Organic Chemistry 6th Edition by Janice G Smith. All Chapters 1-29

Organic Chemistry, 6e (Smith) Chapter 1 Structure and Bonding 1) What is the ground-state electronic configuration of a carbon atom? A) 1s2, 2s2, 2p5 B) 1s2, 2s2, 2p2 C) 1s2, 2s2, 2p6 D) 1s2, 2s2, 2p4 2) What is the ground-state electronic configuration of a fluorine atom? A) 1s2, 2s2, 2p2 B) 1s2, 2s2, 2p3 C) 1s2, 2s2, 2p4 D) 1s2, 2s2, 2p5 3) What is the ground-state electronic configuration of a magnesium cation (Mg2+)? A) 1s2, 2s2, 2p6 B) 1s2, 2s2, 2p6, 3s1 C) 1s2, 2s2, 2p6, 3s2 D) 1s2, 2s2, 2p6, 3s2, 3p2 4) What is the ground-state electronic configuration of a chlorine anion (Cl—)? A) 1s2, 2s2, 2p6 B) 1s2, 2s2, 2p6, 3s2, 3p6 C) 1s2, 2s2, 2p6, 3s2, 3p5 D) 1s2, 2s2, 2p6, 3s2, 3p4 5) Which of the following statements about valence electrons is true? A) They are the most tightly held electrons. B) They do not participate in chemical reactions. C) They are the outermost electrons. D) They reveal the period number of a second-row element. 6) Which of the following atoms will have a full 3s orbital in the ground state? A) Hydrogen B) Lithium C) Potassium D) Rubidium 7) Which of the following statements about bonding is true? A) Covalent bonds result from the transfer of electrons from one element to another. B) Ionic bonds result from the transfer of electrons from a metal to a non-metal. C) Ionic bonds result from the sharing of electrons between two non-metals. D) Covalent bonds result from the sharing of electrons between two metals. 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

8) Which of the following would you expect to have ionic bonds? A) CO B) FBr C) NF3 D) NaCl 9) Which of the following molecules has nonpolar covalent bonds? A) HCl B) N2 C) CHCl3 D) NO 10) Which of the following molecules contain both covalent and ionic bonds?

A) I, II B) I, IV C) II, III D) II, IV 11) Which of the following would most likely form an ionic bond?

A) I B) II C) III D) IV 12) Which of the following statements correctly describes the typical number of bonds for carbon, nitrogen, and oxygen in most neutral organic molecules? A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds, and oxygen forms 3 covalent bonds. B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds, and oxygen forms 2 covalent bonds. C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds, and oxygen forms 2 covalent bonds. D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds, and oxygen forms 4 covalent bonds. 2 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

13) Which is not an acceptable Lewis structure for the anion CH2NCO—?

A) I B) II C) III D) IV 14) Which of the following Lewis structures is correct?

A) I B) II C) III D) IV 15) Which of the following Lewis structures is correct?

A) I, II B) I, III C) II, III D) III, IV

16) Which is the correct Lewis structure for acetic acid (CH3CO2H)?

A) I B) II C) III D) IV 17) In which of the following ions does carbon have a formal charge?

A) I B) II C) III D) None of these 18) In which of the following ions does carbon have a formal charge?

A) I B) II C) III D) None of these 19) What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple bond? A) 0 B) -2 C) -1 D) +1

20) What is the formal charge of the carbon in carbon dioxide (CO2) when drawn with two double bonds? A) +1 B) 0 C) -1 D) -2 21) Which of the following statements about constitutional isomers is true? A) Constitutional isomers are different molecules having the different molecular formula. B) Constitutional isomers are different molecules having the same molecular formula. C) Constitutional isomers are same molecules having the different molecular formula. D) Constitutional isomers are same molecules having the same molecular formula. 22) How many constitutional isomers are there for a molecule having the molecular formula C2H6O? A) 1 B) 2 C) 3 D) 4 23) How many constitutional isomers are there for a molecule having the molecular formula C3H8O? A) 1 B) 2 C) 3 D) 4 24) How many constitutional isomers are there for a molecule having the molecular formula C3H6? A) 1 B) 2 C) 3 D) 4 25) How many constitutional isomers are there for a molecule having the molecular formula C2H4Cl2? A) 1 B) 2 C) 3 D) 4

26) How many different isomers are there for a compound having the molecular formula C3H6O? A) 4 B) 5 C) 6 D) 7 27) Which of the following molecules are constitutional isomers?

A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III 28) Which of the following compounds has an atom with an unfilled valence shell of electrons? A) H2O B) BCl3 C) CH4 D) CO2 29) Which of the following compounds has an atom with more than eight valence electrons? A) H2CO3 B) H2SO4 C) H2O D) HBr 30) How many electrons are around phosphorus in phosphoric acid (H3PO4)? A) 6 B) 8 C) 10 D) 12

31) Which of the following statements about resonance structures is true? A) Resonance structures have the same placement of electrons but different arrangement of atoms. B) Resonance structures have the same placement of atoms but different arrangement of electrons. C) Resonance structures have the same placement of atoms and the same arrangement of electrons. D) Resonance structures have different placement of atoms and different arrangement of electrons. 32) Which of the following statements about resonance structures is not true? A) There is no movement of electrons from one form to another. B) Resonance structures are not isomers. C) Resonance structures differ only in the arrangement of electrons. D) Resonance structures are in equilibrium with each other. 33) Which of the following pair does not represent resonance structures?

A) I B) II C) III D) IV 34) What 2 things will change between two resonance structures? A) The position of multiple bonds and non-bonded electrons. B) The position of multiple bonds and single bonds. C) The placement of atoms and single bonds. D) The placement of atoms and non-bonded electrons.

35) Which of the following is a resonance structure of the compound below?

A) I B) II C) III D) IV 36) Which of the following resonance structures is the least important contributor to the resonance hybrid of the formate anion, HCOO—?

A) I B) II C) III D) IV 37) Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H2CO.

A) I > II > III B) I > III > II C) II > I > III D) III > II > I

38) Follow the curved arrows to draw the second resonance structure for the ion below.

A) I B) II C) III D) IV 39) Which is more important in each pair of contributing resonance structures?

A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V 40) What is the approximate value of the H-C-H bond angle in methane, CH4? A) 90° B) 109.5° C) 120° D) 180°

41) What is the approximate C-C-C bond angle in propene, CH3CH = CH2? A) 90° B) 109.5° C) 120° D) 180° 42) What is the approximate H-C-O bond angle in formaldehyde, H2CO? A) 90° B) 109.5° C) 120° D) 180° 43) Determine the geometry around the indicated atom in each species.

A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral 44) What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN? A) 90° B) 109.5° C) 120° D) 180° 45) What is the molecular geometry around the boron atom in BH3? A) Tetrahedral B) Trigonal Planar C) Trigonal Pyramidal D) Linear 46) What is the molecular geometry around the carbon atom in CH4? A) Tetrahedral B) Trigonal Planar C) Trigonal Pyramidal D) Linear

47) Which of the following is the appropriate conversion of the condensed structure, CH3COCH3, to a Lewis structure?

A) I B) II C) III D) IV 48) Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a skeletal structure?

A) I B) II C) III D) IV 49) Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?

A) I B) II C) III D) IV

50) What is the condensed formula of the compound below?

A) I B) II C) III D) IV 51) Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a skeletal structure?

A) I B) II C) III D) IV

52) Convert the following skeletal structure to a condensed structure.

A) I B) II C) III D) IV 53) Avobenzone is an active ingredient in some common sunscreens. Which of the following is the correct molecular formula for avobenzone?

A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3 54) In which structure is the hybridization incorrect?

A) I B) II C) III D) IV

55) What is the hybridization for each of the indicated atoms in the following compound?

A) I = sp2; II = sp2; III = sp2. B) I = sp2; II = sp3; III = sp3. C) I = sp; II = sp2; III = sp3. D) I = sp2; II = sp2; III = sp3. 56) What is the hybridization of the carbon atom in the methyl cation, (CH3+)? A) sp3 B) sp2 C) sp D) p 57) What is the hybridization of the nitrogen atom in the ammonium cation, NH4+? A) sp3 B) sp2 C) sp D) p 58) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethane, CH3CH3? A) Csp2 + H1s B) Csp3 + H1s C) C2p + H1s D) Csp + H1s 59) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethylene, H2C=CH2? A) C2p + H1s B) Csp + H1s C) Csp3 + H1s D) Csp2 + H1s 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

60) Which atomic orbitals overlap to form the carbon-carbon s and p bonding molecular orbitals of ethylene, H2C=CH2? A) Csp3 + Csp3, and C2p + C2p B) Csp3 + Csp3, and Csp2 + Csp2 C) Csp2 + Csp2, and C2p + C2p D) Csp2 + Csp2, and Csp2 + Csp2 61) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of acetylene, C2H2? A) Csp + H1s B) C2p +H1s C) Csp3 + H1s D) Csp2 + H1s 62) Which atomic orbitals overlap to form the carbon-carbon s bonding molecular orbital of acetylene, C2H2? A) Csp2 + Csp2 B) Csp + Csp C) Csp3 + Csp3 D) C2p + C2p 63) When forming molecular orbitals from atomic orbitals, what is the order of increasing C-H bond strength for the following set?

A) II < I < III B) III < I < II C) III < II < I D) I < II < III 64) What is the order of decreasing bond length for a C-C bond composed of the following molecular orbitals?

A) I > III > II B) I > II > III C) III > II > I D) II > III > I

65) Which of the following statements about electronegativity and the periodic table is true? A) Electronegativity decreases across a row of the periodic table. B) Electronegativity increases down a column of the periodic table. C) Electronegativity increases across a row of the periodic table. D) Electronegativity does not change down a column of the periodic table. 66) Rank the following atoms in order of increasing electronegativity, putting the least electronegative first.

A) I < II < III < IV B) I < IV < II < III C) III < II < IV < I D) I < II < IV < III 67) Rank the following atoms in order of decreasing electronegativity, putting the most electronegative first.

A) I > IV > II > III B) II > III > IV > I C) III > IV > II > I D) III > II > IV > I 68) Which molecule has the greatest difference in electronegativity (DE) between the two different elements? A) CO2 B) H2S C) NH3 D) H2O 69) Which compound contains the most polar bond?

70) Which of the following compounds are non-polar?

A) I, IV B) I, II C) II, III D) II, IV 71) Which of the following molecules has non-polar covalent bonds? A) CO2 B) N2 C) CCl4 D) HF 72) Which of the following molecules has polar covalent bonds? A) MgO B) NH3 C) Cl2 D) NaBr 73) Which of the following covalent bonds has the largest dipole moment? A) C-H B) C-C C) C-O D) H-F 74) Which of the following molecules has the smallest dipole moment? A) CO2 B) HCl C) H2O D) NH3 75) Which of the following molecules does not have a net dipole moment of zero? A) CCl4 B) BF3 C) CO2 D) NH3

76) Which of the following molecules has a net dipole moment of zero?

A) I B) II C) III D) IV 77) Consider compounds which contain both a heteroatom and a double bond. For which compound is no additional Lewis structure possible?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 1 Structure and Bonding 1) What is the ground-state electronic configuration of a carbon atom? A) 1s2, 2s2, 2p5 B) 1s2, 2s2, 2p2 C) 1s2, 2s2, 2p6 D) 1s2, 2s2, 2p4 Answer: B Difficulty: 1 Easy Section: 01.01 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 2) What is the ground-state electronic configuration of a fluorine atom? A) 1s2, 2s2, 2p2 B) 1s2, 2s2, 2p3 C) 1s2, 2s2, 2p4 D) 1s2, 2s2, 2p5 Answer: D Difficulty: 1 Easy Section: 01.01 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 3) What is the ground-state electronic configuration of a magnesium cation (Mg2+)? A) 1s2, 2s2, 2p6 B) 1s2, 2s2, 2p6, 3s1 C) 1s2, 2s2, 2p6, 3s2 D) 1s2, 2s2, 2p6, 3s2, 3p2 Answer: A Difficulty: 1 Easy Section: 01.01 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

4) What is the ground-state electronic configuration of a chlorine anion (Cl—)? A) 1s2, 2s2, 2p6 B) 1s2, 2s2, 2p6, 3s2, 3p6 C) 1s2, 2s2, 2p6, 3s2, 3p5 D) 1s2, 2s2, 2p6, 3s2, 3p4 Answer: B Difficulty: 1 Easy Section: 01.01 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 5) Which of the following statements about valence electrons is true? A) They are the most tightly held electrons. B) They do not participate in chemical reactions. C) They are the outermost electrons. D) They reveal the period number of a second-row element. Answer: C Difficulty: 1 Easy Section: 01.01 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 6) Which of the following atoms will have a full 3s orbital in the ground state? A) Hydrogen B) Lithium C) Potassium D) Rubidium Answer: D Difficulty: 2 Medium Section: 01.01 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

7) Which of the following statements about bonding is true? A) Covalent bonds result from the transfer of electrons from one element to another. B) Ionic bonds result from the transfer of electrons from a metal to a non-metal. C) Ionic bonds result from the sharing of electrons between two non-metals. D) Covalent bonds result from the sharing of electrons between two metals. Answer: B Difficulty: 1 Easy Section: 01.02 Topic: Structure and Bonding Bloom's: 1. Remember Chapter: 01 Accessibility: Keyboard Navigation 8) Which of the following would you expect to have ionic bonds? A) CO B) FBr C) NF3 D) NaCl Answer: D Difficulty: 1 Easy Section: 01.02 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation 9) Which of the following molecules has nonpolar covalent bonds? A) HCl B) N2 C) CHCl3 D) NO Answer: B Difficulty: 1 Easy Section: 01.02 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

10) Which of the following molecules contain both covalent and ionic bonds?

A) I, II B) I, IV C) II, III D) II, IV Answer: D Difficulty: 1 Easy Section: 01.02 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 11) Which of the following would most likely form an ionic bond?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 01.02 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01

12) Which of the following statements correctly describes the typical number of bonds for carbon, nitrogen, and oxygen in most neutral organic molecules? A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds, and oxygen forms 3 covalent bonds. B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds, and oxygen forms 2 covalent bonds. C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds, and oxygen forms 2 covalent bonds. D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds, and oxygen forms 4 covalent bonds. Answer: B Difficulty: 1 Easy Section: 01.02 Topic: Structure and Bonding Bloom's: 1. Remember Chapter: 01 Accessibility: Keyboard Navigation 13) Which is not an acceptable Lewis structure for the anion CH2NCO—?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 01.03 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01

14) Which of the following Lewis structures is correct?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 01.03 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 15) Which of the following Lewis structures is correct?

A) I, II B) I, III C) II, III D) III, IV Answer: C Difficulty: 2 Medium Section: 01.03 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01

16) Which is the correct Lewis structure for acetic acid (CH3CO2H)?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 01.03 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 17) In which of the following ions does carbon have a formal charge?

A) I B) II C) III D) None of these Answer: D Difficulty: 1 Easy Section: 01.03 Topic: Structure and Bonding Bloom's: 1. Remember Chapter: 01

18) In which of the following ions does carbon have a formal charge?

A) I B) II C) III D) None of these Answer: B Difficulty: 1 Easy Section: 01.03 Topic: Structure and Bonding Bloom's: 1. Remember Chapter: 01 19) What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple bond? A) 0 B) -2 C) -1 D) +1 Answer: C Difficulty: 2 Medium Section: 01.03 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation

20) What is the formal charge of the carbon in carbon dioxide (CO2) when drawn with two double bonds? A) +1 B) 0 C) -1 D) -2 Answer: B Difficulty: 2 Medium Section: 01.03 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 21) Which of the following statements about constitutional isomers is true? A) Constitutional isomers are different molecules having the different molecular formula. B) Constitutional isomers are different molecules having the same molecular formula. C) Constitutional isomers are same molecules having the different molecular formula. D) Constitutional isomers are same molecules having the same molecular formula. Answer: B Difficulty: 1 Easy Section: 01.04 Topic: Structure and Bonding Bloom's: 1. Remember Chapter: 01 Accessibility: Keyboard Navigation 22) How many constitutional isomers are there for a molecule having the molecular formula C2H6O? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation

23) How many constitutional isomers are there for a molecule having the molecular formula C3H8O? A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 1 Easy Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 24) How many constitutional isomers are there for a molecule having the molecular formula C3H6? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 25) How many constitutional isomers are there for a molecule having the molecular formula C2H4Cl2? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 2 Medium Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation

26) How many different isomers are there for a compound having the molecular formula C3H6O? A) 4 B) 5 C) 6 D) 7 Answer: D Difficulty: 2 Medium Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 27) Which of the following molecules are constitutional isomers?

A) I, II, IV B) II, III, IV C) I, III, IV D) I, II, III Answer: D Difficulty: 1 Easy Section: 01.04 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01

28) Which of the following compounds has an atom with an unfilled valence shell of electrons? A) H2O B) BCl3 C) CH4 D) CO2 Answer: B Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 29) Which of the following compounds has an atom with more than eight valence electrons? A) H2CO3 B) H2SO4 C) H2O D) HBr Answer: B Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 30) How many electrons are around phosphorus in phosphoric acid (H3PO4)? A) 6 B) 8 C) 10 D) 12 Answer: C Difficulty: 2 Medium Section: 01.05 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation

31) Which of the following statements about resonance structures is true? A) Resonance structures have the same placement of electrons but different arrangement of atoms. B) Resonance structures have the same placement of atoms but different arrangement of electrons. C) Resonance structures have the same placement of atoms and the same arrangement of electrons. D) Resonance structures have different placement of atoms and different arrangement of electrons. Answer: B Difficulty: 1 Easy Section: 01.06 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 32) Which of the following statements about resonance structures is not true? A) There is no movement of electrons from one form to another. B) Resonance structures are not isomers. C) Resonance structures differ only in the arrangement of electrons. D) Resonance structures are in equilibrium with each other. Answer: D Difficulty: 1 Easy Section: 01.06 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

33) Which of the following pair does not represent resonance structures?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 01.06 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 34) What 2 things will change between two resonance structures? A) The position of multiple bonds and non-bonded electrons. B) The position of multiple bonds and single bonds. C) The placement of atoms and single bonds. D) The placement of atoms and non-bonded electrons. Answer: A Difficulty: 1 Easy Section: 01.06 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

35) Which of the following is a resonance structure of the compound below?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 01.06 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 36) Which of the following resonance structures is the least important contributor to the resonance hybrid of the formate anion, HCOO—?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 01.06 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01

37) Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H2CO.

A) I > II > III B) I > III > II C) II > I > III D) III > II > I Answer: A Difficulty: 3 Hard Section: 01.06 Topic: Structure and Bonding Bloom's: 3. Apply Chapter: 01 38) Follow the curved arrows to draw the second resonance structure for the ion below.

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 01.06 Topic: Structure and Bonding Bloom's: 2. Understand Chapter: 01 16 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

39) Which is more important in each pair of contributing resonance structures?

A) II, IV, V B) II, III, V C) II, III, VI D) I, IV, V Answer: B Difficulty: 2 Medium Section: 01.06 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01 40) What is the approximate value of the H-C-H bond angle in methane, CH4? A) 90° B) 109.5° C) 120° D) 180° Answer: B Difficulty: 1 Easy Section: 01.07 Topic: Molecular Shape Bloom's: 1. Remember Chapter: 01 Accessibility: Keyboard Navigation

41) What is the approximate C-C-C bond angle in propene, CH3CH = CH2? A) 90° B) 109.5° C) 120° D) 180° Answer: C Difficulty: 1 Easy Section: 01.07 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 42) What is the approximate H-C-O bond angle in formaldehyde, H2CO? A) 90° B) 109.5° C) 120° D) 180° Answer: C Difficulty: 2 Medium Section: 01.07 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

43) Determine the geometry around the indicated atom in each species.

A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral Answer: A Difficulty: 1 Easy Section: 01.07 Topic: Molecular Shape Bloom's: 1. Remember Chapter: 01 44) What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN? A) 90° B) 109.5° C) 120° D) 180° Answer: D Difficulty: 2 Medium Section: 01.07 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation

45) What is the molecular geometry around the boron atom in BH3? A) Tetrahedral B) Trigonal Planar C) Trigonal Pyramidal D) Linear Answer: B Difficulty: 2 Medium Section: 01.07 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation 46) What is the molecular geometry around the carbon atom in CH4? A) Tetrahedral B) Trigonal Planar C) Trigonal Pyramidal D) Linear Answer: A Difficulty: 2 Medium Section: 01.07 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 Accessibility: Keyboard Navigation

47) Which of the following is the appropriate conversion of the condensed structure, CH3COCH3, to a Lewis structure?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 48) Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a skeletal structure?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01

49) Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 50) What is the condensed formula of the compound below?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01

51) Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a skeletal structure?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01 52) Convert the following skeletal structure to a condensed structure.

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 2. Understand Chapter: 01

53) Avobenzone is an active ingredient in some common sunscreens. Which of the following is the correct molecular formula for avobenzone?

A) C22O22O3 B) C20H22O3 C) C21H23O3 D) C20H24O3 Answer: B Difficulty: 2 Medium Section: 01.08 Topic: Drawing Organic Molecules Bloom's: 3. Apply Chapter: 01 54) In which structure is the hybridization incorrect?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 01.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01

55) What is the hybridization for each of the indicated atoms in the following compound?

A) I = sp2; II = sp2; III = sp2. B) I = sp2; II = sp3; III = sp3. C) I = sp; II = sp2; III = sp3. D) I = sp2; II = sp2; III = sp3. Answer: D Difficulty: 2 Medium Section: 01.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 56) What is the hybridization of the carbon atom in the methyl cation, (CH3+)? A) sp3 B) sp2 C) sp D) p Answer: B Difficulty: 2 Medium Section: 01.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

57) What is the hybridization of the nitrogen atom in the ammonium cation, NH4+? A) sp3 B) sp2 C) sp D) p Answer: A Difficulty: 2 Medium Section: 01.09 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 58) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethane, CH3CH3? A) Csp2 + H1s B) Csp3 + H1s C) C2p + H1s D) Csp + H1s Answer: B Difficulty: 2 Medium Section: 01.10 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation 59) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethylene, H2C=CH2? A) C2p + H1s B) Csp + H1s C) Csp3 + H1s D) Csp2 + H1s Answer: D Difficulty: 2 Medium Section: 01.10 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation

60) Which atomic orbitals overlap to form the carbon-carbon s and p bonding molecular orbitals of ethylene, H2C=CH2? A) Csp3 + Csp3, and C2p + C2p B) Csp3 + Csp3, and Csp2 + Csp2 C) Csp2 + Csp2, and C2p + C2p D) Csp2 + Csp2, and Csp2 + Csp2 Answer: C Difficulty: 2 Medium Section: 01.10 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation 61) Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of acetylene, C2H2? A) Csp + H1s B) C2p +H1s C) Csp3 + H1s D) Csp2 + H1s Answer: A Difficulty: 2 Medium Section: 01.10 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation 62) Which atomic orbitals overlap to form the carbon-carbon s bonding molecular orbital of acetylene, C2H2? A) Csp2 + Csp2 B) Csp + Csp C) Csp3 + Csp3 D) C2p + C2p Answer: B Difficulty: 2 Medium Section: 01.10 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation 27 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

63) When forming molecular orbitals from atomic orbitals, what is the order of increasing C-H bond strength for the following set?

A) II < I < III B) III < I < II C) III < II < I D) I < II < III Answer: D Difficulty: 2 Medium Section: 01.11 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 64) What is the order of decreasing bond length for a C-C bond composed of the following molecular orbitals?

A) I > III > II B) I > II > III C) III > II > I D) II > III > I Answer: B Difficulty: 2 Medium Section: 01.11 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01

65) Which of the following statements about electronegativity and the periodic table is true? A) Electronegativity decreases across a row of the periodic table. B) Electronegativity increases down a column of the periodic table. C) Electronegativity increases across a row of the periodic table. D) Electronegativity does not change down a column of the periodic table. Answer: C Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 66) Rank the following atoms in order of increasing electronegativity, putting the least electronegative first.

A) I < II < III < IV B) I < IV < II < III C) III < II < IV < I D) I < II < IV < III Answer: B Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01

67) Rank the following atoms in order of decreasing electronegativity, putting the most electronegative first.

A) I > IV > II > III B) II > III > IV > I C) III > IV > II > I D) III > II > IV > I Answer: D Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 68) Which molecule has the greatest difference in electronegativity (DE) between the two different elements? A) CO2 B) H2S C) NH3 D) H2O Answer: D Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation

69) Which compound contains the most polar bond?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 70) Which of the following compounds are non-polar?

A) I, IV B) I, II C) II, III D) II, IV Answer: A Difficulty: 2 Medium Section: 01.13 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01

71) Which of the following molecules has non-polar covalent bonds? A) CO2 B) N2 C) CCl4 D) HF Answer: B Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 72) Which of the following molecules has polar covalent bonds? A) MgO B) NH3 C) Cl2 D) NaBr Answer: B Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 73) Which of the following covalent bonds has the largest dipole moment? A) C-H B) C-C C) C-O D) H-F Answer: D Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 3. Apply Chapter: 01 Accessibility: Keyboard Navigation

74) Which of the following molecules has the smallest dipole moment? A) CO2 B) HCl C) H2O D) NH3 Answer: A Difficulty: 2 Medium Section: 01.12 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation 75) Which of the following molecules does not have a net dipole moment of zero? A) CCl4 B) BF3 C) CO2 D) NH3 Answer: D Difficulty: 2 Medium Section: 01.13 Topic: Molecular Shape Bloom's: 2. Understand Chapter: 01 Accessibility: Keyboard Navigation

76) Which of the following molecules has a net dipole moment of zero?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 01.13 Topic: Molecular Shape Bloom's: 4. Analyze Chapter: 01 77) Consider compounds which contain both a heteroatom and a double bond. For which compound is no additional Lewis structure possible?

A) I B) II C) III D) IV Answer: C Difficulty: 3 Hard Section: 01.06 Topic: Structure and Bonding Bloom's: 4. Analyze Chapter: 01

Organic Chemistry, 6e (Smith) Chapter 2 Acids and Bases 1) Which of the following statements is a correct definition for a Brønsted-Lowry acid? A) Proton acceptor B) Electron pair donor C) Electron pair acceptor D) Proton donor 2) Which of the following statements about a Brønsted-Lowry base is true? A) The net charge may be zero, positive, or negative. B) All Brønsted-Lowry bases contain a lone pair of electrons or a π bond. C) All Brønsted-Lowry bases contain a proton. D) The net charge may be zero or positive. 3) Which of the following compounds is both a Brønsted-Lowry acid and base?

A) I, II B) I, III C) II, IV D) I, IV 4) Which of the following species cannot act as both a Brønsted-Lowry acid and base? A) HCO3B) HSO4C) HOD) H2PO45) Which of the following species is not a Brønsted-Lowry base? A) BF3 B) NH3 C) H2O D) PO436) Which of the following statements about Brønsted-Lowry acids and bases is true? A) Loss of a proton from a base forms its conjugate acid. B) Loss of a proton from an acid forms its conjugate base. C) Gain of a proton by an acid forms its conjugate base. D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a base to an acid. 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

7) Which of the following species is the conjugate base of methanol, CH3OH? A) CH3OH2+ B) CH3OC) CH3D) CH4 8) Which of the following species is the conjugate base of the hydronium ion, H3O+? A) H3O B) H2OC) H2O D) HO9) Which of the following species is the conjugate acid of ammonia, NH3? A) H4N B) H3N+ C) H2ND) H4N+ 10) Which is the conjugate acid in the following reaction?

A) I B) II C) III D) IV 11) Which is the conjugate base in the following reaction?

A) I B) II C) III D) IV

12) Which is the conjugate acid in the following reaction?

A) I B) II C) III D) IV 13) Which is the conjugate base in the following reaction?

A) I B) II C) III D) IV 14) Which of the following statements about acid strength is true? A) The stronger the acid, the further the equilibrium lies to the left. B) The stronger the acid, the smaller the Ka. C) The stronger the acid, the larger the pKa. D) The stronger the acid, the smaller the pKa. 15) Which of the following compounds is the strongest acid?

A) I B) II C) III D) IV 16) Which of the following compounds is the strongest acid? A) CH3OH B) BrCH2OH C) CH3NH2 D) CH3Cl 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

17) Which of the following compounds is the weakest acid? A) HF B) HCl C) HBr D) HI 18) Which of the following compounds is the weakest acid? A) H2S B) PH3 C) HCl D) SiH4 19) Which of the following species is the strongest base? A) HOB) H2NC) CH3COOD) Cl20) Which of the following ranks the compounds in order of increasing basicity, putting the least basic first? A) CH3NH2 < CH3OH < CH4 B) CH3OH < CH3NH2 < CH4 C) CH4 < CH3NH2 < CH3OH D) CH4 < CH3OH < CH3NH2 21) Consider the following molecule with protons labeled, I-III. Rank these protons in order of decreasing acidity, putting the most acidic first.

A) I > II > III B) I > III > II C) III > II > I D) III > I > II

22) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) III < I < IV < II B) III < IV < I < II C) II < I < IV < III D) III < I < II < IV 23) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) I < IV < III < II B) I < III < IV < II C) II < III < IV < I D) II < IV < III < I 24) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > II > III > I B) III > II > IV > I C) I > II > IV > III D) III > IV > II > I 25) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > II > III > I B) IV > III > II > I C) III > IV > II > I D) III > IV > I > II

26) Rank the following conjugate bases in order of increasing basicity, putting the least basic first.

A) II < I < III B) II < III < I C) I < II < III D) I < III < II 27) Rank the following conjugate bases in order of decreasing basicity, putting the most basic first.

A) II > I > III B) I > II > III C) III > I > II D) III > II > I 28) Which of the following is the strongest base? A) CH3COCH3 B) CH3COOH C) NH3 D) H2O 29) What is the direction of equilibrium when acetylene (C2H2) reacts with H2N- in an acid-base reaction?

A) Left B) Right C) Neither D) Cannot be determined

30) What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide (CH3CH2O-) in an acid-base reaction?

A) Left B) Right C) Neither D) Cannot be determined 31) Which of the following statements explains why H2O is a stronger acid than CH4? A) H2O can form hydrogen bonds while CH4 cannot. B) H2O forms a less stable conjugate base, HO-. C) CH4 forms a more stable conjugate base, CH3-. D) H2O forms a more stable conjugate base, HO-. 32) Which of the following statements explain why HBr is a stronger acid than HF? A) Br- is more stable than F- because Br- is larger than F-. B) Br- is less stable than F- because Br- is larger than F-. C) Br- is more stable than F- because Br- is less electronegative than F-. D) Br- is less stable than F- because Br- is less electronegative than F-. 33) Which of the following compounds has the lowest pKa? A) H2O B) H2S C) NH3 D) CH4 34) Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH) and ethanol (CH3CH2OH)? A) Hybridization B) Electronegativity C) Resonance D) Size 35) Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2) and ethylene (C2H4)? A) Size B) Resonance C) Inductive effect D) Hybridization 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

36) Which of the following concepts can be used to explain the difference in acidity between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)? A) Size B) Inductive effect C) Resonance D) Hybridization 37) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) I > II > III B) III > II > I C) II > III > I D) III > I > II 38) Which of the following statements about Lewis acids is true? A) Lewis acids are proton donors. B) Lewis acids are proton acceptors. C) Lewis acids are electron pair donors. D) Lewis acids are electron pair acceptors. 39) Which of the following statements about Lewis bases is true? A) Lewis bases are electron pair acceptors. B) Lewis bases are electron pair donors. C) Lewis bases are proton donors. D) Lewis bases are proton acceptors. 40) Which of the following is a Lewis acid but not a Brønsted-Lowry acid? A) CH3OH B) H2O C) CH3COOH D) BF3

41) Which of the following species can be both Lewis acid and Lewis base?

A) I, III, IV B) I, II, IV C) II, III, IV D) I, II, III 42) What is the correct classification of the following compound? CH3-O-CH3 A) Brønsted-Lowry acid and Lewis acid B) Brønsted-Lowry base and Lewis base C) Brønsted-Lowry base D) Lewis base 43) Identify the Lewis acid in the following reaction.

A) I B) II C) III D) IV 44) Identify the Lewis base in the following reaction.

A) I B) II C) III D) IV 45) Which of the following compounds is not a Lewis acid? A) AlCl3 B) HCl C) H2O D) CBr4 9 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

46) What is the role of methylchloride (CH3Cl) in the following reaction?

A) Lewis acid B) Lewis base C) Brønsted-Lowry acid D) Brønsted-Lowry base 47) What is the electrophilic site in the following compounds?

A) I = Carbon; II = carbon; III = boron. B) I = Chlorine; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron. D) I = Carbon; II = carbon; III = fluorine. 48) What is the nucleophilic site in the following compounds?

50) What are the products of the following proton transfer reaction?

A) I B) II C) III D) IV 51) What is the correct rank of the following compounds in order of increasing acidity?

A) I > II > III > IV B) IV > III > II > I C) IV > I > II > III D) III > I > IV > II 52) Consider the following structures I-IV. Which two species represent a conjugate acid-base pair?

A) I and II B) I and III C) I and IV D) II and III

53) Consider the following structures I-IV. Which two species represent resonance structures?

A) I and II B) I and III C) I and IV D) II and IV 54) Consider the following structures I-IV. Which two species represent constitutional isomers?

A) I and II B) I and III C) I and IV D) II and IV 55) Identify the acid/conjugate acid (in that order) in the following reaction:

A) I, III B) I, IV C) II, III D) II, IV

56) Identify the base/conjugate base (in that order) in the following reaction:

A) I, III B) I, IV C) II, III D) II, IV 57) Which of the following ranks the compounds in order of increasing acidity, putting the least acidic first? A) CH4 < H2O < NH3 B) H2O < NH3 < CH4 C) NH3 < CH4 < H2O D) CH4 < NH3 < H2O 58) Which of the following will proceed as written? A) CH3ONa + HCl → CH3OH + NaCl B) CH3OH + NaCl → NaOEt + HCl C) CH3OH + H2O → CH3O- + H3O+ D) CH3OH + NH3 → CH3O- + NH4± 59) Which of the following would have the lowest pKa? A) ClCH2CH2CH2CH2COOH B) CH3CHClCH2CH2COOH C) CH3CH2CHClCH2COOH D) CH3CH2CH2CHClCOOH

Organic Chemistry, 6e (Smith) Chapter 2 Acids and Bases 1) Which of the following statements is a correct definition for a Brønsted-Lowry acid? A) Proton acceptor B) Electron pair donor C) Electron pair acceptor D) Proton donor Answer: D Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 1. Remember Chapter: 02 Accessibility: Keyboard Navigation 2) Which of the following statements about a Brønsted-Lowry base is true? A) The net charge may be zero, positive, or negative. B) All Brønsted-Lowry bases contain a lone pair of electrons or a π bond. C) All Brønsted-Lowry bases contain a proton. D) The net charge may be zero or positive. Answer: B Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 1. Remember Chapter: 02 Accessibility: Keyboard Navigation

3) Which of the following compounds is both a Brønsted-Lowry acid and base?

A) I, II B) I, III C) II, IV D) I, IV Answer: B Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 4) Which of the following species cannot act as both a Brønsted-Lowry acid and base? A) HCO3B) HSO4C) HOD) H2PO4Answer: C Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

5) Which of the following species is not a Brønsted-Lowry base? A) BF3 B) NH3 C) H2O D) PO43Answer: A Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 6) Which of the following statements about Brønsted-Lowry acids and bases is true? A) Loss of a proton from a base forms its conjugate acid. B) Loss of a proton from an acid forms its conjugate base. C) Gain of a proton by an acid forms its conjugate base. D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a base to an acid. Answer: B Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 7) Which of the following species is the conjugate base of methanol, CH3OH? A) CH3OH2+ B) CH3OC) CH3D) CH4 Answer: B Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

8) Which of the following species is the conjugate base of the hydronium ion, H3O+? A) H3O B) H2OC) H2O D) HOAnswer: C Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 9) Which of the following species is the conjugate acid of ammonia, NH3? A) H4N B) H3N+ C) H2ND) H4N+ Answer: D Difficulty: 1 Easy Section: 02.01 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

10) Which is the conjugate acid in the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 02.02 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 11) Which is the conjugate base in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 02.02 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

12) Which is the conjugate acid in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 02.02 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 13) Which is the conjugate base in the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 02.02 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

14) Which of the following statements about acid strength is true? A) The stronger the acid, the further the equilibrium lies to the left. B) The stronger the acid, the smaller the Ka. C) The stronger the acid, the larger the pKa. D) The stronger the acid, the smaller the pKa. Answer: D Difficulty: 1 Easy Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 15) Which of the following compounds is the strongest acid?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 16) Which of the following compounds is the strongest acid? A) CH3OH B) BrCH2OH C) CH3NH2 D) CH3Cl Answer: B Difficulty: 1 Easy Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

17) Which of the following compounds is the weakest acid? A) HF B) HCl C) HBr D) HI Answer: A Difficulty: 1 Easy Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 18) Which of the following compounds is the weakest acid? A) H2S B) PH3 C) HCl D) SiH4 Answer: D Difficulty: 1 Easy Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 19) Which of the following species is the strongest base? A) HOB) H2NC) CH3COOD) ClAnswer: B Difficulty: 1 Easy Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

20) Which of the following ranks the compounds in order of increasing basicity, putting the least basic first? A) CH3NH2 < CH3OH < CH4 B) CH3OH < CH3NH2 < CH4 C) CH4 < CH3NH2 < CH3OH D) CH4 < CH3OH < CH3NH2 Answer: D Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 21) Consider the following molecule with protons labeled, I-III. Rank these protons in order of decreasing acidity, putting the most acidic first.

A) I > II > III B) I > III > II C) III > II > I D) III > I > II Answer: C Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

22) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) III < I < IV < II B) III < IV < I < II C) II < I < IV < III D) III < I < II < IV Answer: B Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 23) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) I < IV < III < II B) I < III < IV < II C) II < III < IV < I D) II < IV < III < I Answer: A Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

24) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > II > III > I B) III > II > IV > I C) I > II > IV > III D) III > IV > II > I Answer: D Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 25) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > II > III > I B) IV > III > II > I C) III > IV > II > I D) III > IV > I > II Answer: B Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

26) Rank the following conjugate bases in order of increasing basicity, putting the least basic first.

A) II < I < III B) II < III < I C) I < II < III D) I < III < II Answer: A Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 27) Rank the following conjugate bases in order of decreasing basicity, putting the most basic first.

A) II > I > III B) I > II > III C) III > I > II D) III > II > I Answer: C Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

28) Which of the following is the strongest base? A) CH3COCH3 B) CH3COOH C) NH3 D) H2O Answer: C Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 29) What is the direction of equilibrium when acetylene (C2H2) reacts with H2N- in an acid-base reaction?

A) Left B) Right C) Neither D) Cannot be determined Answer: B Difficulty: 1 Easy Section: 02.04 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

30) What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide (CH3CH2O-) in an acid-base reaction?

A) Left B) Right C) Neither D) Cannot be determined Answer: A Difficulty: 1 Easy Section: 02.04 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 31) Which of the following statements explains why H2O is a stronger acid than CH4? A) H2O can form hydrogen bonds while CH4 cannot. B) H2O forms a less stable conjugate base, HO-. C) CH4 forms a more stable conjugate base, CH3-. D) H2O forms a more stable conjugate base, HO-. Answer: D Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

32) Which of the following statements explain why HBr is a stronger acid than HF? A) Br- is more stable than F- because Br- is larger than F-. B) Br- is less stable than F- because Br- is larger than F-. C) Br- is more stable than F- because Br- is less electronegative than F-. D) Br- is less stable than F- because Br- is less electronegative than F-. Answer: A Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 33) Which of the following compounds has the lowest pKa? A) H2O B) H2S C) NH3 D) CH4 Answer: B Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 34) Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH) and ethanol (CH3CH2OH)? A) Hybridization B) Electronegativity C) Resonance D) Size Answer: C Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

35) Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2) and ethylene (C2H4)? A) Size B) Resonance C) Inductive effect D) Hybridization Answer: D Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 36) Which of the following concepts can be used to explain the difference in acidity between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)? A) Size B) Inductive effect C) Resonance D) Hybridization Answer: B Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

37) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) I > II > III B) III > II > I C) II > III > I D) III > I > II Answer: D Difficulty: 2 Medium Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 38) Which of the following statements about Lewis acids is true? A) Lewis acids are proton donors. B) Lewis acids are proton acceptors. C) Lewis acids are electron pair donors. D) Lewis acids are electron pair acceptors. Answer: D Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 02 Accessibility: Keyboard Navigation 39) Which of the following statements about Lewis bases is true? A) Lewis bases are electron pair acceptors. B) Lewis bases are electron pair donors. C) Lewis bases are proton donors. D) Lewis bases are proton acceptors. Answer: B Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 2. Understand Chapter: 02 Accessibility: Keyboard Navigation 17 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

40) Which of the following is a Lewis acid but not a Brønsted-Lowry acid? A) CH3OH B) H2O C) CH3COOH D) BF3 Answer: D Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 41) Which of the following species can be both Lewis acid and Lewis base?

A) I, III, IV B) I, II, IV C) II, III, IV D) I, II, III Answer: A Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

42) What is the correct classification of the following compound? CH3-O-CH3 A) Brønsted-Lowry acid and Lewis acid B) Brønsted-Lowry base and Lewis base C) Brønsted-Lowry base D) Lewis base Answer: B Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 43) Identify the Lewis acid in the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

44) Identify the Lewis base in the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 45) Which of the following compounds is not a Lewis acid? A) AlCl3 B) HCl C) H2O D) CBr4 Answer: D Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

46) What is the role of methylchloride (CH3Cl) in the following reaction?

A) Lewis acid B) Lewis base C) Brønsted-Lowry acid D) Brønsted-Lowry base Answer: B Difficulty: 1 Easy Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 47) What is the electrophilic site in the following compounds?

A) I = Carbon; II = carbon; III = boron. B) I = Chlorine; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron. D) I = Carbon; II = carbon; III = fluorine. Answer: A Difficulty: 2 Medium Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

48) What is the nucleophilic site in the following compounds?

A) I = Hydrogen; II = π electrons in bond; III = nitrogen. B) I = Oxygen; II = carbon; III = nitrogen. C) I = Hydrogen; II = carbon; III = carbon. D) I = Oxygen; II = π electrons in bond; III = nitrogen. Answer: D Difficulty: 2 Medium Section: 02.08 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 49) What is the conjugate base of HSO4-? SO42- H2SO4 SO3 H2O I II III IV A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 02.08 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 02 Accessibility: Keyboard Navigation

50) What are the products of the following proton transfer reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 02.04 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 02 51) What is the correct rank of the following compounds in order of increasing acidity?

A) I > II > III > IV B) IV > III > II > I C) IV > I > II > III D) III > I > IV > II Answer: C Difficulty: 3 Hard Section: 02.05 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 02

52) Consider the following structures I-IV. Which two species represent a conjugate acid-base pair?

A) I and II B) I and III C) I and IV D) II and III Answer: A Difficulty: 2 Medium Section: 02.02 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 02 53) Consider the following structures I-IV. Which two species represent resonance structures?

A) I and II B) I and III C) I and IV D) II and IV Answer: C Difficulty: 2 Medium Section: 02.02 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 02

54) Consider the following structures I-IV. Which two species represent constitutional isomers?

A) I and II B) I and III C) I and IV D) II and IV Answer: B Difficulty: 2 Medium Section: 02.02 Topic: Acids and Bases Bloom's: 4. Analyze Chapter: 02 55) Identify the acid/conjugate acid (in that order) in the following reaction:

A) I, III B) I, IV C) II, III D) II, IV Answer: C Difficulty: 1 Easy Section: 02.02 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02

56) Identify the base/conjugate base (in that order) in the following reaction:

A) I, III B) I, IV C) II, III D) II, IV Answer: B Difficulty: 1 Easy Section: 02.02 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 57) Which of the following ranks the compounds in order of increasing acidity, putting the least acidic first? A) CH4 < H2O < NH3 B) H2O < NH3 < CH4 C) NH3 < CH4 < H2O D) CH4 < NH3 < H2O Answer: D Difficulty: 2 Medium Section: 02.03 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

58) Which of the following will proceed as written? A) CH3ONa + HCl → CH3OH + NaCl B) CH3OH + NaCl → NaOEt + HCl C) CH3OH + H2O → CH3O- + H3O+ D) CH3OH + NH3 → CH3O- + NH4± Answer: A Difficulty: 1 Easy Section: 02.04 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation 59) Which of the following would have the lowest pKa? A) ClCH2CH2CH2CH2COOH B) CH3CHClCH2CH2COOH C) CH3CH2CHClCH2COOH D) CH3CH2CH2CHClCOOH Answer: D Difficulty: 1 Easy Section: 02.05 Topic: Acids and Bases Bloom's: 3. Apply Chapter: 02 Accessibility: Keyboard Navigation

Organic Chemistry, 6e (Smith) Chapter 3 Introduction to Organic Molecules and Functional Groups 1) Which of the following lists contains common heteroatoms found in organic molecules? A) N, O, S, P, Cl B) Na, O, S, P, Cl C) Na, Mg, S, N, Cl D) Na, Mg, O, N, Cl 2) Why do heteroatoms confer reactivity on a particular molecule? A) Because they have lone pairs and create electron-rich sites on carbon. B) Because they have lone pairs and create electron-deficient sites on carbon. C) Because they are electronegative and act as electrophiles. D) Because they are electropositive and act as nucleophiles. 3) Why do π bonds confer reactivity on a particular molecule? A) Because π bonds are difficult to break in chemical reactions. B) Because π bonds make a molecule an acid. C) Because π bonds are easily broken in chemical reactions. D) Because π bonds make a molecule an electrophile. 4) Which of the following molecules contain the same functional groups?

A) I, II, III B) I, II, IV C) II, III, IV D) I, III, IV 5) Which of the following molecules contain the same functional groups?

A) I, II, IV B) I, II, III C) II, III, IV D) I, III, IV

6) Which of the following molecules are aliphatic hydrocarbons?

A) I, II, III B) I and III C) II, III, IV D) II and IV 7) Which of the following molecules are aromatic hydrocarbons?

A) I B) II C) III D) I and III 8) Which of the following correctly matches the molecules to the names of the functional group? I. II. III. IV.

CH3OH CH3CO2CH3 CH3COCH3 H2CO

Carboxylic acid Ester Ketone Alcohol

A) I and II B) III and IV C) II and III D) II and IV

9) Which of the following correctly matches the molecules to the names of the functional group? I. CH3OCH3 II. CH3CONH2 III. CH3SH IV. CH3CHO

Ether Amine Thiol Alcohol

A) I and II B) II and III C) III and IV D) I and III 10) Which of the following correctly matches the molecules to the names of the functional group? I. CH3NH2 II. CH3SCH3 III. CH3CONH2 IV. CH3CO2CH3

Amide Sulfide Amine Ester

A) I and II B) II and IV C) III and IV D) II and III 11) Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the following lists the correct functional groups present in donepezil?

A) Amide, aromatic, ether, ketone B) Amide, aromatic, ester, ketone C) Amine, aromatic, ester, ketone D) Amine, aromatic, ether, ketone

12) Consider the molecule atenolol (a β blocker used to treat hypertension). Which of the following lists the correct functional groups present in atenolol?

A) Primary alcohol, amide, primary amine, aromatic, ether B) Secondary alcohol, amide, secondary amine, aromatic, ether C) Secondary alcohol, amide, primary amine, aromatic, ether D) Secondary alcohol, amide, secondary amine, aromatic, ester 13) Which of the following structures contains a secondary amine?

A) I B) II C) III D) IV 14) Which of the following structures contains a primary amine?

A) I B) II C) III D) IV

15) Which of the following structures contains an amide?

A) I B) II C) III D) IV 16) Which of the following structures contains an alkene?

A) I B) II C) III D) IV 17) Which of the following is a tertiary amine?

A) I B) II C) III D) IV

18) Which of the following is a secondary alcohol?

A) I B) II C) III D) IV 19) Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces? A) The larger the surface area, the weaker the intermolecular forces. B) The larger the surface area, the stronger the intermolecular forces. C) The smaller the surface area, the stronger the intermolecular forces. D) There is no relationship between surface area and intermolecular forces. 20) Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first.

A) I < II < III B) II < I < III C) I < III < II D) II < III < I 21) Which of the following compounds has the lowest boiling point?

A) I B) II C) III D) IV

22) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV 23) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV 24) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV 25) Which of the following compounds has the highest boiling point?

26) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > II > III > IV B) III > IV > II > I C) III > II > IV > I D) I > IV > II > III 27) Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself?

