 Easy Section: 26.08 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication) 14) Approximately 30% of the bases found in human DNA are adenine. Based on this, what is the approximate percentage of guanine found in human DNA? A) 20% B) 30% C) 60% D) 70% Answer: A Difficulty: 2 Medium Section: 26.08 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication); Base pairing

15) A certain type of yeast has DNA that contains 18% cytosine. Based on this, what is the percentage of adenine in the DNA of this yeast? A) 9% B) 18% C) 32% D) 36% Answer: C Difficulty: 2 Medium Section: 26.08 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Composition of nucleic acids; Base pairing 16) Which of the following DNA base sequences is the complementary strand to the DNA sequence shown below? (Recall: DNA strands run antiparallel.) (5') GGATTCGA (3') A) (5') CCTAAGCT (3') B) (5') TGCAATGG (3') C) (5') TCGAATCC (3') D) (5') CCTAAGGT (3') Answer: C Difficulty: 2 Medium Section: 26.08 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication); Base pairing

17) Which of the following are correct in describing the structure of DNA? I. The purine and pyrimidine bases of one strand are connected to their complementary bases by hydrogen bonds. II. The purine and pyrimidine bases are connected to 2-deoxy-D-ribose by an N-glycoside bond. III. The 2-deoxy-D-ribose sugars are connected by phosphate ester linkages to each other. A) I and II B) I and III C) II and III D) All of the answers are correct. Answer: D Difficulty: 2 Medium Section: 26.08 Topic: Nucleic Acids Bloom's: 2. Understand Chapter: 26 Subtopic: Composition of nucleic acids; DNA (includes replication); Base pairing 18) The base pairs present in DNA are A) A----G and C----T. B) A----C and G----T. C) A----T and G----C. D) A----A and T----T. Answer: C Difficulty: 1 Easy Section: 26.08 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: DNA (includes replication); Base pairing 19) The repeating unit found in the backbone structure of DNA is A) [base-sugar]. B) [base-phosphate]. C) [sugar-phosphate]. D) [base-phosphate-sugar]. Answer: C Difficulty: 1 Easy Section: 26.08 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: Composition of nucleic acids 8 Copyright © 2019

20) The structures of cytosine and guanine are shown below. In DNA the -NH2 group on guanine hydrogen bonds with the

A) -NH2 group on cytosine. B) doubly bonded ring nitrogen on cytosine. C) -NH- ring nitrogen on cytosine. D) carbonyl oxygen on cytosine. Answer: D Difficulty: 2 Medium Section: 26.08 Topic: Nucleic Acids Bloom's: 2. Understand Chapter: 26 Subtopic: DNA (includes replication); Base pairing 21) How many bases constitute a codon in messenger RNA? A) one B) two C) three D) four Answer: C Difficulty: 1 Easy Section: 26.11 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription)

22) In which of the following is a sequence of bases termed anticodon located? A) DNA B) messenger RNA C) ribosomal RNA D) transfer RNA Answer: D Difficulty: 1 Easy Section: 26.11 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription) 23) How many types of RNA are involved in gene expression? A) one B) two C) three D) four Answer: C Difficulty: 1 Easy Section: 26.11 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription) 24) How many "start" and "stop" codons, respectively, are there in the genetic code? A) one of each B) one "start" and three "stop" C) two "start" and two "stop" D) two "start" and one "stop" Answer: B Difficulty: 1 Easy Section: 26.11 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription)

25) What is the total number of codons in the genetic code? A) 8 B) 16 C) 32 D) 64 Answer: D Difficulty: 1 Easy Section: 26.11 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription) 26) A codon in a segment of mRNA is shown below. Which of the following is the corresponding anticodon? (5') G-A-U (3') A) (5') A-U-C (3') B) (5') C-G-A (3') C) (5') C-U-A (3') D) (5') G-C-A (3') Answer: A Difficulty: 2 Medium Section: 26.11 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: Base pairing; RNA (includes transcription)

27) The codon sequences on a segment of mRNA are shown below. Which of the following amino acid sequences is coded by this mRNA segment? (Recall: the mRNA chain runs 5' to 3'. Refer to table 26.4 in the textbook.) -UAC-GCA-CCC-ACG-AGC-CAGA) tyr-arg-ala-pro-thr-pro B) ser-gly-ala-ile-thr-lys C) gln-ser-pro-ala-arg-tyr D) tyr-ala-pro-thr-ser-gln Answer: D Difficulty: 2 Medium Section: 26.11 Topic: Nucleic Acids Bloom's: 3. Apply Chapter: 26 Subtopic: RNA (includes transcription) 28) What amino acid sequence is coded for by the following DNA template strand? (Recall: the DNA template strand runs 5' to 3' and the mRNA strand runs antiparallel to the DNA template strand. Refer to table 26.4 in the textbook.) TTG-CGA-CCA-GAC-CAG-TTT A) gln-ser-trp-val-leu-lys B) lys-leu-val-trp-ser-gln C) his-pro-met-cys-ile-try D) asn-ala-leu-glu-thr-ser Answer: B Difficulty: 3 Hard Section: 26.11 Topic: Nucleic Acids Bloom's: 4. Analyze Chapter: 26 Subtopic: Base pairing; RNA (includes transcription)