A) I B) II C) III D) IV 28) What is the strongest intermolecular force present in 1-propanol?

A) Ion-ion B) Hydrogen bonding C) Dipole-dipole D) Induced dipole-induced dipole 29) What intermolecular force is generally considered the strongest? A) Hydrogen bonding B) London dispersion forces C) Covalent bonds D) Dipole-dipole

30) What intermolecular force is generally considered the weakest? A) Hydrogen bonding B) London dispersion forces C) Dipole-dipole D) Ion-ion 31) Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first.

A) II < I < III B) I < III < II C) I < II < III D) III < II < I 32) Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first.

A) I > II > III B) II > III > I C) III > II > I D) III > I > II 33) Which of the following intermolecular forces would not form between similar molecules of the structure below?

A) London dispersion forces B) Ion-ion C) Hydrogen bonding D) Dipole-dipole

34) Which of the following alkanes is expected to have the highest melting point?

A) I B) II C) III D) IV 35) Which of the following compounds is expected to be the least soluble in H2O?

A) I B) II C) III D) IV 36) Which of the following compounds is expected to be the most soluble in H2O?

A) I B) II C) III D) IV 37) Which of the following compounds would be expected to be more soluble in hexane (C6H14)?

38) Which of the following statements about the solubility of organic compounds in H2O is true? A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic. B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic. C) The polar part of a molecule that can that can bond hydrogen to water is said to be hydrophobic. D) For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has 35 carbons. 39) Which of the following compounds is expected to be H2O soluble?

A) I B) II C) III D) IV 40) What molecular features are required for soap to properly dissolve grease and oil? A) The molecule must be large. B) The molecule must contain a polar head. C) The molecule must contain a non-polar tail. D) The molecule must contain both a polar head and a non-polar tail. 41) Which of the following statements about vitamin A, drawn below, is true?

A) Vitamin A is soluble in H2O. B) Vitamin A is insoluble in organic solvents. C) Vitamin A contains an aromatic ring. D) Vitamin A is insoluble in H2O.

42) Which of the following statements about vitamin C, drawn below, is true?

A) Vitamin C is insoluble in H2O. B) Vitamin C is soluble in H2O. C) Vitamin C is an aliphatic hydrocarbon. D) Vitamin C contains a ketone functional group. 43) Which of the following could most likely serve as an ionophore?

A) I B) II C) III D) IV 44) The indicated carbon atom is:

A) Electrophilic because it is electron-deficient. B) Nucleophilic because it is electron-deficient. C) Electrophilic because it is electron-rich. D) Nucleophilic because it is electron-rich.

45) The indicated bond is:

A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-rich. C) Nucleophilic because it is electron-rich. D) Electrophilic because it is electron-deficient. 47) Which of the following lists the correct functional groups found in aspartame, the artificial sweetener?

A) Amine, aromatic, carboxylic acid, ether, ketone B) Amine, amide, aromatic, carboxylic acid, ester C) Amide, alcohol, aromatic, carboxylic acid, ether D) Amine, aromatic, carboxylic acid, ester, nitrile 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

48) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > III > IV > II B) IV > II > I > III C) IV > I > II > III D) I > IV > II > III 49) Rank the following compounds in order of increasing strength of intermolecular forces.

A) I > III > IV > II B) IV > II > I > III C) IV > I > III > II D) I > IV > II > III 50) Which of the following molecules can bond hydrogen to another molecule of itself?

A) I B) II C) III D) IV

51) Which C=O functional group is present in the following molecule?

A) Carboxylic Acid B) Ester C) Ketone D) Aldehyde 52) Which C=O functional group is present in the following molecule?

A) Carboxylic acid B) Ester C) Ketone D) Aldehyde 53) Which C=O functional group is present in the following molecule?

A) Carboxylic acid B) Ester C) Ketone D) Aldehyde

54) List the intermolecular forces present in the following molecule:

A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct. 55) List the intermolecular forces present in the following molecule:

A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct. 56) List the intermolecular forces present in the following molecule:

A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct.

Organic Chemistry, 6e (Smith) Chapter 3 Introduction to Organic Molecules and Functional Groups 1) Which of the following lists contains common heteroatoms found in organic molecules? A) N, O, S, P, Cl B) Na, O, S, P, Cl C) Na, Mg, S, N, Cl D) Na, Mg, O, N, Cl Answer: A Difficulty: 1 Easy Section: 03.01 Topic: Functional Groups Bloom's: 2. Understand Chapter: 03 Accessibility: Keyboard Navigation 2) Why do heteroatoms confer reactivity on a particular molecule? A) Because they have lone pairs and create electron-rich sites on carbon. B) Because they have lone pairs and create electron-deficient sites on carbon. C) Because they are electronegative and act as electrophiles. D) Because they are electropositive and act as nucleophiles. Answer: B Difficulty: 1 Easy Section: 03.01 Topic: Functional Groups Bloom's: 2. Understand Chapter: 03 Accessibility: Keyboard Navigation 3) Why do π bonds confer reactivity on a particular molecule? A) Because π bonds are difficult to break in chemical reactions. B) Because π bonds make a molecule an acid. C) Because π bonds are easily broken in chemical reactions. D) Because π bonds make a molecule an electrophile. Answer: C Difficulty: 1 Easy Section: 03.01 Topic: Functional Groups Bloom's: 2. Understand Chapter: 03 Accessibility: Keyboard Navigation

4) Which of the following molecules contain the same functional groups?

A) I, II, III B) I, II, IV C) II, III, IV D) I, III, IV Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 5) Which of the following molecules contain the same functional groups?

A) I, II, IV B) I, II, III C) II, III, IV D) I, III, IV Answer: A Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

6) Which of the following molecules are aliphatic hydrocarbons?

A) I, II, III B) I and III C) II, III, IV D) II and IV Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 7) Which of the following molecules are aromatic hydrocarbons?

A) I B) II C) III D) I and III Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

8) Which of the following correctly matches the molecules to the names of the functional group? I. II. III. IV.

CH3OH CH3CO2CH3 CH3COCH3 H2CO

Carboxylic acid Ester Ketone Alcohol

A) I and II B) III and IV C) II and III D) II and IV Answer: C Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation 9) Which of the following correctly matches the molecules to the names of the functional group? I. CH3OCH3 II. CH3CONH2 III. CH3SH IV. CH3CHO

Ether Amine Thiol Alcohol

A) I and II B) II and III C) III and IV D) I and III Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation

10) Which of the following correctly matches the molecules to the names of the functional group? I. CH3NH2 II. CH3SCH3 III. CH3CONH2 IV. CH3CO2CH3

Amide Sulfide Amine Ester

A) I and II B) II and IV C) III and IV D) II and III Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation 11) Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the following lists the correct functional groups present in donepezil?

A) Amide, aromatic, ether, ketone B) Amide, aromatic, ester, ketone C) Amine, aromatic, ester, ketone D) Amine, aromatic, ether, ketone Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

12) Consider the molecule atenolol (a β blocker used to treat hypertension). Which of the following lists the correct functional groups present in atenolol?

A) Primary alcohol, amide, primary amine, aromatic, ether B) Secondary alcohol, amide, secondary amine, aromatic, ether C) Secondary alcohol, amide, primary amine, aromatic, ether D) Secondary alcohol, amide, secondary amine, aromatic, ester Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 13) Which of the following structures contains a secondary amine?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

14) Which of the following structures contains a primary amine?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 15) Which of the following structures contains an amide?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

16) Which of the following structures contains an alkene?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 17) Which of the following is a tertiary amine?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

18) Which of the following is a secondary alcohol?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 19) Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces? A) The larger the surface area, the weaker the intermolecular forces. B) The larger the surface area, the stronger the intermolecular forces. C) The smaller the surface area, the stronger the intermolecular forces. D) There is no relationship between surface area and intermolecular forces. Answer: B Difficulty: 1 Easy Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation

20) Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first.

A) I < II < III B) II < I < III C) I < III < II D) II < III < I Answer: C Difficulty: 2 Medium Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 21) Which of the following compounds has the lowest boiling point?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

22) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 23) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

24) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 25) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

26) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > II > III > IV B) III > IV > II > I C) III > II > IV > I D) I > IV > II > III Answer: C Difficulty: 1 Easy Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 27) Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

28) What is the strongest intermolecular force present in 1-propanol?

A) Ion-ion B) Hydrogen bonding C) Dipole-dipole D) Induced dipole-induced dipole Answer: B Difficulty: 2 Medium Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 29) What intermolecular force is generally considered the strongest? A) Hydrogen bonding B) London dispersion forces C) Covalent bonds D) Dipole-dipole Answer: A Difficulty: 1 Easy Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation 30) What intermolecular force is generally considered the weakest? A) Hydrogen bonding B) London dispersion forces C) Dipole-dipole D) Ion-ion Answer: B Difficulty: 2 Medium Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

31) Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first.

A) II < I < III B) I < III < II C) I < II < III D) III < II < I Answer: C Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 32) Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first.

A) I > II > III B) II > III > I C) III > II > I D) III > I > II Answer: D Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

33) Which of the following intermolecular forces would not form between similar molecules of the structure below?

A) London dispersion forces B) Ion-ion C) Hydrogen bonding D) Dipole-dipole Answer: B Difficulty: 2 Medium Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 34) Which of the following alkanes is expected to have the highest melting point?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

35) Which of the following compounds is expected to be the least soluble in H2O?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 36) Which of the following compounds is expected to be the most soluble in H2O?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

37) Which of the following compounds would be expected to be more soluble in hexane (C6H14)?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 38) Which of the following statements about the solubility of organic compounds in H2O is true? A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic. B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic. C) The polar part of a molecule that can that can bond hydrogen to water is said to be hydrophobic. D) For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has 35 carbons. Answer: B Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 Accessibility: Keyboard Navigation

39) Which of the following compounds is expected to be H2O soluble?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 40) What molecular features are required for soap to properly dissolve grease and oil? A) The molecule must be large. B) The molecule must contain a polar head. C) The molecule must contain a non-polar tail. D) The molecule must contain both a polar head and a non-polar tail. Answer: D Difficulty: 2 Medium Section: 03.06 Topic: Functional Groups Bloom's: 2. Understand Chapter: 03 Accessibility: Keyboard Navigation

41) Which of the following statements about vitamin A, drawn below, is true?

A) Vitamin A is soluble in H2O. B) Vitamin A is insoluble in organic solvents. C) Vitamin A contains an aromatic ring. D) Vitamin A is insoluble in H2O. Answer: D Difficulty: 2 Medium Section: 03.05 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 42) Which of the following statements about vitamin C, drawn below, is true?

A) Vitamin C is insoluble in H2O. B) Vitamin C is soluble in H2O. C) Vitamin C is an aliphatic hydrocarbon. D) Vitamin C contains a ketone functional group. Answer: B Difficulty: 2 Medium Section: 03.05 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

43) Which of the following could most likely serve as an ionophore?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 03.07 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 44) The indicated carbon atom is:

A) Electrophilic because it is electron-deficient. B) Nucleophilic because it is electron-deficient. C) Electrophilic because it is electron-rich. D) Nucleophilic because it is electron-rich. Answer: A Difficulty: 1 Easy Section: 03.08 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

45) The indicated bond is:

A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-deficient. C) Nucleophilic because it electron-rich. D) Electrophilic because it is electron-rich. Answer: C Difficulty: 1 Easy Section: 03.08 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 46) The indicated bond is:

A) Nucleophilic because it is electron-deficient. B) Electrophilic because it is electron-rich. C) Nucleophilic because it is electron-rich. D) Electrophilic because it is electron-deficient. Answer: D Difficulty: 1 Easy Section: 03.08 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

47) Which of the following lists the correct functional groups found in aspartame, the artificial sweetener?

A) Amine, aromatic, carboxylic acid, ether, ketone B) Amine, amide, aromatic, carboxylic acid, ester C) Amide, alcohol, aromatic, carboxylic acid, ether D) Amine, aromatic, carboxylic acid, ester, nitrile Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 48) Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > III > IV > II B) IV > II > I > III C) IV > I > II > III D) I > IV > II > III Answer: D Difficulty: 1 Easy Section: 03.04 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

49) Rank the following compounds in order of increasing strength of intermolecular forces.

A) I > III > IV > II B) IV > II > I > III C) IV > I > III > II D) I > IV > II > III Answer: C Difficulty: 1 Easy Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 50) Which of the following molecules can bond hydrogen to another molecule of itself?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

51) Which C=O functional group is present in the following molecule?

A) Carboxylic Acid B) Ester C) Ketone D) Aldehyde Answer: A Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 52) Which C=O functional group is present in the following molecule?

A) Carboxylic acid B) Ester C) Ketone D) Aldehyde Answer: C Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

53) Which C=O functional group is present in the following molecule?

A) Carboxylic acid B) Ester C) Ketone D) Aldehyde Answer: B Difficulty: 1 Easy Section: 03.02 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03 54) List the intermolecular forces present in the following molecule:

A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct. Answer: D Difficulty: 1 Easy Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

55) List the intermolecular forces present in the following molecule:

A) Van der Waals B) Dipole-dipole interactions C) Hydrogen bonding D) More than one of these answer choices is correct. Answer: A Difficulty: 1 Easy Section: 03.03 Topic: Functional Groups Bloom's: 3. Apply Chapter: 03

Organic Chemistry, 6e (Smith) Chapter 4 Alkanes 1) Which of the following statements about alkanes is not true? A) Alkanes are aliphatic hydrocarbons. B) Alkanes contain only C-C and C-H s bonds. C) Alkanes are acyclic or cyclic. D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons. 2) Which of the following statements about alkanes is true? A) Alkanes are aliphatic hydrocarbons having only C-C and C-H p bonds. B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of carbons. C) Acyclic alkanes contain carbons joined in one or more rings. D) Acyclic alkanes have the general molecular formula CnH2n. 3) What is the molecular formula of an alkane that has twenty-three carbon atoms? A) C23H46 B) C23H48 C) C23H50 D) C23H44 4) What is the molecular formula of a cycloalkane that has six carbon atoms? A) C6H14 B) C6H10 C) C6H12 D) C6H16 5) What is the approximate C-C-C bond angle in propane? A) 90° B) 109.5° C) 120° D) 180° 6) What is the hybridization of a carbon atom in an alkane? A) sp3 B) sp2 C) sp D) p

7) How many constitutional isomers are there with the molecular formula C5H12? A) 2 B) 3 C) 4 D) 5 8) How many constitutional isomers are there with the molecular formula C6H14? A) 2 B) 3 C) 4 D) 5 9) Which of the following is not another representation for 2-methylbutane?

A) I B) II C) III D) IV 10) Which of the following compounds has primary, secondary, tertiary, and quaternary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane 11) Which of the following compounds has only primary and secondary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,3,3-Trimethylpentane 12) Which of the following compounds has only primary, secondary, and tertiary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane

13) Which of the following compounds has only primary, secondary, and quaternary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane 14) Which of the following compounds has primary, secondary, and tertiary hydrogen atoms? A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane 15) Which of the following compounds has only primary and secondary hydrogen atoms? A) 2-Methylpentane B) 2,2,3-Trimethylpentane C) 3-Methylpentane D) 2,2-Dimethylpentane 16) How many cycloalkane constitutional isomers (excluding stereoisomers) are there with molecular formula C5H10? A) 2 B) 3 C) 4 D) 5 17) What is the parent chain for the following compound?

A) Hexane B) Heptane C) Octane D) Nonane

18) What is the parent chain for the following compound?

A) Heptane B) Octane C) Nonane D) Decane 19) What is the name of the alkyl group that contains two carbons in a straight chain and onecarbon branch? A) Ethyl B) Propyl C) Isopropyl D) None of these 20) What is the IUPAC name for the following compound?

A) 4-Ethyl-5-methyloctane B) 4-Methyl-5-ethyloctane C) 4-Methyl-3-propylheptane D) 4-Methyl-5-propyloctane 21) What is the IUPAC name for the following compound?

A) 3,5-Diethyl-6-methylheptane B) 3,5-Diethyl-2-methylheptane C) 3-Ethyl-5-isopropylheptane D) 5-Ethyl-3-isopropylheptane

22) What is the IUPAC name for the following compound?

A) 2,3-Dimethyl-4-sec-butylheptane B) 4-sec-Butyl-2,3-dimethylheptane C) 3,5,6-Trimethyl-4-propylheptane D) 2,3,5-Trimethyl-4-propylheptane 23) What is the IUPAC name for the following compound?

A) 5-Ethyl-3,6-dimethylheptane B) 3-Ethyl-2,5-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane D) 5-Ethyl-3,6-dimethyloctane 24) What is the IUPAC name for the following compound?

A) 2,3,5-Trimethylhexane B) 2,4,5-Triethylhexane C) 2,4-Diethyl-5-methylheptane D) 4-Ethyl-3,6-dimethyloctane

25) What is the IUPAC name for the following compound?

A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane 26) What is the IUPAC name for the following compound?

A) 3-Ethyl-1-methylcyclohexane B) 1-Ethyl-3-methylcyclohexane C) 1-Ethyl-3-methylhexane D) 3-Ethyl-1-methylhexane 27) What is the IUPAC name for the following compound?

A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane

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

A) 1,4-Dimethylcyclohexane B) 1,3-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane D) 1,4-Dimethylcyclopentane 29) What is the IUPAC name for the following compound?

A) 1-Butylcyclohexane B) Cyclohexanebutane C) 1-Cyclohexylbutane D) Butylcyclohexane 30) What is the IUPAC name for the following compound?

A) Hexylcyclopentane B) 1-Hexylcyclopentane C) 1-Cyclopentylhexane D) 1-Cyclopentylheptane 31) What is the IUPAC name for the following compound?

A) 1-Butyl-3-methylcyclohexane B) 1-sec-Butyl-3-methylcyclohexane C) 1-Methyl-3-sec-butylcyclohexane D) 1-sec-Butyl-3-methylhexane 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

32) What is the common name of the following alkyl group?

A) Isobutyl B) sec-Butyl C) Isopropyl D) tert-Butyl 33) What is the common name of the following alkyl group?

A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl 34) Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first.

A) I > II > III B) I > III > II C) II > III > I D) III > II > I

35) Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first.

A) I < III < II B) I < II < III C) II < III < I D) III < II < I 36) Which of the following statements about the conformations of acyclic alkanes is true? A) Conformations are the same arrangements of atoms that cannot be interconverted by rotation about single bonds. B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon. C) In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon. D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered conformation, and vice versa. 37) Which of the following statements about the conformations of acyclic alkanes is not true? A) The staggered and eclipsed conformations are equally stable. B) The staggered conformations are more stable than the eclipsed conformations. C) An energy minimum and maximum occur every 60° as the conformation changes from staggered to eclipsed. D) Conformations that are neither staggered nor eclipsed are intermediate in energy. 38) Which of the following statements about the conformations of acyclic alkanes is true? A) A staggered conformation with two larger groups 180° from each other is called gauche. B) Staggered conformations are at energy maxima and eclipsed conformations are energy minima. C) A staggered conformation with two larger groups 60° from each other is called anti. D) Gauche conformations are generally higher in energy than anti conformations.

39) Which of the following is not a conformer of butane?

A) I B) II C) III D) IV 40) Which of the following are gauche conformers?

A) I and II B) I and III C) II and IV D) II and III 41) Which of the following are anti conformers?

A) I and II B) II and III C) I and IV D) II and IV

42) Which of the following conformers has the highest energy?

A) I B) II C) III D) IV 43) Rank the conformers of butane in order of decreasing stability, putting the most stable first.

A) IV > I > II > III B) IV > I > III > II C) II > III > I > IV D) I > IV > II > III 44) Which of the following is the highest energy conformer of 2,3-dimethylbutane?

A) I B) II C) III D) IV

45) Which of the following is the lowest energy conformer of 2,3-dimethybutane?

A) I B) II C) III D) IV 46) Which of the following cycloalkanes has the most angle strain? A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane 47) Which of the following cycloalkanes has the least angle strain? A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane 48) Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?

A) I B) II C) III D) IV

49) Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?

A) I B) II C) III D) IV 50) Which of the following is the most stable conformation of cis-1-ethyl-3isopropylcyclohexane?

A) I B) II C) III D) IV 51) Which of the following is the most stable conformation of trans-1-isopropyl-3methylcyclohexane?

A) I B) II C) III D) IV

52) Select the most stable conformer of cis-1,3-cyclohexanediol.

. A) I B) II C) III D) IV 53) What is the alternate chair conformation of the following compound?

A) I B) II C) III D) IV

54) Which of the following is the most stable conformation of the following compound?

A) I B) II C) III D) IV 55) Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting the most stable first.

A) I > II > III > IV B) III > II > IV > I C) III > IV > II > I D) I > II > IV > III 56) What are the products of the combustion of alkanes? A) Carbon and hydrogen B) Carbon and water C) Carbon dioxide and hydrogen D) Carbon dioxide and water

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

A) Pentane B) 2-Methylpentane C) 2-Methyl-3-ethylpentane D) 3-Ethyl-2-methylpentane 58) Rank the following alkanes in order of increasing boiling point.

A) I > II > III > IV B) IV > III > II > I C) II > III > IV > I D) IV > III > I > II 59) Which of the following conformation is highest in energy?

A) I B) II C) III D) IV

60) What is the relation between the following pair of compounds?

A) Constitutional isomers B) Stereoisomers C) Identical molecules D) Not isomers of each other 61) Which formula represents a cycloalkane with 6 carbons? A) C6H12 B) C6H14 C) C6H16 D) C6H18 62) Which formula represents a cycloalkane with 5 carbons? A) C5H8 B) C5H10 C) C5H12 D) C5H14 63) What is the IUPAC name for the following alkane?

A) 2,5,6,7-tetramethyloctane B) 2,3,4,7-tetramethyloctane C) 2,5,6,7-tetramethylheptane D) 2,3,4,7-tetramethylheptane

64) What is the IUPAC name for the following alkane?

A) 3-isopropyl-6-methyloctane B) 3-isopropyl-3.7-methyloctane C) 3-ethyl-2,6-dimethyloctane D) 6-ethyl-3,7-dimethyloctane

Organic Chemistry, 6e (Smith) Chapter 4 Alkanes 1) Which of the following statements about alkanes is not true? A) Alkanes are aliphatic hydrocarbons. B) Alkanes contain only C-C and C-H s bonds. C) Alkanes are acyclic or cyclic. D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons. Answer: D Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 2. Understand Chapter: 04 Accessibility: Keyboard Navigation 2) Which of the following statements about alkanes is true? A) Alkanes are aliphatic hydrocarbons having only C-C and C-H p bonds. B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of carbons. C) Acyclic alkanes contain carbons joined in one or more rings. D) Acyclic alkanes have the general molecular formula CnH2n. Answer: B Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 2. Understand Chapter: 04 Accessibility: Keyboard Navigation

3) What is the molecular formula of an alkane that has twenty-three carbon atoms? A) C23H46 B) C23H48 C) C23H50 D) C23H44 Answer: B Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 4) What is the molecular formula of a cycloalkane that has six carbon atoms? A) C6H14 B) C6H10 C) C6H12 D) C6H16 Answer: C Difficulty: 1 Easy Section: 04.02 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 5) What is the approximate C-C-C bond angle in propane? A) 90° B) 109.5° C) 120° D) 180° Answer: B Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

6) What is the hybridization of a carbon atom in an alkane? A) sp3 B) sp2 C) sp D) p Answer: A Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 7) How many constitutional isomers are there with the molecular formula C5H12? A) 2 B) 3 C) 4 D) 5 Answer: B Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 8) How many constitutional isomers are there with the molecular formula C6H14? A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

9) Which of the following is not another representation for 2-methylbutane?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 04.01 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 10) Which of the following compounds has primary, secondary, tertiary, and quaternary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane Answer: D Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

11) Which of the following compounds has only primary and secondary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,3,3-Trimethylpentane Answer: A Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 12) Which of the following compounds has only primary, secondary, and tertiary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane Answer: B Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 13) Which of the following compounds has only primary, secondary, and quaternary carbon atoms? A) Pentane B) 2-Methylpentane C) 2,2-Dimethylpentane D) 2,2,3-Trimethylpentane Answer: C Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

14) Which of the following compounds has primary, secondary, and tertiary hydrogen atoms? A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane Answer: C Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 15) Which of the following compounds has only primary and secondary hydrogen atoms? A) 2-Methylpentane B) 2,2,3-Trimethylpentane C) 3-Methylpentane D) 2,2-Dimethylpentane Answer: D Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 16) How many cycloalkane constitutional isomers (excluding stereoisomers) are there with molecular formula C5H10? A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: 04.02 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

17) What is the parent chain for the following compound?

A) Hexane B) Heptane C) Octane D) Nonane Answer: B Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 18) What is the parent chain for the following compound?

A) Heptane B) Octane C) Nonane D) Decane Answer: C Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

19) What is the name of the alkyl group that contains two carbons in a straight chain and onecarbon branch? A) Ethyl B) Propyl C) Isopropyl D) None of these Answer: C Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 20) What is the IUPAC name for the following compound?

A) 4-Ethyl-5-methyloctane B) 4-Methyl-5-ethyloctane C) 4-Methyl-3-propylheptane D) 4-Methyl-5-propyloctane Answer: A Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

21) What is the IUPAC name for the following compound?

A) 3,5-Diethyl-6-methylheptane B) 3,5-Diethyl-2-methylheptane C) 3-Ethyl-5-isopropylheptane D) 5-Ethyl-3-isopropylheptane Answer: B Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 22) What is the IUPAC name for the following compound?

A) 2,3-Dimethyl-4-sec-butylheptane B) 4-sec-Butyl-2,3-dimethylheptane C) 3,5,6-Trimethyl-4-propylheptane D) 2,3,5-Trimethyl-4-propylheptane Answer: D Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

23) What is the IUPAC name for the following compound?

A) 5-Ethyl-3,6-dimethylheptane B) 3-Ethyl-2,5-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane D) 5-Ethyl-3,6-dimethyloctane Answer: B Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 24) What is the IUPAC name for the following compound?

A) 2,3,5-Trimethylhexane B) 2,4,5-Triethylhexane C) 2,4-Diethyl-5-methylheptane D) 4-Ethyl-3,6-dimethyloctane Answer: D Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

25) What is the IUPAC name for the following compound?

A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane Answer: B Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 26) What is the IUPAC name for the following compound?

A) 3-Ethyl-1-methylcyclohexane B) 1-Ethyl-3-methylcyclohexane C) 1-Ethyl-3-methylhexane D) 3-Ethyl-1-methylhexane Answer: B Difficulty: 1 Easy Section: 04.05 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

27) What is the IUPAC name for the following compound?

A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane Answer: A Difficulty: 2 Medium Section: 04.05 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 28) What is the IUPAC name for the following compound?

A) 1,4-Dimethylcyclohexane B) 1,3-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane D) 1,4-Dimethylcyclopentane Answer: C Difficulty: 1 Easy Section: 04.05 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

29) What is the IUPAC name for the following compound?

A) 1-Butylcyclohexane B) Cyclohexanebutane C) 1-Cyclohexylbutane D) Butylcyclohexane Answer: D Difficulty: 1 Easy Section: 04.05 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 30) What is the IUPAC name for the following compound?

A) Hexylcyclopentane B) 1-Hexylcyclopentane C) 1-Cyclopentylhexane D) 1-Cyclopentylheptane Answer: C Difficulty: 1 Easy Section: 04.05 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

31) What is the IUPAC name for the following compound?

A) 1-Butyl-3-methylcyclohexane B) 1-sec-Butyl-3-methylcyclohexane C) 1-Methyl-3-sec-butylcyclohexane D) 1-sec-Butyl-3-methylhexane Answer: B Difficulty: 1 Easy Section: 04.05 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 32) What is the common name of the following alkyl group?

A) Isobutyl B) sec-Butyl C) Isopropyl D) tert-Butyl Answer: B Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

33) What is the common name of the following alkyl group?

A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl Answer: A Difficulty: 1 Easy Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 34) Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first.

A) I > II > III B) I > III > II C) II > III > I D) III > II > I Answer: B Difficulty: 2 Medium Section: 04.08 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

35) Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first.

A) I < III < II B) I < II < III C) II < III < I D) III < II < I Answer: A Difficulty: 2 Medium Section: 04.08 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 36) Which of the following statements about the conformations of acyclic alkanes is true? A) Conformations are the same arrangements of atoms that cannot be interconverted by rotation about single bonds. B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon. C) In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon. D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered conformation, and vice versa. Answer: D Difficulty: 2 Medium Section: 04.09 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

37) Which of the following statements about the conformations of acyclic alkanes is not true? A) The staggered and eclipsed conformations are equally stable. B) The staggered conformations are more stable than the eclipsed conformations. C) An energy minimum and maximum occur every 60° as the conformation changes from staggered to eclipsed. D) Conformations that are neither staggered nor eclipsed are intermediate in energy. Answer: A Difficulty: 2 Medium Section: 04.09 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 38) Which of the following statements about the conformations of acyclic alkanes is true? A) A staggered conformation with two larger groups 180° from each other is called gauche. B) Staggered conformations are at energy maxima and eclipsed conformations are energy minima. C) A staggered conformation with two larger groups 60° from each other is called anti. D) Gauche conformations are generally higher in energy than anti conformations. Answer: D Difficulty: 2 Medium Section: 04.08; 04.09 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

39) Which of the following is not a conformer of butane?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 40) Which of the following are gauche conformers?

A) I and II B) I and III C) II and IV D) II and III Answer: B Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

41) Which of the following are anti conformers?

A) I and II B) II and III C) I and IV D) II and IV Answer: D Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 42) Which of the following conformers has the highest energy?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

43) Rank the conformers of butane in order of decreasing stability, putting the most stable first.

A) IV > I > II > III B) IV > I > III > II C) II > III > I > IV D) I > IV > II > III Answer: B Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 44) Which of the following is the highest energy conformer of 2,3-dimethylbutane?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

45) Which of the following is the lowest energy conformer of 2,3-dimethybutane?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 46) Which of the following cycloalkanes has the most angle strain? A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane Answer: A Difficulty: 1 Easy Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

47) Which of the following cycloalkanes has the least angle strain? A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane Answer: B Difficulty: 1 Easy Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 48) Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 04.12 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

49) Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 04.12 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 50) Which of the following is the most stable conformation of cis-1-ethyl-3isopropylcyclohexane?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

51) Which of the following is the most stable conformation of trans-1-isopropyl-3methylcyclohexane?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 52) Select the most stable conformer of cis-1,3-cyclohexanediol.

. A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 24 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

53) What is the alternate chair conformation of the following compound?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 54) Which of the following is the most stable conformation of the following compound?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 25 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

55) Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting the most stable first.

A) I > II > III > IV B) III > II > IV > I C) III > IV > II > I D) I > II > IV > III Answer: C Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 56) What are the products of the combustion of alkanes? A) Carbon and hydrogen B) Carbon and water C) Carbon dioxide and hydrogen D) Carbon dioxide and water Answer: D Difficulty: 1 Easy Section: 04.14 Topic: Alkanes Bloom's: 1. Remember Chapter: 04 Accessibility: Keyboard Navigation

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

A) Pentane B) 2-Methylpentane C) 2-Methyl-3-ethylpentane D) 3-Ethyl-2-methylpentane Answer: D Difficulty: 2 Medium Section: 04.10 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 58) Rank the following alkanes in order of increasing boiling point.

A) I > II > III > IV B) IV > III > II > I C) II > III > IV > I D) IV > III > I > II Answer: B Difficulty: 2 Medium Section: 04.08 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

59) Which of the following conformation is highest in energy?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 04.09 Topic: Alkanes Bloom's: 2. Understand Chapter: 04 60) What is the relation between the following pair of compounds?

A) Constitutional isomers B) Stereoisomers C) Identical molecules D) Not isomers of each other Answer: B Difficulty: 2 Medium Section: 04.13 Topic: Alkanes Bloom's: 2. Understand Chapter: 04

61) Which formula represents a cycloalkane with 6 carbons? A) C6H12 B) C6H14 C) C6H16 D) C6H18 Answer: A Difficulty: 1 Easy Section: 04.02 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation 62) Which formula represents a cycloalkane with 5 carbons? A) C5H8 B) C5H10 C) C5H12 D) C5H14 Answer: B Difficulty: 1 Easy Section: 04.02 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 Accessibility: Keyboard Navigation

63) What is the IUPAC name for the following alkane?

A) 2,5,6,7-tetramethyloctane B) 2,3,4,7-tetramethyloctane C) 2,5,6,7-tetramethylheptane D) 2,3,4,7-tetramethylheptane Answer: B Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04 64) What is the IUPAC name for the following alkane?

A) 3-isopropyl-6-methyloctane B) 3-isopropyl-3.7-methyloctane C) 3-ethyl-2,6-dimethyloctane D) 6-ethyl-3,7-dimethyloctane Answer: C Difficulty: 2 Medium Section: 04.04 Topic: Alkanes Bloom's: 3. Apply Chapter: 04

Organic Chemistry, 6e (Smith) Chapter 5 Stereochemistry 1) What is the main carbohydrate in the seeds and roots of plants? A) Starch B) Glucose C) Cellulose D) Glycogen 2) Which of the following statements about starch and cellulose is true? A) Starch and cellulose are not stereoisomers. B) In cellulose, the O atom joins two rings using one equatorial and one axial bond. C) In starch, the O atom joins two rings using two equatorial bonds. D) In cellulose, the O atom joins two rings using two equatorial bonds. 3) Which of the following statements about constitutional isomers is not true? A) They have different IUPAC names. B) They always have the same functional groups. C) They have different physical properties. D) They have different chemical properties. 4) Which of the following statements about stereoisomers is not true? A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans. B) Stereoisomers differ in configuration. C) Stereoisomers always have the same functional groups. D) Stereoisomers differ only in their structural formula. 5) What is the relationship between the following two compounds?

A) Stereoisomers B) Constitutional isomers C) Identical D) Not isomers, different compounds

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

A) Constitutional isomers B) Identical C) Stereoisomers D) Not isomers, different compounds 7) What is the relationship between the following two compounds?

A) Constitutional isomers B) Identical C) Stereoisomers D) Not isomers, different compounds 8) What is the relationship between the following two compounds?

A) Constitutional isomers B) Stereoisomers C) Identical D) Not isomers, different compounds 9) Which of the following is the definition of chirality? A) The existence of a molecule with a mirror image. B) The existence of a molecule with a carbon atom that has four different substituents. C) The existence of a molecule that is superimposable on its mirror image. D) The existence of a molecule that is not superimposable on its mirror image. 10) Which of the following statements is not true? A) A molecule that is superimposable on its mirror image is said to achiral. B) A molecule that is not superimposable on its mirror image is said to be chiral. C) A molecule that is superimposable on its mirror image is said to be chiral. D) A carbon atom bonded to four different groups is a stereogenic center. 2 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

11) Which of the following statements is true? A) Enantiomers are mirror images that are not superimposable. B) A molecule that is superimposable on its mirror image is chiral. C) A chiral molecule usually contains a plane of symmetry. D) An achiral molecule does not contain a plane of symmetry. 12) Which of the following statements is true? A) Achiral molecules usually contain a plane of symmetry. B) With one tetrahedral stereogenic center, a molecule may or may not be chiral. C) With two or more stereogenic centers, a molecule is always chiral. D) Chiral molecules usually contain a plane of symmetry. 13) Which of the following is the correct definition for a pair of enantiomers? A) A pair of stereoisomers that have a plane of symmetry. B) A pair of stereoisomers that are not mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are superimposable mirror images of each other. 14) Which of the following molecules has a plane of symmetry?

A) I B) II C) III D) IV 15) Which of the following statements is true? A) The presence of a plane of symmetry makes a molecule chiral. B) An achiral molecule must have one or more stereogenic centers. C) All molecules that have stereogenic centers are chiral. D) Stereoisomers that are not superimposable on their mirror image are enantiomers. 16) Which of the following molecules are chiral? I. cis-1,3-Dibromocyclohexane II. 1-Bromo-1-methylcyclohexane III. trans-1-Bromo-3-methylcyclohexane IV. cis-1-Bromo-3-methylcyclohexane A) I, II B) II, III C) I, IV D) III, IV 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

17) Which of the following molecules are chiral? I. 2-Chlorobutane II. 3-Bromopentane III. 1-Bromo-2-methylpropene IV. 2-Bromo-3-methylbutane A) I, II B) I, IV C) II, III D) III, IV 18) Which of the following molecules are achiral?

A) II, III B) I, II C) I, IV D) III, IV 19) Which of the following molecules are chiral?

A) II, III B) I, II C) I, IV D) III, IV

20) How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?

A) 0 B) 1 C) 2 D) 3 21) How many stereogenic centers are present in the following compound?

A) 0 B) 1 C) 2 D) 3 22) How many stereogenic centers are present in fructose, a simple sugar?

23) How many stereogenic centers are present in the following compound?

A) 1 B) 2 C) 3 D) 4 24) How many stereogenic centers are present in menthol?

A) 1 B) 2 C) 3 D) 4 25) How many stereogenic centers are present in the following compound?

A) 1 B) 2 C) 3 D) 4

26) How many stereogenic centers are present in the following molecule?

A) 1 B) 2 C) 4 D) 5 27) How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH)CH3? A) 1 B) 2 C) 3 D) 4 28) How many stereoisomers can be drawn for a molecule with formula CH3CH(OH)CH(OH)CH3? A) 1 B) 2 C) 3 D) 4 29) What is the total number of possible stereoisomers for the following molecule?

A) 2 B) 4 C) 6 D) 8 30) How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane? A) 2 B) 3 C) 4 D) 6 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

31) How many chiral stereoisomers can be drawn for dimethycyclopropane? A) 1 B) 2 C) 3 D) 4 32) How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

A) 0 B) 1 C) 2 D) 3 33) How many stereogenic centers are present in the following compound?

A) 0 B) 1 C) 2 D) 3 34) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) III > I > II > IV B) I > II > IV > III C) III > II > IV > I D) III > IV > II > I

35) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) I > II > III > IV B) II > I > IV > III C) II > I > III > IV D) I > II > IV > III 36) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) I > III > IV > II B) III > IV > I > II C) IV > III > I > II D) IV > I > III > II 37) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) I > II > IV > III B) IV > II > I > III C) IV > I > II > III D) III > II > I> IV

38) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) IV > III > I > II B) IV > I > III > II C) III > IV > I > II D) II > I > III > IV 39) Which of the following compounds has a plane of symmetry?

A) I and II B) II and III C) II, III, and IV D) III and IV 40) Which of the following structures has a different configuration from the other three?

A) I B) II C) III D) IV

41) Which of the following structures has a different configuration from the other three?

A) I B) II C) III D) IV 42) Which of the following structures has the S configuration?

A) Only I B) Only II C) Only I and II D) I, II, and III 43) Which of the following structures has the R configuration?

A) Only I B) Only II C) Only I and II D) I, II, and III

44) Which of the following structures has the R configuration?

A) Only I B) Only II C) Only I and II D) I, II, and III 45) Which of the following is the definition for a pair of diastereomers? A) A pair of stereoisomers with stereogenic centers but is not chiral. B) A pair of stereoisomers that are superimposable mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are not mirror images of each other. 46) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical 47) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical

48) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical 49) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical 50) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical

51) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical 52) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical 53) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical 54) Which of the following statements about meso compounds is not true? A) A meso compound generally has a plane of symmetry. B) A meso compound and its mirror image are identical. C) A meso compound is achiral. D) A meso compound is chiral. 55) Which of the following compounds is a meso compound? A) (2R, 3S)-dichlorobutane B) (2R, 3R)-dichlorobutane C) (2R, 3S)-3-chloro-2-butanol D) (2R, 3R)-3-chloro-2-butanol 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

56) Which of the following compounds are meso?

A) Only I B) Only II C) I and II D) Neither 57) Which of the following compounds can have a meso stereoisomer?

A) I B) II C) III D) IV 58) How many stereoisomers of 1,3-dibromocyclopentane exist? A) 1 B) 2 C) 3 D) 4 59) Which of the following compounds does not have a plane of symmetry?

A) Only I and II B) Only II C) Only III and IV D) Only I, II, and IV

60) Which of the following cyclic molecules is a meso compound?

A) I B) II C) III D) IV 61) How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane? A) 3 B) 4 C) 5 D) 6 62) A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O. What is the specific rotation of this compound? A) -10° B) +100° C) +10° D) -100° 63) A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer? A) +50° B) -40° C) +40° D) -50° 64) How much of the R enantiomer is present in 10 g of a mixture that has an enantiomeric excess of 30% of the S isomer? A) 3.0 g B) 3.5 g C) 6.5 g D) 7.0 g

65) A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter? A) +5.6° B) +11.2° C) +2.8° D) +1.4° 66) What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other? A) 70 B) 85 C) 40 D) 30 67) If a mixture has an ee of 90%, what is the percentage of each enantiomer? A) 65% : 35% B) 55% : 45% C) 80% : 20% D) 95% : 5% 68) A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture? A) 75 B) 40 C) 65 D) 50 69) Which of the following compounds are chiral?

A) I and II B) II and III C) III and IV D) I and IV

70) Which of the following compounds is identical to compound A?

A) I and II B) II and III C) I and III D) II 71) Give the IUPAC name for the following compound:

A) R-3-methylhexane B) S-3-methylhexane C) R-4-methylhexane D) S-4-methylhexane 72) Give the IUPAC name for the following compound:

A) R-3-methylhexane B) S-3-methylhexane C) R-4-methylhexane D) S-4-methylhexane

73) Give the IUPAC name for the following compound:

A) R-2,3-dimethylhexane B) S-2,3-dimethylhexane C) R-4,5-dimethylhexane D) S-4,5-dimethylhexane 74) Give the IUPAC name for the following compound:

A) (1R,3R)-1-ethyl-3-methylcyclohexane B) (1R,3S)-1-ethyl-3-methylcyclohexane C) (1S,3R)-1-ethyl-3-methylcyclohexane D) (1S,3S)-1-ethyl-3-methylcyclohexane 75) Give the IUPAC name for the following compound:

A) (1R,3R)-1-ethyl-3-methylcyclohexane B) (1R,3S)-1-ethyl-3-methylcyclohexane C) (1S,3R)-1-ethyl-3-methylcyclohexane D) (1S,3S)-1-ethyl-3-methylcyclohexane

76) Give the IUPAC name for the following compound:

A) (1R,2R)-1,2-dimethylcyclopentane B) (1R,2S)-1,2-dimethylcyclopentane C) (1S,2R)-1,2-dimethylcyclopentane D) (1S,2S)-1,2-dimethylcyclopentane

Organic Chemistry, 6e (Smith) Chapter 5 Stereochemistry 1) What is the main carbohydrate in the seeds and roots of plants? A) Starch B) Glucose C) Cellulose D) Glycogen Answer: A Difficulty: 1 Easy Section: 05.01 Topic: Stereochemistry Chapter: 05 Accessibility: Keyboard Navigation 2) Which of the following statements about starch and cellulose is true? A) Starch and cellulose are not stereoisomers. B) In cellulose, the O atom joins two rings using one equatorial and one axial bond. C) In starch, the O atom joins two rings using two equatorial bonds. D) In cellulose, the O atom joins two rings using two equatorial bonds. Answer: D Difficulty: 1 Easy Section: 05.01 Topic: Stereochemistry Chapter: 05 Accessibility: Keyboard Navigation 3) Which of the following statements about constitutional isomers is not true? A) They have different IUPAC names. B) They always have the same functional groups. C) They have different physical properties. D) They have different chemical properties. Answer: B Difficulty: 1 Easy Section: 05.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

4) Which of the following statements about stereoisomers is not true? A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans. B) Stereoisomers differ in configuration. C) Stereoisomers always have the same functional groups. D) Stereoisomers differ only in their structural formula. Answer: D Difficulty: 1 Easy Section: 05.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 5) What is the relationship between the following two compounds?

A) Stereoisomers B) Constitutional isomers C) Identical D) Not isomers, different compounds Answer: B Difficulty: 1 Easy Section: 05.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

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

A) Constitutional isomers B) Identical C) Stereoisomers D) Not isomers, different compounds Answer: A Difficulty: 1 Easy Section: 05.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 7) What is the relationship between the following two compounds?

A) Constitutional isomers B) Identical C) Stereoisomers D) Not isomers, different compounds Answer: B Difficulty: 1 Easy Section: 05.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

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

A) Constitutional isomers B) Stereoisomers C) Identical D) Not isomers, different compounds Answer: B Difficulty: 1 Easy Section: 05.02 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 9) Which of the following is the definition of chirality? A) The existence of a molecule with a mirror image. B) The existence of a molecule with a carbon atom that has four different substituents. C) The existence of a molecule that is superimposable on its mirror image. D) The existence of a molecule that is not superimposable on its mirror image. Answer: D Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 10) Which of the following statements is not true? A) A molecule that is superimposable on its mirror image is said to achiral. B) A molecule that is not superimposable on its mirror image is said to be chiral. C) A molecule that is superimposable on its mirror image is said to be chiral. D) A carbon atom bonded to four different groups is a stereogenic center. Answer: C Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 4 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

11) Which of the following statements is true? A) Enantiomers are mirror images that are not superimposable. B) A molecule that is superimposable on its mirror image is chiral. C) A chiral molecule usually contains a plane of symmetry. D) An achiral molecule does not contain a plane of symmetry. Answer: A Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 12) Which of the following statements is true? A) Achiral molecules usually contain a plane of symmetry. B) With one tetrahedral stereogenic center, a molecule may or may not be chiral. C) With two or more stereogenic centers, a molecule is always chiral. D) Chiral molecules usually contain a plane of symmetry. Answer: A Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 13) Which of the following is the correct definition for a pair of enantiomers? A) A pair of stereoisomers that have a plane of symmetry. B) A pair of stereoisomers that are not mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are superimposable mirror images of each other. Answer: C Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

14) Which of the following molecules has a plane of symmetry?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 15) Which of the following statements is true? A) The presence of a plane of symmetry makes a molecule chiral. B) An achiral molecule must have one or more stereogenic centers. C) All molecules that have stereogenic centers are chiral. D) Stereoisomers that are not superimposable on their mirror image are enantiomers. Answer: D Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

16) Which of the following molecules are chiral? I. cis-1,3-Dibromocyclohexane II. 1-Bromo-1-methylcyclohexane III. trans-1-Bromo-3-methylcyclohexane IV. cis-1-Bromo-3-methylcyclohexane A) I, II B) II, III C) I, IV D) III, IV Answer: D Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 17) Which of the following molecules are chiral? I. 2-Chlorobutane II. 3-Bromopentane III. 1-Bromo-2-methylpropene IV. 2-Bromo-3-methylbutane A) I, II B) I, IV C) II, III D) III, IV Answer: B Difficulty: 1 Easy Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

18) Which of the following molecules are achiral?

A) II, III B) I, II C) I, IV D) III, IV Answer: C Difficulty: 2 Medium Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 19) Which of the following molecules are chiral?

A) II, III B) I, II C) I, IV D) III, IV Answer: A Difficulty: 2 Medium Section: 05.03 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

20) How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?

A) 0 B) 1 C) 2 D) 3 Answer: C Difficulty: 1 Easy Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 21) How many stereogenic centers are present in the following compound?

A) 0 B) 1 C) 2 D) 3 Answer: D Difficulty: 1 Easy Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

22) How many stereogenic centers are present in fructose, a simple sugar?

A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 1 Easy Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 23) How many stereogenic centers are present in the following compound?

A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

24) How many stereogenic centers are present in menthol?

A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 1 Easy Section: 05.05 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 25) How many stereogenic centers are present in the following compound?

A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

26) How many stereogenic centers are present in the following molecule?

A) 1 B) 2 C) 4 D) 5 Answer: B Difficulty: 2 Medium Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 27) How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH)CH3? A) 1 B) 2 C) 3 D) 4 Answer: D Difficulty: 2 Medium Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

28) How many stereoisomers can be drawn for a molecule with formula CH3CH(OH)CH(OH)CH3? A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 2 Medium Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 29) What is the total number of possible stereoisomers for the following molecule?

A) 2 B) 4 C) 6 D) 8 Answer: D Difficulty: 2 Medium Section: 05.04 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

30) How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane? A) 2 B) 3 C) 4 D) 6 Answer: C Difficulty: 2 Medium Section: 05.05 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation 31) How many chiral stereoisomers can be drawn for dimethycyclopropane? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 2 Medium Section: 05.05 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

32) How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?

A) 0 B) 1 C) 2 D) 3 Answer: A Difficulty: 2 Medium Section: 05.05 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 33) How many stereogenic centers are present in the following compound?

A) 0 B) 1 C) 2 D) 3 Answer: B Difficulty: 3 Hard Section: 05.05 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

34) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) III > I > II > IV B) I > II > IV > III C) III > II > IV > I D) III > IV > II > I Answer: D Difficulty: 1 Easy Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 35) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) I > II > III > IV B) II > I > IV > III C) II > I > III > IV D) I > II > IV > III Answer: B Difficulty: 1 Easy Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

36) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) I > III > IV > II B) III > IV > I > II C) IV > III > I > II D) IV > I > III > II Answer: C Difficulty: 1 Easy Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 37) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) I > II > IV > III B) IV > II > I > III C) IV > I > II > III D) III > II > I> IV Answer: C Difficulty: 1 Easy Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

38) Rank the following groups in order of decreasing priority according to the Cahn-IngoldPrelog system.

A) IV > III > I > II B) IV > I > III > II C) III > IV > I > II D) II > I > III > IV Answer: A Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 39) Which of the following compounds has a plane of symmetry?

A) I and II B) II and III C) II, III, and IV D) III and IV Answer: D Difficulty: 2 Medium Section: 05.08 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

40) Which of the following structures has a different configuration from the other three?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 41) Which of the following structures has a different configuration from the other three?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05

42) Which of the following structures has the S configuration?

A) Only I B) Only II C) Only I and II D) I, II, and III Answer: C Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 43) Which of the following structures has the R configuration?

A) Only I B) Only II C) Only I and II D) I, II, and III Answer: B Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05

44) Which of the following structures has the R configuration?

A) Only I B) Only II C) Only I and II D) I, II, and III Answer: C Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 45) Which of the following is the definition for a pair of diastereomers? A) A pair of stereoisomers with stereogenic centers but is not chiral. B) A pair of stereoisomers that are superimposable mirror images of each other. C) A pair of stereoisomers that are not superimposable mirror images of each other. D) A pair of stereoisomers that are not mirror images of each other. Answer: D Difficulty: 1 Easy Section: 05.07 Topic: Stereochemistry Bloom's: 2. Understand Chapter: 05 Accessibility: Keyboard Navigation

46) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: B Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 47) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: C Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05

48) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: B Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 49) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: D Difficulty: 3 Hard Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05

50) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: B Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 51) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: C Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05

52) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: A Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 53) What is the relationship between the following compounds?

A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical Answer: B Difficulty: 2 Medium Section: 05.07 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05

54) Which of the following statements about meso compounds is not true? A) A meso compound generally has a plane of symmetry. B) A meso compound and its mirror image are identical. C) A meso compound is achiral. D) A meso compound is chiral. Answer: D Difficulty: 2 Medium Section: 05.08 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 Accessibility: Keyboard Navigation 55) Which of the following compounds is a meso compound? A) (2R, 3S)-dichlorobutane B) (2R, 3R)-dichlorobutane C) (2R, 3S)-3-chloro-2-butanol D) (2R, 3R)-3-chloro-2-butanol Answer: A Difficulty: 3 Hard Section: 05.08 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 Accessibility: Keyboard Navigation 56) Which of the following compounds are meso?

A) Only I B) Only II C) I and II D) Neither Answer: B Difficulty: 3 Hard Section: 05.08 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 26 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

57) Which of the following compounds can have a meso stereoisomer?

A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 05.08 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 58) How many stereoisomers of 1,3-dibromocyclopentane exist? A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 2 Medium Section: 05.10 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 Accessibility: Keyboard Navigation

59) Which of the following compounds does not have a plane of symmetry?

A) Only I and II B) Only II C) Only III and IV D) Only I, II, and IV Answer: B Difficulty: 2 Medium Section: 05.08 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 60) Which of the following cyclic molecules is a meso compound?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 05.08 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05

61) How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane? A) 3 B) 4 C) 5 D) 6 Answer: D Difficulty: 2 Medium Section: 05.10 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 Accessibility: Keyboard Navigation 62) A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O. What is the specific rotation of this compound? A) -10° B) +100° C) +10° D) -100° Answer: B Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation 63) A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer? A) +50° B) -40° C) +40° D) -50° Answer: D Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation

64) How much of the R enantiomer is present in 10 g of a mixture that has an enantiomeric excess of 30% of the S isomer? A) 3.0 g B) 3.5 g C) 6.5 g D) 7.0 g Answer: B Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation 65) A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter? A) +5.6° B) +11.2° C) +2.8° D) +1.4° Answer: B Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation 66) What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other? A) 70 B) 85 C) 40 D) 30 Answer: C Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation

67) If a mixture has an ee of 90%, what is the percentage of each enantiomer? A) 65% : 35% B) 55% : 45% C) 80% : 20% D) 95% : 5% Answer: D Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation 68) A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture? A) 75 B) 40 C) 65 D) 50 Answer: D Difficulty: 2 Medium Section: 05.12 Topic: Stereochemistry Bloom's: 5. Evaluate Chapter: 05 Accessibility: Keyboard Navigation

69) Which of the following compounds are chiral?

A) I and II B) II and III C) III and IV D) I and IV Answer: B Difficulty: 2 Medium Section: 05.03 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05 70) Which of the following compounds is identical to compound A?

A) I and II B) II and III C) I and III D) II Answer: D Difficulty: 3 Hard Section: 05.11 Topic: Stereochemistry Bloom's: 3. Apply Chapter: 05

71) Give the IUPAC name for the following compound:

A) R-3-methylhexane B) S-3-methylhexane C) R-4-methylhexane D) S-4-methylhexane Answer: B Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 72) Give the IUPAC name for the following compound:

A) R-3-methylhexane B) S-3-methylhexane C) R-4-methylhexane D) S-4-methylhexane Answer: A Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05

73) Give the IUPAC name for the following compound:

A) R-2,3-dimethylhexane B) S-2,3-dimethylhexane C) R-4,5-dimethylhexane D) S-4,5-dimethylhexane Answer: A Difficulty: 2 Medium Section: 05.06 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 74) Give the IUPAC name for the following compound:

A) (1R,3R)-1-ethyl-3-methylcyclohexane B) (1R,3S)-1-ethyl-3-methylcyclohexane C) (1S,3R)-1-ethyl-3-methylcyclohexane D) (1S,3S)-1-ethyl-3-methylcyclohexane Answer: A Difficulty: 3 Hard Section: 05.09 Bloom's: 4. Analyze Chapter: 05

75) Give the IUPAC name for the following compound:

A) (1R,3R)-1-ethyl-3-methylcyclohexane B) (1R,3S)-1-ethyl-3-methylcyclohexane C) (1S,3R)-1-ethyl-3-methylcyclohexane D) (1S,3S)-1-ethyl-3-methylcyclohexane Answer: D Difficulty: 3 Hard Section: 05.09 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05 76) Give the IUPAC name for the following compound:

A) (1R,2R)-1,2-dimethylcyclopentane B) (1R,2S)-1,2-dimethylcyclopentane C) (1S,2R)-1,2-dimethylcyclopentane D) (1S,2S)-1,2-dimethylcyclopentane Answer: A Difficulty: 3 Hard Section: 05.09 Topic: Stereochemistry Bloom's: 4. Analyze Chapter: 05

Organic Chemistry, 6e (Smith) Chapter 6 Understanding Organic Reactions 1) Which of the following statements about substitution reactions is true? A) Substitution reactions involve π bonds. B) Substitution reactions involve σ bonds. C) One σ bond breaks and another forms at a different carbon atom. D) One π bond breaks and another forms at the same carbon atom. 2) What kind of reaction does the conversion of A to B represent?

A) Addition reaction B) Substitution reaction C) Elimination reaction D) Acid-base reaction 3) Which of the following statements about elimination reactions is true? A) Two σ bonds are broken. B) Two σ bonds are formed. C) Two π bonds are broken. D) Two π bonds are formed. 4) What kind of reaction does the conversion of A to B represent?

A) Addition reaction B) Elimination reaction C) Substitution reaction D) Oxidation-reduction reaction 5) Which of the following statements about addition reactions is true? A) Two π bonds are formed. B) Two π bonds are broken. C) Two σ bonds are formed. D) One π bond is formed.

6) What kind of reaction does the conversion of A to B represent?

A) Acid-base reaction B) Elimination reaction C) Substitution reaction D) Addition reaction 7) Which of the following statements about bond breaking is true? A) Homolysis and heterolysis require energy. B) In homolysis, the electrons in the bond are divided unequally. C) In heterolysis, the electrons in the bond are divided equally. D) Homolysis generates charged intermediates. 8) Which of the following statements about bond breaking is not true? A) Homolysis generates uncharged reactive intermediates with unpaired electrons. B) Homolysis require energy but heterolysis does not require energy. C) Heterolysis generates charged intermediates. D) Heterolysis involves unequal sharing of bonding electrons by atoms. 9) Which of the following statements is true? A) Ionic intermediates are formed in radical reactions. B) Radicals are intermediates in polar reactions. C) Carbocations are electrophiles. D) Radicals are nucleophiles. 10) Which of the following statements is not true? A) In polar reactions, a nucleophile reacts with an electrophile. B) Carbocations are electrophiles. C) Carbanions are nucleophiles. D) A half-headed curved arrow shows the movement of an electron pair. 11) Which of the following statements is not true? A) Bond breaking is endothermic. B) The bond dissociation energy for bond breaking is always negative. C) Bond making is exothermic. D) The bond dissociation energy for bond formation is always negative.

12) Which of the following statements is true? A) Bond dissociation energies increase down a column of the periodic table. B) When DH° is positive, more energy is released in forming bonds than is needed to break bonds. C) When DH° is negative, more energy is needed to break bonds than is released in forming bonds. D) Bond dissociation energies decrease down a column of the periodic table. 13) Using the bond dissociation energies given, calculate DH° for the following reaction.

Bond A-B (CH3)3C-Cl

DH° KJ/mol 331

H-OH (CH3)3C-OH

498 401

H-Cl

431

A) +3 KJ/mol B) -3 KJ/mol C) -67 KJ/mol D) +70 KJ/mol 14) Using the bond dissociation energies given, calculate DH° for the following reaction.

Bond A-B CH3CH2-Br

DH° KJ/mol 285

H-OH CH3CH2-OH

498 393

H-Br

368

A) +108 KJ/mol B) -130 KJ/mol C) -22 KJ/mol D) +22 KJ/mol

15) Which of the following statements about the equilibrium constant, Keq, is true? A) When Keq > 1, the equilibrium favors the reactants. B) When Keq < 1, the equilibrium favors the products. C) The size of Keq tells about the position of equilibrium. D) For a reaction to be useful, the equilibrium must favor the reactants. 16) Which of the following statements about equilibrium is true? A) Equilibrium favors the products when the energy of the products is higher than the energy of the reactants. B) Equilibrium favors the reactants when the energy of the product is lower than the energy of the reactants. C) Equilibrium favors the products when they are less stable than the starting material of a reaction. D) Equilibrium favors the products when they are more stable than the starting material of a reaction. 17) Which of the following expressions summarizes the correct relationship between the free energy change, DG°, and the equilibrium constant, Keq? A) Keq > 1 when DG° > 0 B) Keq > 1 when DG° < 0 C) Keq < 1 when DG° < 0 D) Keq < 1 when DG° = 0 18) Which of the Keq corresponds to the lowest value of DG°? A) Keq = 10-3 B) Keq = 10-2 C) Keq = 10-1 D) DG° cannot be determined. 19) Which of the Keq corresponds to the highest value of DG°? A) Keq = 10-1 B) Keq = 10-2 C) Keq = 10-3 D) Keq = 10-5 20) Which of the Keq corresponds to the most negative value of DG°? A) Keq = 1 B) Keq = 101 C) Keq = 102 D) Keq = 103 4 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

21) Which of the following statements is true? A) The product is favored in reaction in which DH° is a positive value. B) Entropy decreases when an acyclic compound forms a ring. C) In homolytic bond cleavage, entropy decreases and favors formation of products. D) The starting material is favored in a reaction in which DH° is a negative value. 22) Which of the following statements is true? A) The size of the activation energy tells us about the reaction mechanism. B) The size of the activation energy tells us about the reaction rate. C) A slow reaction has low activation energy. D) A fast reaction has high activation energy. 23) Which of the following statements is not true? A) Two reactions can have identical values for DH° but very different Ea values. B) The larger the activation energy, the slower the reaction. C) DH° determines the height of the energy barrier. D) The lower the activation energy, the faster the reaction. 24) What is the name given to the reaction species that lies at an energy minimum between steps on a reaction energy diagram? A) Transition state B) Activation energy C) Reactive intermediate D) Equilibrium product 25) Which of the following statements about a two-step reaction mechanism is true? A) The transition states are located at energy minima. B) Each step is characterized by its own value of DH° and Ea. C) The rate-determining step has the lower energy transition state. D) The reactive intermediate is located at an energy maximum. 26) Which reaction is fast and has Keq = 1?

A) A B) B C) C

27) Which reaction has a positive DG°, assuming that entropy changes are negligible compared to enthalpy changes?

A) A B) B C) C 28) Which reaction is slowest?

A) A B) B C) C 29) In which reaction is Keq > 1?

A) A B) B C) C

30) How many transition states are present in the reaction in the energy diagram?

A) 0 B) 1 C) 2 D) 3 31) Which of the following letters represents DH° for the forward reaction in the following energy diagram?

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

32) How many transition states and intermediates would the reaction profile have for the reaction shown below?

A) Three transition states and three intermediates B) Two transition states and two intermediates C) Three transition states and two intermediates D) Two transition states and three intermediates 33) Which step would most likely have the largest energy of activation?

A) Step one B) Step two C) Step three D) It cannot be determined from the information provided 34) A decrease in which of the following results in an increase in the rate of a chemical reaction? A) Energy of activation B) Concentration C) Temperature D) Kinetic energy 35) Which of the following reaction quantities will have an effect on reaction rate? A) DG° B) DH° C) Keq D) Ea

36) Which of the following statements is true? A) Fast reactions have small rate constants. B) Slow reactions have large rate constants. C) A rate equation contains concentration terms for all reactants involved in a one-step mechanism. D) A rate equation contains concentration terms for all the reactants involved in a multi-step reaction. 37) The equilibrium constant for the conversion of A to D is predicted to be which of the following?

A) Keq = 1 B) Keq < 1 C) Keq > 1 D) Cannot be determined from the information provided 38) The DG° (free energy change) for the conversion of A to B is predicted to be which of the following?

A) DG° = 0 B) DG° < 0 C) DG° > 0 D) Cannot be determined from the information provided 39) What kind of reaction does the conversion of A to D represent?

A) Addition reaction B) Substitution reaction C) Elimination reaction D) Oxidation-reduction reaction 9 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

40) If the conversion of A to B is slow and B to C is fast, what is the rate equation for this reaction?

A) Rate = k[(CH3)2CHCl][H2O] B) Rate = k[(CH3)2CHCl] C) Rate = k[(CH3)2CH]+[H2O] D) Rate = k[(CH3)2CH]+ 41) Which compound would you predict to be highest in energy?

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

42) Calculate Ea for the conversion of C ® B.

Ea (A ® B) = +10 kcal Ea (B ® C) = +4 kcal DH (A ® B) = +8 kcal DH (B ® C) = -5 kcal A) +3 kcal B) +7 kcal C) +9 kcal D) None of these 43) The following is an energy diagram for the conversion of A ® B ® C. The energies of activation and DH's for each step are also given. Calculate DH overall as shown on the energy diagram for A ® B ® C.

Ea (A ® B) = +10 kcal Ea (B ® C) = +4 kcal DH (A ® B) = +8 kcal DH (B ® C) = -5 kcal A) +3 kcal B) +7 kcal C) +9 kcal D) None of these 11 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

44) Which of the following statements about a catalyst is true? A) A catalyst accelerates a reaction by changing the amount of reactant and product at equilibrium. B) A catalyst accelerates a reaction by lowering the energy of activation. C) A catalyst accelerates a reaction by raising the energy of activation. D) A catalyst accelerates a reaction by lowering the equilibrium constant. 45) Which of the following statements about enzymes is true? A) Enzymes increase the activation energy for a reaction. B) Enzymes decrease the equilibrium constant. C) Enzymes shift the equilibrium to favor the product. D) Enzymes lower the transition state for the rate-determining step. 46) For which of the following reactions is ΔS° a positive value?

A) I B) II C) III D) IV 47) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

48) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

If the concentration of -OCH3 were increased 5 times, what would happen to the rate of the reaction? A) Rate would become one fifth B) Rate would increase 25 times C) Rate would increase 5 times D) Rate would remain unchanged 49) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

If the concentrations of both -OCH3 and acetyl chloride were increased 2 times, what would happen to the rate of the reaction? A) Rate would become one-fourth B) Rate would increase 4 times C) Rate would increase 16 times D) Rate would increase 2 times 50) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

The conversion of acetyl chloride to methyl acetate would be classified as which of the following? A) Addition B) Elimination C) Substitution D) None of these 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

51) The symbol hν stands for ________ in a chemical reaction. A) light B) heat C) reactant D) product 52) The symbol Δ stands for ________ in a chemical reaction. A) light B) heat C) reactant D) product 53) What type of bond cleavage takes place in/what type of intermediate is produced in the following reaction?

A) Homolysis/Radical B) Homolysis/Carbocation C) Heterolysis/Carbocation D) Heterolysis/Carbanion 54) What type of bond cleavage takes place in/what type of intermediate is produced in the following reaction?

A) Homolysis/Radical B) Homolysis/Carbocation C) Heterolysis/Carbocation D) Heterolysis/Carbanion

55) What type of reaction does the following conversion represent?

A) Addition reaction B) Elimination reaction C) Substitution reaction D) Oxidation-reduction reaction

Organic Chemistry, 6e (Smith) Chapter 6 Understanding Organic Reactions 1) Which of the following statements about substitution reactions is true? A) Substitution reactions involve π bonds. B) Substitution reactions involve σ bonds. C) One σ bond breaks and another forms at a different carbon atom. D) One π bond breaks and another forms at the same carbon atom. Answer: B Difficulty: 1 Easy Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 2) What kind of reaction does the conversion of A to B represent?

A) Addition reaction B) Substitution reaction C) Elimination reaction D) Acid-base reaction Answer: B Difficulty: 1 Easy Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06

3) Which of the following statements about elimination reactions is true? A) Two σ bonds are broken. B) Two σ bonds are formed. C) Two π bonds are broken. D) Two π bonds are formed. Answer: A Difficulty: 1 Easy Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 4) What kind of reaction does the conversion of A to B represent?

A) Addition reaction B) Elimination reaction C) Substitution reaction D) Oxidation-reduction reaction Answer: B Difficulty: 1 Easy Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 5) Which of the following statements about addition reactions is true? A) Two π bonds are formed. B) Two π bonds are broken. C) Two σ bonds are formed. D) One π bond is formed. Answer: C Difficulty: 1 Easy Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 2 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

6) What kind of reaction does the conversion of A to B represent?

A) Acid-base reaction B) Elimination reaction C) Substitution reaction D) Addition reaction Answer: D Difficulty: 1 Easy Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 7) Which of the following statements about bond breaking is true? A) Homolysis and heterolysis require energy. B) In homolysis, the electrons in the bond are divided unequally. C) In heterolysis, the electrons in the bond are divided equally. D) Homolysis generates charged intermediates. Answer: A Difficulty: 1 Easy Section: 06.03 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 8) Which of the following statements about bond breaking is not true? A) Homolysis generates uncharged reactive intermediates with unpaired electrons. B) Homolysis require energy but heterolysis does not require energy. C) Heterolysis generates charged intermediates. D) Heterolysis involves unequal sharing of bonding electrons by atoms. Answer: B Difficulty: 1 Easy Section: 06.03 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

9) Which of the following statements is true? A) Ionic intermediates are formed in radical reactions. B) Radicals are intermediates in polar reactions. C) Carbocations are electrophiles. D) Radicals are nucleophiles. Answer: C Difficulty: 1 Easy Section: 06.03 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 10) Which of the following statements is not true? A) In polar reactions, a nucleophile reacts with an electrophile. B) Carbocations are electrophiles. C) Carbanions are nucleophiles. D) A half-headed curved arrow shows the movement of an electron pair. Answer: D Difficulty: 1 Easy Section: 06.03 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 11) Which of the following statements is not true? A) Bond breaking is endothermic. B) The bond dissociation energy for bond breaking is always negative. C) Bond making is exothermic. D) The bond dissociation energy for bond formation is always negative. Answer: B Difficulty: 1 Easy Section: 06.04 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation

12) Which of the following statements is true? A) Bond dissociation energies increase down a column of the periodic table. B) When DH° is positive, more energy is released in forming bonds than is needed to break bonds. C) When DH° is negative, more energy is needed to break bonds than is released in forming bonds. D) Bond dissociation energies decrease down a column of the periodic table. Answer: D Difficulty: 1 Easy Section: 06.04 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 13) Using the bond dissociation energies given, calculate DH° for the following reaction.

Bond A-B (CH3)3C-Cl

DH° KJ/mol 331

H-OH (CH3)3C-OH

498 401

H-Cl

431

A) +3 KJ/mol B) -3 KJ/mol C) -67 KJ/mol D) +70 KJ/mol Answer: B Difficulty: 2 Medium Section: 06.04 Topic: Chemical Reactions Bloom's: 5. Evaluate Chapter: 06

14) Using the bond dissociation energies given, calculate DH° for the following reaction.

Bond A-B CH3CH2-Br

DH° KJ/mol 285

H-OH CH3CH2-OH

498 393

H-Br

368

A) +108 KJ/mol B) -130 KJ/mol C) -22 KJ/mol D) +22 KJ/mol Answer: D Difficulty: 2 Medium Section: 06.04 Topic: Chemical Reactions Bloom's: 5. Evaluate Chapter: 06 15) Which of the following statements about the equilibrium constant, Keq, is true? A) When Keq > 1, the equilibrium favors the reactants. B) When Keq < 1, the equilibrium favors the products. C) The size of Keq tells about the position of equilibrium. D) For a reaction to be useful, the equilibrium must favor the reactants. Answer: C Difficulty: 1 Easy Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation

16) Which of the following statements about equilibrium is true? A) Equilibrium favors the products when the energy of the products is higher than the energy of the reactants. B) Equilibrium favors the reactants when the energy of the product is lower than the energy of the reactants. C) Equilibrium favors the products when they are less stable than the starting material of a reaction. D) Equilibrium favors the products when they are more stable than the starting material of a reaction. Answer: D Difficulty: 1 Easy Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 17) Which of the following expressions summarizes the correct relationship between the free energy change, DG°, and the equilibrium constant, Keq? A) Keq > 1 when DG° > 0 B) Keq > 1 when DG° < 0 C) Keq < 1 when DG° < 0 D) Keq < 1 when DG° = 0 Answer: B Difficulty: 1 Easy Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation

18) Which of the Keq corresponds to the lowest value of DG°? A) Keq = 10-3 B) Keq = 10-2 C) Keq = 10-1 D) DG° cannot be determined. Answer: C Difficulty: 1 Easy Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 19) Which of the Keq corresponds to the highest value of DG°? A) Keq = 10-1 B) Keq = 10-2 C) Keq = 10-3 D) Keq = 10-5 Answer: D Difficulty: 1 Easy Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 20) Which of the Keq corresponds to the most negative value of DG°? A) Keq = 1 B) Keq = 101 C) Keq = 102 D) Keq = 103 Answer: D Difficulty: 1 Easy Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation

21) Which of the following statements is true? A) The product is favored in reaction in which DH° is a positive value. B) Entropy decreases when an acyclic compound forms a ring. C) In homolytic bond cleavage, entropy decreases and favors formation of products. D) The starting material is favored in a reaction in which DH° is a negative value. Answer: B Difficulty: 2 Medium Section: 06.06 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 22) Which of the following statements is true? A) The size of the activation energy tells us about the reaction mechanism. B) The size of the activation energy tells us about the reaction rate. C) A slow reaction has low activation energy. D) A fast reaction has high activation energy. Answer: B Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 23) Which of the following statements is not true? A) Two reactions can have identical values for DH° but very different Ea values. B) The larger the activation energy, the slower the reaction. C) DH° determines the height of the energy barrier. D) The lower the activation energy, the faster the reaction. Answer: C Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation

24) What is the name given to the reaction species that lies at an energy minimum between steps on a reaction energy diagram? A) Transition state B) Activation energy C) Reactive intermediate D) Equilibrium product Answer: C Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 25) Which of the following statements about a two-step reaction mechanism is true? A) The transition states are located at energy minima. B) Each step is characterized by its own value of DH° and Ea. C) The rate-determining step has the lower energy transition state. D) The reactive intermediate is located at an energy maximum. Answer: B Difficulty: 1 Easy Section: 06.08 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation

26) Which reaction is fast and has Keq = 1?

A) A B) B C) C Answer: B Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 27) Which reaction has a positive DG°, assuming that entropy changes are negligible compared to enthalpy changes?

A) A B) B C) C Answer: A Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06

28) Which reaction is slowest?

A) A B) B C) C Answer: A Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 29) In which reaction is Keq > 1?

A) A B) B C) C Answer: C Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06

30) How many transition states are present in the reaction in the energy diagram?

A) 0 B) 1 C) 2 D) 3 Answer: C Difficulty: 1 Easy Section: 06.08 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 31) Which of the following letters represents DH° for the forward reaction in the following energy diagram?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

32) How many transition states and intermediates would the reaction profile have for the reaction shown below?

A) Three transition states and three intermediates B) Two transition states and two intermediates C) Three transition states and two intermediates D) Two transition states and three intermediates Answer: C Difficulty: 1 Easy Section: 06.08 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 33) Which step would most likely have the largest energy of activation?

A) Step one B) Step two C) Step three D) It cannot be determined from the information provided Answer: A Difficulty: 1 Easy Section: 06.08 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06

34) A decrease in which of the following results in an increase in the rate of a chemical reaction? A) Energy of activation B) Concentration C) Temperature D) Kinetic energy Answer: A Difficulty: 1 Easy Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 35) Which of the following reaction quantities will have an effect on reaction rate? A) DG° B) DH° C) Keq D) Ea Answer: D Difficulty: 1 Easy Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation 36) Which of the following statements is true? A) Fast reactions have small rate constants. B) Slow reactions have large rate constants. C) A rate equation contains concentration terms for all reactants involved in a one-step mechanism. D) A rate equation contains concentration terms for all the reactants involved in a multi-step reaction. Answer: C Difficulty: 1 Easy Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 Accessibility: Keyboard Navigation

37) The equilibrium constant for the conversion of A to D is predicted to be which of the following?

A) Keq = 1 B) Keq < 1 C) Keq > 1 D) Cannot be determined from the information provided Answer: C Difficulty: 2 Medium Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 38) The DG° (free energy change) for the conversion of A to B is predicted to be which of the following?

A) DG° = 0 B) DG° < 0 C) DG° > 0 D) Cannot be determined from the information provided Answer: C Difficulty: 2 Medium Section: 06.05 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06

39) What kind of reaction does the conversion of A to D represent?

A) Addition reaction B) Substitution reaction C) Elimination reaction D) Oxidation-reduction reaction Answer: C Difficulty: 2 Medium Section: 06.02 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 40) If the conversion of A to B is slow and B to C is fast, what is the rate equation for this reaction?

A) Rate = k[(CH3)2CHCl][H2O] B) Rate = k[(CH3)2CHCl] C) Rate = k[(CH3)2CH]+[H2O] D) Rate = k[(CH3)2CH]+ Answer: B Difficulty: 2 Medium Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06

41) Which compound would you predict to be highest in energy?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 42) Calculate Ea for the conversion of C ® B.

Ea (A ® B) = +10 kcal Ea (B ® C) = +4 kcal DH (A ® B) = +8 kcal DH (B ® C) = -5 kcal A) +3 kcal B) +7 kcal C) +9 kcal D) None of these Answer: C Difficulty: 2 Medium Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 18 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

43) The following is an energy diagram for the conversion of A ® B ® C. The energies of activation and DH's for each step are also given. Calculate DH overall as shown on the energy diagram for A ® B ® C.

Ea (A ® B) = +10 kcal Ea (B ® C) = +4 kcal DH (A ® B) = +8 kcal DH (B ® C) = -5 kcal A) +3 kcal B) +7 kcal C) +9 kcal D) None of these Answer: A Difficulty: 2 Medium Section: 06.07 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 44) Which of the following statements about a catalyst is true? A) A catalyst accelerates a reaction by changing the amount of reactant and product at equilibrium. B) A catalyst accelerates a reaction by lowering the energy of activation. C) A catalyst accelerates a reaction by raising the energy of activation. D) A catalyst accelerates a reaction by lowering the equilibrium constant. Answer: B Difficulty: 1 Easy Section: 06.10 Topic: Chemical Reactions Bloom's: 1. Remember Chapter: 06 Accessibility: Keyboard Navigation

45) Which of the following statements about enzymes is true? A) Enzymes increase the activation energy for a reaction. B) Enzymes decrease the equilibrium constant. C) Enzymes shift the equilibrium to favor the product. D) Enzymes lower the transition state for the rate-determining step. Answer: D Difficulty: 1 Easy Section: 06.11 Topic: Chemical Reactions Bloom's: 1. Remember Chapter: 06 Accessibility: Keyboard Navigation 46) For which of the following reactions is ΔS° a positive value?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 06.06 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06

47) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

What is the rate equation for this reaction if the first step is rate determining? A) Rate = k [acetyl chloride] [-OCH3] B) Rate = k [acetyl chloride] C) Rate = k [-OCH3] D) Rate = k [acetyl chloride] [-OCH3]2 Answer: A Difficulty: 2 Medium Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 48) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

If the concentration of -OCH3 were increased 5 times, what would happen to the rate of the reaction? A) Rate would become one fifth B) Rate would increase 25 times C) Rate would increase 5 times D) Rate would remain unchanged Answer: C Difficulty: 1 Easy Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06

49) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

If the concentrations of both -OCH3 and acetyl chloride were increased 2 times, what would happen to the rate of the reaction? A) Rate would become one-fourth B) Rate would increase 4 times C) Rate would increase 16 times D) Rate would increase 2 times Answer: B Difficulty: 1 Easy Section: 06.09 Topic: Chemical Reactions Bloom's: 3. Apply Chapter: 06 50) The conversion of acetyl chloride to methyl acetate occurs via the following two-step mechanism:

The conversion of acetyl chloride to methyl acetate would be classified as which of the following? A) Addition B) Elimination C) Substitution D) None of these Answer: C Difficulty: 2 Medium Section: 06.02 Topic: Chemical Reactions Bloom's: 2. Understand; 3. Apply Chapter: 06

51) The symbol hν stands for ________ in a chemical reaction. A) light B) heat C) reactant D) product Answer: A Difficulty: 1 Easy Section: 06.01 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation 52) The symbol Δ stands for ________ in a chemical reaction. A) light B) heat C) reactant D) product Answer: B Difficulty: 1 Easy Section: 06.01 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 Accessibility: Keyboard Navigation

53) What type of bond cleavage takes place in/what type of intermediate is produced in the following reaction?

A) Homolysis/Radical B) Homolysis/Carbocation C) Heterolysis/Carbocation D) Heterolysis/Carbanion Answer: C Difficulty: 2 Medium Section: 06.03 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06 54) What type of bond cleavage takes place in/what type of intermediate is produced in the following reaction?

A) Homolysis/Radical B) Homolysis/Carbocation C) Heterolysis/Carbocation D) Heterolysis/Carbanion Answer: A Difficulty: 2 Medium Section: 06.03 Topic: Chemical Reactions Bloom's: 2. Understand Chapter: 06

55) What type of reaction does the following conversion represent?

Organic Chemistry, 6e (Smith) Chapter 7 Alkyl Halides and Nucleophilic Substitution 1) Which of the following alkyl halides is a primary alkyl halide?

A) I B) II C) III D) IV 2) Which of the following alkyl halides is a secondary alkyl halide?

A) I B) II C) III D) IV 3) Which of the following alkyl halides is a tertiary alkyl halide?

A) I B) II C) III D) IV

4) Which of the following alkyl halides is a vinyl alkyl halide?

A) I B) II C) III D) IV 5) Which of the following structures have the correct common name?

A) I and II B) II and IV C) II and III D) III and IV 6) Which of the following structures have the correct common name?

A) I and II B) II and III C) I and III D) III and IV

7) Which of the following structures have the correct common name?

A) I and II B) II and III C) II and IV D) III and IV 8) What is the IUPAC name of the following compound?

A) 2-Methyl-4-chloropentane B) 2-Chloro-4-methylpentane C) 2-Chloro-1-isopropylpropane D) 2-Chloro-2-methylpentane 9) What is the IUPAC name of the following compound?

A) 2-Bromo-5-methyloctane B) 2-Bromo-3-methylheptane C) 2-Bromo-5-methylheptane D) 6-Bromo-3-methylheptane

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

A) 2-Bromo-5,5-dimethylheptane B) 3,3-Dimethyl-6-bromoheptane C) 6-Bromo-3,3-dimethylheptane D) 2-Bromo-5,5-dimethyloctane 11) What is the IUPAC name of the following compound?

A) (R)-3-Chloro-6-ethyloctane B) (S)-3-Chloro-6-ethyloctane C) (S)-6-Chloro-3-ethyloctane D) (R)-6-Chloro-3-ethyloctane

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

A) trans-4-Methylcyclohexyl chloride B) trans-p-Chloromethylcyclohexane C) trans-4-Methyl-1-chlorocyclohexane D) trans-1-Chloro-4-methylcyclohexane 14) What is the IUPAC name of the following compound?

A) (R)-3-Bromo-1-methylcyclohexene B) (S)-3-Bromo-1-methylcyclohexene C) (S)-1-Bromo-3-methyl-2-cyclohexene D) (R)-1-Bromo-3-methyl-2-cyclohexene 15) What is the IUPAC name of the following compound?

A) (E)-2-Bromo-3,4-dimethyl-2-pentene B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene C) (Z)-2-Bromo-3,4-dimethyl-2-pentene D) (E)-1-Bromo-1,2,3-trimethyl-1-butene

16) Rank the following halides in order of decreasing polarity, putting the most polar first.

A) II > IV > I > III B) IV > II > I > III C) I > II > III > IV D) IV > III > II > I 17) Rank the following molecules in order of increasing polarity, putting the least polar first.

A) IV < III < II < I B) I < IV < III < II C) I < II < III < IV D) II < I < III < IV 18) Which of the following statements about the reactions of alkyl halides is true? A) The characteristic reactions of alkyl halides are addition and elimination. B) The characteristic reactions of alkyl halides are addition and substitution. C) The characteristic reactions of alkyl halides are elimination and substitution. D) The characteristic reactions of alkyl halides are oxidation and reduction. 19) Which of the following statements is true? A) All good leaving groups are strong bases with weak conjugate acids. B) Left-to-right across a row of the periodic table, leaving group ability decreases. C) Down a column of the periodic table, leaving group ability decreases. D) The conjugate bases of strong acids are good leaving groups. 20) Rank the following in order of decreasing leaving group ability, putting the best first.

A) III > II > IV > I B) III > II > I > IV C) IV > I > II > III D) II > III > I > IV 6 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

21) Which of the following statements is not true? A) All good leaving groups are weak bases with strong conjugate acids. B) Left-to-right across a row of the periodic table, leaving group ability increases. C) Down a column of the periodic table, leaving group ability increases. D) Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile. 22) Rank the following in order of increasing leaving group ability, putting the worst leaving group first.

A) IV < II < III < I B) III < IV < I < II C) II < IV < I < III D) I < III < II < IV 23) Which of the following statements is not true? A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. C) Sterically hindered bases are also called nonnucleophilic bases. D) Steric hindrance decreases basicity but not nucleophilicity. 24) Which of the following statements is not true? A) In polar protic solvents, nucleophilicity decreases down a column of the periodic table as the size of the anion increases. B) Nucleophilicity is affected by the solvent used in a substitution reaction. C) Polar protic solvents are capable of intermolecular hydrogen bonding. D) Polar protic solvents solvate both cations and anions. 25) Which of the following solvents is not a polar protic solvent?

A) I B) II C) III D) IV

26) Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.

A) I < II < III < IV B) IV < III < II < I C) I < II < IV < III D) IV < III < I < II 27) Which of the following anions is the most nucleophilic in polar aprotic solvents? A) FB) ClC) BrD) I28) Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first.

A) II > III > I > IV B) III > II > IV > I C) II > III > IV > I D) III > II > I > IV 29) Which of the following is the most nucleophilic? A) CH4 B) H2O C) NH3 D) HF

30) Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.

A) II < IV < I < III B) IV < III < II < I C) III < IV < I < II D) II < I < IV < III 31) The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate. What is the effect of doubling the concentration of sodium acetate on the rate of the reaction? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. 32) The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1butanol. What would happen to the rate of the reaction if the concentration of both 1bromobutane and sodium hydroxide were doubled? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. 33) The reaction of tert-butyl bromide, (CH3)3CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH3)3COCH2CH3, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. 34) Which of the following statements about SN2 reactions is true? A) The rate of reaction is dependent on just the substrate. B) The fastest reaction will occur with a tertiary alkyl halide. C) The mechanism is a two-step process. D) Displacement occurs with inversion of configuration.

A) I > II > III B) II > I > III C) III > I > II D) I > III > II 39) Given the following substitution reaction, what would be the effect of changing the solvent from CH3OH to (CH3)2S=O? CH3(CH2)5Br + NaOH ® CH3(CH2)5OH + BrA) The rate would decrease because SN1 reactions are favored by polar protic solvents. B) The rate would increase because SN2 reactions are favored by polar aprotic solvents. C) The rate would increase because SN1 reactions are favored by polar protic solvents. D) The rate would decrease because SN2 reactions are favored by polar aprotic solvents.

40) Which of the following is a polar aprotic solvent?

A) I B) II C) III D) IV 41) Which of the following statements about an SN1 reaction mechanism is true? A) The reaction is fastest with primary alkyl halide. B) The reaction exhibits a one-step mechanism. C) The reaction rate increases as the leaving group ability increases. D) The reaction rate increases as the strength of the nucleophile increases. 42) Which of the following statements about an SN1 reaction mechanism is true? A) The reaction involves two steps and occurs fastest with primary alkyl halides. B) The reaction involves one step and occurs fastest with primary alkyl halides. C) The reaction involves one step and occurs fastest with tertiary alkyl halides. D) The reaction involves two steps and occurs fastest with tertiary alkyl halides. 43) Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism?

A) I B) II C) III D) IV 44) What is the rate-determining step of an SN1 reaction mechanism? A) Reaction of the nucleophile with the carbocation to form the product. B) Breaking the bond between the carbon and the leaving group to generate a carbocation. C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. D) None of these.

45) Which of the following rate laws describes the kinetics of an SN1 reaction? A) Rate = k[alkyl halide] B) Rate = k[alkyl halide][nucleophile] C) Rate = k[nucleophile] D) Rate = k[solvent] 46) Which of the following carbocations is the most stable?

A) I B) II C) III D) IV 47) Rank the following carbocations in order of decreasing stability, putting the most stable first.

A) I > II > III B) II > I > III C) III > I > II D) III > II > I 48) Which of the following is not a characteristic of an SN1 reaction? A) The rate is proportional to the concentration of substrate. B) The reaction is favored in polar protic solvents. C) The rate is independent of the concentration of the nucleophile. D) The electrophilic carbon undergoes inversion of stereochemistry. 49) Which of the following statements about carbocation stability is true? A) Carbocations are stabilized by electron-withdrawing inductive effects only. B) Carbocations are stabilized by electron-withdrawing inductive effects and hyperconjugation. C) Carbocations are stabilized by electron-donating inductive effects only. D) Carbocations are stabilized by electro-donating inductive effects and hyperconjugation.

50) Which of the following statements about the Hammond postulate is not true? A) The Hammond postulate provides a quantitative estimate of the energy of a transition state. B) In endothermic reactions, the transition state is closer in energy to the products. C) In exothermic reactions, the transition state is closer in energy to the reactants. D) The Hammond postulate provides a qualitative estimate of the energy of a transition state. 51) Which of the following statements about the Hammond postulate is true? A) In an exothermic reaction, lowering the energy of the transition state increases the activation energy, Ea. B) In an endothermic reaction, the more stable product forms faster. C) In an endothermic reaction, the less stable product forms faster. D) In an endothermic reaction, the activation energy, Ea, is similar for both products. 52) The reaction of what nucleophile and substrate is represented by the following transition state?

A) Methanol with 2-bromopropane B) Methoxide with 2-bromopropane C) Methoxide with 1-bromopropane D) Methanol with 1-bromopropane 53) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.

A) SN1, CH3OH B) SN1, DMSO C) SN2, CH3OH D) SN2, DMSO

54) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.

A) SN1, H2O B) SN1, DMF C) SN2, H2O D) SN2, DMF 55) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.

A) SN1, CH3OH B) SN1, HMPA C) SN2, CH3OH D) SN2, HMPA 56) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

57) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None 58) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

59) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None 60) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

61) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None 62) What is the starting material in the reaction shown below?

A) I B) II C) III D) IV

63) What is the starting material in the reaction shown below?

A) I B) II C) III D) IV 64) Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism? A) They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and stronger. B) They don't undergo SN2 reactions because a higher percent s-character makes the bond shorter and stronger. C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. D) They don't undergo SN1 reactions because the carbocation is highly electronegative. 65) Which of the following alkyl halides would react the fastest with –OH in SN2 reaction? CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I A) CH3CH2Br B) CH3CH2Cl C) CH3CH2F D) CH3CH2I 66) Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and –OCH3. A) CH2CH2OH B) CH3OH C) DMSO D) H2O

67) Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br, (CH3)2CHCH2Br, CH3CH2CH(CH3)Br, (CH3)3CBr A) CH3CH2CH2CH2Br B) (CH3)2CHCH2Br C) CH3CH2CH(CH3)Br D) (CH3)3CBr 68) Rank the following compounds in order of increasing SN2 reactivity?

A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV 69) Rank the following compounds in order of increasing SN1 reactivity?

A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV 70) What is the IUPAC name of the following compound?

A) (3R,4R)-3-chloro-4-methylhexane B) (3R,4S)-3-chloro-4-methylhexane C) (3S,4R)-3-chloro-4-methylhexane D) (3S,4S)-3-chloro-4-methylhexane 19 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) (1R,3R)-1-bromo-3-isopropylcyclopentane B) (1R,3S)-1-bromo-3-isopropylcyclopentane C) (1S,3R)-1-bromo-3-isopropylcyclopentane D) (1S,3S)-1-bromo-3-isopropylcyclopentane 72) Identify the nucleophile and type of substitution reaction in the following:

A) CN-, Sn1 B) CN-, Sn2 C) Br-, Sn1 D) Br-, Sn2 73) Which alkyl halide will form the most stable carbocation?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 7 Alkyl Halides and Nucleophilic Substitution 1) Which of the following alkyl halides is a primary alkyl halide?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 07.01 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 2) Which of the following alkyl halides is a secondary alkyl halide?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 07.01 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

3) Which of the following alkyl halides is a tertiary alkyl halide?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 07.01 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 4) Which of the following alkyl halides is a vinyl alkyl halide?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 07.01 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

5) Which of the following structures have the correct common name?

A) I and II B) II and IV C) II and III D) III and IV Answer: C Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 6) Which of the following structures have the correct common name?

A) I and II B) II and III C) I and III D) III and IV Answer: B Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

7) Which of the following structures have the correct common name?

A) I and II B) II and III C) II and IV D) III and IV Answer: D Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 8) What is the IUPAC name of the following compound?

A) 2-Methyl-4-chloropentane B) 2-Chloro-4-methylpentane C) 2-Chloro-1-isopropylpropane D) 2-Chloro-2-methylpentane Answer: B Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

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

A) 2-Bromo-5-methyloctane B) 2-Bromo-3-methylheptane C) 2-Bromo-5-methylheptane D) 6-Bromo-3-methylheptane Answer: C Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 10) What is the IUPAC name of the following compound?

A) 2-Bromo-5,5-dimethylheptane B) 3,3-Dimethyl-6-bromoheptane C) 6-Bromo-3,3-dimethylheptane D) 2-Bromo-5,5-dimethyloctane Answer: A Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

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

A) 2-Chloro-4-isopropyl-2,6-dimethyloctane B) 2-Chloro-4-isopropyl-2,7-dimethylnonane C) 2,6-Dimethyl-2-chloro-4-isopropyloctane D) 7-Chloro-5-isopropyl-3,7-dimethyloctane Answer: A Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 12) What is the IUPAC name of the following compound?

A) (R)-3-Chloro-6-ethyloctane B) (S)-3-Chloro-6-ethyloctane C) (S)-6-Chloro-3-ethyloctane D) (R)-6-Chloro-3-ethyloctane Answer: B Difficulty: 1 Easy Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

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

A) trans-4-Methylcyclohexyl chloride B) trans-p-Chloromethylcyclohexane C) trans-4-Methyl-1-chlorocyclohexane D) trans-1-Chloro-4-methylcyclohexane Answer: D Difficulty: 2 Medium Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 14) What is the IUPAC name of the following compound?

A) (R)-3-Bromo-1-methylcyclohexene B) (S)-3-Bromo-1-methylcyclohexene C) (S)-1-Bromo-3-methyl-2-cyclohexene D) (R)-1-Bromo-3-methyl-2-cyclohexene Answer: B Difficulty: 2 Medium Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

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

A) (E)-2-Bromo-3,4-dimethyl-2-pentene B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene C) (Z)-2-Bromo-3,4-dimethyl-2-pentene D) (E)-1-Bromo-1,2,3-trimethyl-1-butene Answer: C Difficulty: 2 Medium Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 16) Rank the following halides in order of decreasing polarity, putting the most polar first.

A) II > IV > I > III B) IV > II > I > III C) I > II > III > IV D) IV > III > II > I Answer: D Difficulty: 1 Easy Section: 07.03 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

17) Rank the following molecules in order of increasing polarity, putting the least polar first.

A) IV < III < II < I B) I < IV < III < II C) I < II < III < IV D) II < I < III < IV Answer: B Difficulty: 1 Easy Section: 07.03 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 18) Which of the following statements about the reactions of alkyl halides is true? A) The characteristic reactions of alkyl halides are addition and elimination. B) The characteristic reactions of alkyl halides are addition and substitution. C) The characteristic reactions of alkyl halides are elimination and substitution. D) The characteristic reactions of alkyl halides are oxidation and reduction. Answer: C Difficulty: 1 Easy Section: 07.05 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 19) Which of the following statements is true? A) All good leaving groups are strong bases with weak conjugate acids. B) Left-to-right across a row of the periodic table, leaving group ability decreases. C) Down a column of the periodic table, leaving group ability decreases. D) The conjugate bases of strong acids are good leaving groups. Answer: D Difficulty: 1 Easy Section: 07.06 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 9 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

20) Rank the following in order of decreasing leaving group ability, putting the best first.

A) III > II > IV > I B) III > II > I > IV C) IV > I > II > III D) II > III > I > IV Answer: B Difficulty: 1 Easy Section: 07.07 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 21) Which of the following statements is not true? A) All good leaving groups are weak bases with strong conjugate acids. B) Left-to-right across a row of the periodic table, leaving group ability increases. C) Down a column of the periodic table, leaving group ability increases. D) Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile. Answer: D Difficulty: 2 Medium Section: 07.07 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

22) Rank the following in order of increasing leaving group ability, putting the worst leaving group first.

A) IV < II < III < I B) III < IV < I < II C) II < IV < I < III D) I < III < II < IV Answer: A Difficulty: 1 Easy Section: 07.07 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 23) Which of the following statements is not true? A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. C) Sterically hindered bases are also called nonnucleophilic bases. D) Steric hindrance decreases basicity but not nucleophilicity. Answer: D Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

24) Which of the following statements is not true? A) In polar protic solvents, nucleophilicity decreases down a column of the periodic table as the size of the anion increases. B) Nucleophilicity is affected by the solvent used in a substitution reaction. C) Polar protic solvents are capable of intermolecular hydrogen bonding. D) Polar protic solvents solvate both cations and anions. Answer: A Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 25) Which of the following solvents is not a polar protic solvent?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

26) Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.

A) I < II < III < IV B) IV < III < II < I C) I < II < IV < III D) IV < III < I < II Answer: A Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 27) Which of the following anions is the most nucleophilic in polar aprotic solvents? A) FB) ClC) BrD) IAnswer: A Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

28) Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first.

A) II > III > I > IV B) III > II > IV > I C) II > III > IV > I D) III > II > I > IV Answer: B Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 29) Which of the following is the most nucleophilic? A) CH4 B) H2O C) NH3 D) HF Answer: C Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

30) Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.