29) Peptide biosynthesis is mechanistically similar to the A) Claisen condensation. B) Fischer esterification reaction. C) aldol condensation. D) ammonolysis of an ester. Answer: D Difficulty: 2 Medium Section: 26.12 Topic: Nucleic Acids Bloom's: 2. Understand Chapter: 26 Subtopic: RNA (includes transcription) 30) All proteins are initially formed with what amino acid at their N-terminal end? (it is generally cleaved off later) A) serine B) threonine C) cysteine D) methionine Answer: D Difficulty: 1 Easy Section: 26.12 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription) 31) The term retrovirus refers to what? A) a virus that reverse copies its host's DNA B) a virus whose DNA does not reside in an antiparallel arrangement C) a virus that uses RNA as its genetic material D) a virus that contains cyclic DNA Answer: C Difficulty: 1 Easy Section: 26.13 Topic: Nucleic Acids Bloom's: 1. Remember Chapter: 26 Subtopic: RNA (includes transcription)

Organic Chemistry, 11e (Carey) Chapter 27 Synthetic Polymers 1) Which one of the following is used to make Teflon? A) fluoroethene B) 1,2-difluoroethene C) 1,1,4,4-tetrafluorobutadiene D) tetrafluoroethylene Answer: D Difficulty: 1 Easy Section: 27.02 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Classes of synthetic polymers 2) Which of the following is the monomer that gives the polymer shown below?

3) The repeating unit of poly (methyl methacrylate) is shown below. Which one of the following is the monomer used to make poly (methyl methacrylate)?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 27.02 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers

4) Identify the following polymer.

A) polyethylene B) polypropylene C) polyisobutylene D) polybutylene Answer: B Difficulty: 2 Medium Section: 27.02 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers

5) A super-absorbent polymer used in diapers is the sodium salt of a crosslinked form of the polymer shown below. From what monomer is it made?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 27.02 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers

6) Which of the following is the repeating unit in poly(vinyl chloride) (PV)?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 27.02 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Classes of synthetic polymers

7) Which of the following is the repeating unit of the polymer formed in the polymerization reaction shown below?

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 27.02 Topic: Synthetic polymers Bloom's: 3. Apply Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms)

8) Which one of the following monomers is used to make the polymer carbowax, shown below?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 27.02 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers

9) Which of the following are addition polymers? I. polypropylene II. Teflon III. Nylon A) only I B) only II C) only III D) both I and II Answer: D Difficulty: 1 Easy Section: 27.03 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms) 10) Which of the following are repeating units of step-growth polymers?

A) only I B) only II C) only III D) I and II Answer: D Difficulty: 2 Medium Section: 27.04 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms)

11) Which of the following are condensation polymers? I. polypropylene II. Teflon III. Nylon A) only I B) only II C) only III D) both II and III Answer: C Difficulty: 1 Easy Section: 27.03 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms) 12) Vulcanization is the process of cross-linking polymer chains in rubber using A) sulfur. B) formaldehyde. C) benzoyl peroxide. D) ethylene glycol. Answer: A Difficulty: 1 Easy Section: 27.05 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms) 13) Crosslinking polymer chains makes the polymer A) more soluble. B) more rigid. C) more flexible. D) more elastic. Answer: B Difficulty: 1 Easy Section: 27.05 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Physical properties of polymers

14) What modification occurs when a small amount of p-divinylbenzene is added to the polymerization reaction of styrene to polystyrene? (Recall: the vinyl group is -CH=CH2.) A) cross-linking of the polystyrene B) isotactic stereochemistry of the polystyrene C) syndiotactic stereochemistry of the polystyrene D) "softening" of the polystyrene by a plasticizer Answer: A Difficulty: 3 Hard Section: 27.05 Topic: Synthetic polymers Bloom's: 3. Apply Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms) 15) What is the purpose of plasticizers? A) harden plastics B) initiate polymerizations C) soften plastics D) cross-link polymer chains Answer: B Difficulty: 1 Easy Section: 27.06 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Physical properties of polymers 16) Polymers which soften on heating and harden when cooled are A) cross-linked polymers. B) thermosetting polymers. C) copolymers. D) thermoplastics. Answer: D Difficulty: 1 Easy Section: 27.06 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Classes of synthetic polymers; Physical properties of polymers

17) Which one of the following best describes the polymer chain shown below?

A) atactic polypropylene B) syndiotactic polypropylene C) isotactic polypropylene D) cross-linked polypropylene Answer: B Difficulty: 1 Easy Section: 27.07 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers 18) Which one of the following best describes the polymer chain shown below?

A) atactic polypropylene B) syndiotactic polypropylene C) isotactic polypropylene D) cross-linked polypropylene Answer: C Difficulty: 1 Easy Section: 27.07 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers

19) Which of the following monomers can form a stereoregular polymer? A) H2C=CH2 B) F2C=CF2 C) H2C=CHCH3 D) H2C=CCl2 Answer: C Difficulty: 2 Medium Section: 27.07 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers 20) Which one of the following initiators is used to make isotactic polypropylene? A) benzoyl peroxide B) CH3CH2CH2CH2Li C) BF3 D) Al(CH2CH3)3, TiCl4 Answer: D Difficulty: 2 Medium Section: 27.07 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Polymerization methods (mechanisms)

21) The compound shown below is used to initiate what type of polymerizations?