A) II < IV < I < III B) IV < III < II < I C) III < IV < I < II D) II < I < IV < III Answer: C Difficulty: 1 Easy Section: 07.08 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 31) The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate. What is the effect of doubling the concentration of sodium acetate on the rate of the reaction? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. Answer: C Difficulty: 1 Easy Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

32) The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1butanol. What would happen to the rate of the reaction if the concentration of both 1bromobutane and sodium hydroxide were doubled? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. Answer: D Difficulty: 2 Medium Section: 07.12 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 33) The reaction of tert-butyl bromide, (CH3)3CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH3)3COCH2CH3, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled? A) The rate remains the same. B) The rate decreases by a factor of 2. C) The rate increases by a factor of 2. D) The rate increases by a factor of 4. Answer: A Difficulty: 2 Medium Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 34) Which of the following statements about SN2 reactions is true? A) The rate of reaction is dependent on just the substrate. B) The fastest reaction will occur with a tertiary alkyl halide. C) The mechanism is a two-step process. D) Displacement occurs with inversion of configuration. Answer: D Difficulty: 1 Easy Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 16 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

35) Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true? A) Involves one step and occurs with retention of configuration. B) Involves two steps and occurs with inversion of configuration. C) Involves one step and occurs with inversion of configuration. D) Involves one step and occurs with racemization. Answer: C Difficulty: 1 Easy Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 36) Which compound is most likely to follow second-order kinetics in a substitution reaction? A) CH3Br B) (CH3)3CCH2Br C) CH3CH2Br D) (CH3)2CHBr Answer: A Difficulty: 1 Easy Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 37) Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide? A) 1-Iodobutane B) 1-Chlorobutane C) 1-Fluorobutane D) 1-Bromobutane Answer: A Difficulty: 1 Easy Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

38) Rank the alkyl halides in order of decreasing SN2 reactivity, putting the most reactive first.

A) I > II > III B) II > I > III C) III > I > II D) I > III > II Answer: B Difficulty: 1 Easy Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 39) Given the following substitution reaction, what would be the effect of changing the solvent from CH3OH to (CH3)2S=O? CH3(CH2)5Br + NaOH ® CH3(CH2)5OH + BrA) The rate would decrease because SN1 reactions are favored by polar protic solvents. B) The rate would increase because SN2 reactions are favored by polar aprotic solvents. C) The rate would increase because SN1 reactions are favored by polar protic solvents. D) The rate would decrease because SN2 reactions are favored by polar aprotic solvents. Answer: B Difficulty: 1 Easy Section: 07.10 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

40) Which of the following is a polar aprotic solvent?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 41) Which of the following statements about an SN1 reaction mechanism is true? A) The reaction is fastest with primary alkyl halide. B) The reaction exhibits a one-step mechanism. C) The reaction rate increases as the leaving group ability increases. D) The reaction rate increases as the strength of the nucleophile increases. Answer: C Difficulty: 1 Easy Section: 07.12 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

42) Which of the following statements about an SN1 reaction mechanism is true? A) The reaction involves two steps and occurs fastest with primary alkyl halides. B) The reaction involves one step and occurs fastest with primary alkyl halides. C) The reaction involves one step and occurs fastest with tertiary alkyl halides. D) The reaction involves two steps and occurs fastest with tertiary alkyl halides. Answer: D Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 43) Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

44) What is the rate-determining step of an SN1 reaction mechanism? A) Reaction of the nucleophile with the carbocation to form the product. B) Breaking the bond between the carbon and the leaving group to generate a carbocation. C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. D) None of these. Answer: B Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 45) Which of the following rate laws describes the kinetics of an SN1 reaction? A) Rate = k[alkyl halide] B) Rate = k[alkyl halide][nucleophile] C) Rate = k[nucleophile] D) Rate = k[solvent] Answer: A Difficulty: 1 Easy Section: 07.14 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 46) Which of the following carbocations is the most stable?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 21 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

47) Rank the following carbocations in order of decreasing stability, putting the most stable first.

A) I > II > III B) II > I > III C) III > I > II D) III > II > I Answer: A Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 48) Which of the following is not a characteristic of an SN1 reaction? A) The rate is proportional to the concentration of substrate. B) The reaction is favored in polar protic solvents. C) The rate is independent of the concentration of the nucleophile. D) The electrophilic carbon undergoes inversion of stereochemistry. Answer: D Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 49) Which of the following statements about carbocation stability is true? A) Carbocations are stabilized by electron-withdrawing inductive effects only. B) Carbocations are stabilized by electron-withdrawing inductive effects and hyperconjugation. C) Carbocations are stabilized by electron-donating inductive effects only. D) Carbocations are stabilized by electro-donating inductive effects and hyperconjugation. Answer: D Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

50) Which of the following statements about the Hammond postulate is not true? A) The Hammond postulate provides a quantitative estimate of the energy of a transition state. B) In endothermic reactions, the transition state is closer in energy to the products. C) In exothermic reactions, the transition state is closer in energy to the reactants. D) The Hammond postulate provides a qualitative estimate of the energy of a transition state. Answer: A Difficulty: 1 Easy Section: 07.14 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 51) Which of the following statements about the Hammond postulate is true? A) In an exothermic reaction, lowering the energy of the transition state increases the activation energy, Ea. B) In an endothermic reaction, the more stable product forms faster. C) In an endothermic reaction, the less stable product forms faster. D) In an endothermic reaction, the activation energy, Ea, is similar for both products. Answer: B Difficulty: 1 Easy Section: 07.14 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

52) The reaction of what nucleophile and substrate is represented by the following transition state?

A) Methanol with 2-bromopropane B) Methoxide with 2-bromopropane C) Methoxide with 1-bromopropane D) Methanol with 1-bromopropane Answer: B Difficulty: 1 Easy Section: 07.14 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 53) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.

A) SN1, CH3OH B) SN1, DMSO C) SN2, CH3OH D) SN2, DMSO Answer: A Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

54) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.

A) SN1, H2O B) SN1, DMF C) SN2, H2O D) SN2, DMF Answer: D Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 55) For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.

A) SN1, CH3OH B) SN1, HMPA C) SN2, CH3OH D) SN2, HMPA Answer: D Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

56) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

57) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None Answer: A Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

58) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None Answer: C Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 59) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None Answer: D Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 28 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

60) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None Answer: C Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 61) What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 29 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

62) What is the starting material in the reaction shown below?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

63) What is the starting material in the reaction shown below?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 64) Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism? A) They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and stronger. B) They don't undergo SN2 reactions because a higher percent s-character makes the bond shorter and stronger. C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. D) They don't undergo SN1 reactions because the carbocation is highly electronegative. Answer: B Difficulty: 2 Medium Section: 07.17 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation

65) Which of the following alkyl halides would react the fastest with –OH in SN2 reaction? CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I A) CH3CH2Br B) CH3CH2Cl C) CH3CH2F D) CH3CH2I Answer: D Difficulty: 2 Medium Section: 07.07 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 66) Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and –OCH3. A) CH2CH2OH B) CH3OH C) DMSO D) H2O Answer: C Difficulty: 2 Medium Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 67) Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br, (CH3)2CHCH2Br, CH3CH2CH(CH3)Br, (CH3)3CBr A) CH3CH2CH2CH2Br B) (CH3)2CHCH2Br C) CH3CH2CH(CH3)Br D) (CH3)3CBr Answer: D Difficulty: 2 Medium Section: 07.12 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 Accessibility: Keyboard Navigation 32 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

68) Rank the following compounds in order of increasing SN2 reactivity?

A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV Answer: B Difficulty: 2 Medium Section: 07.11 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 69) Rank the following compounds in order of increasing SN1 reactivity?

A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV Answer: D Difficulty: 2 Medium Section: 07.12 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

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

A) (3R,4R)-3-chloro-4-methylhexane B) (3R,4S)-3-chloro-4-methylhexane C) (3S,4R)-3-chloro-4-methylhexane D) (3S,4S)-3-chloro-4-methylhexane Answer: C Difficulty: 2 Medium Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07 71) What is the IUPAC name of the following compound?

A) (1R,3R)-1-bromo-3-isopropylcyclopentane B) (1R,3S)-1-bromo-3-isopropylcyclopentane C) (1S,3R)-1-bromo-3-isopropylcyclopentane D) (1S,3S)-1-bromo-3-isopropylcyclopentane Answer: A Difficulty: 2 Medium Section: 07.02 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 2. Understand Chapter: 07

72) Identify the nucleophile and type of substitution reaction in the following:

A) CN-, Sn1 B) CN-, Sn2 C) Br-, Sn1 D) Br-, Sn2 Answer: B Difficulty: 2 Medium Section: 07.15 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07 73) Which alkyl halide will form the most stable carbocation?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 07.13 Topic: Alkyl Halides and Nucleophilic Substitution Bloom's: 3. Apply Chapter: 07

Organic Chemistry, 6e (Smith) Chapter 8 Alkyl Halides and Elimination Reactions 1) Which of the following statements about an E1 mechanism is not true? A) It is a two-step process and has the same first step as an SN1 mechanism. B) It involves the formation of a carbocation from eliminating a good leaving group. C) A common competing reaction is rearrangement of a less stable carbocation to a more stable carbocation. D) The loss of a proton by the carbocation is a slow step. 2) How many unique β carbons are found in the alkyl halide below?

A) 1 B) 2 C) 3 D) 4 3) How many unique β carbons are found in the alkyl halide below?

A) 1 B) 2 C) 3 D) 4

4) Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents bonded to the double bond.

A) I = Disubstituted; II = trisubstituted; III = trisubstituted B) I = Monosubstituted; II = disubstituted; III = trisubstituted C) I = Disubstituted; II = disubstituted; III = trisubstituted D) I = Disubstituted; II = trisubstituted; III = disubstituted 5) Which of the following represents the rate law for an E2 reaction? A) Rate = k[alkyl halide] B) Rate = k[alkyl halide][base] C) Rate = k[alkyl halide]2 D) Rate = k[base]2 6) Which of the following statements about the mechanism of an E2 reaction is true? A) All bonds are broken and formed in multiple steps. B) The reaction is not concerted. C) Entropy favors the reactants of an E2 reaction. D) Entropy favors the products of an E2 reaction. 7) How many different E2 products can form from the dehydrohalogenation of 2-bromobutane? A) 1 B) 2 C) 3 D) 4

8) What is the major elimination product in the reaction of 1-bromobutane with potassium tertbutoxide in tert-butanol? A) cis-2-Butene B) 1-Butene C) trans-2-Butene D) Butanol 9) What is the major product of the following reaction?

A) I B) II C) III D) IV 10) Which of the following statements about the mechanism of an E2 reaction is not true? A) It is fastest with tertiary halides. B) It exhibits first-order kinetics. C) A better leaving group should make a faster reaction. D) All bonds are broken and formed in a single step. 11) What is the major elimination product obtained from the following reaction?

12) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV 13) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV

14) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV 15) Which of the following is the most reactive substrate in an E2 reaction?

A) I B) II C) III D) IV 16) Which of the following is the least reactive substrate in an E2 reaction?

A) I B) II C) III D) IV 17) Which of the following statements about an E1 mechanism is not true? A) The reaction is fastest with tertiary alkyl halides. B) A better leaving group makes the reaction rate increase. C) The reaction follows first-order kinetics. D) Stronger bases favor the E1 reaction. 5 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

A) I B) II C) III D) IV 20) Which of the following is the major elimination product of the following reaction?

A) I B) II C) III D) IV

21) Which of the following alkyl halides would afford the indicated product upon reaction with sodium methoxide?

A) I B) II C) III D) IV 22) Which of the following is the major E2 product formed from the following alkyl halide?

A) I B) II C) III D) IV

23) Which of the labeled protons in the compound below is most readily abstracted under E2 conditions?

A) Ha B) Hb C) Hc D) Hd 24) Which of the following alkyl halides will afford the product below as the major product in an E2 reaction?

A) I B) II C) III D) IV

25) What is the product of the following reaction?

A) I B) II C) III D) IV 26) What is the product of the following reaction?

A) I B) II C) III D) IV

27) What is the product of the following reaction?

A) I B) II C) III D) IV 28) What is the product of the following reaction?

A) Only I B) Only II C) Only III D) II and III 29) Which of the following is most likely to react as a base rather than a nucleophile?

30) Which of the following is most likely to react as a nucleophile rather than a base?

A) I B) II C) III D) IV 31) Which of the following is the dihalide that can be used to prepare the alkyne below?

A) Only I B) Only II C) Only III D) II and III 32) Which of the following is the dihalide that can be used to prepare the alkyne below?

A) I and II B) II and III C) I and III D) I, II, and III

33) Select the elimination product(s) formed by treating the indicated alkyl halide with a base.

A) Only I B) Only II C) Only III D) I, II, and III 34) What is (are) the product(s) of the following reaction?

A) I and II B) II and III C) I and III D) I, II, and III

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

A) Only I B) Only II C) Only III D) II and III 36) What is (are) the elimination product(s) of the following reaction?

A) Only I B) Only II C) Only III D) II and III

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

A) Only I B) Only II C) Only III D) II and III 38) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) I and II 39) What is (are) the product(s) of the following reaction?

40) What is (are) the starting material(s) in the reaction below?

A) Only I B) Only II C) Only III D) II and III 41) Which alkyl halide(s) would give the following alkene as the only product in an elimination reaction?

A) Only I B) Only II C) Only III D) I and II 42) What is the most likely mechanism for the reaction below?

43) What is the most likely mechanism for the reaction below?

A) SN1 B) SN2 C) E1 D) E2 44) Consider the following E2 reaction. What rate equation would be observed for this reaction?

A) Rate = k[CH3CH2CH2Br] B) Rate = k[CH3CH2CH2Br][KOC(CH3)3] C) Rate = k[CH3CH2CH2Br][KOC(CH3)3]2 D) Rate = k[CH3CH2CH2Br]2[KOC(CH3)3] 45) Which of the following alkenes is the most stable?

A) I B) II C) III D) IV

46) Which of the following alkyl chloride affords alkene A exclusively under E2 reaction condition?

A) I B) II C) III D) IV 47) Which of the following alkyl halide would react the fastest with –OH in E2 reaction?

A) I B) II C) III D) IV 48) Which of the following alkyl halide reacts the fastest in an E2 reaction?

A) I B) II C) III D) IV

49) Which of the following is the most stable alkene?

A) I B) II C) III D) IV 50) Which is the most likely mechanism for the following reaction?

A) SN1 B) SN2 C) E1 D) E2 51) What is the major product and likely mechanism for the following reaction?

A) I, E1 B) I, E2 C) II, E1 D) II, E2

52) What is the most likely mechanism for the following reaction?

A) SN1 B) SN2 C) E1 D) E2

Organic Chemistry, 6e (Smith) Chapter 8 Alkyl Halides and Elimination Reactions 1) Which of the following statements about an E1 mechanism is not true? A) It is a two-step process and has the same first step as an SN1 mechanism. B) It involves the formation of a carbocation from eliminating a good leaving group. C) A common competing reaction is rearrangement of a less stable carbocation to a more stable carbocation. D) The loss of a proton by the carbocation is a slow step. Answer: D Difficulty: 1 Easy Section: 08.01 Topic: Alkyl Halides and Elimination Reactions Bloom's: 2. Understand Chapter: 08 Accessibility: Keyboard Navigation 2) How many unique β carbons are found in the alkyl halide below?

A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 08.01 Topic: Alkyl Halides and Elimination Reactions Bloom's: 2. Understand Chapter: 08

3) How many unique β carbons are found in the alkyl halide below?

A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 08.01 Topic: Alkyl Halides and Elimination Reactions Bloom's: 2. Understand Chapter: 08

4) Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents bonded to the double bond.

A) I = Disubstituted; II = trisubstituted; III = trisubstituted B) I = Monosubstituted; II = disubstituted; III = trisubstituted C) I = Disubstituted; II = disubstituted; III = trisubstituted D) I = Disubstituted; II = trisubstituted; III = disubstituted Answer: A Difficulty: 1 Easy Section: 08.02 Topic: Alkyl Halides and Elimination Reactions Bloom's: 2. Understand Chapter: 08 5) Which of the following represents the rate law for an E2 reaction? A) Rate = k[alkyl halide] B) Rate = k[alkyl halide][base] C) Rate = k[alkyl halide]2 D) Rate = k[base]2 Answer: B Difficulty: 1 Easy Section: 08.03 Topic: Alkyl Halides and Elimination Reactions Bloom's: 2. Understand Chapter: 08 Accessibility: Keyboard Navigation

6) Which of the following statements about the mechanism of an E2 reaction is true? A) All bonds are broken and formed in multiple steps. B) The reaction is not concerted. C) Entropy favors the reactants of an E2 reaction. D) Entropy favors the products of an E2 reaction. Answer: D Difficulty: 1 Easy Section: 08.04 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 Accessibility: Keyboard Navigation 7) How many different E2 products can form from the dehydrohalogenation of 2-bromobutane? A) 1 B) 2 C) 3 D) 4 Answer: C Difficulty: 1 Easy Section: 08.04 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 Accessibility: Keyboard Navigation 8) What is the major elimination product in the reaction of 1-bromobutane with potassium tertbutoxide in tert-butanol? A) cis-2-Butene B) 1-Butene C) trans-2-Butene D) Butanol Answer: B Difficulty: 1 Easy Section: 08.05 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 Accessibility: Keyboard Navigation

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

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 08.05 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 10) Which of the following statements about the mechanism of an E2 reaction is not true? A) It is fastest with tertiary halides. B) It exhibits first-order kinetics. C) A better leaving group should make a faster reaction. D) All bonds are broken and formed in a single step. Answer: B Difficulty: 1 Easy Section: 08.04; 08.05 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 Accessibility: Keyboard Navigation

11) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

12) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 13) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

14) What is the major elimination product obtained from the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 15) Which of the following is the most reactive substrate in an E2 reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 08.09 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

16) Which of the following is the least reactive substrate in an E2 reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 17) Which of the following statements about an E1 mechanism is not true? A) The reaction is fastest with tertiary alkyl halides. B) A better leaving group makes the reaction rate increase. C) The reaction follows first-order kinetics. D) Stronger bases favor the E1 reaction. Answer: D Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 Accessibility: Keyboard Navigation

18) Which of the following statements about an E1 mechanism is true? A) The identity of the leaving group affects the rate of reaction. B) The reaction follows second-order kinetics. C) The reaction is slowest with tertiary substrates. D) Polar aprotic solvents favor the E1 mechanism. Answer: A Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 Accessibility: Keyboard Navigation 19) Which of the following is the most reactive substrate in an E1 reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

20) Which of the following is the major elimination product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

21) Which of the following alkyl halides would afford the indicated product upon reaction with sodium methoxide?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 08.06 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

22) Which of the following is the major E2 product formed from the following alkyl halide?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 08.08 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

23) Which of the labeled protons in the compound below is most readily abstracted under E2 conditions?

A) Ha B) Hb C) Hc D) Hd Answer: D Difficulty: 2 Medium Section: 08.08 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

24) Which of the following alkyl halides will afford the product below as the major product in an E2 reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 08.08 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

25) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 08.10 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 26) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 08.10 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 16 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

27) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 08.10 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

28) What is the product of the following reaction?

A) Only I B) Only II C) Only III D) II and III Answer: D Difficulty: 2 Medium Section: 08.10 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 29) Which of the following is most likely to react as a base rather than a nucleophile?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 08.07 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

30) Which of the following is most likely to react as a nucleophile rather than a base?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 08.07 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 31) Which of the following is the dihalide that can be used to prepare the alkyne below?

A) Only I B) Only II C) Only III D) II and III Answer: D Difficulty: 1 Easy Section: 08.10 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

32) Which of the following is the dihalide that can be used to prepare the alkyne below?

A) I and II B) II and III C) I and III D) I, II, and III Answer: D Difficulty: 1 Easy Section: 08.10 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 33) Select the elimination product(s) formed by treating the indicated alkyl halide with a base.

A) Only I B) Only II C) Only III D) I, II, and III Answer: D Difficulty: 1 Easy Section: 08.09 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

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

A) I and II B) II and III C) I and III D) I, II, and III Answer: D Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 35) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) II and III Answer: D Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 21 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) Only I B) Only II C) Only III D) II and III Answer: D Difficulty: 2 Medium Section: 08.09 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 37) What is (are) the elimination product(s) of the following reaction?

A) Only I B) Only II C) Only III D) II and III Answer: D Difficulty: 2 Medium Section: 08.09 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) Only I B) Only II C) Only III D) I and II Answer: A Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 39) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) I and II Answer: B Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 23 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

40) What is (are) the starting material(s) in the reaction below?

A) Only I B) Only II C) Only III D) II and III Answer: A Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 41) Which alkyl halide(s) would give the following alkene as the only product in an elimination reaction?

A) Only I B) Only II C) Only III D) I and II Answer: B Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 24 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) What is the most likely mechanism for the reaction below?

A) SN1 B) SN2 C) E1 D) E2 Answer: B Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 43) What is the most likely mechanism for the reaction below?

A) SN1 B) SN2 C) E1 D) E2 Answer: D Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

44) Consider the following E2 reaction. What rate equation would be observed for this reaction?

A) Rate = k[CH3CH2CH2Br] B) Rate = k[CH3CH2CH2Br][KOC(CH3)3] C) Rate = k[CH3CH2CH2Br][KOC(CH3)3]2 D) Rate = k[CH3CH2CH2Br]2[KOC(CH3)3] Answer: B Difficulty: 1 Easy Section: 08.04 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 45) Which of the following alkenes is the most stable?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 08.05 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

46) Which of the following alkyl chloride affords alkene A exclusively under E2 reaction condition?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 08.05 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 47) Which of the following alkyl halide would react the fastest with –OH in E2 reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 08.04 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

48) Which of the following alkyl halide reacts the fastest in an E2 reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 08.08 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 49) Which of the following is the most stable alkene?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 08.05 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

50) Which is the most likely mechanism for the following reaction?

A) SN1 B) SN2 C) E1 D) E2 Answer: D Difficulty: 1 Easy Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08 51) What is the major product and likely mechanism for the following reaction?

A) I, E1 B) I, E2 C) II, E1 D) II, E2 Answer: B Difficulty: 2 Medium Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

52) What is the most likely mechanism for the following reaction?

A) SN1 B) SN2 C) E1 D) E2 Answer: A Difficulty: 1 Easy Section: 08.11 Topic: Alkyl Halides and Elimination Reactions Bloom's: 3. Apply Chapter: 08

Organic Chemistry, 6e (Smith) Chapter 9 Alcohols, Ethers, and Related Compounds 1) Which of the following compounds is (are) primary alcohols?

A) Only I B) Only II C) Only I and II D) Only II and III 2) Which of the following compounds is (are) secondary alcohols?

A) Only I B) Only II C) Only II and III D) Only III and IV 3) Which of the following compounds are ethers?

A) Only I and II B) Only III and IV C) Only I, II, and III D) I, II, III, and IV

4) Which of the following compounds are epoxides?

A) Only I and III B) Only III and IV C) Only I, III, and IV D) I, II, III, and IV 5) Which of the following compounds is (are) symmetrical ethers?

A) Only I B) Only IV C) Only III and IV D) Only I, III, and IV 6) Which of the following explains why epoxides are much more reactive than ethers? A) The C-O-C bond angle of an epoxide is 109°, making epoxides to have angle strain. B) The oxygen atom of an epoxide is sp2 hybridized. C) The C-O-C bond angle of an epoxide is 120°, making epoxides to have angle strain. D) The C-O-C bond angle of an epoxide is 60°, making epoxides to have angle strain. 7) What is the IUPAC of the following compound? (CH3CH2)3COH A) 2-Ethyl-2-pentanol B) 2-Ethyl-3-pentanol C) 3-Ethyl-3-pentanol D) 2,2-Diethyl-1-butanol

8) What is the IUPAC of the following compound?

A) 3,3,6-Trimethylcyclohexanol B) 2,5,5-Trimethylcyclohexanol C) 1,4,4-Trimethyl-2-cyclohexanol D) 1,1,4-Trimethyl-2-cyclohexanol 9) What is the IUPAC of the following compound?

A) 5-Hydroxy-3-methyl-1-pentene B) 3-Methyl-5-penten-1-ol C) 3-Methyl-1-penten-5-ol D) 3-Methyl-4-penten-1-ol 10) What is the IUPAC of the following compound?

A) (S)-2,2-Dimethyl-3-pentanol B) (R)-2,2-Dimethyl-3-pentanol C) (R)-4,4-Dimethyl-3-pentanol D) (S)-1-tert-Butyl-1-propanol

11) What is the IUPAC of the following compound?

A) Ethoxyoctane B) 5-Ethoxyoctane C) 4-Ethoxyoctane D) Ethyl octyl ether 12) What is the common name of the following compound?

A) Isobutyl isopropyl ether B) Diisobutyl ether C) Di-sec-butyl ether D) Diisopropyl ether 13) What is the common name of the following compound?

A) Methyl sec-butyl ether B) Isobutyl methyl ether C) sec-Butyl methyl ether D) Butyl methyl ether 14) What is the common name of the following compound?

A) Methyl vinyl ether B) Allyl methyl ether C) Propenyl methyl ether D) Methylene propylene ether

15) What is the IUPAC of the following compound?

A) 1,2-Epoxy-4-methylcyclohexane B) 3,4-Epoxy-1-methylcyclohexane C) 1,2-Epoxy-3-methylcyclohexane D) 1,2-Epoxy-5-methylcyclohexane 16) What is the IUPAC of the following compound?

A) 1,2-Epoxy-2-methylcyclopentane B) 1,2-Epoxy-1-methylcyclopentane C) 1,2-Epoxy-1-methylpentane D) 1,2-Epoxy-2-methylpentane 17) What is the IUPAC of the following compound?

A) 1,1-Dimethyloxirane B) 2-Methylpropylane C) 2-Methylpropylene oxide D) 2,2-Dimethyloxirane 18) Which of the following compounds has the highest boiling point?

19) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV 20) Rank the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

A) III < II < I < IV B) II < III < I < IV C) IV < I < II < III D) I < II < III < IV 21) Which of the following statements about a crown ether-cation complex is not true? A) It is a host-guest complex. B) The crown ether is the guest and the cation is the host. C) The crown ether is the host and the cation is the guest. D) The host-guest complex is soluble in nonpolar solvents. 22) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis? A) Sodium methoxide and tert-butyl bromide. B) Sodium tert-butoxide and iodomethane. C) Methanol and tert-butyl alcohol in the presence of KOH. D) Iodomethane and tert-butyl bromide in the presence of KOH. 23) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis? A) Bromobenzene and sodium methoxide B) Phenol and sodium methoxide C) Bromobenzene and bromomethane D) Sodium phenoxide and bromomethane

A) I B) II C) III D) IV

26) Which of the following would be a reasonable synthesis of 2-butanol?

A) I B) II C) III D) IV 27) What is the best choice of reagent to accomplish the following transformation?

A) HCl B) SOCl2, pyridine C) Cl2 D) H3O+, H2O

28) What is the product of the following reaction?

A) I B) II C) III D) IV 29) What is the major organic product(s) obtained in the following reaction?

A) I B) II C) III D) I and II 30) What is the best choice of reagent to accomplish the following transformation?

A) HCl B) H2SO4 C) NaOH D) TsCl, pyridine

31) Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl halide?

A) I B) II C) III D) IV 32) What is the major organic product obtained from the following sequence of reactions?

A) 2-Methyl-1-butene B) 3-Methyl-3-butene C) 1-Chloro-2-methylbutane D) 1-Bromo-2-methylbutane 33) Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only II and III

34) Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only I and II 35) Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting the least reactive first.

A) I < III < II B) I < II < III C) II < III < I D) III < II < I 36) Which of the following statements about carbocation rearrangement is not true? A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation. D) The migrating group in a 1,2-shift moves with one bonding electron.

37) Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?

A) I B) II C) III D) IV 38) What is the best choice of reagent to accomplish the following transformation?

A) TsCl, pyridine B) POCl3, pyridine C) HCl, ZnCl2 D) NaOH 39) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV

40) What is the major organic product obtained from the following reaction?

A) (±)-2-Chlorobutane B) (R)-2-Chlorobutane C) (S)-2-Chlorobutane D) trans-2-Butene 41) What is the major organic product obtained from the following sequence of reactions?

A) (R)-2-Methylpentanenitrile B) (S)-2-Methylpentanenitrile C) (±)-2-Methylpentanenitrile D) trans-2-Butene 42) What is the major organic product obtained from the following sequence of reactions?

A) (S)-2-Methoxypentane B) (R)-2-Methoxypentane C) (±)-2-Methoxypentane D) trans-2-Butene 43) What are the major products obtained upon treatment of ethyl methyl ether with excess HBr? A) Bromomethane and ethanol B) Bromoethane and methanol C) Bromoethane and bromomethane D) Ethanol and methanol 44) What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI? A) tert-Butyl alcohol and iodomethane B) tert-Butyl iodide and iodomethane C) tert-Butyl alcohol and methanol D) tert-Butyl iodide and methanol 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

45) Which of the following statements about the reaction of ethers with strong acids is true? A) HCl, HBr, and HI can all be used. B) The mechanism of ether cleavage is SN1 only. C) The mechanism of ether cleavage is SN2 only. D) The mechanism of ether cleavage is SN1 and SN2. 46) What are the major products obtained upon treatment of methyl phenyl ether with excess HBr? A) Phenol and bromomethane B) Phenol and methanol C) Bromobenzene and bromomethane D) Bromobenzene and methanol 47) Determine the product in the following reaction (ignoring possible stereoisomers).

A) I B) II C) III D) IV 48) Determine the product in the following reaction (ignoring possible stereoisomers).

49) What is the product of the following reaction?

A) I B) II C) III D) IV 50) What is the major alkene formed when compound A is dehydrated with H2SO4?

A) I B) II C) III D) IV 51) What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine?

A) I B) II C) III D) IV

52) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 53) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 54) What is the IUPAC name of the following compound?

A) 5-Ethylthio-4-isopropylpentane B) 1-Ethylthio-3-methyl-2-propylbutane C) 1-Ethylthio-2-isopropylpentane D) Isooctylthioethane 55) What is the IUPAC name of the following compound?

A) 3-Ethyl-5-methylcyclohexanethiol B) 3-Ethyl-5-methylcyclohexane-1-thiol C) 5-Ethyl-2-methylcyclohexanethiol D) 5-Ethyl-2-methylcyclohexylthiol 16 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) (2R, 4R)-4-chloro-2-pentanol B) (2R, 4S)-4-chloro-2-pentanol C) (2S, 4R)-4-chloro-2-pentanol D) (2S, 4S)-4-chloro-2-pentanol 57) What is the IUPAC name of the following compound?

A) R-2,2-dimethylcyclohexanol B) S-2,2-dimethylcyclohexanol C) R-1,1-dimethyl-2-cyclohexanol D) S-1,1-dimethyl-2-cyclohexanol 58) What is the IUPAC name of the following compound?

A) R-2-methoxy-5,5-dimethylhexane B) S-2-methoxy-5,5-dimethylhexane C) R-5-methoxy-2,2-dimethylhexane D) S-5-methoxy-2,2-dimethylhexane

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

A) I B) II C) III D) IV 60) What is the major product of the following reaction?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 9 Alcohols, Ethers, and Related Compounds 1) Which of the following compounds is (are) primary alcohols?

A) Only I B) Only II C) Only I and II D) Only II and III Answer: B Difficulty: 1 Easy Section: 09.01 Topic: Alcohols Bloom's: 2. Understand Chapter: 09 2) Which of the following compounds is (are) secondary alcohols?

A) Only I B) Only II C) Only II and III D) Only III and IV Answer: D Difficulty: 1 Easy Section: 09.01 Topic: Alcohols Bloom's: 2. Understand Chapter: 09

3) Which of the following compounds are ethers?

A) Only I and II B) Only III and IV C) Only I, II, and III D) I, II, III, and IV Answer: D Difficulty: 1 Easy Section: 09.01 Topic: Ethers Bloom's: 2. Understand Chapter: 09 4) Which of the following compounds are epoxides?

A) Only I and III B) Only III and IV C) Only I, III, and IV D) I, II, III, and IV Answer: B Difficulty: 1 Easy Section: 09.01 Topic: Epoxides Bloom's: 2. Understand Chapter: 09

5) Which of the following compounds is (are) symmetrical ethers?

A) Only I B) Only IV C) Only III and IV D) Only I, III, and IV Answer: B Difficulty: 1 Easy Section: 09.01 Topic: Ethers Bloom's: 2. Understand Chapter: 09 6) Which of the following explains why epoxides are much more reactive than ethers? A) The C-O-C bond angle of an epoxide is 109°, making epoxides to have angle strain. B) The oxygen atom of an epoxide is sp2 hybridized. C) The C-O-C bond angle of an epoxide is 120°, making epoxides to have angle strain. D) The C-O-C bond angle of an epoxide is 60°, making epoxides to have angle strain. Answer: D Difficulty: 1 Easy Section: 09.02 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation

7) What is the IUPAC of the following compound? (CH3CH2)3COH A) 2-Ethyl-2-pentanol B) 2-Ethyl-3-pentanol C) 3-Ethyl-3-pentanol D) 2,2-Diethyl-1-butanol Answer: C Difficulty: 1 Easy Section: 09.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 8) What is the IUPAC of the following compound?

A) 3,3,6-Trimethylcyclohexanol B) 2,5,5-Trimethylcyclohexanol C) 1,4,4-Trimethyl-2-cyclohexanol D) 1,1,4-Trimethyl-2-cyclohexanol Answer: B Difficulty: 1 Easy Section: 09.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

9) What is the IUPAC of the following compound?

A) 5-Hydroxy-3-methyl-1-pentene B) 3-Methyl-5-penten-1-ol C) 3-Methyl-1-penten-5-ol D) 3-Methyl-4-penten-1-ol Answer: D Difficulty: 1 Easy Section: 09.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 10) What is the IUPAC of the following compound?

A) (S)-2,2-Dimethyl-3-pentanol B) (R)-2,2-Dimethyl-3-pentanol C) (R)-4,4-Dimethyl-3-pentanol D) (S)-1-tert-Butyl-1-propanol Answer: B Difficulty: 2 Medium Section: 09.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

11) What is the IUPAC of the following compound?

A) Ethoxyoctane B) 5-Ethoxyoctane C) 4-Ethoxyoctane D) Ethyl octyl ether Answer: C Difficulty: 2 Medium Section: 09.03 Topic: Ethers Bloom's: 3. Apply Chapter: 09 12) What is the common name of the following compound?

A) Isobutyl isopropyl ether B) Diisobutyl ether C) Di-sec-butyl ether D) Diisopropyl ether Answer: B Difficulty: 1 Easy Section: 09.03 Topic: Ethers Bloom's: 3. Apply Chapter: 09

13) What is the common name of the following compound?

A) Methyl sec-butyl ether B) Isobutyl methyl ether C) sec-Butyl methyl ether D) Butyl methyl ether Answer: C Difficulty: 2 Medium Section: 09.03 Topic: Ethers Bloom's: 3. Apply Chapter: 09 14) What is the common name of the following compound?

A) Methyl vinyl ether B) Allyl methyl ether C) Propenyl methyl ether D) Methylene propylene ether Answer: B Difficulty: 2 Medium Section: 09.03 Topic: Ethers Bloom's: 3. Apply Chapter: 09

15) What is the IUPAC of the following compound?

A) 1,2-Epoxy-4-methylcyclohexane B) 3,4-Epoxy-1-methylcyclohexane C) 1,2-Epoxy-3-methylcyclohexane D) 1,2-Epoxy-5-methylcyclohexane Answer: A Difficulty: 2 Medium Section: 09.03 Topic: Epoxides Bloom's: 3. Apply Chapter: 09 16) What is the IUPAC of the following compound?

A) 1,2-Epoxy-2-methylcyclopentane B) 1,2-Epoxy-1-methylcyclopentane C) 1,2-Epoxy-1-methylpentane D) 1,2-Epoxy-2-methylpentane Answer: B Difficulty: 2 Medium Section: 09.03 Topic: Epoxides Bloom's: 3. Apply Chapter: 09

17) What is the IUPAC of the following compound?

A) 1,1-Dimethyloxirane B) 2-Methylpropylane C) 2-Methylpropylene oxide D) 2,2-Dimethyloxirane Answer: D Difficulty: 1 Easy Section: 09.03 Topic: Epoxides Bloom's: 3. Apply Chapter: 09 18) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 09.04 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

19) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 09.04 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 20) Rank the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

A) III < II < I < IV B) II < III < I < IV C) IV < I < II < III D) I < II < III < IV Answer: A Difficulty: 1 Easy Section: 09.04 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

21) Which of the following statements about a crown ether-cation complex is not true? A) It is a host-guest complex. B) The crown ether is the guest and the cation is the host. C) The crown ether is the host and the cation is the guest. D) The host-guest complex is soluble in nonpolar solvents. Answer: B Difficulty: 1 Easy Section: 09.05 Topic: Ethers Bloom's: 1. Remember Chapter: 09 Accessibility: Keyboard Navigation 22) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis? A) Sodium methoxide and tert-butyl bromide. B) Sodium tert-butoxide and iodomethane. C) Methanol and tert-butyl alcohol in the presence of KOH. D) Iodomethane and tert-butyl bromide in the presence of KOH. Answer: B Difficulty: 1 Easy Section: 09.06 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 23) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis? A) Bromobenzene and sodium methoxide B) Phenol and sodium methoxide C) Bromobenzene and bromomethane D) Sodium phenoxide and bromomethane Answer: D Difficulty: 1 Easy Section: 09.06 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation

24) Which of the following ethers cannot be prepared by the Williamson ether synthesis? A) Isopropyl methyl ether B) tert-Butyl methyl ether C) tert-Butyl phenyl ether D) Methyl phenyl ether Answer: C Difficulty: 2 Medium Section: 09.06 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 25) Which of the following would be a reasonable synthesis of 1-butanol?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 09.06 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

26) Which of the following would be a reasonable synthesis of 2-butanol?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 09.06 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 27) What is the best choice of reagent to accomplish the following transformation?

A) HCl B) SOCl2, pyridine C) Cl2 D) H3O+, H2O Answer: B Difficulty: 1 Easy Section: 09.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

28) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 09.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 29) What is the major organic product(s) obtained in the following reaction?

A) I B) II C) III D) I and II Answer: D Difficulty: 2 Medium Section: 09.11 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

30) What is the best choice of reagent to accomplish the following transformation?

A) HCl B) H2SO4 C) NaOH D) TsCl, pyridine Answer: B Difficulty: 1 Easy Section: 09.08 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 31) Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl halide?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 09.11 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

32) What is the major organic product obtained from the following sequence of reactions?

A) 2-Methyl-1-butene B) 3-Methyl-3-butene C) 1-Chloro-2-methylbutane D) 1-Bromo-2-methylbutane Answer: D Difficulty: 1 Easy Section: 09.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 33) Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only II and III Answer: D Difficulty: 1 Easy Section: 09.08 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

34) Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 09.13 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 35) Rank the alcohols in order of increasing reactivity when dehydrated with H2SO4, putting the least reactive first.

A) I < III < II B) I < II < III C) II < III < I D) III < II < I Answer: A Difficulty: 2 Medium Section: 09.08 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

36) Which of the following statements about carbocation rearrangement is not true? A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom. B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group. C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation. D) The migrating group in a 1,2-shift moves with one bonding electron. Answer: D Difficulty: 1 Easy Section: 09.09 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 37) Which of the following alcohols is most likely to yield a carbocation that is susceptible to rearrangements?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 09.09 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

38) What is the best choice of reagent to accomplish the following transformation?

A) TsCl, pyridine B) POCl3, pyridine C) HCl, ZnCl2 D) NaOH Answer: B Difficulty: 1 Easy Section: 09.10 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 39) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 09.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

40) What is the major organic product obtained from the following reaction?

A) (±)-2-Chlorobutane B) (R)-2-Chlorobutane C) (S)-2-Chlorobutane D) trans-2-Butene Answer: B Difficulty: 2 Medium Section: 09.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 41) What is the major organic product obtained from the following sequence of reactions?

A) (R)-2-Methylpentanenitrile B) (S)-2-Methylpentanenitrile C) (±)-2-Methylpentanenitrile D) trans-2-Butene Answer: A Difficulty: 2 Medium Section: 09.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

42) What is the major organic product obtained from the following sequence of reactions?

A) (S)-2-Methoxypentane B) (R)-2-Methoxypentane C) (±)-2-Methoxypentane D) trans-2-Butene Answer: B Difficulty: 2 Medium Section: 09.13 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 43) What are the major products obtained upon treatment of ethyl methyl ether with excess HBr? A) Bromomethane and ethanol B) Bromoethane and methanol C) Bromoethane and bromomethane D) Ethanol and methanol Answer: C Difficulty: 1 Easy Section: 09.14 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 44) What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI? A) tert-Butyl alcohol and iodomethane B) tert-Butyl iodide and iodomethane C) tert-Butyl alcohol and methanol D) tert-Butyl iodide and methanol Answer: B Difficulty: 1 Easy Section: 09.14 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 21 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

45) Which of the following statements about the reaction of ethers with strong acids is true? A) HCl, HBr, and HI can all be used. B) The mechanism of ether cleavage is SN1 only. C) The mechanism of ether cleavage is SN2 only. D) The mechanism of ether cleavage is SN1 and SN2. Answer: D Difficulty: 1 Easy Section: 09.14 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation 46) What are the major products obtained upon treatment of methyl phenyl ether with excess HBr? A) Phenol and bromomethane B) Phenol and methanol C) Bromobenzene and bromomethane D) Bromobenzene and methanol Answer: A Difficulty: 1 Easy Section: 09.14 Topic: Ethers Bloom's: 3. Apply Chapter: 09 Accessibility: Keyboard Navigation

47) Determine the product in the following reaction (ignoring possible stereoisomers).

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 09.16 Topic: Epoxides Bloom's: 3. Apply Chapter: 09 48) Determine the product in the following reaction (ignoring possible stereoisomers).

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 09.16 Topic: Epoxides Bloom's: 3. Apply Chapter: 09 23 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

49) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 09.16 Topic: Epoxides Bloom's: 3. Apply Chapter: 09 50) What is the major alkene formed when compound A is dehydrated with H2SO4?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 09.08 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

51) What is the major alkene formed when compound A is dehydrated with POCl3 and pyridine?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 09.10 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 52) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 09.15 Topic: Thiols Bloom's: 3. Apply Chapter: 09

53) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 09.15 Topic: Thiols Bloom's: 3. Apply Chapter: 09 54) What is the IUPAC name of the following compound?

A) 5-Ethylthio-4-isopropylpentane B) 1-Ethylthio-3-methyl-2-propylbutane C) 1-Ethylthio-2-isopropylpentane D) Isooctylthioethane Answer: C Difficulty: 2 Medium Section: 09.15 Topic: Sulfides (Thioethers) Bloom's: 3. Apply Chapter: 09

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

A) 3-Ethyl-5-methylcyclohexanethiol B) 3-Ethyl-5-methylcyclohexane-1-thiol C) 5-Ethyl-2-methylcyclohexanethiol D) 5-Ethyl-2-methylcyclohexylthiol Answer: C Difficulty: 2 Medium Section: 09.15 Topic: Thiols; Sulfides (Thioethers) Bloom's: 3. Apply Chapter: 09 56) What is the IUPAC name of the following compound?

A) (2R, 4R)-4-chloro-2-pentanol B) (2R, 4S)-4-chloro-2-pentanol C) (2S, 4R)-4-chloro-2-pentanol D) (2S, 4S)-4-chloro-2-pentanol Answer: D Difficulty: 3 Hard Section: 09.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

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

A) R-2,2-dimethylcyclohexanol B) S-2,2-dimethylcyclohexanol C) R-1,1-dimethyl-2-cyclohexanol D) S-1,1-dimethyl-2-cyclohexanol Answer: A Difficulty: 2 Medium Section: 09.03 Topic: Alcohols Bloom's: 3. Apply Chapter: 09 58) What is the IUPAC name of the following compound?

A) R-2-methoxy-5,5-dimethylhexane B) S-2-methoxy-5,5-dimethylhexane C) R-5-methoxy-2,2-dimethylhexane D) S-5-methoxy-2,2-dimethylhexane Answer: A Difficulty: 2 Medium Section: 09.03 Topic: Epoxides Bloom's: 3. Apply Chapter: 09

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

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 09.11 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

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

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 09.11 Topic: Alcohols Bloom's: 3. Apply Chapter: 09

Organic Chemistry, 6e (Smith) Chapter 10 Alkenes 1) Which of the following alkenes are terminal alkenes?

A) I and II B) II and III C) I and IV D) I and III 2) Which of the following alkenes are internal alkenes?

A) I and II B) II and III C) I and III D) II and IV 3) Which of the statements about the properties of the carbon-carbon double bond is not true? A) There is restricted rotation around the carbon-carbon double bond. B) Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible. C) Trans alkenes are generally more stable than cis alkenes. D) The stability of the carbon-carbon double bond increases as the number of substituent groups increases. 4) Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl. A) 1 B) 2 C) 3 D) 0 5) Calculate the degree of unsaturation for a molecule with molecular formula C8H9N. A) 2 B) 3 C) 4 D) 5

6) What is the IUPAC name for the following compound?

A) 6-Ethyl-1-heptene B) 2-Ethyl-1-heptene C) 2-Ethyl-1-octene D) 6-Ethyl-6-heptene 7) What is the IUPAC name for the following compound?

A) 1-Methylcyclopentene B) 2-Methyl-1-cyclopentene C) 1-Methylene-1-methylcyclopentane D) 1-Methylcyclohexene 8) What is the IUPAC name for the following compound?

A) 1,2-Dimethylcyclohexene B) 2,3-Dimethylcyclohexene C) 1,6-Dimethylcyclohexene D) 1,2-Dimethyl-3-cyclohexene 9) What is the IUPAC name for the following compound?

A) 5-Methyl-5-hexen-2-ol B) 6-Methyl-6-hepten-2-ol C) 6-Hydroxy-2-methylheptene D) 6-Hydroxy-2-methyl-1-heptene 2 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

10) What is the IUPAC name for the following compound?

A) 4-Ethyl-3-methyl-1-octen-5-ol B) 3-Ethyl-4-methyl-2-octen-5-ol C) 5-Ethyl-6-methyl-7-octen-4-ol D) 4-Ethyl-6-methyl-1-octen-5-ol 11) Label each C-C double bond in Kavain, a naturally occurring relaxant, as E or Z.

A) I = Z and II = Z B) I = Z and II = E C) I = E and II = E D) I = E and II = Z 12) What is the common name of the following compound?

A) 2-Vinylcyclohexene B) 2-Allylcyclohexene C) 1-Allylcyclohexene D) 1-Vinylcyclohexene

13) Rank the following isomers in order of increasing boiling point, putting the least first.

A) I < II < III B) I < III < II C) II < III < I D) II < I < III 14) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV 15) Which of the following is a terpene?

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV 17) Which of the following statements about alkenes is not true? A) They are less reactive than alkanes. B) They can exist as cis/trans isomers. C) The bond angle around the C-C double bond is approximately 120°. D) The carbon of the C-C double bond is sp2 hybridized. 18) Which of the following statements about alkenes is true? A) Alkenes react with nucleophiles and bases. B) Alkenes contain double bonds from two sp-hybridized carbon atoms. C) In the reactions of alkenes, the D) Alkenes react with electrophiles.

bond is not always broken.

19) Rank the following compounds in order of decreasing stability, putting the most stable first.

A) I > II > III B) II > I > III C) III > II > I D) III > I > II

20) Which of the following reaction conditions would result in anti-Markovnikov addition to an alkene? A) H2O/H3O+ B) HBr C) HCl D) [1] BH3; [2] H2O2/HO21) Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III 22) In which of the following alkene addition reactions will carbocation rearrangements occur? A) Addition of Br2 and H2O B) Addition of Br2 C) Addition of Cl2 and H2O D) Addition of H2O in the presence of H2SO4 23) Markovnikov addition of HBr to CH3CH=CH2 involves which of the following? A) Initial attack by bromide anion (Br-). B) Initial attack by bromine radical (Br•). C) Formation of a primary carbocation. D) Formation of a secondary carbocation. 24) Rearrangements can occur in which of the following reactions? A) Addition of Cl2 to an alkene. B) Addition of HOBr to an alkene. C) Addition of H2O/H3O+ to an alkene. D) None of these.

25) Which of the following alkenes reacts fastest with HCl?

A) I B) II C) III D) IV 26) Predict the major product of the following reaction.

A) I B) II C) III D) IV 27) Predict the product(s) of the following reaction.

A) Only I and II B) Only I and III C) Only II and III D) Only III and IV 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

28) Predict the product of the following reaction.

A) I B) II C) III D) IV 29) Predict the major product of the following reaction.

A) I B) II C) III D) IV 30) Predict the major product of the following reaction.

31) Predict the major product(s) of the following reaction.

A) Only I and II B) Only II and III C) Only III and IV D) Only I and IV 32) Predict the major product(s) of the following reaction.

A) Only I and II B) Only II and IV C) Only II and III D) Only I and IV

33) What is the major product obtained from the following reaction?

A) I B) II C) III D) IV 34) What is the major product obtained from the following reaction (assume enantiomer is also formed)?

A) I B) II C) III D) IV

35) What is (are) the major product(s) obtained from the following reaction?

A) Only I B) Only II C) Only III D) Only I and II 36) What is (are) the major product(s) obtained from the following reaction?

A) Only I B) Only II C) Only III D) Only I and II 37) What is the best choice of reagent to accomplish the following transformation?

A) HBr B) Br2, H2O C) Br2 D) H2O2/Br2

38) What is the best choice of reagent to accomplish the following transformation?

A) H2O, Br2 B) [1] BH3; [2] H2O2/HOC) H2O, H2SO4 D) [1] BH3; [2] H2O 39) What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane? A) Carbanion B) Carbocation C) Cyclic bromonium ion D) Radical 40) What type of reactive intermediate is formed in the reaction of an alkene with Br2 and H2O to give a bromohydrin? A) Carbanion B) Radical C) Carbocation D) Cyclic bromonium ion 41) Rank the carbocation in order of increasing stability, putting the least stable first.

A) III < I < II B) III < II < I C) I < II < III D) I < III < II 42) Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true? A) Achiral starting materials yield an unequal mixture of two enantiomers. B) Hydrohalogenation occurs with syn stereochemistry only. C) Hydrohalogenation occurs with anti stereochemistry only. D) Hydrohalogenation occurs with syn and anti addition of HX. 12 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

A) I B) II C) III D) IV 45) What is the starting material in the following reaction?

A) I B) II C) III D) IV

46) What is (are) the missing reagent(s) in the following reaction?

A) Br2/CCl4 B) NBS, DMSO/H2O C) [1] Br2; [2] H2O D) [1] BH3; [2] H2O2/HO47) Which of the following statements about hydroboration/oxidation of alkenes is true? A) In hydroboration, the boron atom bonds to the more substituted carbon. B) Hydroboration occurs with anti addition. C) Oxidation occurs with retention of configuration. D) 9-BBN does not undergo hydroboration in the same manner as BH3. 48) Which of the following alkenes is an E alkene?

A) I B) II C) III D) IV 49) Which alkene reacts fastest with HBr?

50) Calculate the degree of unsaturation for the following molecule:

A) 2 B) 3 C) 4 D) 5 51) Calculate the degree of unsaturation for the following molecule:

A) 2 B) 3 C) 4 D) 5 52) What is the IUPAC name of the following compound?

A) (E,R)-4-bromo-4-hexen-2-ol B) (Z,R)-4-bromo-4-hexen-2-ol C) (E,S)-4-bromo-4-hexen-2-ol D) (Z,S)-4-bromo-4-hexen-2-ol

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

A) R-4,4-dibromo-2-cyclohexen-1-ol B) S-4,4-dibromo-2-cyclohexen-1-ol C) R-4,4-dibromo-5-cyclohexen-1-ol D) S-4,4-dibromo-5-cyclohexen-1-ol 54) What is the major product of the following reaction?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 10 Alkenes 1) Which of the following alkenes are terminal alkenes?

A) I and II B) II and III C) I and IV D) I and III Answer: D Difficulty: 1 Easy Section: 10.01 Topic: Alkenes Bloom's: 2. Understand Chapter: 10 2) Which of the following alkenes are internal alkenes?

A) I and II B) II and III C) I and III D) II and IV Answer: D Difficulty: 1 Easy Section: 10.01 Topic: Alkenes Bloom's: 2. Understand Chapter: 10

3) Which of the statements about the properties of the carbon-carbon double bond is not true? A) There is restricted rotation around the carbon-carbon double bond. B) Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible. C) Trans alkenes are generally more stable than cis alkenes. D) The stability of the carbon-carbon double bond increases as the number of substituent groups increases. Answer: B Difficulty: 1 Easy Section: 10.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 4) Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl. A) 1 B) 2 C) 3 D) 0 Answer: A Difficulty: 1 Easy Section: 10.02 Topic: Alkenes Bloom's: 5. Evaluate Chapter: 10 Accessibility: Keyboard Navigation 5) Calculate the degree of unsaturation for a molecule with molecular formula C8H9N. A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: 10.02 Topic: Alkenes Bloom's: 5. Evaluate Chapter: 10 Accessibility: Keyboard Navigation

6) What is the IUPAC name for the following compound?

A) 6-Ethyl-1-heptene B) 2-Ethyl-1-heptene C) 2-Ethyl-1-octene D) 6-Ethyl-6-heptene Answer: B Difficulty: 1 Easy Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 7) What is the IUPAC name for the following compound?

A) 1-Methylcyclopentene B) 2-Methyl-1-cyclopentene C) 1-Methylene-1-methylcyclopentane D) 1-Methylcyclohexene Answer: A Difficulty: 1 Easy Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

8) What is the IUPAC name for the following compound?

A) 1,2-Dimethylcyclohexene B) 2,3-Dimethylcyclohexene C) 1,6-Dimethylcyclohexene D) 1,2-Dimethyl-3-cyclohexene Answer: C Difficulty: 1 Easy Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 9) What is the IUPAC name for the following compound?

A) 5-Methyl-5-hexen-2-ol B) 6-Methyl-6-hepten-2-ol C) 6-Hydroxy-2-methylheptene D) 6-Hydroxy-2-methyl-1-heptene Answer: B Difficulty: 1 Easy Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

10) What is the IUPAC name for the following compound?

A) 4-Ethyl-3-methyl-1-octen-5-ol B) 3-Ethyl-4-methyl-2-octen-5-ol C) 5-Ethyl-6-methyl-7-octen-4-ol D) 4-Ethyl-6-methyl-1-octen-5-ol Answer: C Difficulty: 2 Medium Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 11) Label each C-C double bond in Kavain, a naturally occurring relaxant, as E or Z.

A) I = Z and II = Z B) I = Z and II = E C) I = E and II = E D) I = E and II = Z Answer: C Difficulty: 2 Medium Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

12) What is the common name of the following compound?

A) 2-Vinylcyclohexene B) 2-Allylcyclohexene C) 1-Allylcyclohexene D) 1-Vinylcyclohexene Answer: D Difficulty: 1 Easy Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 13) Rank the following isomers in order of increasing boiling point, putting the least first.

A) I < II < III B) I < III < II C) II < III < I D) II < I < III Answer: B Difficulty: 1 Easy Section: 10.04 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

14) Which of the following compounds has the highest boiling point?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 10.04 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 15) Which of the following is a terpene?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 10.05 Topic: Alkenes Bloom's: 1. Remember Chapter: 10

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

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 10.07 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 17) Which of the following statements about alkenes is not true? A) They are less reactive than alkanes. B) They can exist as cis/trans isomers. C) The bond angle around the C-C double bond is approximately 120°. D) The carbon of the C-C double bond is sp2 hybridized. Answer: A Difficulty: 1 Easy Section: 10.07 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation

18) Which of the following statements about alkenes is true? A) Alkenes react with nucleophiles and bases. B) Alkenes contain double bonds from two sp-hybridized carbon atoms. C) In the reactions of alkenes, the D) Alkenes react with electrophiles.

bond is not always broken.

Answer: D Difficulty: 1 Easy Section: 10.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 19) Rank the following compounds in order of decreasing stability, putting the most stable first.

A) I > II > III B) II > I > III C) III > II > I D) III > I > II Answer: B Difficulty: 1 Easy Section: 10.01 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

20) Which of the following reaction conditions would result in anti-Markovnikov addition to an alkene? A) H2O/H3O+ B) HBr C) HCl D) [1] BH3; [2] H2O2/HOAnswer: D Difficulty: 1 Easy Section: 10.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 21) Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III Answer: C Difficulty: 2 Medium Section: 10.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

22) In which of the following alkene addition reactions will carbocation rearrangements occur? A) Addition of Br2 and H2O B) Addition of Br2 C) Addition of Cl2 and H2O D) Addition of H2O in the presence of H2SO4 Answer: D Difficulty: 1 Easy Section: 10.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 23) Markovnikov addition of HBr to CH3CH=CH2 involves which of the following? A) Initial attack by bromide anion (Br-). B) Initial attack by bromine radical (Br•). C) Formation of a primary carbocation. D) Formation of a secondary carbocation. Answer: D Difficulty: 2 Medium Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 24) Rearrangements can occur in which of the following reactions? A) Addition of Cl2 to an alkene. B) Addition of HOBr to an alkene. C) Addition of H2O/H3O+ to an alkene. D) None of these. Answer: C Difficulty: 2 Medium Section: 10.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation

25) Which of the following alkenes reacts fastest with HCl?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 26) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

27) Predict the product(s) of the following reaction.

A) Only I and II B) Only I and III C) Only II and III D) Only III and IV Answer: A Difficulty: 2 Medium Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 28) Predict the product of the following reaction.

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

29) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 10.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 30) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 10.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

31) Predict the major product(s) of the following reaction.

A) Only I and II B) Only II and III C) Only III and IV D) Only I and IV Answer: A Difficulty: 2 Medium Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 32) Predict the major product(s) of the following reaction.

A) Only I and II B) Only II and IV C) Only II and III D) Only I and IV Answer: B Difficulty: 1 Easy Section: 10.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 15 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

33) What is the major product obtained from the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 10.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 34) What is the major product obtained from the following reaction (assume enantiomer is also formed)?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 10.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 16 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

35) What is (are) the major product(s) obtained from the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 2 Medium Section: 10.13 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 36) What is (are) the major product(s) obtained from the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: C Difficulty: 2 Medium Section: 10.13 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

37) What is the best choice of reagent to accomplish the following transformation?

A) HBr B) Br2, H2O C) Br2 D) H2O2/Br2 Answer: B Difficulty: 2 Medium Section: 10.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 38) What is the best choice of reagent to accomplish the following transformation?

A) H2O, Br2 B) [1] BH3; [2] H2O2/HOC) H2O, H2SO4 D) [1] BH3; [2] H2O Answer: B Difficulty: 2 Medium Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

39) What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane? A) Carbanion B) Carbocation C) Cyclic bromonium ion D) Radical Answer: B Difficulty: 1 Easy Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 40) What type of reactive intermediate is formed in the reaction of an alkene with Br2 and H2O to give a bromohydrin? A) Carbanion B) Radical C) Carbocation D) Cyclic bromonium ion Answer: D Difficulty: 1 Easy Section: 10.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation

41) Rank the carbocation in order of increasing stability, putting the least stable first.

A) III < I < II B) III < II < I C) I < II < III D) I < III < II Answer: B Difficulty: 1 Easy Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 42) Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true? A) Achiral starting materials yield an unequal mixture of two enantiomers. B) Hydrohalogenation occurs with syn stereochemistry only. C) Hydrohalogenation occurs with anti stereochemistry only. D) Hydrohalogenation occurs with syn and anti addition of HX. Answer: D Difficulty: 2 Medium Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation

43) Which of the following reactions of alkenes takes place with anti stereochemistry only? A) Addition of HBr B) Addition of H2O in the presence of H2SO4 C) Addition of BH3 followed by H2O2/HOD) Addition of Br2 Answer: D Difficulty: 1 Easy Section: 10.13 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 44) Predict the product of the following reaction, ignoring stereochemistry.

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

45) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 46) What is (are) the missing reagent(s) in the following reaction?

A) Br2/CCl4 B) NBS, DMSO/H2O C) [1] Br2; [2] H2O D) [1] BH3; [2] H2O2/HOAnswer: D Difficulty: 1 Easy Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

47) Which of the following statements about hydroboration/oxidation of alkenes is true? A) In hydroboration, the boron atom bonds to the more substituted carbon. B) Hydroboration occurs with anti addition. C) Oxidation occurs with retention of configuration. D) 9-BBN does not undergo hydroboration in the same manner as BH3. Answer: C Difficulty: 2 Medium Section: 10.16 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 Accessibility: Keyboard Navigation 48) Which of the following alkenes is an E alkene?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

49) Which alkene reacts fastest with HBr?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 10.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 10 50) Calculate the degree of unsaturation for the following molecule:

A) 2 B) 3 C) 4 D) 5 Answer: B Difficulty: 1 Easy Section: 10.02 Topic: Alkenes Bloom's: 5. Evaluate Chapter: 10

51) Calculate the degree of unsaturation for the following molecule:

A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: 10.02 Topic: Alkenes Bloom's: 5. Evaluate Chapter: 10 52) What is the IUPAC name of the following compound?

A) (E,R)-4-bromo-4-hexen-2-ol B) (Z,R)-4-bromo-4-hexen-2-ol C) (E,S)-4-bromo-4-hexen-2-ol D) (Z,S)-4-bromo-4-hexen-2-ol Answer: B Difficulty: 3 Hard Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

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

A) R-4,4-dibromo-2-cyclohexen-1-ol B) S-4,4-dibromo-2-cyclohexen-1-ol C) R-4,4-dibromo-5-cyclohexen-1-ol D) S-4,4-dibromo-5-cyclohexen-1-ol Answer: A Difficulty: 3 Hard Section: 10.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

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

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 10.12 Topic: Alkenes Bloom's: 3. Apply Chapter: 10

Organic Chemistry, 6e (Smith) Chapter 11 Alkynes 1) Which of the following molecular formulas is consistent with the formula for a molecule containing one alkyne and no other degrees of unsaturation?

A) I B) II C) III D) IV 2) Which of the following represents a terminal alkyne?

A) Only I and II B) Only II and III C) Only I and III D) Only II and IV 3) Which of the following represents an internal alkyne?

A) Only I and II B) Only I and III C) Only II and IV D) Only II and III

4) Which of the following alkynes is a symmetrical alkyne?

A) I B) II C) III D) IV 5) How many degrees of unsaturation are introduced by a triple bond? A) 0 B) 1 C) 2 D) 3 6) How many s bonds and p bonds are present in a triple bond? A) One s bond and one p bond. B) One s bond and two p bonds. C) Two s bonds and one p bond. D) Two s bonds and two p bonds. 7) Which of the following statements about alkynes is not true? A) Alkynes undergo many addition reactions. B) Alkynes are more polarizable than alkenes. C) Both p bonds of a C-C triple bond are weaker than a C-C s bond. D) The electrons in the p bonds of alkynes are more tightly held than those of alkenes. 8) Give the IUPAC name for the following compound.

A) 6,6-Dimethyl-3-octyne B) 3,3-Dimethyl-3-octyne C) 3,3-Dimethy-5-octyne D) 6-Ethyl-6-methyl-3-heptyne

9) Give the IUPAC name for the following compound.

A) 4,4-Diethyl-1-octyne B) 4,4-Dipropyl-1-heptyne C) 4,4-Dipropyl-6-heptyne D) 4,4-Diethyl-6-octyne 10) Give the IUPAC name for the following compound.

A) 4-Chloro-4-methyl-2-heptyne B) 3-Chloro-3-methyl-4-heptyne C) 3-Chloro-3-methyl-4-hexyne D) 4-Chloro-4-methyl-2-hexyne 11) Give the IUPAC name for the following compound.

A) 3-sec-Butyl-1,4-octadiyne B) 3-Isopropyl-1,5-octadiyne C) 3-Isopropyl-1,5-nonadiyne D) 3-sec-Butyl-1,4-nonadiyne

12) Give the IUPAC name for the following compound.

A) trans-2-Acetylenecyclohexanol B) trans-2-Ethynylcyclohexanol C) trans-2-Acetylene-1-cyclohexanol D) trans-2-Ethylenecyclohexanol 13) Give the IUPAC name for the following compound.

A) 2,5-Dimethyl-3-heptyne B) 3,6-Dimethy-4-heptyne C) 2,5-Dimethyl-3-octyne D) 3,6-Dimethyl-4-octyne 14) Give the IUPAC name for the following compound.

A) 4-Methyl-4-penten-1-yne B) 2-Methyl-2-hexen-5-yne C) 5-Methyl-4-hexen-1-yne D) 2-Methyl-2-penten-4-yne 15) Which of the following about the physical properties of alkynes is not true? A) Alkynes have low melting and boiling points. B) Melting and boiling points increase as the number of carbons increases. C) Alkynes are soluble in organic solvents. D) Alkynes are soluble in water.

16) Which of the following explains why 1-pentyne has a slightly higher boiling point than 1pentene? A) 1-Pentyne has more carbons than 1-pentene. B) 1-Pentyne has more carbons per hydrogen than 1-pentene. C) 1-Pentyne is linear while 1-pentene is trigonal planar. D) The C-C triple bond in 1-pentyne is more polar than the C-C double bond in 1-pentene. 17) What is the product of the following reaction?

A) I B) II C) III D) IV 18) What is the product of the following sequence of reactions?

A) I B) II C) III D) IV

19) What is the product of the following reaction?

A) I B) II C) III D) IV 20) Which method would work the best in accomplishing the following transformation?

A) [1] HBr; [2] 2eq. NaNH2 B) [1] Br2; [2] 2eq. NaNH2 C) [1] Br2, H2O; [2] NaNH2 D) [1]BH3, THF; [2] H2O2, NaOH; [3] NaNH2 21) Which of the following statements about the reactions of alkynes is not true? A) Alkynes contain easily broken p bonds. B) Alkynes undergo addition reactions. C) When alkynes undergo two sequential addition reactions, four new s bonds are formed. D) When alkynes undergo two sequential addition reactions, two new s bonds and a p bond are formed.

22) Which of the indicated hydrogen in the following compounds is the least acidic?

A) I B) II C) III D) IV 23) Which of the indicated hydrogen in the following compounds is the most acidic?

A) I B) II C) III D) IV 24) Rank the following compounds in order of decreasing basicity, putting the most basic first.

A) I > II > III B) III > II > I C) III > I > II D) II > III > I

25) Which of the following anions is the most basic?

A) I B) II C) III D) IV 26) Which of the following bases can deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.

A) Only I and II B) Only I and III C) Only II and III D) Only II and IV 27) Which of the following bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.

A) Only I and II B) Only I and III C) Only II and III D) Only II and IV

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

A) Only I B) Only II C) Only III D) I, II, and III 29) What is the reagent required to accomplish the following transformation?

A) SOCl2 B) 2eq. HCl C) Cl2 D) Br2/CCl4 30) In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is A) the Csp-H1s bond of 1-butyne. B) the C-C triple bond of 1-butyne. C) the H atom in HBr. D) the Br ion. 31) In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is A) the Csp-H1s bond of 1-butyne. B) the C-C triple bond of 1-butyne. C) the H atom in HBr. D) the Br ion.

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

A) Only I B) Only II C) Only III D) I, II, and III 33) Which of the following statements about tautomers is true? A) Tautomers differ in the position of a single bond and a hydrogen atom. B) Tautomers differ in the position of a double bond and a carbon atom. C) Tautomers differ in the position of a double bond and a hydrogen atom. D) Tautomers differ in the position of a single bond and a carbon atom. 34) What is the relationship between the keto and enol forms of acetone, CH3COCH3? A) Same compounds B) Diastereomers C) Enantiomers D) Constitutional isomers 35) Which of the following compounds is a tautomer of 2-hexanone?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III

36) Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III 37) Which of the following represents a keto-enol tautomeric pair?

A) I B) II C) III D) IV

38) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 39) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 40) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV 42) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 43) What is (are) the major organic product(s) of the following reaction?

A) Only I and II B) Only II and III C) Only I and III D) I, II, and III 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

44) Determine the product of the following reaction.

A) I B) II C) III D) IV 45) What is the starting material in the following reaction?

A) I B) II C) III D) IV 46) What is the major product of the following reaction?

A) I B) II C) III D) IV

47) Give the IUPAC name for the following compound.

A) R-4-bromo-1-pentyne B) S-4-bromo-1-pentyne C) R-3-bromo-5-pentyne D) S-3-bromo-5-pentyne 48) Give the IUPAC name for the following compound.

A) R-1-butyn-3-ol B) S-1-butyn-3-ol C) R-3-butyn-1-ol D) S-3-butyn-1-ol

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

A) I B) II C) III D) IV 50) What is the major product of the following reaction?

A) I B) II C) III D) IV

51) What is the major product of the following reaction sequence?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 11 Alkynes 1) Which of the following molecular formulas is consistent with the formula for a molecule containing one alkyne and no other degrees of unsaturation?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 2. Understand Chapter: 11 2) Which of the following represents a terminal alkyne?

A) Only I and II B) Only II and III C) Only I and III D) Only II and IV Answer: D Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

3) Which of the following represents an internal alkyne?

A) Only I and II B) Only I and III C) Only II and IV D) Only II and III Answer: B Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 4) Which of the following alkynes is a symmetrical alkyne?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

5) How many degrees of unsaturation are introduced by a triple bond? A) 0 B) 1 C) 2 D) 3 Answer: C Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 5. Evaluate Chapter: 11 Accessibility: Keyboard Navigation 6) How many s bonds and p bonds are present in a triple bond? A) One s bond and one p bond. B) One s bond and two p bonds. C) Two s bonds and one p bond. D) Two s bonds and two p bonds. Answer: B Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation 7) Which of the following statements about alkynes is not true? A) Alkynes undergo many addition reactions. B) Alkynes are more polarizable than alkenes. C) Both p bonds of a C-C triple bond are weaker than a C-C s bond. D) The electrons in the p bonds of alkynes are more tightly held than those of alkenes. Answer: D Difficulty: 1 Easy Section: 11.01 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation

8) Give the IUPAC name for the following compound.

A) 6,6-Dimethyl-3-octyne B) 3,3-Dimethyl-3-octyne C) 3,3-Dimethy-5-octyne D) 6-Ethyl-6-methyl-3-heptyne Answer: A Difficulty: 1 Easy Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 9) Give the IUPAC name for the following compound.

A) 4,4-Diethyl-1-octyne B) 4,4-Dipropyl-1-heptyne C) 4,4-Dipropyl-6-heptyne D) 4,4-Diethyl-6-octyne Answer: B Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

10) Give the IUPAC name for the following compound.

A) 4-Chloro-4-methyl-2-heptyne B) 3-Chloro-3-methyl-4-heptyne C) 3-Chloro-3-methyl-4-hexyne D) 4-Chloro-4-methyl-2-hexyne Answer: D Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 11) Give the IUPAC name for the following compound.

A) 3-sec-Butyl-1,4-octadiyne B) 3-Isopropyl-1,5-octadiyne C) 3-Isopropyl-1,5-nonadiyne D) 3-sec-Butyl-1,4-nonadiyne Answer: B Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

12) Give the IUPAC name for the following compound.

A) trans-2-Acetylenecyclohexanol B) trans-2-Ethynylcyclohexanol C) trans-2-Acetylene-1-cyclohexanol D) trans-2-Ethylenecyclohexanol Answer: B Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 13) Give the IUPAC name for the following compound.

A) 2,5-Dimethyl-3-heptyne B) 3,6-Dimethy-4-heptyne C) 2,5-Dimethyl-3-octyne D) 3,6-Dimethyl-4-octyne Answer: A Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

14) Give the IUPAC name for the following compound.

A) 4-Methyl-4-penten-1-yne B) 2-Methyl-2-hexen-5-yne C) 5-Methyl-4-hexen-1-yne D) 2-Methyl-2-penten-4-yne Answer: C Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 15) Which of the following about the physical properties of alkynes is not true? A) Alkynes have low melting and boiling points. B) Melting and boiling points increase as the number of carbons increases. C) Alkynes are soluble in organic solvents. D) Alkynes are soluble in water. Answer: D Difficulty: 1 Easy Section: 11.03 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 11.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

18) What is the product of the following sequence of reactions?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 11.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 19) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 11.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

20) Which method would work the best in accomplishing the following transformation?

A) [1] HBr; [2] 2eq. NaNH2 B) [1] Br2; [2] 2eq. NaNH2 C) [1] Br2, H2O; [2] NaNH2 D) [1]BH3, THF; [2] H2O2, NaOH; [3] NaNH2 Answer: B Difficulty: 2 Medium Section: 11.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 21) Which of the following statements about the reactions of alkynes is not true? A) Alkynes contain easily broken p bonds. B) Alkynes undergo addition reactions. C) When alkynes undergo two sequential addition reactions, four new s bonds are formed. D) When alkynes undergo two sequential addition reactions, two new s bonds and a p bond are formed. Answer: D Difficulty: 1 Easy Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation

22) Which of the indicated hydrogen in the following compounds is the least acidic?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 23) Which of the indicated hydrogen in the following compounds is the most acidic?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

24) Rank the following compounds in order of decreasing basicity, putting the most basic first.

A) I > II > III B) III > II > I C) III > I > II D) II > III > I Answer: B Difficulty: 2 Medium Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 25) Which of the following anions is the most basic?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

26) Which of the following bases can deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.

A) Only I and II B) Only I and III C) Only II and III D) Only II and IV Answer: B Difficulty: 1 Easy Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 27) Which of the following bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.

A) Only I and II B) Only I and III C) Only II and III D) Only II and IV Answer: D Difficulty: 1 Easy Section: 11.06 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

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

A) Only I B) Only II C) Only III D) I, II, and III Answer: A Difficulty: 1 Easy Section: 11.07 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 29) What is the reagent required to accomplish the following transformation?

A) SOCl2 B) 2eq. HCl C) Cl2 D) Br2/CCl4 Answer: B Difficulty: 1 Easy Section: 11.07 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

30) In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is A) the Csp-H1s bond of 1-butyne. B) the C-C triple bond of 1-butyne. C) the H atom in HBr. D) the Br ion. Answer: C Difficulty: 1 Easy Section: 11.07 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation 31) In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is A) the Csp-H1s bond of 1-butyne. B) the C-C triple bond of 1-butyne. C) the H atom in HBr. D) the Br ion. Answer: B Difficulty: 1 Easy Section: 11.07 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation

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

A) Only I B) Only II C) Only III D) I, II, and III Answer: A Difficulty: 1 Easy Section: 11.08 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 33) Which of the following statements about tautomers is true? A) Tautomers differ in the position of a single bond and a hydrogen atom. B) Tautomers differ in the position of a double bond and a carbon atom. C) Tautomers differ in the position of a double bond and a hydrogen atom. D) Tautomers differ in the position of a single bond and a carbon atom. Answer: C Difficulty: 1 Easy Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation

34) What is the relationship between the keto and enol forms of acetone, CH3COCH3? A) Same compounds B) Diastereomers C) Enantiomers D) Constitutional isomers Answer: D Difficulty: 2 Medium Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 Accessibility: Keyboard Navigation 35) Which of the following compounds is a tautomer of 2-hexanone?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III Answer: A Difficulty: 1 Easy Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

36) Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III Answer: B Difficulty: 2 Medium Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

37) Which of the following represents a keto-enol tautomeric pair?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 38) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 19 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

39) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 11.09 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 40) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 11.10 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

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

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 11.10 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 42) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 11.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

43) What is (are) the major organic product(s) of the following reaction?

A) Only I and II B) Only II and III C) Only I and III D) I, II, and III Answer: A Difficulty: 1 Easy Section: 11.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 44) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 11.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

45) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 11.12 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 46) What is the major product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 11.12 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

47) Give the IUPAC name for the following compound.

A) R-4-bromo-1-pentyne B) S-4-bromo-1-pentyne C) R-3-bromo-5-pentyne D) S-3-bromo-5-pentyne Answer: B Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11 48) Give the IUPAC name for the following compound.

A) R-1-butyn-3-ol B) S-1-butyn-3-ol C) R-3-butyn-1-ol D) S-3-butyn-1-ol Answer: D Difficulty: 2 Medium Section: 11.02 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

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

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 11.08 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

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

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 11.10 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

51) What is the major product of the following reaction sequence?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 11.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 11

Organic Chemistry, 6e (Smith) Chapter 12 Oxidation and Reduction 1) Which of the following statements about oxidation and reduction is not true? A) The conversion of an alkyne to an alkene is reduction. B) The conversion of an alkene to an alkane is reduction. C) Oxidation results in a decrease in the number of C-H bonds. D) Reduction results in an increase in the number of C-Z bonds. 2) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 3) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 4) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction

5) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 6) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 7) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 8) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction

9) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 10) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction 11) Rank the following compounds in order of increasing oxidation level (from lowest to highest).

A) I < III < II < IV B) II < III < I < IV C) IV < I < III < II D) II < IV < III < I 12) What happens to the carbon atom in the transformation of chloromethane to methyllithium? CH3Cl + 2Li ® CH3Li + LiCl A) Oxidized B) Reduced C) Oxidized and reduced D) Neither oxidized nor reduced

13) Rank the following compounds in order of decreasing oxidation level, putting the compound with the highest oxidation level first.

A) II > IV > I > III B) I > III > IV > II C) III > I > II > IV D) III > I > IV > II 14) Which of the following classes of organic compounds cannot undergo reduction easily? A) Alkanes B) Alkenes C) Alkynes D) Carboxylic acids 15) Determine the product(s) of the following reaction.

A) I and III B) II and III C) I, II, and III D) I or II 16) Rank the following alkenes in order of decreasing heat of hydrogenation.

A) I > II > III B) III > I > II C) II > I > III D) III > II > I 4 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

17) Which of the following explains why heats of hydrogenation cannot be used to determine the relative stability of compounds A and B below?

A) Compound A is trisubstituted while compound B is monosubstituted. B) Compound A has E configuration while compound B has no E/Z configuration. C) Both compounds A and B have no E/Z configurations. D) Hydrogenation of A and B give different alkanes. 18) Rank the following alkenes in order of increasing rate of hydrogenation.

A) I < III < IV < II B) IV < III < II < I C) I < II < III < IV D) IV < II < III < I 19) A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula C8H14. What can be inferred about the structure of compound X? A) Compound X has 3 rings. B) Compound X has 3 p bonds. C) Compound X has 1 ring and 2 p bonds. D) Compound X has 2 rings and 1 p bond.

20) Determine the product of the following reaction.

A) I B) II C) III D) IV 21) What reagent is required to accomplish the following transformation?

A) Na, NH3 B) H2, Pd-C C) H2, Ni D) H2, Lindlar catalyst 22) What reagent is required to accomplish the following transformation?

A) Na, NH3 B) H2, Pd-C C) H2, Ni D) H2, Lindlar catalyst

23) What is the starting material in the following reaction?

A) I B) II C) III D) IV 24) Determine the product of the following reaction.

A) I B) II C) III D) IV 25) Which of the following statements about the reduction of epoxides with LiA1H4 is true? A) The nucleophile is a hydride (H-). B) In unsymmetrical epoxides, nucleophilic attack of H- occurs at the more substituted carbon atom. C) The reaction follows SN1 mechanism. D) The nucleophile, H-, is a weak nucleophile.

26) Which is (are) the product(s) of the following reaction?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III 27) Which of the following products do not form in the following reaction?

A) Only I B) Only II C) Only III and IV D) Only I and II 28) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II 8 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

29) Determine the product of the following reaction, ignoring stereochemistry.

A) I B) II C) III D) IV 30) What is (are) the product(s) of the following reaction?

A) I B) II C) III D) IV 31) What is the reagent required to accomplish the following transformation?

A) LiA1H4 B) [1] OsO4; [2] NaHSO3, H2O C) RCO3H, H2O/HOD) PCC/CH2Cl2

32) What is the reagent required to accomplish the following transformation?

A) [1] OsO4; [2] NaHSO3, H2O B) KMnO4, H2O/HOC) RCO3H/H2O/HOD) PCC/CH2Cl2 33) Determine the product of the following reaction.

A) I B) II C) III D) IV 34) After ozonolysis and treatment of the unstable ozonide with CH3SCH3, compound A was converted to the compound below. What is the structure of compound A?

A) I B) II C) III D) IV

35) What is the starting material in the following sequence of reactions?

A) I B) II C) III D) IV 36) Which of the following is (are) formed by ozonolysis of compound A?

A) Only I B) Only II C) Only I and II D) I, II, and III

37) Which of the following is (are) formed by ozonolysis of compound A?

A) Only I B) Only II C) I and II D) I, II, and III 38) Which of the following is (are) formed by ozonolysis of the following alkyne?

A) Only I and II B) Only III and IV C) Only I and IV D) Only II and III 39) Which of the following is (are) formed by ozonolysis of the following alkyne?

A) Only I B) Only II C) I and II D) I, II, and III 12 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

40) Determine the product of the following reaction.

A) I B) II C) III D) IV 41) Determine the product of the following reaction.

A) I B) II C) III D) IV

42) What is the product of the following reaction?

A) I B) II C) III D) IV 43) Predict the major product of the following reaction.

A) I B) II C) III D) IV

44) Predict the major product of the following reaction.

A) I B) II C) III D) IV 45) What is the starting material in the following reaction?

A) I B) II C) III D) IV

46) What is the starting material in the following reaction?

A) I B) II C) III D) IV 47) What reagents are necessary to perform the following reaction?

A) H2, Lindlar's B) Na, NH3 C) O3 D) KMnO4

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

A) I B) II C) III D) IV 49) What reagents are necessary to perform the following reaction?

A) LiAlH4, H2O B) O2 C) KMnO4 D) PCC

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

A) Only I B) Only I and IV C) Only II D) Only III 51) What reagents are necessary to perform the following reaction?

A) PCC B) K2Cr2O7, H2SO4, H2O C) LiAlH4, H2O D) Na, NH3

Organic Chemistry, 6e (Smith) Chapter 12 Oxidation and Reduction 1) Which of the following statements about oxidation and reduction is not true? A) The conversion of an alkyne to an alkene is reduction. B) The conversion of an alkene to an alkane is reduction. C) Oxidation results in a decrease in the number of C-H bonds. D) Reduction results in an increase in the number of C-Z bonds. Answer: D Difficulty: 1 Easy Section: 12.01 Topic: Alkenes; Alkynes Bloom's: 2. Understand Chapter: 12 Accessibility: Keyboard Navigation 2) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Alkenes Bloom's: 2. Understand Chapter: 12

3) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Alkyl Halides Bloom's: 2. Understand Chapter: 12 4) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: B Difficulty: 1 Easy Section: 12.01 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 12

5) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Alkyl Halides Bloom's: 2. Understand Chapter: 12 6) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: B Difficulty: 1 Easy Section: 12.01 Topic: Alkenes Bloom's: 2. Understand Chapter: 12

7) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Alcohols Bloom's: 2. Understand Chapter: 12 8) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: B Difficulty: 1 Easy Section: 12.01 Topic: Alkanes Bloom's: 2. Understand Chapter: 12

9) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 12 10) What is the correct classification of the following reaction?

A) Reduction reaction B) Oxidation reaction C) Elimination reaction D) Substitution reaction Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Alkenes Bloom's: 2. Understand Chapter: 12

11) Rank the following compounds in order of increasing oxidation level (from lowest to highest).

A) I < III < II < IV B) II < III < I < IV C) IV < I < III < II D) II < IV < III < I Answer: D Difficulty: 1 Easy Section: 12.01 Topic: Alkenes; Aldehydes and Ketones; Alkanes; Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 12 12) What happens to the carbon atom in the transformation of chloromethane to methyllithium? CH3Cl + 2Li ® CH3Li + LiCl A) Oxidized B) Reduced C) Oxidized and reduced D) Neither oxidized nor reduced Answer: B Difficulty: 1 Easy Section: 12.01 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 12 Accessibility: Keyboard Navigation

13) Rank the following compounds in order of decreasing oxidation level, putting the compound with the highest oxidation level first.

A) II > IV > I > III B) I > III > IV > II C) III > I > II > IV D) III > I > IV > II Answer: C Difficulty: 1 Easy Section: 12.01 Topic: Alkenes; Aldehydes and Ketones; Alkanes; Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 12 14) Which of the following classes of organic compounds cannot undergo reduction easily? A) Alkanes B) Alkenes C) Alkynes D) Carboxylic acids Answer: A Difficulty: 1 Easy Section: 12.01 Topic: Alkenes; Aldehydes and Ketones; Alkanes; Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 12 Accessibility: Keyboard Navigation

15) Determine the product(s) of the following reaction.

A) I and III B) II and III C) I, II, and III D) I or II Answer: D Difficulty: 2 Medium Section: 12.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 16) Rank the following alkenes in order of decreasing heat of hydrogenation.

A) I > II > III B) III > I > II C) II > I > III D) III > II > I Answer: B Difficulty: 2 Medium Section: 12.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

17) Which of the following explains why heats of hydrogenation cannot be used to determine the relative stability of compounds A and B below?

A) Compound A is trisubstituted while compound B is monosubstituted. B) Compound A has E configuration while compound B has no E/Z configuration. C) Both compounds A and B have no E/Z configurations. D) Hydrogenation of A and B give different alkanes. Answer: D Difficulty: 2 Medium Section: 12.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 18) Rank the following alkenes in order of increasing rate of hydrogenation.

A) I < III < IV < II B) IV < III < II < I C) I < II < III < IV D) IV < II < III < I Answer: B Difficulty: 2 Medium Section: 12.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

19) A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula C8H14. What can be inferred about the structure of compound X? A) Compound X has 3 rings. B) Compound X has 3 p bonds. C) Compound X has 1 ring and 2 p bonds. D) Compound X has 2 rings and 1 p bond. Answer: D Difficulty: 2 Medium Section: 12.03 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 Accessibility: Keyboard Navigation 20) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 12.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 12

21) What reagent is required to accomplish the following transformation?

A) Na, NH3 B) H2, Pd-C C) H2, Ni D) H2, Lindlar catalyst Answer: D Difficulty: 2 Medium Section: 12.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 12 22) What reagent is required to accomplish the following transformation?

A) Na, NH3 B) H2, Pd-C C) H2, Ni D) H2, Lindlar catalyst Answer: A Difficulty: 2 Medium Section: 12.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 12

23) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 12.05 Topic: Alkenes; Alkynes Bloom's: 3. Apply Chapter: 12 24) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 12.06 Topic: Epoxides Bloom's: 3. Apply Chapter: 12

25) Which of the following statements about the reduction of epoxides with LiA1H4 is true? A) The nucleophile is a hydride (H-). B) In unsymmetrical epoxides, nucleophilic attack of H- occurs at the more substituted carbon atom. C) The reaction follows SN1 mechanism. D) The nucleophile, H-, is a weak nucleophile. Answer: A Difficulty: 2 Medium Section: 12.06 Topic: Epoxides Bloom's: 3. Apply Chapter: 12 Accessibility: Keyboard Navigation 26) Which is (are) the product(s) of the following reaction?

A) Only I and II B) Only I and III C) Only II and III D) I, II, and III Answer: A Difficulty: 2 Medium Section: 12.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

27) Which of the following products do not form in the following reaction?

A) Only I B) Only II C) Only III and IV D) Only I and II Answer: C Difficulty: 2 Medium Section: 12.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 28) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 2 Medium Section: 12.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

29) Determine the product of the following reaction, ignoring stereochemistry.

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 12.08 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 30) What is (are) the product(s) of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 12.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

31) What is the reagent required to accomplish the following transformation?

A) LiA1H4 B) [1] OsO4; [2] NaHSO3, H2O C) RCO3H, H2O/HOD) PCC/CH2Cl2 Answer: B Difficulty: 2 Medium Section: 12.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 32) What is the reagent required to accomplish the following transformation?

A) [1] OsO4; [2] NaHSO3, H2O B) KMnO4, H2O/HOC) RCO3H/H2O/HOD) PCC/CH2Cl2 Answer: C Difficulty: 2 Medium Section: 12.09 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

33) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 12.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 34) After ozonolysis and treatment of the unstable ozonide with CH3SCH3, compound A was converted to the compound below. What is the structure of compound A?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 12.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 17 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

35) What is the starting material in the following sequence of reactions?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 12.10 Topic: Alkenes; Alkyl Halides Bloom's: 3. Apply Chapter: 12 36) Which of the following is (are) formed by ozonolysis of compound A?

A) Only I B) Only II C) Only I and II D) I, II, and III Answer: C Difficulty: 2 Medium Section: 12.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 18 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

37) Which of the following is (are) formed by ozonolysis of compound A?

A) Only I B) Only II C) I and II D) I, II, and III Answer: C Difficulty: 2 Medium Section: 12.10 Topic: Alkenes Bloom's: 3. Apply Chapter: 12 38) Which of the following is (are) formed by ozonolysis of the following alkyne?

A) Only I and II B) Only III and IV C) Only I and IV D) Only II and III Answer: A Difficulty: 2 Medium Section: 12.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 12

39) Which of the following is (are) formed by ozonolysis of the following alkyne?

A) Only I B) Only II C) I and II D) I, II, and III Answer: A Difficulty: 2 Medium Section: 12.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 12 40) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 12.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 12

41) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 12.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 12

42) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 12.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 12

43) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 12.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

44) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 12.15 Topic: Alkenes Bloom's: 3. Apply Chapter: 12

45) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 12.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 12

46) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 12.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 12 47) What reagents are necessary to perform the following reaction?

A) H2, Lindlar's B) Na, NH3 C) O3 D) KMnO4 Answer: B Difficulty: 1 Easy Section: 12.05 Topic: Alkynes Bloom's: 3. Apply Chapter: 12

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

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 12.06 Topic: Reduction Bloom's: 3. Apply Chapter: 12 49) What reagents are necessary to perform the following reaction?

A) LiAlH4, H2O B) O2 C) KMnO4 D) PCC Answer: A Difficulty: 1 Easy Section: 12.06 Topic: Reduction Bloom's: 3. Apply Chapter: 12 27 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) Only I B) Only I and IV C) Only II D) Only III Answer: B Difficulty: 2 Medium Section: 12.11 Topic: Alkynes Bloom's: 3. Apply Chapter: 12 51) What reagents are necessary to perform the following reaction?

A) PCC B) K2Cr2O7, H2SO4, H2O C) LiAlH4, H2O D) Na, NH3 Answer: A Difficulty: 2 Medium Section: 12.12 Topic: Alcohols Bloom's: 3. Apply Chapter: 12

Organic Chemistry, 6e (Smith) Chapter 13 Radical Reactions 1) Which of the following statements about radicals and radical reactions is not true? A) Most radicals are unstable. B) A radical contains an atom that has an octet of electrons. C) Half-headed arrows are used to show the movement of lone electrons. D) A radical is formed by homolysis of a covalent bond. 2) Which of the following statements about carbon radicals is not true? A) Carbon radicals are classified as primary, secondary, tertiary, or quaternary. B) A carbon radical is sp2 hybridized. C) The geometry of a carbon radical is trigonal planar. D) The unhybridized p orbital in a carbon radical contains the unpaired electron. 3) Which of the following statements about radicals is true? A) Cleavage of a stronger bond forms the more stable radical. B) The stability of a radical increases as the number of alkyl groups bonded to the radical carbon decreases. C) The higher the bond dissociation energy for a C-H bond, the more stable the resulting carbon radical. D) Less stable radicals generally do not rearrange to more stable radicals. 4) Which of the following compounds contain primary (1°) radical carbons?

A) Only I B) Only II C) Only III D) Only II and IV 5) Which of the following compounds contain secondary (2°) radical carbons?

A) Only I B) Only II C) Only III D) Only II and IV 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

6) Which of the following compounds contain tertiary (3°) radical carbons?

A) Only I B) Only II C) Only III D) Only II and IV 7) Which of the following is a radical scavenger? A) O3 B) O2 C) Vitamin C D) CO2 8) How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH3)2CHCH2CH3 with Cl2 and hn? A) 2 B) 3 C) 4 D) 5 9) How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and hn? A) 3 B) 4 C) 5 D) 6 10) How many monochlorination products can be formed from the reaction of (CH3)3CH with Cl2 and hn? A) 1 B) 2 C) 3 D) 4 11) Which of the following statements about radical reactions is not true? A) Light or heat provides the energy needed for homolytic bond cleavage to form radicals. B) Breaking the weak O-O bond of peroxides initiates radical reactions. C) The diradical O2 removes radicals from a reaction mixture. D) Radicals rearrange. 2 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

12) Which steps are the rate-determining step in the mechanism of radical halogenation? A) Initiation B) Propagation C) Termination D) Initiation and propagation 13) Which of the following statements about the propagation steps in the chlorination of ethane is true? A) Radical chlorination consists of two propagation steps. B) The energy diagram for the propagation steps has three energy barriers. C) The first of the propagation steps is rate-determining because its transition state is at lower energy. D) The second of the propagation steps is rate-determining because its transition state is at higher energy. 14) Which of the following statements about chlorination and bromination is true? A) Bromination is unselective, yielding a mixture of products. B) Chlorination is often selective, yielding one major product. C) Chlorination is faster than bromination. D) Bromination is faster than chlorination. 15) Which of the following statements about bromination is true? A) The rate-determining step in bromination is exothermic. B) Both radicals are formed. C) A mixture of products results. D) A single radical halogenation product predominates. 16) Which of the following statements about chlorination is true? A) The rate-determining step in chlorination is endothermic. B) The transition state resembles the product. C) The more stable radical is formed faster. D) A mixture of products results.

17) What is the product in the following sequence of reactions?

A) I B) II C) III D) IV 18) What is the product in the following sequence of reactions?

A) I B) II C) III D) IV 19) Which of the following statements about the stereochemistry of halogenation reactions is true? A) An achiral starting material always gives an achiral product only. B) An achiral starting material always gives a racemic product only. C) The configuration at a stereogenic center of a product must change even if a reaction does not occur at a stereogenic center. D) An achiral starting material always gives either an achiral or a racemic product. 20) How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl2 and hn? A) 2 B) 3 C) 4 D) 5

21) How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl2 and hn? A) 2 B) 3 C) 4 D) 5 22) Rank the following radicals in order of increasing stability, putting the least stable first.

A) III< I < II B) I < II < III C) III < II < I D) I < III < II 23) Rank the following radicals in order of decreasing stability, putting the most stable first.

A) II > IV > III > I B) III > II > IV > I C) IV > III > II > I D) IV > III > I > II 24) What is the product of the following reaction?

25) What is the product of the following reaction?

A) I B) II C) III D) IV 26) How many allylic halides can be formed when 3-methycyclohexene undergoes allylic halogenation with one equivalent of NBS and light? A) 1 B) 2 C) 3 D) 4 27) What is the product of the following reaction?

A) I B) II C) III D) IV

28) Identify the monomer used to make the following polymer.

A) I B) II C) III D) IV 29) Identify the monomer used to make the following polymer.

A) I B) II C) III D) IV

30) Identify the monomer used to make the following polymer.

A) I B) II C) III D) IV 31) Determine the monochlorination product(s).

A) Only I B) Only II C) Only III D) Only I and II

32) Determine the product of the following reaction.

A) I B) II C) III D) IV 33) Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only I and II 34) Which of the following statements is (are) true about free radical halogenation of alkanes? A) The first of the chain-propagating steps is rate-determining. B) The reaction proceeds by way of a flat sp2 hybridized free radical. C) The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a hydrogen atom. D) Statements (The first of the chain-propagating steps is rate-determining) and (The reaction proceeds by way of a flat sp2 hybridized free radical) are both true.

35) Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?

A) Ha B) Hb C) Hc D) Hd 36) Which of the indicated hydrogens is most readily abstracted in a free radical halogenation reaction?

A) I B) II C) III D) IV

37) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain initiating step(s) is (are) ________.

A) Only [1] B) Only [2] C) Only [3] D) Only [1] and [2] 38) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain propagating step(s) is (are) ________.

A) Only [1] and [2] B) Only [2] and [3] C) Only [1] and [3] D) Only [3]

39) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine DH for step [1].

Bond dissociation energies (kcal/mol):

A) -5 kcal/mol B) +58 kcal/mol C) -28 kcal/mol D) None of the choices are correct.

40) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine DH for step [2].

Bond dissociation energies (kcal/mol):

A) -5 kcal/mol B) +58 kcal/mol C) -28 kcal/mol D) None of the choices are correct. 41) Select the route that would most likely produce the desired results from the given starting material.

I.(1) H2SO4 and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr III.(1) H2SO4 and heat; (2) HBr + peroxides IV.(1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides A) I B) II C) III D) IV 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) What type of reactive intermediate is formed in the reaction of propene with Nbromosuccinimide (NBS) to give 3-bromo-1-propene? A) Cyclic bromonium ion B) Allylic carbocation C) Allylic carbanion D) Allylic radical 43) Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

A) I B) II C) III D) IV 44) How many monochlorination products, including stereoisomers, are formed from (S,S)-1,2dimethylcyclopropane?