A) anionic B) cationic C) radical D) condensation Answer: C Difficulty: 2 Medium Section: 27.07 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Polymerization methods (mechanisms) 22) A gas cylinder of CF2=CF2 is unexpectedly found to have lost all pressure. Upon being sawn open, what was discovered? (a true story) A) plexiglass B) Bakelite C) styrofoam D) Teflon Answer: D Difficulty: 2 Medium Section: 27.07 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms)

23) The repeating unit of a polymer is shown below. This polymer is formed by

A) addition of ethylene. B) 1,2 addition of butadiene. C) addition of trans-2-butene. D) 1,4 addition of butadiene. Answer: D Difficulty: 3 Hard Section: 27.07 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms) 24) Which one of the following is the monomer that gives the polymer shown below?

A) A B) B C) C D) D Answer: D Difficulty: 3 Hard Section: 27.07 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers

25) Identify the repeating unit in the polymer formed from the following reaction sequence.

A) A B) B C) C D) D Answer: B Difficulty: 3 Hard Section: 27.07 Topic: Synthetic polymers Bloom's: 3. Apply Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms)

26) Bakelite is formed by the acid-catalyzed polymerization of phenol with formaldehyde. What is(are) the product(s) of the first step in this polymerization, shown below? (Note: in the answers below the hydroxymethyl group is -CH2OH.)

A) ortho and para-hydroxybenzaldehyde B) meta-hydroxybenzaldehyde C) ortho and para-(hydroxymethyl)phenol D) meta-(hydroxymethyl)phenol Answer: C Difficulty: 3 Hard Section: 27.07 Topic: Synthetic polymers Bloom's: 3. Apply Chapter: 27 Subtopic: Polymerization methods (mechanisms) 27) Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an initiator? A) free-radical chain-growth B) anionic chain-growth C) cationic chain-growth D) acid-catalyzed step-growth Answer: A Difficulty: 1 Easy Section: 27.08 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Polymerization methods (mechanisms)

28) Which one of the following initiators can be used for free radical chain-growth polymerization? A) benzoyl peroxide B) CH3CH2CH2CH2Li C) BF3 D) Al(CH2CH3)3, TiCl4 Answer: A Difficulty: 1 Easy Section: 27.08 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Polymerization methods (mechanisms) 29) Which one of the following initiators can be used for anionic chain-growth polymerization? A) benzoyl peroxide B) CH3CH2CH2CH2Li C) BF3 D) Al(CH2CH3)3, TiCl4 Answer: B Difficulty: 1 Easy Section: 27.09 Topic: Synthetic polymers Bloom's: 1. Remember Chapter: 27 Subtopic: Polymerization methods (mechanisms) 30) Which one of the following monomers undergoes anionic polymerization most readily? A) H2C=CH2 B) H2C=CHCH3 C) H2C=C(CH3)2 D) H2C=CHCN Answer: D Difficulty: 2 Medium Section: 27.09 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Polymerization methods (mechanisms)

31) The monomer used to make superglue is shown below. Which one of the following methods of polymerization is most suitable for this type of monomer?

A) free-radical chain-growth B) anionic chain-growth C) cationic chain-growth D) acid-catalyzed step-growth Answer: C Difficulty: 2 Medium Section: 27.09 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Polymerization methods (mechanisms) 32) Which one of the following monomers undergoes cationic polymerization most readily? A) H2C=CH2 B) H2C=CHCH3 C) H2C=C(CH3)2 D) H2C=CHCN Answer: C Difficulty: 3 Hard Section: 27.10 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Polymerization methods (mechanisms)

33) Which polymer would be compatible with prolonged exposure to aqueous base?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 27.11 Topic: Synthetic polymers Bloom's: 2. Understand Chapter: 27 Subtopic: Classes of synthetic polymers

34) Identify the monomer(s) used to make the following polymer.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 27.11 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers

35) What monomer(s) would be used to make the polyester shown below?

A) butanedioic acid B) 4-hydroxybutanoic acid C) 4-hydroxybutanal D) butanedioic acid and 1,4-butanediol Answer: C Difficulty: 2 Medium Section: 27.12 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers

36) Which one of the following is the repeating unit of the polymer formed in the polymerization of para-hydroxybenzoic acid?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 27.12 Topic: Synthetic polymers Bloom's: 3. Apply Chapter: 27 Subtopic: Classes of synthetic polymers; Polymerization methods (mechanisms)

37) Identify the monomer(s) needed to make the following polyester.

A) 3-hydroxybutanoic acid B) butanedioic acid and 1,2-ethanediol C) butanedioic acid D) butanedioic acid and ethanol Answer: C Difficulty: 3 Hard Section: 27.12 Topic: Synthetic polymers Bloom's: 4. Analyze Chapter: 27 Subtopic: Classes of synthetic polymers