A) 4 B) 3 C) 6 D) 5 45) How many products, including stereoisomers, are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides? A) 1 B) 2 C) 3 D) 4 46) How many products, including stereoisomers, are formed when (R)-2,4-dimethylhex-2-ene is treated with HBr in presence of peroxides? A) 1 B) 2 C) 3 D) 4 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

47) Rank the following in order of increasing stability.

A) I < II < III < IV B) II < I < III < IV C) I < II < IV < III D) IV < III < II < I 48) What is/are the product(s) of the following monochlorination?

A) I B) II C) III D) All of the choices are correct.

49) For a radical reaction, put the following steps in the correct order: 1. Initiation 2. Propagation 3. Termination A) 1, 2, 3 B) 1, 3, 2 C) 2, 3, 1 D) 3, 2, 1 50) Which of the following would be the fastest to form a radical?

A) I B) II C) III D) IV

51) Find the major product of the following reaction.

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 13 Radical Reactions 1) Which of the following statements about radicals and radical reactions is not true? A) Most radicals are unstable. B) A radical contains an atom that has an octet of electrons. C) Half-headed arrows are used to show the movement of lone electrons. D) A radical is formed by homolysis of a covalent bond. Answer: B Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 2) Which of the following statements about carbon radicals is not true? A) Carbon radicals are classified as primary, secondary, tertiary, or quaternary. B) A carbon radical is sp2 hybridized. C) The geometry of a carbon radical is trigonal planar. D) The unhybridized p orbital in a carbon radical contains the unpaired electron. Answer: A Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 3) Which of the following statements about radicals is true? A) Cleavage of a stronger bond forms the more stable radical. B) The stability of a radical increases as the number of alkyl groups bonded to the radical carbon decreases. C) The higher the bond dissociation energy for a C-H bond, the more stable the resulting carbon radical. D) Less stable radicals generally do not rearrange to more stable radicals. Answer: D Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

4) Which of the following compounds contain primary (1°) radical carbons?

A) Only I B) Only II C) Only III D) Only II and IV Answer: C Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 5) Which of the following compounds contain secondary (2°) radical carbons?

A) Only I B) Only II C) Only III D) Only II and IV Answer: D Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

6) Which of the following compounds contain tertiary (3°) radical carbons?

A) Only I B) Only II C) Only III D) Only II and IV Answer: A Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 7) Which of the following is a radical scavenger? A) O3 B) O2 C) Vitamin C D) CO2 Answer: B Difficulty: 1 Easy Section: 13.02 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation

8) How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH3)2CHCH2CH3 with Cl2 and hn? A) 2 B) 3 C) 4 D) 5 Answer: C Difficulty: 1 Easy Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 9) How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and hn? A) 3 B) 4 C) 5 D) 6 Answer: A Difficulty: 1 Easy Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 10) How many monochlorination products can be formed from the reaction of (CH3)3CH with Cl2 and hn? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 1 Easy Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation

11) Which of the following statements about radical reactions is not true? A) Light or heat provides the energy needed for homolytic bond cleavage to form radicals. B) Breaking the weak O-O bond of peroxides initiates radical reactions. C) The diradical O2 removes radicals from a reaction mixture. D) Radicals rearrange. Answer: D Difficulty: 1 Easy Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 12) Which steps are the rate-determining step in the mechanism of radical halogenation? A) Initiation B) Propagation C) Termination D) Initiation and propagation Answer: B Difficulty: 1 Easy Section: 13.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 13) Which of the following statements about the propagation steps in the chlorination of ethane is true? A) Radical chlorination consists of two propagation steps. B) The energy diagram for the propagation steps has three energy barriers. C) The first of the propagation steps is rate-determining because its transition state is at lower energy. D) The second of the propagation steps is rate-determining because its transition state is at higher energy. Answer: A Difficulty: 1 Easy Section: 13.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation

14) Which of the following statements about chlorination and bromination is true? A) Bromination is unselective, yielding a mixture of products. B) Chlorination is often selective, yielding one major product. C) Chlorination is faster than bromination. D) Bromination is faster than chlorination. Answer: C Difficulty: 1 Easy Section: 13.06 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 15) Which of the following statements about bromination is true? A) The rate-determining step in bromination is exothermic. B) Both radicals are formed. C) A mixture of products results. D) A single radical halogenation product predominates. Answer: D Difficulty: 1 Easy Section: 13.06 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 16) Which of the following statements about chlorination is true? A) The rate-determining step in chlorination is endothermic. B) The transition state resembles the product. C) The more stable radical is formed faster. D) A mixture of products results. Answer: D Difficulty: 1 Easy Section: 13.06 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation

17) What is the product in the following sequence of reactions?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 13.07 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 18) What is the product in the following sequence of reactions?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 13.07 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

19) Which of the following statements about the stereochemistry of halogenation reactions is true? A) An achiral starting material always gives an achiral product only. B) An achiral starting material always gives a racemic product only. C) The configuration at a stereogenic center of a product must change even if a reaction does not occur at a stereogenic center. D) An achiral starting material always gives either an achiral or a racemic product. Answer: D Difficulty: 1 Easy Section: 13.08 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 20) How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl2 and hn? A) 2 B) 3 C) 4 D) 5 Answer: B Difficulty: 2 Medium Section: 13.08 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 21) How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl2 and hn? A) 2 B) 3 C) 4 D) 5 Answer: C Difficulty: 2 Medium Section: 13.08 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 8 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

22) Rank the following radicals in order of increasing stability, putting the least stable first.

A) III< I < II B) I < II < III C) III < II < I D) I < III < II Answer: C Difficulty: 1 Easy Section: 13.02 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 23) Rank the following radicals in order of decreasing stability, putting the most stable first.

A) II > IV > III > I B) III > II > IV > I C) IV > III > II > I D) IV > III > I > II Answer: A Difficulty: 1 Easy Section: 13.02 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

24) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 13.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 25) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 13.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

26) How many allylic halides can be formed when 3-methycyclohexene undergoes allylic halogenation with one equivalent of NBS and light? A) 1 B) 2 C) 3 D) 4 Answer: D Difficulty: 1 Easy Section: 13.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 27) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 13.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

28) Identify the monomer used to make the following polymer.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 13.14 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

29) Identify the monomer used to make the following polymer.

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 13.14 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 30) Identify the monomer used to make the following polymer.

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 13.14 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

31) Determine the monochlorination product(s).

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 13.05 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 32) Determine the product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 13.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

33) Determine the product(s) of the following reaction.

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 13.10 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 34) Which of the following statements is (are) true about free radical halogenation of alkanes? A) The first of the chain-propagating steps is rate-determining. B) The reaction proceeds by way of a flat sp2 hybridized free radical. C) The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a hydrogen atom. D) Statements (The first of the chain-propagating steps is rate-determining) and (The reaction proceeds by way of a flat sp2 hybridized free radical) are both true. Answer: D Difficulty: 1 Easy Section: 13.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation

35) Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?

A) Ha B) Hb C) Hc D) Hd Answer: B Difficulty: 2 Medium Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 36) Which of the indicated hydrogens is most readily abstracted in a free radical halogenation reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

37) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain initiating step(s) is (are) ________.

A) Only [1] B) Only [2] C) Only [3] D) Only [1] and [2] Answer: A Difficulty: 1 Easy Section: 13.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

38) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain propagating step(s) is (are) ________.

A) Only [1] and [2] B) Only [2] and [3] C) Only [1] and [3] D) Only [3] Answer: B Difficulty: 1 Easy Section: 13.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

39) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine DH for step [1].

Bond dissociation energies (kcal/mol):

A) -5 kcal/mol B) +58 kcal/mol C) -28 kcal/mol D) None of the choices are correct. Answer: B Difficulty: 2 Medium Section: 13.04 Topic: Radical Reactions Bloom's: 5. Evaluate Chapter: 13

40) A possible reaction of ethane with chlorine is shown below.

This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. Determine DH for step [2].

Bond dissociation energies (kcal/mol):

A) -5 kcal/mol B) +58 kcal/mol C) -28 kcal/mol D) None of the choices are correct. Answer: A Difficulty: 2 Medium Section: 13.04 Topic: Radical Reactions Bloom's: 5. Evaluate Chapter: 13

41) Select the route that would most likely produce the desired results from the given starting material.

I.(1) H2SO4 and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr III.(1) H2SO4 and heat; (2) HBr + peroxides IV.(1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 13.07 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 42) What type of reactive intermediate is formed in the reaction of propene with Nbromosuccinimide (NBS) to give 3-bromo-1-propene? A) Cyclic bromonium ion B) Allylic carbocation C) Allylic carbanion D) Allylic radical Answer: D Difficulty: 3 Hard Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation

43) Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 44) How many monochlorination products, including stereoisomers, are formed from (S,S)-1,2dimethylcyclopropane?

A) 4 B) 3 C) 6 D) 5 Answer: C Difficulty: 3 Hard Section: 13.08 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 13

45) How many products, including stereoisomers, are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 2 Medium Section: 13.13 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 13 Accessibility: Keyboard Navigation 46) How many products, including stereoisomers, are formed when (R)-2,4-dimethylhex-2-ene is treated with HBr in presence of peroxides? A) 1 B) 2 C) 3 D) 4 Answer: B Difficulty: 3 Hard Section: 13.13 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 13 Accessibility: Keyboard Navigation

47) Rank the following in order of increasing stability.

A) I < II < III < IV B) II < I < III < IV C) I < II < IV < III D) IV < III < II < I Answer: A Difficulty: 1 Easy Section: 13.01 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

48) What is/are the product(s) of the following monochlorination?

A) I B) II C) III D) All of the choices are correct. Answer: D Difficulty: 1 Easy Section: 13.03 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13

49) For a radical reaction, put the following steps in the correct order: 1. Initiation 2. Propagation 3. Termination A) 1, 2, 3 B) 1, 3, 2 C) 2, 3, 1 D) 3, 2, 1 Answer: A Difficulty: 1 Easy Section: 13.04 Topic: Radical Reactions Bloom's: 3. Apply Chapter: 13 Accessibility: Keyboard Navigation 50) Which of the following would be the fastest to form a radical?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 13.05 Topic: Radical Reactions Chapter: 13

51) Find the major product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 13.13 Topic: Radical Reactions Bloom's: 4. Analyze Chapter: 13

Organic Chemistry, 6e (Smith) Chapter 14 Conjugation, Resonance, and Dienes 1) Which of the following dienes contain conjugated double bonds?

A) Only I and II B) Only II and III C) Only I and III D) Only II and IV 2) Which of the following dienes contain isolated double bonds?

A) Only I and II B) Only II and III C) Only I and III D) Only II and IV 3) Which of the following statements about resonance structures is true? A) The placement of atoms is different. B) The placement of p bonds is different. C) The placement of s bonds is different. D) The placement of nonbonded electrons is the same. 4) What is the hybridization around the indicated carbon atom in the following anion?

5) What is the hybridization around the indicated oxygen atom in the following anion?

A) sp3 B) sp2 C) sp D) p 6) Which of the following is (are) conjugated dienes?

A) Only I B) Only II C) Only I and II D) I, II, and III 7) Which of the following compounds is conjugated?

A) I B) II C) III D) IV

8) Which of the following conjugated dienes represent two conformations?

A) Only I and II B) Only I and III C) Only II and III D) None of the choices 9) Rank the following dienes in order of decreasing heat of hydrogenation, putting the diene with the highest heat of hydrogenation first.

A) I > II > III B) III > II > I C) II > I > III D) III > I > II 10) Rank the following compounds in order of increasing stability, putting the least stable first.

A) I < II < III B) III < II < I C) II < I < III D) III < I < II 11) What is the reactive intermediate in the reaction of 1,3-diene with HBr, resulting in 1,4addition? A) Allylic radical B) Cyclic bromonium C) Dienophile D) Allylic carbocation

12) Which of the following is the appropriate term for the mechanism of the addition of HBr to 1,3-dienes? A) Nucleophilic addition B) Electrophilic addition C) Free radical addition D) Conjugate addition 13) What is (are) the major product(s) of the following reaction?

A) Only I B) Only II and IV C) Only I and III D) Only I, II, and III 14) What is (are) the major product(s) of the following reaction?

A) Only I B) Only I and III C) Only II and IV D) Only I, II, and III

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

A) Only I B) Only II C) Only I and II D) I, II, and III 16) Which of the following is not a product obtained from the addition of 1 equivalent of HBr to (E)-1,3-pentadiene? A) (E)-4-Bromo-2-pentene B) (E)-1-Bromo-2-pentene C) 3-Bromo-1-pentene D) (E)-3-Bromo-2-pentene 17) What is the thermodynamic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene? A) 3-Bromo-1-butene B) 1-Bromo-2-butene C) 2-Bromo-2-butene D) 2-Bromo-1-butene 18) What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3butadiene? A) 3-Bromo-1-butene B) 1-Bromo-2-butene C) 2-Bromo-2-butene D) 2-Bromo-1-butene 19) Which of the following statements about kinetic vs. thermodynamic products is true? A) The product that is formed faster is the thermodynamic product. B) The kinetic product predominates at low temperature. C) The product that predominates at equilibrium is the kinetic product. D) The thermodynamic product is less stable.

20) Which of the following statements about the mechanism of the Diels-Alder reaction is true? A) Three π bonds break; two σ bonds and one π bond form. B) Three π bonds break; one σ bond and two π bonds form. C) Two π bonds break; one σ bond and one π bond form. D) Two π bonds break; two σ bonds and one π bond form. 21) Which of the following is not a feature of the Diels-Alder reaction? A) They are initiated by peroxides. B) They form new six-membered rings. C) Three π bonds break. D) They are concerted. 22) Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

A) I< II < III B) III < I < II C) II < I < III D) I < III < II 23) Which of the following is the least reactive diene in a Diels-Alder reaction?

A) I B) II C) III D) IV 24) Which of the following statements about the Diels-Alder reaction is true? A) The diene can react only when it adopts the s-trans conformation. B) Electron-withdrawing substituents in the diene increase reaction rate. C) Electron-donating substituents in the dienophile increase the reaction rate. D) The stereochemistry of the dienophile is retained in the product.

25) Rank the following dienophile in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

A) I < II < III B) III < I < II C) II < I < III D) III < II < I 26) Which of the following compounds is the least reactive dienophile in a Diels-Alder reaction?

A) I B) II C) III D) IV 27) Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction?

A) I B) II C) III D) IV

28) Which of the following is the most reactive diene in a Diels-Alder reaction?

A) I B) II C) III D) IV 29) Which of the following is the least reactive diene in a Diels-Alder reaction?

A) I B) II C) III D) IV 30) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

31) What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II 32) What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II

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

A) Only I B) Only I and II C) Only II and III D) I, II, and III 34) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

35) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 36) What diene and dienophile are used in a Diels-Alder reaction to prepare the following compound?

37) Which of the following compound absorbs UV light at the longest wavelength?

A) I B) II C) III D) IV 38) Which of the following compound absorbs UV light at the longest wavelength?

A) I B) II C) III D) IV 39) Which of the following electronic transitions is common in the UV spectrum of 1,3butadiene? A) s®p B) s®p* C) n ®p* D) p®p* 40) What is the definition of a resonance structure? A) Compounds with the same molecular formula B) Compounds with different carbon frameworks C) Structures that differ only in the placement of π and nonbonding electrons D) Structures that differ only in the location of bonds 41) Rank the following anions from most to least stable, listing the most stable first.

A) I> II > III B) III > II > I C) I > III > II D) III > I > II 12 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) How would you favor the formation of the kinetic product of the following reaction?

A) Excess HBr B) Long reaction time C) Low temperature D) High pressure 43) Which of the following is an example of a bridged bicyclic system?

A) I B) II C) III D) IV 44) Why would the compound below not react with a dienophile in a Diels-Alder reaction?

45) Which of the following is not a resonance structure of acetic anhydride?

A) I B) II C) III D) IV 46) Which triene has the largest heat of hydrogenation?

A) I B) II C) III D) IV 47) Which triene has the smallest heat of hydrogenation?

A) I B) II C) III D) IV

48) Which triene absorbs the longest wavelength of UV light?

A) I B) II C) III D) IV 49) Which of the following is a major resonance contributor to the first structure?

A) I B) II C) III D) IV 50) What is the major product of the following reaction?

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV 52) What is the major product of the following reaction?

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 14 Conjugation, Resonance, and Dienes 1) Which of the following dienes contain conjugated double bonds?

A) Only I and II B) Only II and III C) Only I and III D) Only II and IV Answer: C Difficulty: 1 Easy Section: 14.01 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 2) Which of the following dienes contain isolated double bonds?

A) Only I and II B) Only II and III C) Only I and III D) Only II and IV Answer: D Difficulty: 1 Easy Section: 14.01 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

3) Which of the following statements about resonance structures is true? A) The placement of atoms is different. B) The placement of p bonds is different. C) The placement of s bonds is different. D) The placement of nonbonded electrons is the same. Answer: B Difficulty: 1 Easy Section: 14.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 14 Accessibility: Keyboard Navigation 4) What is the hybridization around the indicated carbon atom in the following anion?

A) sp3 B) sp2 C) sp D) p Answer: B Difficulty: 1 Easy Section: 14.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

5) What is the hybridization around the indicated oxygen atom in the following anion?

A) sp3 B) sp2 C) sp D) p Answer: B Difficulty: 1 Easy Section: 14.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 6) Which of the following is (are) conjugated dienes?

A) Only I B) Only II C) Only I and II D) I, II, and III Answer: B Difficulty: 1 Easy Section: 14.06 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

7) Which of the following compounds is conjugated?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.06 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 8) Which of the following conjugated dienes represent two conformations?

A) Only I and II B) Only I and III C) Only II and III D) None of the choices Answer: C Difficulty: 1 Easy Section: 14.06 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

9) Rank the following dienes in order of decreasing heat of hydrogenation, putting the diene with the highest heat of hydrogenation first.

A) I > II > III B) III > II > I C) II > I > III D) III > I > II Answer: D Difficulty: 2 Medium Section: 14.09 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 10) Rank the following compounds in order of increasing stability, putting the least stable first.

A) I < II < III B) III < II < I C) II < I < III D) III < I < II Answer: A Difficulty: 2 Medium Section: 14.09 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

11) What is the reactive intermediate in the reaction of 1,3-diene with HBr, resulting in 1,4addition? A) Allylic radical B) Cyclic bromonium C) Dienophile D) Allylic carbocation Answer: D Difficulty: 1 Easy Section: 14.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 12) Which of the following is the appropriate term for the mechanism of the addition of HBr to 1,3-dienes? A) Nucleophilic addition B) Electrophilic addition C) Free radical addition D) Conjugate addition Answer: B Difficulty: 1 Easy Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation

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

A) Only I B) Only II and IV C) Only I and III D) Only I, II, and III Answer: B Difficulty: 1 Easy Section: 14.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

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

A) Only I B) Only I and III C) Only II and IV D) Only I, II, and III Answer: D Difficulty: 1 Easy Section: 14.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 15) What is (are) the major product(s) of the following reaction?

A) Only I B) Only II C) Only I and II D) I, II, and III Answer: C Difficulty: 1 Easy Section: 14.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 8 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

16) Which of the following is not a product obtained from the addition of 1 equivalent of HBr to (E)-1,3-pentadiene? A) (E)-4-Bromo-2-pentene B) (E)-1-Bromo-2-pentene C) 3-Bromo-1-pentene D) (E)-3-Bromo-2-pentene Answer: D Difficulty: 1 Easy Section: 14.10 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 17) What is the thermodynamic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene? A) 3-Bromo-1-butene B) 1-Bromo-2-butene C) 2-Bromo-2-butene D) 2-Bromo-1-butene Answer: B Difficulty: 1 Easy Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 18) What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3butadiene? A) 3-Bromo-1-butene B) 1-Bromo-2-butene C) 2-Bromo-2-butene D) 2-Bromo-1-butene Answer: A Difficulty: 1 Easy Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation

19) Which of the following statements about kinetic vs. thermodynamic products is true? A) The product that is formed faster is the thermodynamic product. B) The kinetic product predominates at low temperature. C) The product that predominates at equilibrium is the kinetic product. D) The thermodynamic product is less stable. Answer: B Difficulty: 1 Easy Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 20) Which of the following statements about the mechanism of the Diels-Alder reaction is true? A) Three π bonds break; two σ bonds and one π bond form. B) Three π bonds break; one σ bond and two π bonds form. C) Two π bonds break; one σ bond and one π bond form. D) Two π bonds break; two σ bonds and one π bond form. Answer: A Difficulty: 1 Easy Section: 14.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 21) Which of the following is not a feature of the Diels-Alder reaction? A) They are initiated by peroxides. B) They form new six-membered rings. C) Three π bonds break. D) They are concerted. Answer: A Difficulty: 1 Easy Section: 14.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation

22) Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

A) I< II < III B) III < I < II C) II < I < III D) I < III < II Answer: B Difficulty: 1 Easy Section: 14.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 23) Which of the following is the least reactive diene in a Diels-Alder reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

24) Which of the following statements about the Diels-Alder reaction is true? A) The diene can react only when it adopts the s-trans conformation. B) Electron-withdrawing substituents in the diene increase reaction rate. C) Electron-donating substituents in the dienophile increase the reaction rate. D) The stereochemistry of the dienophile is retained in the product. Answer: D Difficulty: 2 Medium Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 25) Rank the following dienophile in order of increasing reactivity in a Diels-Alder reaction, listing the least reactive first.

A) I < II < III B) III < I < II C) II < I < III D) III < II < I Answer: B Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

26) Which of the following compounds is the least reactive dienophile in a Diels-Alder reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 27) Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

28) Which of the following is the most reactive diene in a Diels-Alder reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 29) Which of the following is the least reactive diene in a Diels-Alder reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

30) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 31) What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: C Difficulty: 2 Medium Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 15 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

32) What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 2 Medium Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

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

A) Only I B) Only I and II C) Only II and III D) I, II, and III Answer: A Difficulty: 2 Medium Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

34) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

35) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 14.13 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

36) What diene and dienophile are used in a Diels-Alder reaction to prepare the following compound?

A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 14.14 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

37) Which of the following compound absorbs UV light at the longest wavelength?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 14.15 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 38) Which of the following compound absorbs UV light at the longest wavelength?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.15 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

39) Which of the following electronic transitions is common in the UV spectrum of 1,3butadiene? A) s®p B) s®p* C) n ®p* D) p®p* Answer: D Difficulty: 1 Easy Section: 14.15 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 40) What is the definition of a resonance structure? A) Compounds with the same molecular formula B) Compounds with different carbon frameworks C) Structures that differ only in the placement of π and nonbonding electrons D) Structures that differ only in the location of bonds Answer: C Difficulty: 1 Easy Section: 14.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 Accessibility: Keyboard Navigation 41) Rank the following anions from most to least stable, listing the most stable first.

A) I> II > III B) III > II > I C) I > III > II D) III > I > II Answer: B Difficulty: 2 Medium Section: 14.06 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) How would you favor the formation of the kinetic product of the following reaction?

A) Excess HBr B) Long reaction time C) Low temperature D) High pressure Answer: C Difficulty: 1 Easy Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 43) Which of the following is an example of a bridged bicyclic system?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 14.07 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

44) Why would the compound below not react with a dienophile in a Diels-Alder reaction?

A) The compound is not a conjugated diene. B) There are no electron withdrawing groups on the compound. C) There are no electron donating groups on the compound. D) The compound cannot adopt the s-cis conformation. Answer: D Difficulty: 1 Easy Section: 14.12 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14 45) Which of the following is not a resonance structure of acetic anhydride?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 14.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

46) Which triene has the largest heat of hydrogenation?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 14.09 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 14 47) Which triene has the smallest heat of hydrogenation?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 14.09 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 14

48) Which triene absorbs the longest wavelength of UV light?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 14.15 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 14 49) Which of the following is a major resonance contributor to the first structure?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 14.04 Topic: Conjugated Dienes and Pericyclic Reactions Chapter: 14

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

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

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

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

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

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

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

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 14.11 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 14

Organic Chemistry, 6e (Smith) Chapter 15 Benzene and Aromatic Compounds 1) Which of the following statements about benzene is true? A) Benzene is a saturated hydrocarbon. B) Benzene undergoes addition reactions. C) Benzene has five degrees of unsaturation. D) Benzene undergoes substitution reactions. 2) Which of the following statements about the structure of benzene is not true? A) Benzene is planar. B) Benzene has three short double bonds alternating with three longer single bonds. C) The electrons in the pi bonds are delocalized around the ring. D) Benzene has six pi electrons. 3) What orbitals are used to form the bond indicated in the following molecule?

A) Csp2¾Csp2 B) Csp2¾ C2p C) C2p¾C2p D) Csp3¾Csp3 4) What is the IUPAC name of the following compound?

A) 3,6-Dichloroaniline B) 2,5-Dichloroaniline C) 2,5-Dichloroaminobenzene D) 2,5-Dichloroanisole

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

A) 2-Nitro-5-carboxychlorobenzene B) 2-Chloro-4-carboxynitrobenzene C) 2-Chloro-1-nitro-4-benzoic acid D) 3-Chloro-4-nitrobenzoic acid 6) What is the IUPAC name of the following compound?

A) 1-Chloro-4-ethyl-3-propylbenzene B) 1-Chloro-4-ethyl-5-propylbenzene C) 4-Chloro-1-ethyl-2-propylbenzene D) 4-Chloro-2-propyltoluene 7) What is the IUPAC name of the following compound?

A) 3-Bromo-1-chloro-4-toluene B) 2-Bromo-4-chlorotoluene C) 4-Chloro-2-bromo-1-toluene D) 2-Bromo-4-chloroanisole

8) What is the correct assignment of the names of the following substituted benzenes?

A) I = Phenol; II = anisole; III = toluene B) I = Benzaldehyde; II = phenol; III = anisole C) I = Benzaldehyde; II = phenol; III = toluene D) I = Phenol; II = anisole; III = styrene 9) What is the correct assignment of the names of the following substituted benzenes?

A) I = Styrene; II = aniline; III = anisole B) I = Toluene; II = anisole; III = styrene C) I = Styrene; II = anisole; III = phenol D) I = Toluene; II = aniline; III = anisole 10) How many 13CNMR signals does the following compound exhibit?

A) 4 B) 5 C) 6 D) 8

11) What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 ¾2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm?

A) I B) II C) III D) IV 12) What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?

A) I = 3 signals; II = 3 signals; III = 2 signals B) I = 3 signals; II = 4 signals; III = 2 signals C) I = 6 signals; II = 6 signals; III = 6 signals D) I = 3 signals; II = 4 signals; III = 3 signals 13) Which of the following is not one of the Hückel's criteria for aromaticity? A) The molecule must be cyclic. B) The molecule must be planar. C) The molecule must be completely conjugated. D) The molecule must have 4n pi electrons. 14) Which of the following is not a criterion for antiaromaticity? A) The molecule must be cyclic. B) The molecule must have (4n + 2) pi electrons. C) The molecule must be planar. D) The molecule must be completely conjugated.

15) What is the correct assignment of the names of the following aromatic heterocycles?

A) I = pyridine; II = pyrimidine; III = furan B) I = pyrimidine; II =pyrrole; III = furan C) I = pyridine; II = pyrrole; III = furan D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran 16) What is the correct assignment of the names of the following fused aromatic compounds?

A) I = naphthalene; II = anthracene; III = phenanthrene B) I = naphthalene; II = phenanthrene; III = anthracene C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene D) I = anthracene; II = naphthalene; III = phenanthrene 17) Which of the following heterocycles is not aromatic?

A) I B) II C) III D) IV

18) Which of the following ions is aromatic?

A) I B) II C) III D) IV 19) Which of the following molecules has the most acidic hydrogen atoms?

A) I B) II C) III D) IV 20) Rank the following compounds in order of decreasing acidity, starting with the most acidic.

A) I > II > III B) III > II > I C) III > I > II D) I > III > II

21) Which of the following ions is aromatic?

A) Only I and II B) Only II and III C) Only III and IV D) Only II and IV 22) Which of the following statements about the molecular orbital (MO) theory is true?

A) When two p orbitals of similar phase overlap side-by-side, a p* antibonding molecular orbital is formed. B) When two p orbitals of opposite phase overlap side-by-side, a p bonding molecular orbital is formed. C) A p bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. D) A p* antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. 23) What orbitals are used to form the indicated bond?

24) What orbitals are used to form the indicated bond?

A) sp3 B) sp2 C) p D) sp3 and sp2 25) What is the name of the following compound?

A) 2,6-Dimethylbenzene B) 5-Methyltoluene C) Anisole D) 1,3-Dimethylbenzene 26) What is the name of the following compound?

A) Meta-bromophenol B) Para-hydroxybenzene C) 3-bromoanisole D) 6-methoxy-2-bromobenzene

27) What is the correct structure for aniline?

A) I B) II C) III D) IV 28) What is the correct structure for anisole?

A) I B) II C) III D) IV 29) What is the correct structure for toluene?

A) I B) II C) III D) IV

30) What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

A) I B) II C) III D) IV 31) Where do the protons in benzene appear in the 1H NMR spectrum? A) Around 1600 cm-1 B) Around 120 ppm C) Around 0 ppm D) Around 7 ppm 32) How many different proton signals would the following compound show in its 1H NMR spectrum?

A) 1 B) 3 C) 5 D) 6

33) What compound is consistent with the following 1H NMR spectrum?

A) Phenol B) Anisole C) 4-bromoanisole D) 4-bromotoluene 34) What is the correct structure for para-bromotoluene?

A) I B) II C) III D) IV 35) Which of the following compounds is not aromatic?

A) I B) II C) III D) IV

36) Which of the following compounds is not aromatic?

A) I B) II C) III D) IV 37) Which of the following compounds is aromatic?

A) I B) II C) III D) IV 38) Which of the following compounds is aromatic?

A) I B) II C) III D) IV

39) Why is the following compound not aromatic?

A) It has 4n pi electrons. B) It is not cyclic. C) It has 4n+2 pi electrons. D) The pi electron system is not continuous. 40) Why is the following compound not aromatic?

A) It has 4n electrons. B) It is not cyclic. C) It has 4n+2 electrons. D) The pi electron system is not continuous. 41) What is the hybridization of the indicated N atom in the following compound?

A) p B) sp C) sp2 D) sp3

42) What is the hybridization of the indicated N atom in the following compound?

A) p B) sp C) sp2 D) sp3 43) In what type of orbital does the lone pair on the indicated N atom reside?

A) p B) sp C) sp2 D) sp3 44) In what type of orbital does the lone pair on the indicated N atom reside?

A) p B) sp C) sp2 D) sp3

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

A) o-nitroanisole B) m-nitroanisole C) p-nitroanisole D) 2-nitroaniline 46) What is the IUPAC name of the following compound?

A) o-nitroaniline B) m-nitroaniline C) p-nitroaniline D) 4-nitroanilsole

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

A) o-nitrotoluene B) m-nitrotoluene C) p-nitrotoluene D) 3-nitroanisole

Organic Chemistry, 6e (Smith) Chapter 15 Benzene and Aromatic Compounds 1) Which of the following statements about benzene is true? A) Benzene is a saturated hydrocarbon. B) Benzene undergoes addition reactions. C) Benzene has five degrees of unsaturation. D) Benzene undergoes substitution reactions. Answer: D Difficulty: 1 Easy Section: 15.02 Topic: Aromatic Compounds Bloom's: 2. Understand Chapter: 15 Accessibility: Keyboard Navigation 2) Which of the following statements about the structure of benzene is not true? A) Benzene is planar. B) Benzene has three short double bonds alternating with three longer single bonds. C) The electrons in the pi bonds are delocalized around the ring. D) Benzene has six pi electrons. Answer: B Difficulty: 1 Easy Section: 15.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 Accessibility: Keyboard Navigation

3) What orbitals are used to form the bond indicated in the following molecule?

A) Csp2¾Csp2 B) Csp2¾ C2p C) C2p¾C2p D) Csp3¾Csp3 Answer: A Difficulty: 1 Easy Section: 15.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 4) What is the IUPAC name of the following compound?

A) 3,6-Dichloroaniline B) 2,5-Dichloroaniline C) 2,5-Dichloroaminobenzene D) 2,5-Dichloroanisole Answer: B Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

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

A) 2-Nitro-5-carboxychlorobenzene B) 2-Chloro-4-carboxynitrobenzene C) 2-Chloro-1-nitro-4-benzoic acid D) 3-Chloro-4-nitrobenzoic acid Answer: D Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 6) What is the IUPAC name of the following compound?

A) 1-Chloro-4-ethyl-3-propylbenzene B) 1-Chloro-4-ethyl-5-propylbenzene C) 4-Chloro-1-ethyl-2-propylbenzene D) 4-Chloro-2-propyltoluene Answer: C Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

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

A) 3-Bromo-1-chloro-4-toluene B) 2-Bromo-4-chlorotoluene C) 4-Chloro-2-bromo-1-toluene D) 2-Bromo-4-chloroanisole Answer: B Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 8) What is the correct assignment of the names of the following substituted benzenes?

A) I = Phenol; II = anisole; III = toluene B) I = Benzaldehyde; II = phenol; III = anisole C) I = Benzaldehyde; II = phenol; III = toluene D) I = Phenol; II = anisole; III = styrene Answer: C Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

9) What is the correct assignment of the names of the following substituted benzenes?

A) I = Styrene; II = aniline; III = anisole B) I = Toluene; II = anisole; III = styrene C) I = Styrene; II = anisole; III = phenol D) I = Toluene; II = aniline; III = anisole Answer: A Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 10) How many 13CNMR signals does the following compound exhibit?

A) 4 B) 5 C) 6 D) 8 Answer: C Difficulty: 1 Easy Section: 15.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 15.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 12) What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?

A) I = 3 signals; II = 3 signals; III = 2 signals B) I = 3 signals; II = 4 signals; III = 2 signals C) I = 6 signals; II = 6 signals; III = 6 signals D) I = 3 signals; II = 4 signals; III = 3 signals Answer: B Difficulty: 1 Easy Section: 15.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 6 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

13) Which of the following is not one of the Hückel's criteria for aromaticity? A) The molecule must be cyclic. B) The molecule must be planar. C) The molecule must be completely conjugated. D) The molecule must have 4n pi electrons. Answer: D Difficulty: 1 Easy Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 Accessibility: Keyboard Navigation 14) Which of the following is not a criterion for antiaromaticity? A) The molecule must be cyclic. B) The molecule must have (4n + 2) pi electrons. C) The molecule must be planar. D) The molecule must be completely conjugated. Answer: B Difficulty: 1 Easy Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 Accessibility: Keyboard Navigation 15) What is the correct assignment of the names of the following aromatic heterocycles?

A) I = pyridine; II = pyrimidine; III = furan B) I = pyrimidine; II =pyrrole; III = furan C) I = pyridine; II = pyrrole; III = furan D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran Answer: C Difficulty: 1 Easy Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

16) What is the correct assignment of the names of the following fused aromatic compounds?

A) I = naphthalene; II = anthracene; III = phenanthrene B) I = naphthalene; II = phenanthrene; III = anthracene C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene D) I = anthracene; II = naphthalene; III = phenanthrene Answer: A Difficulty: 1 Easy Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 17) Which of the following heterocycles is not aromatic?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

18) Which of the following ions is aromatic?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 19) Which of the following molecules has the most acidic hydrogen atoms?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

20) Rank the following compounds in order of decreasing acidity, starting with the most acidic.

A) I > II > III B) III > II > I C) III > I > II D) I > III > II Answer: B Difficulty: 1 Easy Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 21) Which of the following ions is aromatic?

A) Only I and II B) Only II and III C) Only III and IV D) Only II and IV Answer: D Difficulty: 1 Easy Section: 15.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

22) Which of the following statements about the molecular orbital (MO) theory is true?

A) When two p orbitals of similar phase overlap side-by-side, a p* antibonding molecular orbital is formed. B) When two p orbitals of opposite phase overlap side-by-side, a p bonding molecular orbital is formed. C) A p bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. D) A p* antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. Answer: D Difficulty: 1 Easy Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 23) What orbitals are used to form the indicated bond?

A) sp3 B) sp2 C) p D) sp3 and sp2 Answer: D Difficulty: 1 Easy Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 11 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

24) What orbitals are used to form the indicated bond?

A) sp3 B) sp2 C) p D) sp3 and sp2 Answer: B Difficulty: 1 Easy Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 25) What is the name of the following compound?

A) 2,6-Dimethylbenzene B) 5-Methyltoluene C) Anisole D) 1,3-Dimethylbenzene Answer: D Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

26) What is the name of the following compound?

A) Meta-bromophenol B) Para-hydroxybenzene C) 3-bromoanisole D) 6-methoxy-2-bromobenzene Answer: A Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 27) What is the correct structure for aniline?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

28) What is the correct structure for anisole?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 29) What is the correct structure for toluene?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

30) What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 31) Where do the protons in benzene appear in the 1H NMR spectrum? A) Around 1600 cm-1 B) Around 120 ppm C) Around 0 ppm D) Around 7 ppm Answer: D Difficulty: 1 Easy Section: 15.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 Accessibility: Keyboard Navigation

32) How many different proton signals would the following compound show in its 1H NMR spectrum?

A) 1 B) 3 C) 5 D) 6 Answer: B Difficulty: 1 Easy Section: 15.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 33) What compound is consistent with the following 1H NMR spectrum?

A) Phenol B) Anisole C) 4-bromoanisole D) 4-bromotoluene Answer: C Difficulty: 2 Medium Section: 15.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 16 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

34) What is the correct structure for para-bromotoluene?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 15.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 35) Which of the following compounds is not aromatic?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

36) Which of the following compounds is not aromatic?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 37) Which of the following compounds is aromatic?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

38) Which of the following compounds is aromatic?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 39) Why is the following compound not aromatic?

A) It has 4n pi electrons. B) It is not cyclic. C) It has 4n+2 pi electrons. D) The pi electron system is not continuous. Answer: D Difficulty: 1 Easy Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

40) Why is the following compound not aromatic?

A) It has 4n electrons. B) It is not cyclic. C) It has 4n+2 electrons. D) The pi electron system is not continuous. Answer: A Difficulty: 1 Easy Section: 15.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 41) What is the hybridization of the indicated N atom in the following compound?

A) p B) sp C) sp2 D) sp3 Answer: C Difficulty: 2 Medium Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

42) What is the hybridization of the indicated N atom in the following compound?

A) p B) sp C) sp2 D) sp3 Answer: C Difficulty: 2 Medium Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 43) In what type of orbital does the lone pair on the indicated N atom reside?

A) p B) sp C) sp2 D) sp3 Answer: C Difficulty: 2 Medium Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

44) In what type of orbital does the lone pair on the indicated N atom reside?

A) p B) sp C) sp2 D) sp3 Answer: A Difficulty: 2 Medium Section: 15.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 45) What is the IUPAC name of the following compound?

A) o-nitroanisole B) m-nitroanisole C) p-nitroanisole D) 2-nitroaniline Answer: A Difficulty: 1 Easy Section: 15.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) o-nitroaniline B) m-nitroaniline C) p-nitroaniline D) 4-nitroanilsole Answer: C Difficulty: 1 Easy Section: 15.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

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

A) o-nitrotoluene B) m-nitrotoluene C) p-nitrotoluene D) 3-nitroanisole Answer: B Difficulty: 1 Easy Section: 15.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 15

Organic Chemistry, 6e (Smith) Chapter 16 Reactions of Aromatic Compounds 1) What is the first step in the general mechanism for electrophilic aromatic substitution? A) Protonation of the aromatic ring B) Deprotonation of the aromatic ring C) Addition of the electrophile to the aromatic ring D) Loss of the electrophile from the aromatic ring 2) What is the driving force for losing a proton as the last step in electrophilic aromatic substitution? A) To neutralize the base that is present B) To make room for the electrophile C) To make the ring more reactive D) To rearomatize the ring system 3) What is the electrophile in aromatic nitration? A) NO+ B) NO2+ C) NO3+ D) NO2H 4) What is the electrophile in aromatic sulfonation? A) H2SO3 B) H2SO4 C) SO3+ D) HSO3+ 5) Why is sulfuric acid used in aromatic nitration? A) To keep the reaction from getting too basic B) To form the active electrophile NO2+ C) To protonate the aromatic ring D) To keep the reaction from getting too acidic 6) What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride? A) The tert-butyl cation B) A complex of tert-butylchloride and aluminum chloride C) A proton D) Aluminum chloride

7) Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction?

A) I B) II C) III D) IV 8) What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution? A) Steric and electronic B) Inductive and steric C) Inductive and resonance D) Resonance and electronic 9) Why is the nitro group a meta director? A) Because it is sterically very large B) Because it adds electron density to the meta position, thus activating it C) Because it stabilizes the intermediate cation D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less 10) What is a major problem with Friedel-Crafts alkylation? A) It requires high temperatures. B) The conditions are too acidic. C) The starting material is frequently over-alkylated. D) The products coordinate with the aluminum chloride. 11) Which of the following statements about the mechanism of electrophilic aromatic substitution is not true? A) All electrophilic aromatic substitution reactions occur via a two-step mechanism. B) The transition state of the first step is lower in energy. C) The first step is the rate-determining step. D) The second step is the fast step.

12) What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?

A) I B) II C) III D) IV 13) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV

14) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV 15) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV

16) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV 17) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV

18) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV 19) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV

20) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV 21) Which of the following substituents are activators in electrophilic aromatic substitution? A) CH3O ¾ B) Cl ¾ C) NO2 ¾ D) HSO3¾ 22) Which of the following substituents are deactivators in electrophilic aromatic substitution? A) HO ¾ B) CH3NH ¾ C) CH3O ¾ D) (CH3)3N+¾ 23) Which of the following substituents is an ortho, para director? A) ¾ CHO B) ¾ COOH C) ¾ NHCOR D) ¾ CN 24) Which of the following substituents is a meta director? A) ¾ N(CH3)2 B) ¾ OCH3 C) ¾ NHCOCH3 D) ¾ SO3H

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

A) Only I B) Only II C) Only III D) Only I and III 26) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II

27) Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

A) I < II < III < IV B) II < I < IV < III C) III < IV < I < II D) II < I < III < IV 28) Rank the following compounds in order of decreasing reactivity in electrophilic aromatic substitution.

A) II > IV > I > III B) II > III > IV > I C) IV > II > I > III D) IV > I > II > III 29) Rank the following activating groups in order of decreasing strength of activation, listing the most activating first.

A) IV > II > III > I B) II > III > IV > I C) III > IV > II > I D) II > IV > III > I

30) Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first.

A) I < II < III < IV B) II < III < IV < I C) II < I < III < IV D) IV < III < I < II 31) What are the product(s) of the following reaction?

A) Only I B) Only II C) Only I and II D) Only III 32) What are the product(s) of the following reaction?

A) Only I and II B) Only I and III C) Only II and III D) Only IV 10 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

33) How can polyalkylation be minimized in Friedel-Crafts alkylation? A) Use a large excess of alkyl halide relative to the aromatic compound. B) Use a large excess of benzene relative to the alkyl halide. C) Use an alkyl halide without a Lewis acid catalyst. D) Use a large excess of the Lewis acid catalyst. 34) What is the major product of the following reaction?

A) I B) II C) III D) IV 35) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II

36) What are the two distinct pathways for nucleophilic aromatic substitution? A) Addition-substitution and substitution-addition B) Addition-elimination and elimination-addition C) Addition-addition and elimination-elimination D) Elimination-substitution and substitution-elimination 37) What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution? A) Carbocation B) Radical C) Benzyne D) Carbanion 38) What is the reactive intermediate formed in the elimination-addition mechanism of nucleophilic aromatic substitution? A) Carbocation B) Radical C) Benzyne D) Carbanion 39) Which of the following statements about nucleophilic aromatic substitution is not true? A) Increasing the electronegativity of the halogen increases the reactivity of the aryl halide. B) Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide. C) Electron-withdrawing groups stabilize the intermediate carbanion, and lower the energy of the transition state. D) When a nitro group is located meta to the halogen, the negative charge of the intermediate carbanion can be delocalized onto the NO2 group, thus stabilizing it. 40) Which of the following statements about nucleophilic aromatic substitution is true? A) For the addition-elimination pathway, the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. B) For the elimination-addition pathway, the nucleophile becomes attached only at the site bearing the leaving group. C) The elimination-addition mechanism is not as common as the addition-elimination mechanism. D) In the addition-elimination mechanism, the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate.

41) Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.

A) III < II < I B) I < II < III C) III < I < II D) I < III < II 42) What is the major product of the following reaction?

A) I B) II C) III D) IV 43) Which aryl fluoride reacts the fastest with NaOH?

A) I B) II C) III D) IV

44) In addition to the product shown, what other product is formed in the following reaction?

A) I B) II C) III D) IV 45) Which set of reagents would most likely bring about the following transformation?

A) Br2 and FeBr3 B) NBS and light C) Br2 in CCl4 D) NaBr and H2O

46) What is the product of the following sequence of reactions?

A) I B) II C) III D) IV 47) What is the product of the following reaction?

A) I B) II C) III D) IV

48) What is the product of the following reaction?

A) I B) II C) III D) None of these 49) What is the best choice of reagent to bring about the following transformation?

A) [1] LiAlH4; [2] H2O B) Zn (Hg), HCl C) NH3, NaOH D) H2, Pd-C 50) What is the best choice of reagent to bring about the following transformation?

A) [1] LiAlH4; [2]H2O B) Zn (Hg), HCl C) NH3, NaOH D) H2, Pd-C

51) What is the product of the following reaction?

A) I B) II C) III D) IV 52) What is the major product of electrophilic addition of HBr to the following alkene?

A) I B) II C) III D) IV

53) Consider the tetracyclic aromatic compound drawn below, with rings labelled as I, II, III, and IV. Which of the four rings is most reactive in electrophilic aromatic substitution?

A) I B) II C) III D) IV 54) Consider the tetracyclic aromatic compound drawn below, with rings labelled as I, II, III, and IV. Which of the four rings is least reactive in electrophilic aromatic substitution?

A) I B) II C) III D) IV 55) What is the structure of compound A?

A) I B) II C) III D) IV

56) What is the product of the following monobromonation reaction?

A) Only I B) Only II C) Only III D) Only I and III

57) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

58) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 59) What reagents would be necessary to produce the following product from benzene?

A) CH3Cl, AlCl3 2. HNO3, H2SO4 3. KMnO4 B) HNO3, H2SO4 2. CH3Cl, AlCl3 3. KMnO4 C) KMnO4 2. CH3Cl, AlCl3 3. HNO3, H2SO4 D) KMnO4 2. HNO3, H2SO4 3.CH3Cl, AlCl3

60) What reagents would be necessary to produce the following product from benzene?

Organic Chemistry, 6e (Smith) Chapter 16 Reactions of Aromatic Compounds 1) What is the first step in the general mechanism for electrophilic aromatic substitution? A) Protonation of the aromatic ring B) Deprotonation of the aromatic ring C) Addition of the electrophile to the aromatic ring D) Loss of the electrophile from the aromatic ring Answer: C Difficulty: 1 Easy Section: 16.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 2) What is the driving force for losing a proton as the last step in electrophilic aromatic substitution? A) To neutralize the base that is present B) To make room for the electrophile C) To make the ring more reactive D) To rearomatize the ring system Answer: D Difficulty: 1 Easy Section: 16.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 3) What is the electrophile in aromatic nitration? A) NO+ B) NO2+ C) NO3+ D) NO2H Answer: B Difficulty: 1 Easy Section: 16.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

4) What is the electrophile in aromatic sulfonation? A) H2SO3 B) H2SO4 C) SO3+ D) HSO3+ Answer: D Difficulty: 1 Easy Section: 16.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 5) Why is sulfuric acid used in aromatic nitration? A) To keep the reaction from getting too basic B) To form the active electrophile NO2+ C) To protonate the aromatic ring D) To keep the reaction from getting too acidic Answer: B Difficulty: 1 Easy Section: 16.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 6) What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride? A) The tert-butyl cation B) A complex of tert-butylchloride and aluminum chloride C) A proton D) Aluminum chloride Answer: A Difficulty: 1 Easy Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

7) Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 8) What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution? A) Steric and electronic B) Inductive and steric C) Inductive and resonance D) Resonance and electronic Answer: C Difficulty: 1 Easy Section: 16.06 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

9) Why is the nitro group a meta director? A) Because it is sterically very large B) Because it adds electron density to the meta position, thus activating it C) Because it stabilizes the intermediate cation D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less Answer: D Difficulty: 1 Easy Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 10) What is a major problem with Friedel-Crafts alkylation? A) It requires high temperatures. B) The conditions are too acidic. C) The starting material is frequently over-alkylated. D) The products coordinate with the aluminum chloride. Answer: C Difficulty: 1 Easy Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 11) Which of the following statements about the mechanism of electrophilic aromatic substitution is not true? A) All electrophilic aromatic substitution reactions occur via a two-step mechanism. B) The transition state of the first step is lower in energy. C) The first step is the rate-determining step. D) The second step is the fast step. Answer: B Difficulty: 1 Easy Section: 16.02 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

12) What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

13) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 16.03 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

14) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 16.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

15) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 16.04 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

16) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

17) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

18) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 19) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 11 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

20) What is the major organic product obtained from the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 16.09 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 21) Which of the following substituents are activators in electrophilic aromatic substitution? A) CH3O ¾ B) Cl ¾ C) NO2 ¾ D) HSO3¾ Answer: A Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

22) Which of the following substituents are deactivators in electrophilic aromatic substitution? A) HO ¾ B) CH3NH ¾ C) CH3O ¾ D) (CH3)3N+¾ Answer: D Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 23) Which of the following substituents is an ortho, para director? A) ¾ CHO B) ¾ COOH C) ¾ NHCOR D) ¾ CN Answer: C Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 24) Which of the following substituents is a meta director? A) ¾ N(CH3)2 B) ¾ OCH3 C) ¾ NHCOCH3 D) ¾ SO3H Answer: D Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

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

A) Only I B) Only II C) Only III D) Only I and III Answer: D Difficulty: 1 Easy Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

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

A) Only I B) Only II C) Only III D) Only I and II Answer: A Difficulty: 1 Easy Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 27) Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

A) I < II < III < IV B) II < I < IV < III C) III < IV < I < II D) II < I < III < IV Answer: B Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 15 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

28) Rank the following compounds in order of decreasing reactivity in electrophilic aromatic substitution.

A) II > IV > I > III B) II > III > IV > I C) IV > II > I > III D) IV > I > II > III Answer: D Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 29) Rank the following activating groups in order of decreasing strength of activation, listing the most activating first.

A) IV > II > III > I B) II > III > IV > I C) III > IV > II > I D) II > IV > III > I Answer: B Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

30) Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first.

A) I < II < III < IV B) II < III < IV < I C) II < I < III < IV D) IV < III < I < II Answer: C Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 31) What are the product(s) of the following reaction?

A) Only I B) Only II C) Only I and II D) Only III Answer: D Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

32) What are the product(s) of the following reaction?

A) Only I and II B) Only I and III C) Only II and III D) Only IV Answer: A Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 33) How can polyalkylation be minimized in Friedel-Crafts alkylation? A) Use a large excess of alkyl halide relative to the aromatic compound. B) Use a large excess of benzene relative to the alkyl halide. C) Use an alkyl halide without a Lewis acid catalyst. D) Use a large excess of the Lewis acid catalyst. Answer: B Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

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

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

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

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 16.08 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 36) What are the two distinct pathways for nucleophilic aromatic substitution? A) Addition-substitution and substitution-addition B) Addition-elimination and elimination-addition C) Addition-addition and elimination-elimination D) Elimination-substitution and substitution-elimination Answer: B Difficulty: 1 Easy Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation

37) What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution? A) Carbocation B) Radical C) Benzyne D) Carbanion Answer: D Difficulty: 1 Easy Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 38) What is the reactive intermediate formed in the elimination-addition mechanism of nucleophilic aromatic substitution? A) Carbocation B) Radical C) Benzyne D) Carbanion Answer: C Difficulty: 1 Easy Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 39) Which of the following statements about nucleophilic aromatic substitution is not true? A) Increasing the electronegativity of the halogen increases the reactivity of the aryl halide. B) Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide. C) Electron-withdrawing groups stabilize the intermediate carbanion, and lower the energy of the transition state. D) When a nitro group is located meta to the halogen, the negative charge of the intermediate carbanion can be delocalized onto the NO2 group, thus stabilizing it. Answer: D Difficulty: 1 Easy Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 21 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

40) Which of the following statements about nucleophilic aromatic substitution is true? A) For the addition-elimination pathway, the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. B) For the elimination-addition pathway, the nucleophile becomes attached only at the site bearing the leaving group. C) The elimination-addition mechanism is not as common as the addition-elimination mechanism. D) In the addition-elimination mechanism, the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate. Answer: C Difficulty: 1 Easy Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 Accessibility: Keyboard Navigation 41) Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.

A) III < II < I B) I < II < III C) III < I < II D) I < III < II Answer: B Difficulty: 1 Easy Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

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

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 43) Which aryl fluoride reacts the fastest with NaOH?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

44) In addition to the product shown, what other product is formed in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 45) Which set of reagents would most likely bring about the following transformation?

A) Br2 and FeBr3 B) NBS and light C) Br2 in CCl4 D) NaBr and H2O Answer: B Difficulty: 1 Easy Section: 16.14 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

46) What is the product of the following sequence of reactions?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

47) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 16.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

48) What is the product of the following reaction?

A) I B) II C) III D) None of these Answer: D Difficulty: 1 Easy Section: 16.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 49) What is the best choice of reagent to bring about the following transformation?

A) [1] LiAlH4; [2] H2O B) Zn (Hg), HCl C) NH3, NaOH D) H2, Pd-C Answer: B Difficulty: 1 Easy Section: 16.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

50) What is the best choice of reagent to bring about the following transformation?

A) [1] LiAlH4; [2]H2O B) Zn (Hg), HCl C) NH3, NaOH D) H2, Pd-C Answer: D Difficulty: 1 Easy Section: 16.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16 51) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 16.15 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

52) What is the major product of electrophilic addition of HBr to the following alkene?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 16.08 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 16 53) Consider the tetracyclic aromatic compound drawn below, with rings labelled as I, II, III, and IV. Which of the four rings is most reactive in electrophilic aromatic substitution?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 16.08 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 16 29 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

54) Consider the tetracyclic aromatic compound drawn below, with rings labelled as I, II, III, and IV. Which of the four rings is least reactive in electrophilic aromatic substitution?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 16.08 Topic: Aromatic Compounds Bloom's: 4. Analyze Chapter: 16 55) What is the structure of compound A?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 16.13 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

56) What is the product of the following monobromonation reaction?

A) Only I B) Only II C) Only III D) Only I and III Answer: B Difficulty: 1 Easy Section: 16.07 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

57) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

58) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 16.05 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

59) What reagents would be necessary to produce the following product from benzene?

A) CH3Cl, AlCl3 2. HNO3, H2SO4 3. KMnO4 B) HNO3, H2SO4 2. CH3Cl, AlCl3 3. KMnO4 C) KMnO4 2. CH3Cl, AlCl3 3. HNO3, H2SO4 D) KMnO4 2. HNO3, H2SO4 3.CH3Cl, AlCl3 Answer: A Difficulty: 3 Hard Section: 16.16 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

60) What reagents would be necessary to produce the following product from benzene?

A) CH3CH2C(O)Cl, AlCl3 2. HNO3, H2SO4 3. Zn(Hg), HCl B) HNO3, H2SO4 2. CH3CH2C(O)Cl, AlCl3 3. Zn(Hg), HCl C) CH3CH2C(O)Cl, AlCl3 2. Zn(Hg), HCl 3. HNO3, H2SO4 D) Zn(Hg), HCl 2. CH3CH2C(O)Cl, AlCl3 3. HNO3, H2SO4 Answer: A Difficulty: 3 Hard Section: 16.16 Topic: Aromatic Compounds Bloom's: 3. Apply Chapter: 16

Organic Chemistry, 6e (Smith) Chapter 17 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 1) What is the name of the general reaction type that aldehydes and ketones undergo? A) Electrophilic addition B) Nucleophilic addition C) Nucleophilic substitution D) Electrophilic substitution 2) What is the name of the general reaction type that carboxylic acids, esters, and amides undergo? A) Electrophilic acyl addition B) Nucleophilic acyl addition C) Nucleophilic acyl substitution D) Electrophilic acyl substitution 3) What are the two steps in a nucleophilic addition mechanism? A) Nucleophilic attack followed by protonation B) Nucleophilic attack followed by deprotonation C) Nucleophilic attack followed by substitution D) Nucleophilic attack followed by elimination 4) Which of the following terms explain why aldehydes are more reactive than ketones? A) Electronegativity and resonance B) Hybridization and resonance C) Electronegativity and hybridization D) Sterics and electronics 5) Why are ketones less reactive than aldehydes? A) Ketones are more sterically hindered B) Ketones are less electron deficient due to donation from the two alkyl groups C) The statement is false; ketones are more reactive than aldehydes D) Both Ketones are more sterically hindered and Ketones are less electron deficient due to donation from the two alkyl groups 6) If a compound is reduced, what is the result? A) Fewer C-H bonds B) Increased number of C-H bonds C) Fewer C-Z bonds D) Both increased number of C-H bonds and fewer C-Z bonds

7) Rank the following compounds in order of decreasing reactivity in nucleophilic addition reactions, starting with the most reactive compound.

A) III > I > IV > II B) II > IV > I > III C) IV > II > III > I D) II > IV > III > I 8) Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution reactions, starting with the least reactive compound.

A) III < II < I B) II < III < I C) III < I < II D) II < I < III 9) What is the product of the following reaction?

A) I B) II C) III D) IV

10) What is the product of the following reaction?

A) I B) II C) III D) IV 11) What is the starting material in the following reaction?

A) I B) II C) III D) IV 12) Which reagent can be used to reduce the alkene in cyclopentenone? A) NaBH4 B) LiAlH4 C) H2 and Pd-C D) DIBAL-H 13) Which reagent can be used to reduce the carbonyl in methyl vinyl ketone? A) NaBH4/CH3OH B) H2 and Pd-C C) FeCl3 D) NaH 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

14) Which reagent can be used to reduce an acid chloride to an aldehyde? A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3 15) What reagent would be used to reduce an amide to an amine? A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3 16) What is the product of the following reaction?

A) I B) II C) III D) IV 17) What is the product of the following reaction?

A) I B) II C) III D) IV

18) What will be the product of the following reaction (before any aqueous work-up)?

A) I B) II C) III D) IV 19) Why would the alcohol in the following compound need to be protected before reaction?

A) If it isn't protected, the product will be a carboxylic acid. B) The Grignard reagent will react with the alcohol before the ketone. C) Magnesium is Lewis acidic and will coordinate with the alcohol. D) There is no need to protect the alcohol. 20) What is the purpose of a silyl ether? A) To protect esters from organometallic reagents and other reagents B) To protect ketones from organometallic reagents and other reagents C) To protect alcohols from organometallic reagents and other reagents D) To prevent the formation of carboxylic acids 21) What reagent can be used to cleave a silyl ether protecting group? A) NaOMe B) MeMgBr C) Bu4NF D) Pd/C

22) What is the product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II 23) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

24) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 25) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

26) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 27) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

28) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 29) Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity, starting with the most polar.

A) II > I > III B) II > III > I C) III > I > II D) III > II > I 30) Which of the following statements about organometallic reagents is not true? A) Organometallic reagents contain a carbon atom bonded to a metal. B) The more polar the carbon-metal bond, the more reactive the organometallic reagent. C) Organometallic reagents react as bases and nucleophiles. D) Organometallic reagents are strong acids that readily donate a proton to water.

31) What is the product of the following reaction?

A) I B) II C) III D) IV 32) What is the product of the following reaction?

A) I B) II C) III D) IV 33) What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II 10 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

34) What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?

A) Only I B) Only II C) Only III D) Only I and II 35) What is the major organic product in the following sequence of reactions?

A) I B) II C) III D) IV 36) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

37) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 38) What is the major organic product in the following sequence of reactions?

A) I B) II C) III D) IV 39) What is the missing reagent in the reaction below?

A) [1] Mg, [2] CO2, [3] acidic work-up B) [1] CO2, [2] NaOH C) [1] CO2, [2] acidic work-up D) LiAlH4

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

A) I B) II C) III D) IV 41) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

42) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 43) What is the missing reagent in the reaction below?

A) Et2CuLi then H2O B) EtMgBr then H2O C) NaBH4/CH3OH D) H2, Pd-C 44) What is the missing reagent in the reaction below?

A) PhMgBr then H2O B) Benzene, AlCl3 C) Ph2CuLi then H2O D) PhLi then H2O

45) What is the missing reagent in the reaction below?

A) NaBH4/CH3OH B) H2, Pd-C C) LiAlH4 then H2O D) MeMgBr then H2O 46) What is the starting material in the reaction below?

A) Bromobenzene B) Benzyl bromide C) Benzoic acid D) Lithium benzoate 47) What is the missing reagent in the reaction below?

A) NaBH4/CH3OH B) DIBAL-H C) H2, Pd-C D) LiAlH4 then H2O

48) Rank the following compounds in order of increasing reactivity toward the nucleophilic hydride reagent, NaBH4.

A) I < II < III B) III < II < I C) II < III < I D) II < I < III 49) A carbonyl group, C=O, and an alkene, C=C, double bonds are both sp2 hybridized. However, the chemistry of these two functional groups is very different. This can be explained by which of the following statements? A) The bond angle of the carbonyl is larger than the bond angle of the alkene. B) The electronegative oxygen of the C=O group makes this bond polar. C) The bond of the C=C is longer that the bond of the C=O. D) There is more steric crowding in the carbonyl than in the alkene. 50) Both LiAlH4 and NaBH4 are reducing agents. Which statement about these reagents is true? A) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent. B) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent. C) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent. D) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent. 51) If the starting material has no stereogenic centers, when carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed, what will the composition of the product mixture be? A) Forms a racemic mixture of the two possible enantiomers B) Forms more of one enantiomer than another because of steric reactions around the carbonyl C) Forms more of one enantiomer than another depending on the temperature of the reaction D) Forms different products depending on the solvent used

52) Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate II. benzoylchloride III. benzamide A) III< I < II B) II < I < III C) II < III < I D) I < III < II 53) The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because A) the acid chloride contains a better leaving group B) the aldehyde is more easily oxidized C) the carbonyl of the aldehyde is more positive D) the carbonyl of the aldehyde is less hindered 54) What is the missing reagent in the reaction below?

A) [1] LiAlH4, [2] H2O B) [1] CH3MgBr (excess), [2] H2O C) [1] (CH3)2CuLi (excess), [2] H2O D) [1] DIBAL-H, [2] H2O 55) What is the missing reagent in the reaction below?

A) [1] LiAlH4, [2] H2O B) [1] CH2=CHLi, [2] H2O C) [1] (CH2=CH)2CuLi, [2] H2O D) [1] DIBAL-H, [2] H2O

56) What is the major product from the following reaction?

A) I B) II C) III D) IV 57) What is the major product from the following reaction?

58) What is the major product from the following reaction?

A) I B) II C) III D) IV

59) What is the major product from the following reaction?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 17 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 1) What is the name of the general reaction type that aldehydes and ketones undergo? A) Electrophilic addition B) Nucleophilic addition C) Nucleophilic substitution D) Electrophilic substitution Answer: B Difficulty: 1 Easy Section: 17.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 2) What is the name of the general reaction type that carboxylic acids, esters, and amides undergo? A) Electrophilic acyl addition B) Nucleophilic acyl addition C) Nucleophilic acyl substitution D) Electrophilic acyl substitution Answer: C Difficulty: 1 Easy Section: 17.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 3) What are the two steps in a nucleophilic addition mechanism? A) Nucleophilic attack followed by protonation B) Nucleophilic attack followed by deprotonation C) Nucleophilic attack followed by substitution D) Nucleophilic attack followed by elimination Answer: A Difficulty: 1 Easy Section: 17.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

4) Which of the following terms explain why aldehydes are more reactive than ketones? A) Electronegativity and resonance B) Hybridization and resonance C) Electronegativity and hybridization D) Sterics and electronics Answer: D Difficulty: 1 Easy Section: 17.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 5) Why are ketones less reactive than aldehydes? A) Ketones are more sterically hindered B) Ketones are less electron deficient due to donation from the two alkyl groups C) The statement is false; ketones are more reactive than aldehydes D) Both Ketones are more sterically hindered and Ketones are less electron deficient due to donation from the two alkyl groups Answer: D Difficulty: 1 Easy Section: 17.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 6) If a compound is reduced, what is the result? A) Fewer C-H bonds B) Increased number of C-H bonds C) Fewer C-Z bonds D) Both increased number of C-H bonds and fewer C-Z bonds Answer: D Difficulty: 1 Easy Section: 17.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation

7) Rank the following compounds in order of decreasing reactivity in nucleophilic addition reactions, starting with the most reactive compound.

A) III > I > IV > II B) II > IV > I > III C) IV > II > III > I D) II > IV > III > I Answer: B Difficulty: 1 Easy Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 8) Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution reactions, starting with the least reactive compound.

A) III < II < I B) II < III < I C) III < I < II D) II < I < III Answer: D Difficulty: 1 Easy Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

9) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 10) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 4 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

11) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 12) Which reagent can be used to reduce the alkene in cyclopentenone? A) NaBH4 B) LiAlH4 C) H2 and Pd-C D) DIBAL-H Answer: C Difficulty: 2 Medium Section: 17.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation

13) Which reagent can be used to reduce the carbonyl in methyl vinyl ketone? A) NaBH4/CH3OH B) H2 and Pd-C C) FeCl3 D) NaH Answer: A Difficulty: 2 Medium Section: 17.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 14) Which reagent can be used to reduce an acid chloride to an aldehyde? A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3 Answer: B Difficulty: 1 Easy Section: 17.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 15) What reagent would be used to reduce an amide to an amine? A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3 Answer: C Difficulty: 1 Easy Section: 17.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation

16) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 17.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 17) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 17.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

18) What will be the product of the following reaction (before any aqueous work-up)?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 17.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 19) Why would the alcohol in the following compound need to be protected before reaction?

A) If it isn't protected, the product will be a carboxylic acid. B) The Grignard reagent will react with the alcohol before the ketone. C) Magnesium is Lewis acidic and will coordinate with the alcohol. D) There is no need to protect the alcohol. Answer: B Difficulty: 2 Medium Section: 17.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

20) What is the purpose of a silyl ether? A) To protect esters from organometallic reagents and other reagents B) To protect ketones from organometallic reagents and other reagents C) To protect alcohols from organometallic reagents and other reagents D) To prevent the formation of carboxylic acids Answer: C Difficulty: 1 Easy Section: 17.12 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 21) What reagent can be used to cleave a silyl ether protecting group? A) NaOMe B) MeMgBr C) Bu4NF D) Pd/C Answer: C Difficulty: 1 Easy Section: 17.12 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation

22) What is the product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 17.14 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 23) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 10 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

24) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 25) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 17.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 11 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

26) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 17.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 27) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 17.14 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

28) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 17.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 29) Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity, starting with the most polar.

A) II > I > III B) II > III > I C) III > I > II D) III > II > I Answer: A Difficulty: 2 Medium Section: 17.09 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17

30) Which of the following statements about organometallic reagents is not true? A) Organometallic reagents contain a carbon atom bonded to a metal. B) The more polar the carbon-metal bond, the more reactive the organometallic reagent. C) Organometallic reagents react as bases and nucleophiles. D) Organometallic reagents are strong acids that readily donate a proton to water. Answer: D Difficulty: 2 Medium Section: 17.09 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 31) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 17.14 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17

32) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 17.14 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17 33) What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 17.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

34) What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 17.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 35) What is the major organic product in the following sequence of reactions?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

36) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 17.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 37) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 17.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

38) What is the major organic product in the following sequence of reactions?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 39) What is the missing reagent in the reaction below?

A) [1] Mg, [2] CO2, [3] acidic work-up B) [1] CO2, [2] NaOH C) [1] CO2, [2] acidic work-up D) LiAlH4 Answer: A Difficulty: 1 Easy Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

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

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 17.15 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

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

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 17.15 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 42) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 17.14 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 20 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

43) What is the missing reagent in the reaction below?

A) Et2CuLi then H2O B) EtMgBr then H2O C) NaBH4/CH3OH D) H2, Pd-C Answer: A Difficulty: 2 Medium Section: 17.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 44) What is the missing reagent in the reaction below?

A) PhMgBr then H2O B) Benzene, AlCl3 C) Ph2CuLi then H2O D) PhLi then H2O Answer: C Difficulty: 2 Medium Section: 17.15 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

45) What is the missing reagent in the reaction below?

A) NaBH4/CH3OH B) H2, Pd-C C) LiAlH4 then H2O D) MeMgBr then H2O Answer: C Difficulty: 2 Medium Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 46) What is the starting material in the reaction below?

A) Bromobenzene B) Benzyl bromide C) Benzoic acid D) Lithium benzoate Answer: B Difficulty: 2 Medium Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

47) What is the missing reagent in the reaction below?

A) NaBH4/CH3OH B) DIBAL-H C) H2, Pd-C D) LiAlH4 then H2O Answer: D Difficulty: 1 Easy Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 48) Rank the following compounds in order of increasing reactivity toward the nucleophilic hydride reagent, NaBH4.

A) I < II < III B) III < II < I C) II < III < I D) II < I < III Answer: D Difficulty: 1 Easy Section: 17.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

49) A carbonyl group, C=O, and an alkene, C=C, double bonds are both sp2 hybridized. However, the chemistry of these two functional groups is very different. This can be explained by which of the following statements? A) The bond angle of the carbonyl is larger than the bond angle of the alkene. B) The electronegative oxygen of the C=O group makes this bond polar. C) The bond of the C=C is longer that the bond of the C=O. D) There is more steric crowding in the carbonyl than in the alkene. Answer: B Difficulty: 1 Easy Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 50) Both LiAlH4 and NaBH4 are reducing agents. Which statement about these reagents is true? A) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent. B) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is greater than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent. C) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent. D) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent. Answer: C Difficulty: 1 Easy Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation

51) If the starting material has no stereogenic centers, when carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed, what will the composition of the product mixture be? A) Forms a racemic mixture of the two possible enantiomers B) Forms more of one enantiomer than another because of steric reactions around the carbonyl C) Forms more of one enantiomer than another depending on the temperature of the reaction D) Forms different products depending on the solvent used Answer: A Difficulty: 2 Medium Section: 17.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 52) Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate II. benzoylchloride III. benzamide A) III< I < II B) II < I < III C) II < III < I D) I < III < II Answer: A Difficulty: 2 Medium Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation

53) The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because A) the acid chloride contains a better leaving group B) the aldehyde is more easily oxidized C) the carbonyl of the aldehyde is more positive D) the carbonyl of the aldehyde is less hindered Answer: A Difficulty: 1 Easy Section: 17.16 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17 Accessibility: Keyboard Navigation 54) What is the missing reagent in the reaction below?

A) [1] LiAlH4, [2] H2O B) [1] CH3MgBr (excess), [2] H2O C) [1] (CH3)2CuLi (excess), [2] H2O D) [1] DIBAL-H, [2] H2O Answer: B Difficulty: 2 Medium Section: 17.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

55) What is the missing reagent in the reaction below?

A) [1] LiAlH4, [2] H2O B) [1] CH2=CHLi, [2] H2O C) [1] (CH2=CH)2CuLi, [2] H2O D) [1] DIBAL-H, [2] H2O Answer: B Difficulty: 3 Hard Section: 17.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 17

56) What is the major product from the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 17.10 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17

57) What is the major product from the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 17.14 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17

58) What is the major product from the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 17.14 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17

59) What is the major product from the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 17.14 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 17

Organic Chemistry, 6e (Smith) Chapter 18 Aldehydes and Ketones - Nucleophilic Addition 1) Which is the most reactive carbonyl compound?

A) I B) II C) III D) IV 2) What is the IUPAC name for the following compound?

A) Pivaldehyde B) 2,2-Dimethylpropanal C) Tert-butyl aldehyde D) 2,2-Dimethylpentanal 3) What is the structure of 3-methylcyclohexanone?

A) I B) II C) III D) IV

4) What is the structure of 2-trifluoromethyl-2-methoxybutanal?

A) I B) II C) III D) IV 5) What is the structure of benzophenone?

A) I B) II C) III D) IV 6) Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde? A) A ketone has no carbonyl stretch at 1720 cm-1. B) An aldehyde has a carbonyl stretch at 1820 cm-1. C) An aldehyde has two C-H stretches between 2700-2850 cm-1. D) A ketone has no C-H stretches. 7) Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?

8) Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone? A) An aldehyde has a C-H stretch (one or two) between 2700-2830 cm-1. B) An aldehyde has a proton signal between 9-10 ppm. C) A ketone has signals around 2-3 ppm. D) A ketone has a signal around 200 ppm. 9) What compound is consistent with the following 1H NMR spectrum?

A) Acetone B) Propanal C) Cyclobutanone D) 2-butanone 10) Which of the following oxidants would work for the following reaction?

A) H2Cr2O7 B) FeCl3 C) I2 D) Ag2O 11) What is the first step in nucleophilic addition under acidic conditions? A) Protonation of the nucleophile B) Addition of the nucleophile C) Loss of water D) Protonation of the carbonyl

12) Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone? A) Because the Grignard reagent will react with the acid and be quenched B) Because the ketone will be protonated and thus unreactive C) Because the ketone will form an unreactive enol D) Because the Grignard reagent won't dissolve in aqueous solutions 13) What is the major organic product obtained from the following sequence of reactions?

A) I B) II C) III D) IV 14) Is the following reaction reversible and, if so, under what conditions?

A) No B) Yes, under acidic conditions C) Yes, using Pd/C D) Yes, under basic conditions

15) What would you use to prepare the following ylide from the starting phosphonium salt?

A) Butyl lithium B) 1-Bromo-2-methylpropane C) Triphenylphosphine D) Acetic acid 16) What is the driving force for the Wittig reaction? A) The formation of an alkene B) The deprotonation of a phosphonium salt C) The elimination of triphenylphosphine oxide D) The formation of a phosphonium salt 17) What is the product of the following reaction?

A) I B) II C) III D) IV 18) Why are strongly acidic conditions not used in the formation of enamines and imines? A) The carbonyl will be protonated. B) The amine will be completely protonated. C) The product is not stable to strong acid. D) An enol will be formed.

19) What is the product of the following reaction?

A) I B) II C) III D) IV 20) What is the product of the following reaction?

A) I B) II C) III D) IV

21) What needs to be done to make the following reaction proceed?

A) Heat the reaction. B) Add an acid catalyst only. C) Add a base catalyst only. D) Heat the reaction and add an acid catalyst. 22) What needs to be done to make the following reaction go to starting materials?

A) Heat the reaction. B) Add aqueous acid. C) Add aqueous base. D) Add water. 23) What sequence of reactions is required for the following transformation?

A) [1] NaOMe, [2] acetone B) [1] Ph3P, [2] acetone C) [1] Ph3P, [2] KOtBu, [3] acetone D) Acetone, heat

24) What is the product?

A) I B) II C) III D) IV 25) What is the product of the following reaction?

A) I B) II C) III D) IV

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

A) I only B) II only C) III only D) II and III 27) What is the product of the following reaction?

A) I B) II C) III D) IV

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

A) I only B) II only C) III only D) II and III 29) What is the product of the following reaction?

A) I B) II C) III D) IV

30) What is the product of the following sequence of reactions?

A) I B) II C) III D) IV 31) What is the missing reagent in the reaction below?

A) Ethyl amine, mild acid B) Diethylamine, mild acid C) Diethylamine, strong acid D) Diethylamine, NaOMe 32) What is the missing reagent in the reaction below?

33) What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

A) I B) II C) III D) IV 34) What is the missing reagent in the reaction below?

A) Methanol, acid B) Ethanol, acid C) NaOEt D) NaOMe 35) Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO with Ph3P CHCH3?

A) Only I B) Only II C) Only III D) Only I and II

36) What is the IUPAC for the following compound?

A) 1-Formyl-2-nitropropane B) 1-Formyl-3-nitrobutane C) 2-Nitrobutanal D) 3-Nitrobutanal 37) What is the product of the following reaction?

A) I B) II C) III D) IV 38) How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?

A) The 1H NMR spectrum of compound I will have two singlets. B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

39) Name the following aldehyde.

A) 1-Methylcyclopentanal B) 2-Methylcyclopentanal C) 2-Methylcyclopentanecarbaldehyde D) 1-Methylcyclopentanylcarbaldehyde 40) Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C. What accounts for this difference in boiling points? A) Butanol is polar while butanal is not polar. B) Butanol can exhibit dipole-dipole interactions while butanal cannot. C) Butanol can hydrogen bond and butanal cannot hydrogen bond. D) Butanal is less sterically hindered than butanol. 41) Identify how you could synthesize an enamine. A) React a ketone or an aldehyde with a secondary amine. B) React a ketone or an aldehyde with a primary amine. C) React a ylide with a primary amine. D) React a ylide with a secondary amine. 42) When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the product called? A) Hemiacetal B) Di-ether C) Di-alkoxy alkane D) Acetal 43) Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except A) aqueous acid. B) aqueous base. C) oxidizing reagents. D) reducing reagents. 44) Which of the following statements about carbohydrates is not true? A) Carbohydrates are sugars and starches. B) Carbohydrates often contain acetals and hemiacetals. C) In solution, glucose is in the cyclic acetal form only. D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde. 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

45) What is the product of the following reaction?

A) I B) II C) III D) IV 46) What product is formed when the following acetal is hydrolyzed with aqueous acid?

A) I B) II C) III D) IV

47) What product is formed when the following compound is hydrolyzed with aqueous acid?

A) I B) II C) III D) IV 48) Give the IUPAC name for the following compound.

A) R-3-methylcyclohexanone B) S-3-methylcyclohexanone C) R-5-methylcyclohexanone D) S-5-methylcyclohexanone

49) Give the IUPAC name for the following compound.

A) R-3-bromobutanal B) S-3-bromobutanal C) R-2-bromobutan-4-al D) S-2-bromobutan-4-al 50) Give the IUPAC name for the following compound.

A) R-4-bromo-2-pentanone B) S-4-bromo-2-pentanone C) R-2-bromo-4-pentanone D) S-2-bromo-4-pentanone 51) Give the IUPAC name for the following compound.

A) R-3-hydroxybutanal B) S-3-hydroxybutanal C) R-2-hydroxybutan-4-al D) S-2-hydroxybutan-4-al

52) Give the IUPAC name for the following compound.

A) R-4-hydroxy-2-pentanone B) S-4-hydroxy-2-pentanone C) R-2-hydroxy-4-pentanone D) S-2-hydroxy-4-pentanone

Organic Chemistry, 6e (Smith) Chapter 18 Aldehydes and Ketones - Nucleophilic Addition 1) Which is the most reactive carbonyl compound?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 18.07 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 2) What is the IUPAC name for the following compound?

A) Pivaldehyde B) 2,2-Dimethylpropanal C) Tert-butyl aldehyde D) 2,2-Dimethylpentanal Answer: B Difficulty: 1 Easy Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

3) What is the structure of 3-methylcyclohexanone?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 4) What is the structure of 2-trifluoromethyl-2-methoxybutanal?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

5) What is the structure of benzophenone?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 6) Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde? A) A ketone has no carbonyl stretch at 1720 cm-1. B) An aldehyde has a carbonyl stretch at 1820 cm-1. C) An aldehyde has two C-H stretches between 2700-2850 cm-1. D) A ketone has no C-H stretches. Answer: C Difficulty: 1 Easy Section: 18.03 Topic: Aldehydes and Ketones Bloom's: 1. Remember Chapter: 18 Accessibility: Keyboard Navigation

7) Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 18.03 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 8) Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone? A) An aldehyde has a C-H stretch (one or two) between 2700-2830 cm-1. B) An aldehyde has a proton signal between 9-10 ppm. C) A ketone has signals around 2-3 ppm. D) A ketone has a signal around 200 ppm. Answer: B Difficulty: 1 Easy Section: 18.03 Topic: Aldehydes and Ketones Bloom's: 1. Remember Chapter: 18 Accessibility: Keyboard Navigation

9) What compound is consistent with the following 1H NMR spectrum?

A) Acetone B) Propanal C) Cyclobutanone D) 2-butanone Answer: C Difficulty: 1 Easy Section: 18.03 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 10) Which of the following oxidants would work for the following reaction?

A) H2Cr2O7 B) FeCl3 C) I2 D) Ag2O Answer: A Difficulty: 2 Medium Section: 18.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

11) What is the first step in nucleophilic addition under acidic conditions? A) Protonation of the nucleophile B) Addition of the nucleophile C) Loss of water D) Protonation of the carbonyl Answer: D Difficulty: 1 Easy Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Accessibility: Keyboard Navigation 12) Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone? A) Because the Grignard reagent will react with the acid and be quenched B) Because the ketone will be protonated and thus unreactive C) Because the ketone will form an unreactive enol D) Because the Grignard reagent won't dissolve in aqueous solutions Answer: A Difficulty: 1 Easy Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation

13) What is the major organic product obtained from the following sequence of reactions?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 18.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 14) Is the following reaction reversible and, if so, under what conditions?

A) No B) Yes, under acidic conditions C) Yes, using Pd/C D) Yes, under basic conditions Answer: D Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

15) What would you use to prepare the following ylide from the starting phosphonium salt?

A) Butyl lithium B) 1-Bromo-2-methylpropane C) Triphenylphosphine D) Acetic acid Answer: A Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 16) What is the driving force for the Wittig reaction? A) The formation of an alkene B) The deprotonation of a phosphonium salt C) The elimination of triphenylphosphine oxide D) The formation of a phosphonium salt Answer: C Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation

17) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 18) Why are strongly acidic conditions not used in the formation of enamines and imines? A) The carbonyl will be protonated. B) The amine will be completely protonated. C) The product is not stable to strong acid. D) An enol will be formed. Answer: B Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation

19) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 18.11 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

20) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 21) What needs to be done to make the following reaction proceed?

A) Heat the reaction. B) Add an acid catalyst only. C) Add a base catalyst only. D) Heat the reaction and add an acid catalyst. Answer: D Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18

22) What needs to be done to make the following reaction go to starting materials?

A) Heat the reaction. B) Add aqueous acid. C) Add aqueous base. D) Add water. Answer: B Difficulty: 2 Medium Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 23) What sequence of reactions is required for the following transformation?

A) [1] NaOMe, [2] acetone B) [1] Ph3P, [2] acetone C) [1] Ph3P, [2] KOtBu, [3] acetone D) Acetone, heat Answer: C Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

24) What is the product?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

25) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

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

A) I only B) II only C) III only D) II and III Answer: D Difficulty: 2 Medium Section: 18.11 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

27) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

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

A) I only B) II only C) III only D) II and III Answer: A Difficulty: 2 Medium Section: 18.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

29) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

30) What is the product of the following sequence of reactions?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 18.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 31) What is the missing reagent in the reaction below?

A) Ethyl amine, mild acid B) Diethylamine, mild acid C) Diethylamine, strong acid D) Diethylamine, NaOMe Answer: B Difficulty: 2 Medium Section: 18.11 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

32) What is the missing reagent in the reaction below?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

33) What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 34) What is the missing reagent in the reaction below?

A) Methanol, acid B) Ethanol, acid C) NaOEt D) NaOMe Answer: B Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 21 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

35) Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO with Ph3P CHCH3?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 2 Medium Section: 18.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 36) What is the IUPAC for the following compound?

A) 1-Formyl-2-nitropropane B) 1-Formyl-3-nitrobutane C) 2-Nitrobutanal D) 3-Nitrobutanal Answer: D Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

37) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

38) How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?

A) The 1H NMR spectrum of compound I will have two singlets. B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. Answer: D Difficulty: 2 Medium Section: 18.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 39) Name the following aldehyde.

A) 1-Methylcyclopentanal B) 2-Methylcyclopentanal C) 2-Methylcyclopentanecarbaldehyde D) 1-Methylcyclopentanylcarbaldehyde Answer: C Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

40) Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C. What accounts for this difference in boiling points? A) Butanol is polar while butanal is not polar. B) Butanol can exhibit dipole-dipole interactions while butanal cannot. C) Butanol can hydrogen bond and butanal cannot hydrogen bond. D) Butanal is less sterically hindered than butanol. Answer: C Difficulty: 2 Medium Section: 18.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 Accessibility: Keyboard Navigation 41) Identify how you could synthesize an enamine. A) React a ketone or an aldehyde with a secondary amine. B) React a ketone or an aldehyde with a primary amine. C) React a ylide with a primary amine. D) React a ylide with a secondary amine. Answer: A Difficulty: 2 Medium Section: 18.11 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation 42) When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the product called? A) Hemiacetal B) Di-ether C) Di-alkoxy alkane D) Acetal Answer: D Difficulty: 2 Medium Section: 18.13 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation

43) Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except A) aqueous acid. B) aqueous base. C) oxidizing reagents. D) reducing reagents. Answer: A Difficulty: 2 Medium Section: 18.14 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation 44) Which of the following statements about carbohydrates is not true? A) Carbohydrates are sugars and starches. B) Carbohydrates often contain acetals and hemiacetals. C) In solution, glucose is in the cyclic acetal form only. D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde. Answer: C Difficulty: 2 Medium Section: 18.16 Topic: Aldehydes and Ketones Bloom's: 2. Understand Chapter: 18 Accessibility: Keyboard Navigation

45) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 18.15 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

46) What product is formed when the following acetal is hydrolyzed with aqueous acid?

A) I B) II C) III D) IV Answer: C Difficulty: 3 Hard Section: 18.15 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

47) What product is formed when the following compound is hydrolyzed with aqueous acid?

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 18.11 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

48) Give the IUPAC name for the following compound.

A) R-3-methylcyclohexanone B) S-3-methylcyclohexanone C) R-5-methylcyclohexanone D) S-5-methylcyclohexanone Answer: A Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 49) Give the IUPAC name for the following compound.

A) R-3-bromobutanal B) S-3-bromobutanal C) R-2-bromobutan-4-al D) S-2-bromobutan-4-al Answer: A Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

50) Give the IUPAC name for the following compound.

A) R-4-bromo-2-pentanone B) S-4-bromo-2-pentanone C) R-2-bromo-4-pentanone D) S-2-bromo-4-pentanone Answer: B Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18 51) Give the IUPAC name for the following compound.

A) R-3-hydroxybutanal B) S-3-hydroxybutanal C) R-2-hydroxybutan-4-al D) S-2-hydroxybutan-4-al Answer: A Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

52) Give the IUPAC name for the following compound.

A) R-4-hydroxy-2-pentanone B) S-4-hydroxy-2-pentanone C) R-2-hydroxy-4-pentanone D) S-2-hydroxy-4-pentanone Answer: B Difficulty: 2 Medium Section: 18.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 18

Organic Chemistry, 6e (Smith) Chapter 19 Carboxylic Acids and the Acidity of the O-H Bond 1) What is the hybridization of the carbon atom in a carboxy group? A) sp B) sp2 C) sp3 D) p 2) Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol? A) The carbon in the alcohol is sp2 hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol. B) The carbon in the carboxylic acid is sp3 hybridized and has a lower percent s-character that shortens the C-O bond in the carboxylic acid. C) The carbon in the carboxylic acid is sp hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid. D) The carbon in the carboxylic acid is sp2 hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid. 3) What two groups make up the carboxylic acid group (RCOOH)? A) Carbon dioxide and hydrogen B) Carbonyl and hydroxyl C) Carbon monoxide and hydroxyl D) Carbonyl oxide and hydrogen 4) What is the correct IUPAC name of the following compound?

A) 4-Isopropyl-3-methylbutanoic acid B) 2,4-Dimethylhexanoic acid C) 3,5-Dimethylhexanoic acid D) 3,5-Dimethy-1-hexanoic acid

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

A) 2-sec-Butyl-4,4-dimethylnonanoic acid B) 4,4-Dimethyl-2-isobutylnonanoic acid C) 4,4-Dimethyl-2-sec-butylnonanoic acid D) 2-Isobutyl-4,4-dimethylnonanoic acid 7) What is the correct IUPAC name of the following compound?

A) 3,4-Dimethylcyclohexanoic acid B) 3,4-Dimethylcyclohexanecarboxylic acid C) 4,5-Dimethylcyclohexanecarboxylic acid D) 1,2-Dimethylcyclohexanecarboxylic acid

8) What is the common name of the following compound?

A) a-Methylbutyric acid B) a-Propylpropionic acid C) a-Methylvaleric acid D) a-Methylcaproic acid 9) What is the common name of the following compound?

A) a,b-Dimethoxyvaleric acid B) 2,3-Dimethoxyvaleric acid C) 2,3-Dimethoxycaproic acid D) a,b-Dimethoxycaproic acid 10) What is the common name of the following compound?

A) b,b-Dimethyl-a-fluorobutyric acid B) a-Fluoro-b,b-dimethylbutyric acid C) a-Fluoro-b,b,b-trimethylpropionic acid D) a-Fluoro-b,b,b-trimethylbutyric acid

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

A) Propanedioic acid B) 1,3-Propanedicarboxylic acid C) Malonic acid D) Succinic acid 12) What is the correct IUPAC name of the following compound?

A) (E)-2-Hexenoic acid B) (Z)-2-Hexenoic acid C) (E)-4-Hexenoic acid D) (Z)-4-Hexenoic acid 13) What is the correct IUPAC name of the following compound?

A) 2-Methoxypentanoic acid B) 2-Methoxybutanoic acid C) 4-Methoxybutanoic acid D) 4-Methoxypentanoic acid

14) Which of the following is the structure of oxalic acid?

A) I B) II C) III D) IV 15) Which of the following is the correct IUPAC name for the following structure?

A) Potassium propanoate B) Butanoic potassium C) Potassium propanoic D) Potassium butanoate 16) Which of the following is the most polar organic compound? A) CH3CH2CH2CH3 B) CH3CH2CHO C) CH3CH2CH2OH D) CH3COOH 17) Arrange the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

A) I < II < III < IV B) I < IV < II < III C) III < II < IV < I D) II < IV < I < III

18) Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.

A) I > II > III > IV B) I > IV > II > III C) I > II > IV > III D) IV > III > II > I 19) Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.

A) I < II < III < IV B) II < I < III < IV C) I < III < II < IV D) IV < II < III < I 20) What two strong absorptions are characteristic of the IR spectrum of carboxylic acids? A) A C=O absorption at 1710 cm-1 and a C-H absorption at 3000 cm-1. B) A C=O absorption at 1710 cm-1 and an O-H absorption at 2500-3500 cm-1. C) A C=O absorption at 1600 cm-1 and an O-H absorption at 2500-3000 cm-1. D) A C-O absorption at 1500 cm-1 and an O-H absorption at 2500-3500 cm-1. 21) Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra? A) Between 10 and 12 ppm for the OH proton and 2-2.5 ppm for the protons on the a carbon to the carboxy group. B) Between 6 and 9 ppm for the OH proton and 2-2.5 ppm for the protons on the a carbon to the carboxy group. C) Between 10 and 12 ppm for the OH proton and 1-1.5 ppm for the protons on the a carbon to the carboxy group. D) Between 6 and 9 ppm for the OH proton and 1-1.5 ppm for the protons on the a carbon to the carboxy group.

22) Why is pure acetic acid often called glacial acetic acid? A) Because it freezes just below 0°C, forming white crystals B) Because it freezes just below 100°C, forming white crystals C) Because it freezes just below room temperature, forming white crystals D) Because it freezes just above room temperature, forming white crystals 23) Which of the following reagents can accomplish the transformation below?

A) PCC, CH2Cl2 B) [1] LiAlH4, THF; [2] H2O C) [1] O3; [2] H2O D) K2Cr2O7, H2SO4, H2O 24) What is the other product formed in the oxidation of the following terminal alkyne?

A) HCOOH B) HCOH C) CO2 D) CO 25) Which of the following cannot be the starting material for the following reaction?

A) I B) II C) III D) IV

26) In the presence of strong acids, which of the oxygen atoms on the carboxyl group is preferentially protonated and why? A) Protonation occurs at the carbonyl oxygen because the resulting conjugate acid is stabilized by resonance. B) Protonation occurs at the carbonyl oxygen because the resulting conjugate base is stabilized by the inductive effect. C) Protonation occurs at the hydroxyl oxygen because the resulting conjugate acid is stabilized by resonance. D) Protonation occurs at the hydroxyl oxygen because the resulting conjugate base is stabilized by the inductive effect. 27) Which of the following structures is the major contributor to the resonance hybrid of the phenoxide anion?

A) I B) II C) III D) IV 28) Arrange the following compounds in order of increasing acidity, putting the least acidic first.

A) I < II < III < IV B) IV < III < II < I C) III < IV < II < I D) IV < II < III < I 29) Which of the following bases are strong enough to significantly deprotonate ethanol, CH3CH2OH (pKa = 16)? A) NaOCH3 B) NaOH C) NaH D) NaOCH2CH3

30) Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic.

A) Ha < Hb < Hc < Hd B) Hb < Hc < Ha < Hd C) Hd < Ha < Hc < Hb D) Hb < Hc < Hd < Ha 31) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > III > I > II B) IV > II > I > III C) II > I > IV > III D) II > I > III > IV 32) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) II < III < I < IV B) II < I < III < IV C) IV < III < I < II D) IV < I < II < III

33) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) III < II < IV < I B) III < IV < II < I C) I < IV < II < III D) I < II < III < IV 34) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > III > II > I B) IV > I > III > II C) I > II > III > IV D) IV > II > III > I 35) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) I < II < III < IV B) III < II < I < IV C) IV < I < II < III D) I < IV < III < II

36) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) III > IV > I > II B) IV > III > I > II C) I > II > III > IV D) IV > III > II > I 37) What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds? A) Physical property = solubility differences; reaction type = acid-base reaction B) Physical property = boiling point; reaction type = acid-base reaction C) Physical property = solubility differences; reaction type = oxidation-reduction D) Physical property = density; reaction type = oxidation-reduction 38) What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a separatory funnel containing H2O and CH2Cl2? A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in the organic layer. B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve in the water layer. C) Both benzoic acid and NaCl would dissolve in the organic layer. D) Both benzoic acid and NaCl would dissolve in the water layer. 39) What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2 is treated with aqueous NaOH solution? A) Benzoic acid would remain in the CH2Cl2 layer, and cyclohexanol would dissolve in the aqueous layer. B) Benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH2Cl2 layer. C) The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH2Cl2 layer. D) The salt of benzoic acid would remain in the CH2Cl2 layer while cyclohexanol would dissolve in the aqueous layer. 40) What is the overall charge of the amino acid, alanine, at pH = 2? A) + 1 B) – 1 C) No overall charge D) + 2 11 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

41) What is the overall charge of the amino acid, alanine, at pH = 10? A) + 1 B) – 1 C) No overall charge D) – 2 42) What is the overall charge of the amino acid, alanine, at pH = 7? A) + 1 B) – 1 C) No overall charge D) + 2 43) As applied to the chemistry of amino acids, what is the definition for the isoelectric point? A) The pH at which the amino acid exists primarily in its acidic form. B) The pH at which the amino acid exists primarily in its basic form. C) The pH at which the amino acid exists as a mixture of isomers. D) The pH at which the amino acid exists primarily in its neutral form. 44) Which of the following compounds is most basic?

A) I B) II C) III D) IV 45) Which of the following compounds is least basic?

A) I B) II C) III D) IV

46) Give the IUPAC name for the following compound.

A) (E,R)-2-bromo-3-pentenoic acid B) (Z,R)-2-bromo-3-pentenoic acid C) (E,S)-2-bromo-3-pentenoic acid D) (Z,S)-2-bromo-3-pentenoic acid 47) Give the IUPAC name for the following compound.

A) (E,R)-2-bromo-3-pentenoic acid B) (Z,R)-2-bromo-3-pentenoic acid C) (E,S)-2-bromo-3-pentenoic acid D) (Z,S)-2-bromo-3-pentenoic acid 48) Give the IUPAC name of the following compound.

A) R-2-methylpentanenitrile B) S-2-methylpentanenitrile C) R-2-nitrilehexane D) S-2-nitrilehexane

49) Give the IUPAC name for the following compound.

A) (E,R)-2-methyl-3-pentenenitrile B) (E,S)-2-methyl-3-pentenenitrile C) (Z,R)-2-methyl-3-pentenenitrile D) (Z,S)-2-methyl-3-pentenenitrile 50) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O 51) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O 52) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

53) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O

Organic Chemistry, 6e (Smith) Chapter 19 Carboxylic Acids and the Acidity of the O-H Bond 1) What is the hybridization of the carbon atom in a carboxy group? A) sp B) sp2 C) sp3 D) p Answer: B Difficulty: 1 Easy Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation 2) Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol? A) The carbon in the alcohol is sp2 hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol. B) The carbon in the carboxylic acid is sp3 hybridized and has a lower percent s-character that shortens the C-O bond in the carboxylic acid. C) The carbon in the carboxylic acid is sp hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid. D) The carbon in the carboxylic acid is sp2 hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid. Answer: D Difficulty: 1 Easy Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation

3) What two groups make up the carboxylic acid group (RCOOH)? A) Carbon dioxide and hydrogen B) Carbonyl and hydroxyl C) Carbon monoxide and hydroxyl D) Carbonyl oxide and hydrogen Answer: B Difficulty: 1 Easy Section: 19.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation 4) What is the correct IUPAC name of the following compound?

A) 4-Isopropyl-3-methylbutanoic acid B) 2,4-Dimethylhexanoic acid C) 3,5-Dimethylhexanoic acid D) 3,5-Dimethy-1-hexanoic acid Answer: C Difficulty: 1 Easy Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

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

A) 3,5,5-Trimethylcyclohexanecarboxylic acid B) 3,3,5-Trimethylcyclohexanecarboxylic acid C) 3,3,5-Trimethylcyclohexanoic acid D) 3,5,5-Trimethylcyclohexanoic acid Answer: B Difficulty: 1 Easy Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 6) What is the correct IUPAC name of the following compound?

A) 2-sec-Butyl-4,4-dimethylnonanoic acid B) 4,4-Dimethyl-2-isobutylnonanoic acid C) 4,4-Dimethyl-2-sec-butylnonanoic acid D) 2-Isobutyl-4,4-dimethylnonanoic acid Answer: A Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

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

A) 3,4-Dimethylcyclohexanoic acid B) 3,4-Dimethylcyclohexanecarboxylic acid C) 4,5-Dimethylcyclohexanecarboxylic acid D) 1,2-Dimethylcyclohexanecarboxylic acid Answer: B Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 8) What is the common name of the following compound?

A) a-Methylbutyric acid B) a-Propylpropionic acid C) a-Methylvaleric acid D) a-Methylcaproic acid Answer: C Difficulty: 1 Easy Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

9) What is the common name of the following compound?

A) a,b-Dimethoxyvaleric acid B) 2,3-Dimethoxyvaleric acid C) 2,3-Dimethoxycaproic acid D) a,b-Dimethoxycaproic acid Answer: D Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 10) What is the common name of the following compound?

A) b,b-Dimethyl-a-fluorobutyric acid B) a-Fluoro-b,b-dimethylbutyric acid C) a-Fluoro-b,b,b-trimethylpropionic acid D) a-Fluoro-b,b,b-trimethylbutyric acid Answer: B Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

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

A) Propanedioic acid B) 1,3-Propanedicarboxylic acid C) Malonic acid D) Succinic acid Answer: C Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 12) What is the correct IUPAC name of the following compound?

A) (E)-2-Hexenoic acid B) (Z)-2-Hexenoic acid C) (E)-4-Hexenoic acid D) (Z)-4-Hexenoic acid Answer: B Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

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

A) 2-Methoxypentanoic acid B) 2-Methoxybutanoic acid C) 4-Methoxybutanoic acid D) 4-Methoxypentanoic acid Answer: D Difficulty: 1 Easy Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 14) Which of the following is the structure of oxalic acid?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

15) Which of the following is the correct IUPAC name for the following structure?

A) Potassium propanoate B) Butanoic potassium C) Potassium propanoic D) Potassium butanoate Answer: D Difficulty: 1 Easy Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 16) Which of the following is the most polar organic compound? A) CH3CH2CH2CH3 B) CH3CH2CHO C) CH3CH2CH2OH D) CH3COOH Answer: D Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Accessibility: Keyboard Navigation

17) Arrange the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

A) I < II < III < IV B) I < IV < II < III C) III < II < IV < I D) II < IV < I < III Answer: B Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 18) Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.

A) I > II > III > IV B) I > IV > II > III C) I > II > IV > III D) IV > III > II > I Answer: C Difficulty: 2 Medium Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19

19) Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.

A) I < II < III < IV B) II < I < III < IV C) I < III < II < IV D) IV < II < III < I Answer: D Difficulty: 2 Medium Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 20) What two strong absorptions are characteristic of the IR spectrum of carboxylic acids? A) A C=O absorption at 1710 cm-1 and a C-H absorption at 3000 cm-1. B) A C=O absorption at 1710 cm-1 and an O-H absorption at 2500-3500 cm-1. C) A C=O absorption at 1600 cm-1 and an O-H absorption at 2500-3000 cm-1. D) A C-O absorption at 1500 cm-1 and an O-H absorption at 2500-3500 cm-1. Answer: B Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 19 Accessibility: Keyboard Navigation

21) Where do the two noteworthy peaks of carboxylic acids appear in 1HNMR spectra? A) Between 10 and 12 ppm for the OH proton and 2-2.5 ppm for the protons on the a carbon to the carboxy group. B) Between 6 and 9 ppm for the OH proton and 2-2.5 ppm for the protons on the a carbon to the carboxy group. C) Between 10 and 12 ppm for the OH proton and 1-1.5 ppm for the protons on the a carbon to the carboxy group. D) Between 6 and 9 ppm for the OH proton and 1-1.5 ppm for the protons on the a carbon to the carboxy group. Answer: A Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 19 Accessibility: Keyboard Navigation 22) Why is pure acetic acid often called glacial acetic acid? A) Because it freezes just below 0°C, forming white crystals B) Because it freezes just below 100°C, forming white crystals C) Because it freezes just below room temperature, forming white crystals D) Because it freezes just above room temperature, forming white crystals Answer: C Difficulty: 1 Easy Section: 19.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 19 Accessibility: Keyboard Navigation

23) Which of the following reagents can accomplish the transformation below?

A) PCC, CH2Cl2 B) [1] LiAlH4, THF; [2] H2O C) [1] O3; [2] H2O D) K2Cr2O7, H2SO4, H2O Answer: D Difficulty: 2 Medium Section: 19.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 24) What is the other product formed in the oxidation of the following terminal alkyne?

A) HCOOH B) HCOH C) CO2 D) CO Answer: C Difficulty: 2 Medium Section: 19.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

25) Which of the following cannot be the starting material for the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 19.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 26) In the presence of strong acids, which of the oxygen atoms on the carboxyl group is preferentially protonated and why? A) Protonation occurs at the carbonyl oxygen because the resulting conjugate acid is stabilized by resonance. B) Protonation occurs at the carbonyl oxygen because the resulting conjugate base is stabilized by the inductive effect. C) Protonation occurs at the hydroxyl oxygen because the resulting conjugate acid is stabilized by resonance. D) Protonation occurs at the hydroxyl oxygen because the resulting conjugate base is stabilized by the inductive effect. Answer: A Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation

27) Which of the following structures is the major contributor to the resonance hybrid of the phenoxide anion?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 28) Arrange the following compounds in order of increasing acidity, putting the least acidic first.

A) I < II < III < IV B) IV < III < II < I C) III < IV < II < I D) IV < II < III < I Answer: B Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

29) Which of the following bases are strong enough to significantly deprotonate ethanol, CH3CH2OH (pKa = 16)? A) NaOCH3 B) NaOH C) NaH D) NaOCH2CH3 Answer: C Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation 30) Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic.

A) Ha < Hb < Hc < Hd B) Hb < Hc < Ha < Hd C) Hd < Ha < Hc < Hb D) Hb < Hc < Hd < Ha Answer: B Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19

31) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > III > I > II B) IV > II > I > III C) II > I > IV > III D) II > I > III > IV Answer: D Difficulty: 2 Medium Section: 19.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 32) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) II < III < I < IV B) II < I < III < IV C) IV < III < I < II D) IV < I < II < III Answer: B Difficulty: 2 Medium Section: 19.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19

33) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) III < II < IV < I B) III < IV < II < I C) I < IV < II < III D) I < II < III < IV Answer: C Difficulty: 2 Medium Section: 19.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 34) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) IV > III > II > I B) IV > I > III > II C) I > II > III > IV D) IV > II > III > I Answer: A Difficulty: 2 Medium Section: 19.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19

35) Rank the following compounds in order of increasing acidity, putting the least acidic first.

A) I < II < III < IV B) III < II < I < IV C) IV < I < II < III D) I < IV < III < II Answer: C Difficulty: 2 Medium Section: 19.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 36) Rank the following compounds in order of decreasing acidity, putting the most acidic first.

A) III > IV > I > II B) IV > III > I > II C) I > II > III > IV D) IV > III > II > I Answer: D Difficulty: 2 Medium Section: 19.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19

37) What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds? A) Physical property = solubility differences; reaction type = acid-base reaction B) Physical property = boiling point; reaction type = acid-base reaction C) Physical property = solubility differences; reaction type = oxidation-reduction D) Physical property = density; reaction type = oxidation-reduction Answer: A Difficulty: 2 Medium Section: 19.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation 38) What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a separatory funnel containing H2O and CH2Cl2? A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in the organic layer. B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve in the water layer. C) Both benzoic acid and NaCl would dissolve in the organic layer. D) Both benzoic acid and NaCl would dissolve in the water layer. Answer: B Difficulty: 2 Medium Section: 19.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Accessibility: Keyboard Navigation

39) What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2 is treated with aqueous NaOH solution? A) Benzoic acid would remain in the CH2Cl2 layer, and cyclohexanol would dissolve in the aqueous layer. B) Benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH2Cl2 layer. C) The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH2Cl2 layer. D) The salt of benzoic acid would remain in the CH2Cl2 layer while cyclohexanol would dissolve in the aqueous layer. Answer: C Difficulty: 2 Medium Section: 19.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 Accessibility: Keyboard Navigation 40) What is the overall charge of the amino acid, alanine, at pH = 2? A) + 1 B) – 1 C) No overall charge D) + 2 Answer: A Difficulty: 2 Medium Section: 19.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation

41) What is the overall charge of the amino acid, alanine, at pH = 10? A) + 1 B) – 1 C) No overall charge D) – 2 Answer: B Difficulty: 2 Medium Section: 19.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation 42) What is the overall charge of the amino acid, alanine, at pH = 7? A) + 1 B) – 1 C) No overall charge D) + 2 Answer: C Difficulty: 2 Medium Section: 19.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 Accessibility: Keyboard Navigation 43) As applied to the chemistry of amino acids, what is the definition for the isoelectric point? A) The pH at which the amino acid exists primarily in its acidic form. B) The pH at which the amino acid exists primarily in its basic form. C) The pH at which the amino acid exists as a mixture of isomers. D) The pH at which the amino acid exists primarily in its neutral form. Answer: D Difficulty: 2 Medium Section: 19.11 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 19 Accessibility: Keyboard Navigation

44) Which of the following compounds is most basic?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19 45) Which of the following compounds is least basic?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 19.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 19

46) Give the IUPAC name for the following compound.

A) (E,R)-2-bromo-3-pentenoic acid B) (Z,R)-2-bromo-3-pentenoic acid C) (E,S)-2-bromo-3-pentenoic acid D) (Z,S)-2-bromo-3-pentenoic acid Answer: C Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19 47) Give the IUPAC name for the following compound.

A) (E,R)-2-bromo-3-pentenoic acid B) (Z,R)-2-bromo-3-pentenoic acid C) (E,S)-2-bromo-3-pentenoic acid D) (Z,S)-2-bromo-3-pentenoic acid Answer: B Difficulty: 2 Medium Section: 19.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 19

48) Give the IUPAC name of the following compound.

A) R-2-methylpentanenitrile B) S-2-methylpentanenitrile C) R-2-nitrilehexane D) S-2-nitrilehexane Answer: A Difficulty: 2 Medium Section: 19.02 Topic: Nitriles Bloom's: 2. Understand Chapter: 19 49) Give the IUPAC name for the following compound.

A) (E,R)-2-methyl-3-pentenenitrile B) (E,S)-2-methyl-3-pentenenitrile C) (Z,R)-2-methyl-3-pentenenitrile D) (Z,S)-2-methyl-3-pentenenitrile Answer: A Difficulty: 2 Medium Section: 19.02 Topic: Nitriles Bloom's: 2. Understand Chapter: 19

50) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O Answer: A Difficulty: 1 Easy Section: 19.12 Topic: Nitriles Bloom's: 2. Understand Chapter: 19 51) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O Answer: B Difficulty: 1 Easy Section: 19.12 Topic: Nitriles Bloom's: 2. Understand Chapter: 19

52) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O Answer: C Difficulty: 1 Easy Section: 19.12 Topic: Nitriles Bloom's: 2. Understand Chapter: 19 53) What reagents are necessary to perform the following reaction?

A) H2O, H+ B) LiAlH4, H2O C) DIBAL-H, H2O D) CH3MgBr, H2O Answer: D Difficulty: 1 Easy Section: 19.12 Topic: Nitriles Bloom's: 2. Understand Chapter: 19

Organic Chemistry, 6e (Smith) Chapter 20 Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution 1) Which of the following is a lactam?

A) I B) II C) III D) IV 2) Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride? A) Nitrogen is a better leaving group. B) Chloride is a better leaving group. C) Nitrogen donates more electron density into the carbonyl. D) The amide anion is less basic. 3) What is the IUPAC name for the following compound?

A) Methyl 3-methylbutanamide B) 5-Methylhexanamide C) N-Methyl 3-methylhexanamide D) N-Methyl 3-methylbutanamide

4) What is the IUPAC name for the following compound?

A) 4-Fluoro-3-methylbenzoate B) 4-Fluoro-3-methylbenzoic acid C) 3-Methyl-4-fluorobenzoic acid D) 4-Fluoro-5-methylbenzoic acid 5) What is the structure for acetic propanoic anhydride?

A) I B) II C) III D) IV 6) What is the structure for ethyl 4-chlorobenzoate?

A) I B) II C) III D) IV

7) What is the structure for 3-cyanocyclopentanone?

A) I B) II C) III D) IV 8) What is the IUPAC name for the following compound?

A) 2-fluorobutanonitrile B) 2-fluoropentanonitrile C) 3-fluoropentanonitrile D) 2-fluorobutylcyanide 9) Where is the carbonyl absorption found in the IR spectrum of a simple ester? A) 2.5 ppm B) 2250 cm-1 C) 3800 cm-1 D) 1740 cm-1 10) Which of the following peaks would you see in the IR spectrum of a carboxylic acid? A) A flat line (carboxylic acids are not IR active) B) A sharp line at 2250 cm-1 C) A broad peak from 3800-2800 cm-1 D) A broad peak from 800-600 cm-1 11) You see an absorption at 2250 cm-1 in the IR spectrum of a compound. What kind of functional group is present? A) A ketone B) An aldehyde C) An ester D) A nitrile 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

12) Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid derivatives? A) 1700 cm-1 B) 180-160 ppm C) 2.5-3.0 ppm D) 100-80 ppm 13) Which structure is consistent with the following 1H NMR spectrum?

A) Ethyl acetate B) 2-Propanone C) 3,3-Dimethyl-2-pentanone D) Ethyl 2,2-dimethylpropionate 14) What is the first step in the general mechanism for nucleophilic acyl substitution? A) Protonation of the carbonyl B) Removal of an a-proton C) Addition of the nucleophile to the carbonyl D) Loss of the leaving group 15) Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate? A) The nucleophile is too basic. B) Reforming the carbonyl is energetically favorable. C) The leaving group is unstable and wants to be negatively charged. D) There is no tetrahedral intermediate.

16) Will the following reaction occur?

A) Yes B) No 17) Will the following reaction occur?

A) Yes B) No 18) Will the following reaction occur?

A) Yes B) No 19) Why is pyridine included in the reaction of an acid chloride and an amine or alcohol? A) Pyridine will deprotonate the amine or alcohol, making it a better nucleophile. B) Pyridine will neutralize the acid by-product of the reaction. C) Pyridine will protonate the carbonyl of the acid chloride, making it more reactive. D) Pyridine will absorb the heat of the reaction.

20) What is the product of the following reaction?

A) I B) II C) III D) IV 21) What is the product of the following reaction?

A) I B) II C) III D) IV 22) How can you convert a carboxylic acid into an ester? A) Heat with an alcohol and catalytic acid. B) Deprotonate with a base and react with an alcohol. C) Deprotonate with a base and react with an alkyl halide. D) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alkyl halide. E) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alcohol.

A) I B) II C) III D) IV 25) What is the direct product of the base-promoted hydrolysis of an ester? A) A nitrile B) A carboxylic acid C) An amide D) A carboxylic acid salt 26) Which of the following two amides will react more readily with a nucleophile? Why?

A) I, because it is less hindered B) II, because it is less hindered C) I, because it is more strained D) II, because it is more strained

27) What is the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate?

A) I B) II C) III D) IV 28) What is the IUPAC name for the following compound?

A) Propionyl phenol B) Phenyl propanoate C) Phenol propanoate D) Phenyl acetate 29) What is the product of the following reaction?

A) I B) II C) III D) IV

30) What is the product of the following reaction?

A) I B) II C) III D) IV 31) What is the product of the following reaction?

A) I B) II C) III D) IV

32) What is the product of the following reaction?

A) I B) II C) III D) IV 33) What is the product of the following reaction?

A) I B) II C) III D) IV 34) What is the missing reagent in the reaction below?

35) Which of the following reaction conditions can be used to synthesize an ester (RCOOR')? A) RCOCl + R'NH2 + pyridine B) RCOOH + R'OH + H+ C) RCOOH + R'OH + OHD) RCONH2 + R'OH 36) Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

A) I < II < III B) III < II < I C) II < III < I D) III < I < II 37) Draw the structure of N-phenyl acetamide.

A) I B) II C) III D) IV 38) Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?

39) From the list below, pick the compound that does not react with acetyl chloride. A) Isopropyl alcohol B) Benzoic acid C) Ammonia D) Triethyl amine 40) Which of the following statements about amides is true? A) Amides react with methyl alcohol in the presence of an acid catalyst to form an ester. B) Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate anions. C) Amides react with thionyl chloride to form the acid chloride. D) Amides do not react under any conditions. They are inert compounds. 41) An unknown compound has a sharp, medium peak at 2250 cm-1. The unknown compound is probably A) an alkane. B) an aldehyde. C) an alkene. D) a nitrile. 42) All of the following contain sp2 hybridized atoms in their functional group except A) a carboxylic acid. B) a nitrile. C) an aldehyde. D) an anhydride. 43) What is the product formed by hydrolysis of the following lactone with acid?

A) I B) II C) III D) IV

44) What is the product formed by hydrolysis of the following lactone with acid?

A) I B) II C) III D) IV 45) Which of the following compounds will have the lowest frequency for carbonyl absorption in IR spectroscopy?

A) I B) II C) III D) IV 46) Give the IUPAC name for the following compound.

A) R-3-methoxybutanoyl chloride B) S-3-methoxybutanoyl chloride C) R-2-methoxy-4-butanoyl chloride D) S-2-methoxy-4-butanoyl chloride

47) Give the IUPAC name for the following compound.

A) Butyl ethanoate B) Ethyl butanoate C) 4-hexanoate D) 3-hexanoate 48) What reagents are necessary to perform the following reaction?

A) EtOH, H+ B) CH3CH2NH2, DCC C) SOCl2 D) Heat 49) What reagents are necessary to perform the following reaction?

A) EtOH, H+ B) CH3CH2NH2, DCC C) SOCl2 D) Heat

50) What reagents are necessary to perform the following reaction?

A) EtOH, H+ B) CH3CH2NH2, DCC C) SOCl2 D) Heat

Organic Chemistry, 6e (Smith) Chapter 20 Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution 1) Which of the following is a lactam?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 20.01 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 1. Remember Chapter: 20 2) Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride? A) Nitrogen is a better leaving group. B) Chloride is a better leaving group. C) Nitrogen donates more electron density into the carbonyl. D) The amide anion is less basic. Answer: C Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation

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

A) Methyl 3-methylbutanamide B) 5-Methylhexanamide C) N-Methyl 3-methylhexanamide D) N-Methyl 3-methylbutanamide Answer: D Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 4) What is the IUPAC name for the following compound?

A) 4-Fluoro-3-methylbenzoate B) 4-Fluoro-3-methylbenzoic acid C) 3-Methyl-4-fluorobenzoic acid D) 4-Fluoro-5-methylbenzoic acid Answer: B Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20

5) What is the structure for acetic propanoic anhydride?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 6) What is the structure for ethyl 4-chlorobenzoate?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20

7) What is the structure for 3-cyanocyclopentanone?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 8) What is the IUPAC name for the following compound?

A) 2-fluorobutanonitrile B) 2-fluoropentanonitrile C) 3-fluoropentanonitrile D) 2-fluorobutylcyanide Answer: C Difficulty: 1 Easy Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20

9) Where is the carbonyl absorption found in the IR spectrum of a simple ester? A) 2.5 ppm B) 2250 cm-1 C) 3800 cm-1 D) 1740 cm-1 Answer: D Difficulty: 1 Easy Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation 10) Which of the following peaks would you see in the IR spectrum of a carboxylic acid? A) A flat line (carboxylic acids are not IR active) B) A sharp line at 2250 cm-1 C) A broad peak from 3800-2800 cm-1 D) A broad peak from 800-600 cm-1 Answer: C Difficulty: 1 Easy Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation 11) You see an absorption at 2250 cm-1 in the IR spectrum of a compound. What kind of functional group is present? A) A ketone B) An aldehyde C) An ester D) A nitrile Answer: D Difficulty: 1 Easy Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation

12) Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid derivatives? A) 1700 cm-1 B) 180-160 ppm C) 2.5-3.0 ppm D) 100-80 ppm Answer: B Difficulty: 1 Easy Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation 13) Which structure is consistent with the following 1H NMR spectrum?

A) Ethyl acetate B) 2-Propanone C) 3,3-Dimethyl-2-pentanone D) Ethyl 2,2-dimethylpropionate Answer: D Difficulty: 1 Easy Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20

14) What is the first step in the general mechanism for nucleophilic acyl substitution? A) Protonation of the carbonyl B) Removal of an a-proton C) Addition of the nucleophile to the carbonyl D) Loss of the leaving group Answer: C Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation 15) Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate? A) The nucleophile is too basic. B) Reforming the carbonyl is energetically favorable. C) The leaving group is unstable and wants to be negatively charged. D) There is no tetrahedral intermediate. Answer: B Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation 16) Will the following reaction occur?

A) Yes B) No Answer: B Difficulty: 1 Easy Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

17) Will the following reaction occur?

A) Yes B) No Answer: A Difficulty: 1 Easy Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 18) Will the following reaction occur?

A) Yes B) No Answer: B Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 19) Why is pyridine included in the reaction of an acid chloride and an amine or alcohol? A) Pyridine will deprotonate the amine or alcohol, making it a better nucleophile. B) Pyridine will neutralize the acid by-product of the reaction. C) Pyridine will protonate the carbonyl of the acid chloride, making it more reactive. D) Pyridine will absorb the heat of the reaction. Answer: B Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Accessibility: Keyboard Navigation 8 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

20) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 20.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

21) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 20.07 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 22) How can you convert a carboxylic acid into an ester? A) Heat with an alcohol and catalytic acid. B) Deprotonate with a base and react with an alcohol. C) Deprotonate with a base and react with an alkyl halide. D) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alkyl halide. E) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alcohol. Answer: D Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Accessibility: Keyboard Navigation

23) How can you convert a carboxylic acid into an acid chloride? A) Heat with hydrochloric acid. B) React with thionyl chloride (SOCl2). C) React with sodium chloride. D) React with Cl2 and FeCl3. Answer: B Difficulty: 1 Easy Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand; 3. Apply Chapter: 20 Accessibility: Keyboard Navigation 24) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

25) What is the direct product of the base-promoted hydrolysis of an ester? A) A nitrile B) A carboxylic acid C) An amide D) A carboxylic acid salt Answer: D Difficulty: 2 Medium Section: 20.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 26) Which of the following two amides will react more readily with a nucleophile? Why?

A) I, because it is less hindered B) II, because it is less hindered C) I, because it is more strained D) II, because it is more strained Answer: C Difficulty: 2 Medium Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

27) What is the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 28) What is the IUPAC name for the following compound?

A) Propionyl phenol B) Phenyl propanoate C) Phenol propanoate D) Phenyl acetate Answer: B Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20

29) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

30) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

31) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

32) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

33) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 34) What is the missing reagent in the reaction below?

A) Acetic acid B) NaOMe C) SOCl2 D) Pyridine Answer: C Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

35) Which of the following reaction conditions can be used to synthesize an ester (RCOOR')? A) RCOCl + R'NH2 + pyridine B) RCOOH + R'OH + H+ C) RCOOH + R'OH + OHD) RCONH2 + R'OH Answer: B Difficulty: 2 Medium Section: 20.09 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Accessibility: Keyboard Navigation 36) Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

A) I < II < III B) III < II < I C) II < III < I D) III < I < II Answer: B Difficulty: 2 Medium Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

37) Draw the structure of N-phenyl acetamide.

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 38) Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

39) From the list below, pick the compound that does not react with acetyl chloride. A) Isopropyl alcohol B) Benzoic acid C) Ammonia D) Triethyl amine Answer: D Difficulty: 2 Medium Section: 20.06 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Accessibility: Keyboard Navigation 40) Which of the following statements about amides is true? A) Amides react with methyl alcohol in the presence of an acid catalyst to form an ester. B) Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate anions. C) Amides react with thionyl chloride to form the acid chloride. D) Amides do not react under any conditions. They are inert compounds. Answer: B Difficulty: 2 Medium Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Accessibility: Keyboard Navigation 41) An unknown compound has a sharp, medium peak at 2250 cm-1. The unknown compound is probably A) an alkane. B) an aldehyde. C) an alkene. D) a nitrile. Answer: D Difficulty: 2 Medium Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 Accessibility: Keyboard Navigation

42) All of the following contain sp2 hybridized atoms in their functional group except A) a carboxylic acid. B) a nitrile. C) an aldehyde. D) an anhydride. Answer: B Difficulty: 2 Medium Section: 20.02 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 Accessibility: Keyboard Navigation 43) What is the product formed by hydrolysis of the following lactone with acid?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 20.10 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

44) What is the product formed by hydrolysis of the following lactone with acid?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 20.12 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 45) Which of the following compounds will have the lowest frequency for carbonyl absorption in IR spectroscopy?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 20.04 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

46) Give the IUPAC name for the following compound.

A) R-3-methoxybutanoyl chloride B) S-3-methoxybutanoyl chloride C) R-2-methoxy-4-butanoyl chloride D) S-2-methoxy-4-butanoyl chloride Answer: A Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20 47) Give the IUPAC name for the following compound.

A) Butyl ethanoate B) Ethyl butanoate C) 4-hexanoate D) 3-hexanoate Answer: B Difficulty: 2 Medium Section: 20.03 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 2. Understand Chapter: 20

48) What reagents are necessary to perform the following reaction?

A) EtOH, H+ B) CH3CH2NH2, DCC C) SOCl2 D) Heat Answer: A Difficulty: 1 Easy Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20 49) What reagents are necessary to perform the following reaction?

A) EtOH, H+ B) CH3CH2NH2, DCC C) SOCl2 D) Heat Answer: B Difficulty: 1 Easy Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

50) What reagents are necessary to perform the following reaction?

A) EtOH, H+ B) CH3CH2NH2, DCC C) SOCl2 D) Heat Answer: C Difficulty: 1 Easy Section: 20.08 Topic: Carboxylic Acids and Carboxylic Acid Derivatives Bloom's: 3. Apply Chapter: 20

Organic Chemistry, 6e (Smith) Chapter 21 Substitution Reactions of Carbonyl Compounds at the a Carbon 1) Which is the more stable form of acetophenone?

A) Only I B) Only II C) Only III D) I and II are equally stable 2) Which is the most stable form of 1,3-cyclohexanedione?

A) I B) II C) III D) IV

3) Which of the following is an enol form of the following compound?

A) I B) II C) III D) IV 4) Why is the enolate of acetone less basic than the allyl anion derived from propene? A) Because there are more atoms in acetone B) Because there are more resonance structures for the enolate of acetone C) It isn't; the allyl anion is less basic. D) One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen. 5) Which of the following four compounds is the most acidic?

A) I B) II C) III D) IV 6) Will acetone be completely deprotonated by potassium tert-butoxide? A) Yes B) No 7) Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)? A) Yes B) No

8) Which is the kinetic enolate of 2-methylcyclohexanone?

A) I B) II C) III D) IV 9) If you want to form a thermodynamic enolate, you want to A) keep the reaction as cold as possible. B) use an aprotic solvent such as THF. C) use a protic solvent such as ethanol. D) use a carboxylic acid. 10) If you want to form a kinetic enolate, you want to A) use a strong, non-nucleophilic base such as LDA. B) use a protic solvent. C) use a low temperature. D) both use a strong, non-nucleophilic base such as LDA and use a low temperature. 11) Which of the following is the intermediate for halogenation of ketones under acidic conditions? A) An enolate B) An enol C) A tautomer D) An epimer 12) Why is it difficult to stop the halogenation of ketones under basic conditions at the monohalogenated stage? A) The ketone undergoes a Bayer-Villigar oxidation. B) The ketone is reduced. C) The ketone undergoes an Aldol reaction. D) The bromine helps to stabilize the second enolate, making the product more acidic than the starting material.

13) Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?

A) Because tert-butyl bromide is too basic. B) Because tert-butyl bromide cannot undergo an SN2 reaction. C) Because tert-butyl bromide is a nucleophile. D) Because tert-butyl bromide is not a stable compound. 14) What are the three steps in the malonic ester synthesis? A) Deprotonation, alkylation, hydrolysis/decarboxylation B) Hydrogenation, alkylation, deprotonation C) Alkylation, hydrolysis/decarboxylation. hydrogenation D) Hydrolysis/decarboxylation, deprotonation, alkylation 15) What is the missing reagent for the following reaction?

A) Br2/HOAc B) Br2/KOH C) Cl2/FeCl3 D) Br2/FeBr3

16) Starting with cyclohexanone, how could you prepare the diketone below?

A) Treat cyclohexanone with a base under thermodynamic conditions. B) Hydrogenate cyclohexanone with Raney nickel. C) Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone. D) Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone. 17) What is the product of the following reaction?

A) I B) II C) III D) IV

18) What is the product of the following reaction?

A) I B) II C) III D) IV 19) What is (are) the product(s) of the following reaction?

A) Only I B) Only II C) Only III D) Only I and III

20) What is the missing reagent in the reaction below?

A) Br2/AcOH B) I2/KOH C) I2 D) KOH 21) What is the starting material in the following reaction?

A) I B) II C) III D) IV

22) What is the starting material for the following reaction?

A) I B) II C) III D) IV 23) Which of the following compounds is an enol of compound X drawn below?

A) Only I B) Only II C) Only III D) Only I and II

24) Which of the following are enol forms of ethyl acetoacetate drawn below?

A) Only I B) Only II C) Only III D) I, II, and III 25) For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound. This is due largely to what? A) The C=O bond is much stronger than the C=C bond. B) The C=C bond is much stronger than the C=O bond. C) The keto form can undergo intramolecular hydrogen bonding. D) The enol form can undergo intramolecular hydrogen bonding. 26) It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by A) the C=C of the enol is conjugated with the carbonyl group. B) the -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. C) Both and above are true. D) None of the choices are true. 27) The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation.

A) The nucleophilic enolate requires a reaction center that has a positive charge. B) Hindered alkyl halides do not undergo SN1 reactions. C) Hindered alkyl halides do not undergo SN2 reactions. D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.

28) The following molecule is called

A) a 1,3-diketopentanoate. B) a diethyl malonate. C) an ethyl acetoacetate. D) a b-keto ester. 29) A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with A) bromine with acetic acid. B) bromine and aqueous hydroxide ion. C) THF, LDA at -78 °C followed by reaction with bromine. D) base and methyl bromide. 30) Which is the thermodynamic enolate of 2-methylcyclohexanone?

A) I B) II C) III D) IV 31) Which of the following compounds is the most acidic? A) Ethyl acetoacetate B) 2-Butanone C) 1-Butanol D) 3-Pentanone

32) Which is the most acidic proton in the following compound?

A) I B) II C) III D) IV 33) Which is the most acidic proton in the following compound?

A) I B) II C) III D) IV 34) Which of the following bases will completely convert 1,4-cyclohexandione into an enolate? A) Sodium hydroxide B) Sodium methoxide C) Sodium tert-butoxide D) Sodium hydride

35) Which of the following compounds would undergo racemization in the presence of a base?

A) I B) II C) III D) IV 36) Which of the following ketones will give a positive iodoform test? A) 3-Heptanone B) 2-Pentanone C) 3-Hexanone D) Cyclohexanone 37) What is the major product of the following reaction?

A) I B) II C) III D) IV

38) Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X (C7H14O) as the major product. X shows a strong absorption in the IR spectrum at 1713 cm-1, and its 1H NMR data is given below. What is the structure of X?

Signal # 1 2 3 4 5 6

Shift (ppm) 0.96 1.16 1.33 1.53 2.09 2.52

Multiplicity triplet doublet multiplet multiplet singlet multiplet

Integration 3H 3H 2H 2H 3H 1H

A) I B) II C) III D) IV

39) The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material. Select the structure of the amino acid produced by the following synthesis.

A) I B) II C) III D) IV 40) Select the appropriate sequence of reactions to accomplish the following synthesis.

41) What is the starting material required to accomplish the following transformation?

A) I B) II C) III D) IV 42) Vitamin C is a stable enediol. Which is the structure of a possible keto form in equilibrium with the enediol form?

A) I B) II C) III D) IV

43) What is the structure of X, product of the following reaction?

A) I B) II C) III D) IV 44) Which of the following is a possible enol form of 2-butanone?

A) I B) II C) III D) II and III

45) Which of the following is the most acidic compound?

A) I B) II C) III D) IV 46) Which of the following is the least acidic compound?

A) I B) II C) III D) IV 47) Which of the following would undergo racemization under basic conditions?

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 21 Substitution Reactions of Carbonyl Compounds at the a Carbon 1) Which is the more stable form of acetophenone?

A) Only I B) Only II C) Only III D) I and II are equally stable Answer: B Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 2) Which is the most stable form of 1,3-cyclohexanedione?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

3) Which of the following is an enol form of the following compound?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 4) Why is the enolate of acetone less basic than the allyl anion derived from propene? A) Because there are more atoms in acetone B) Because there are more resonance structures for the enolate of acetone C) It isn't; the allyl anion is less basic. D) One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen. Answer: D Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

5) Which of the following four compounds is the most acidic?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 6) Will acetone be completely deprotonated by potassium tert-butoxide? A) Yes B) No Answer: B Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation 7) Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)? A) Yes B) No Answer: A Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

8) Which is the kinetic enolate of 2-methylcyclohexanone?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 9) If you want to form a thermodynamic enolate, you want to A) keep the reaction as cold as possible. B) use an aprotic solvent such as THF. C) use a protic solvent such as ethanol. D) use a carboxylic acid. Answer: C Difficulty: 2 Medium Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

10) If you want to form a kinetic enolate, you want to A) use a strong, non-nucleophilic base such as LDA. B) use a protic solvent. C) use a low temperature. D) both use a strong, non-nucleophilic base such as LDA and use a low temperature. Answer: D Difficulty: 2 Medium Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation 11) Which of the following is the intermediate for halogenation of ketones under acidic conditions? A) An enolate B) An enol C) A tautomer D) An epimer Answer: B Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation 12) Why is it difficult to stop the halogenation of ketones under basic conditions at the monohalogenated stage? A) The ketone undergoes a Bayer-Villigar oxidation. B) The ketone is reduced. C) The ketone undergoes an Aldol reaction. D) The bromine helps to stabilize the second enolate, making the product more acidic than the starting material. Answer: D Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

13) Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?

A) Because tert-butyl bromide is too basic. B) Because tert-butyl bromide cannot undergo an SN2 reaction. C) Because tert-butyl bromide is a nucleophile. D) Because tert-butyl bromide is not a stable compound. Answer: B Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 14) What are the three steps in the malonic ester synthesis? A) Deprotonation, alkylation, hydrolysis/decarboxylation B) Hydrogenation, alkylation, deprotonation C) Alkylation, hydrolysis/decarboxylation. hydrogenation D) Hydrolysis/decarboxylation, deprotonation, alkylation Answer: A Difficulty: 1 Easy Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

15) What is the missing reagent for the following reaction?

A) Br2/HOAc B) Br2/KOH C) Cl2/FeCl3 D) Br2/FeBr3 Answer: A Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 16) Starting with cyclohexanone, how could you prepare the diketone below?

17) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

18) What is the product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

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

A) Only I B) Only II C) Only III D) Only I and III Answer: D Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 20) What is the missing reagent in the reaction below?

A) Br2/AcOH B) I2/KOH C) I2 D) KOH Answer: B Difficulty: 2 Medium Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

21) What is the starting material in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

22) What is the starting material for the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

23) Which of the following compounds is an enol of compound X drawn below?

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

24) Which of the following are enol forms of ethyl acetoacetate drawn below?

A) Only I B) Only II C) Only III D) I, II, and III Answer: D Difficulty: 2 Medium Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 25) For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound. This is due largely to what? A) The C=O bond is much stronger than the C=C bond. B) The C=C bond is much stronger than the C=O bond. C) The keto form can undergo intramolecular hydrogen bonding. D) The enol form can undergo intramolecular hydrogen bonding. Answer: A Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

26) It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by A) the C=C of the enol is conjugated with the carbonyl group. B) the -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. C) Both and above are true. D) None of the choices are true. Answer: C Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation 27) The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation.

28) The following molecule is called

A) a 1,3-diketopentanoate. B) a diethyl malonate. C) an ethyl acetoacetate. D) a b-keto ester. Answer: D Difficulty: 1 Easy Section: 21.10 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 29) A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with A) bromine with acetic acid. B) bromine and aqueous hydroxide ion. C) THF, LDA at -78 °C followed by reaction with bromine. D) base and methyl bromide. Answer: B Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

30) Which is the thermodynamic enolate of 2-methylcyclohexanone?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 31) Which of the following compounds is the most acidic? A) Ethyl acetoacetate B) 2-Butanone C) 1-Butanol D) 3-Pentanone Answer: A Difficulty: 2 Medium Section: 21.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation

32) Which is the most acidic proton in the following compound?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 33) Which is the most acidic proton in the following compound?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

34) Which of the following bases will completely convert 1,4-cyclohexandione into an enolate? A) Sodium hydroxide B) Sodium methoxide C) Sodium tert-butoxide D) Sodium hydride Answer: D Difficulty: 2 Medium Section: 21.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation 35) Which of the following compounds would undergo racemization in the presence of a base?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

36) Which of the following ketones will give a positive iodoform test? A) 3-Heptanone B) 2-Pentanone C) 3-Hexanone D) Cyclohexanone Answer: B Difficulty: 1 Easy Section: 21.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 Accessibility: Keyboard Navigation 37) What is the major product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

Signal # 1 2 3 4 5 6

Shift (ppm) 0.96 1.16 1.33 1.53 2.09 2.52

Multiplicity triplet doublet multiplet multiplet singlet multiplet

Integration 3H 3H 2H 2H 3H 1H

A) I B) II C) III D) IV Answer: D Difficulty: 3 Hard Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 21.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

40) Select the appropriate sequence of reactions to accomplish the following synthesis.

A) [1] Br2, CH3CO2H; [2] Li2CO3, LiBr, DMF; [3] CH3CH2CH2CH2Br B) [1] Br2, CH3CO2H; [2] Mg, Et2O; [3] CH3CH2CH2CH2Br C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA Answer: C Difficulty: 2 Medium Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 41) What is the starting material required to accomplish the following transformation?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 23 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) Vitamin C is a stable enediol. Which is the structure of a possible keto form in equilibrium with the enediol form?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

43) What is the structure of X, product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 21.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

44) Which of the following is a possible enol form of 2-butanone?

A) I B) II C) III D) II and III Answer: D Difficulty: 1 Easy Section: 21.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 45) Which of the following is the most acidic compound?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

46) Which of the following is the least acidic compound?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 21.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21 47) Which of the following would undergo racemization under basic conditions?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 21.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 21

Organic Chemistry, 6e (Smith) Chapter 22 Carbonyl Condensation Reactions 1) What is the general name for the reaction product formed in an aldol addition reaction? A) a-Hydroxy carbonyl compound B) b-Hydroxy carbonyl compound C) g-Hydroxy carbonyl compound D) a,b-Hydroxy carbonyl compound 2) In the correct order, what are the three steps in the mechanism of an Aldol reaction? A) Protonation, enolate formation, nucleophilic addition B) Enolate formation, protonation, nucleophilic addition C) Enolate formation, nucleophilic addition, protonation D) Nucleophilic addition, enolate formation, protonation 3) Which of the following statements about Aldol reactions with either aldehydes or ketones is true? A) Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones. B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones. C) Equilibrium favors the products with both aldehydes and ketones. D) Equilibrium favors the starting materials with both aldehydes and ketones. 4) What reaction type is an Aldol reaction? A) Nucleophilic substitution B) Electrophilic substitution C) Electrophilic addition D) Nucleophilic addition 5) What is the Aldol addition product formed from reaction of the following compound with itself?

6) What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with itself?

A) I B) II C) III D) IV 7) What is the Aldol addition product formed from the reaction of acetone, (CH3)2CO, with itself?

A) I B) II C) III D) IV 8) Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

A) I B) II C) III D) None of the choices

9) Which of the following carbonyl compounds does not undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

A) I B) II C) III D) IV 10) Why is the Aldol reaction often called an Aldol condensation? A) The initially formed b-hydroxy carbonyl compound loses a hydroxyl group. B) The initially formed b-hydroxy carbonyl compound loses an oxygen atom. C) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom. D) The initially formed b-hydroxy carbonyl compound loses water. 11) What is the general name for the class of products formed in an Aldol condensation reaction? A) b,g-Unsaturated carbonyl compound B) a,b-Unsaturated carbonyl compound C) a,g-Unsaturated carbonyl compound D) b-Hydroxy carbonyl compound 12) Which is the unsaturated carbonyl compound formed by the dehydration of the following bhydroxy carbonyl compound?

A) I B) II C) I and II D) None of the choices

13) Which is the unsaturated carbonyl compound formed in the dehydration of the following bhydroxy carbonyl compound?

A) I B) II C) I and II D) None of the choices 14) What aldehyde or ketone is needed to prepare the following compound by an Aldol reaction?

A) I B) II C) III D) IV 15) What is the name given to an Aldol reaction between two different carbonyl compounds? A) Multiple Aldol reaction B) Crossed Aldol reaction C) Differential Aldol reaction D) Versatile Aldol reaction 4 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

16) When is a crossed Aldol reaction said to be synthetically useful? A) When both carbonyl compounds have a hydrogens B) When both carbonyl compounds have no a hydrogens C) When one carbonyl compound has no a hydrogens D) When one carbonyl compound has no b hydrogens 17) In what situation can the yield of a single crossed Aldol product be increased? A) The electrophilic carbonyl component is relatively unhindered and is used in excess. B) The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount. C) The nucleophilic carbonyl component is relatively unhindered and is used in excess. D) The nucleophilic carbonyl component is relatively hindered and is used in limited amount. 18) What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

A) I B) II C) III D) IV

19) What cyclic product is formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

A) I B) II C) III D) IV 20) What is the general name for the reaction product formed in a Claisen reaction? A) b-Hydroxy ester B) b-Keto ester C) a-Keto ester D) g-Hydroxy ester 21) What reaction type is a Claisen reaction? A) Electrophilic addition B) Electrophilic substitution C) Nucleophilic addition D) Nucleophilic substitution 22) What type of esters can undergo Claisen reactions? A) All esters can undergo Claisen reactions. B) Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions. C) Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions. D) Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions.

23) What is the product of the following Claisen reaction?

A) I B) II C) III D) IV 24) What is the product of the following Claisen reaction?

A) I B) II C) III D) IV

25) What is the name given to the Claisen reaction between two different esters? A) Multiple Claisen reaction B) Differential Claisen reaction C) Crossed Claisen reaction D) Versatile Claisen reaction 26) When is a crossed Claisen reaction between two different esters synthetically useful? A) When only one of the esters has a hydrogen atoms B) When both esters have a hydrogen atoms C) When only one of the esters has b hydrogen atoms D) When both esters lack a hydrogen atoms 27) What is the general name of the product of a crossed Claisen reaction between a ketone and an ester? A) b-Keto ester B) a,b-Dicarbonyl compound C) g-Dicarbonyl compound D) b-Dicarbonyl compound 28) In the correct order, what are the three general steps in the mechanism of a Claisen reaction? A) Enolate formation, elimination, nucleophilic addition B) Enolate formation, nucleophilic addition, elimination C) Elimination, enolate formation, nucleophilic addition D) Nucleophilic addition, enolate formation, elimination 29) What is an intramolecular Claisen reaction called? A) Michael reaction B) Robinson reaction C) Hoffman reaction D) Dieckmann reaction 30) In a Michael reaction, what is the name given to the a,b-unsaturated carbonyl component? A) Michael donor B) Michael enolate C) Michael nucleophile D) Michael acceptor 31) In a Michael reaction, where does the nucleophile attack the a,b-unsaturated carbonyl component? A) a-Carbon B) b-Carbon C) Carbonyl carbon D) Carbonyl carbon and b-carbon

32) Which of the following compounds cannot serve as a Michael acceptor?

A) I B) II C) III D) IV 33) What are the two starting materials for a Robinson annulation? A) an a,b-Unsaturated carbonyl compound and an enolate B) a b-Ketoester and an enolate C) a 1,5-Dicarbonyl compound and an enolate D) a 1,3-Dicarbonyl compound and an enolate 34) What are the names for the two parts of the mechanism in a Robinson annulation? A) Michael addition and intramolecular Claisen reaction B) Michael addition and intramolecular aldol reaction C) Claisen reaction and intramolecular aldol reaction D) Aldol reaction and intramolecular Claisen reaction 35) Which of the following compounds can undergo an Aldol with itself?

A) I B) II C) III D) Both I and II

36) What is the product of the self-condensation of ethanal (acetaldehyde), shown below?

A) I B) II C) III D) IV 37) The following reaction is an example of what type of reaction?

A) Claisen condensation B) Mixed Aldol reaction C) Robinson annulation D) Dieckmann condensation 38) The following reaction is an example of what type of reaction?

A) Michael reaction B) Aldol self-condensation C) Dieckmann condensation D) Robinson annulation

39) The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result? A) It undergoes elimination, since water is a good leaving group. B) The hydroxy group is oxidized to a carbonyl. C) The hydroxy group reacts with the carbonyl to form a ketal. D) Hydroxide is eliminated via an enolate intermediate. 40) Under basic conditions, the Aldol reaction is reversible, but dehydration is not. What is the reason for this difference in reactivity? A) The initial Aldol product is an alkoxide, so the reaction is not energetically downhill in either direction. B) The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the product. C) The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the starting materials. D) Water is a stable molecule. 41) Would this crossed Aldol reaction work well? Why or why not?

A) Yes, the diketone is significantly more acidic, so this enolate can be formed selectively. B) Yes, the aldehyde is significantly more acidic, so this enolate can be formed selectively. C) No, the aldehyde is significantly more acidic, so this enolate cannot be formed selectively. D) No, the diketone is significantly more acidic, so this enolate cannot be formed selectively. 42) Of the carbonyl compounds; (1) benzaldehyde, (2) acetophenone and (3) dicyclohexyl ketone, which compound has noa-hydrogens? A) Benzaldehyde B) Acetophenone C) Acetone D) All of these compounds contain a-hydrogens. 43) Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that A) the Aldol reaction involves substitution while the Claisen reaction involves addition. B) the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. C) the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. D) the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed.

44) If a Claisen condensation reaction is run using methyl propanoate as the reactant, NaOCH3 is the ideal base. Why is it important to use NaOCH3 and not NaOCH2CH3? A) NaOCH3 is a stronger base than NaOCH2CH3, and this reaction requires a stronger base. B) NaOCH3 is a weaker base than NaOCH2CH3, and this reaction requires a weaker base. C) Transesterfication can occur when esters react, and this transesterfication would result in a mixture of products. D) NaOCH3 is more soluble than NaOCH2CH3 in organic solvents, and this reaction requires a full equivalent of base to proceed. A full equivalent of NaOCH2CH3 would not dissolve, so the reaction would not proceed. 45) There are several variations of the Aldol reaction. Which of the following types of reactants leads to only one possible product with the Aldol condensation reaction? A) Two different aldehydes with a-hydrogens are able to form a single aldol condensation product. B) Two different ketones with a-hydrogens are able to form a single aldol condensation product. C) Any aldehyde and ketone mixed together can react to form a single condensation product. D) Any pair of aldehyde or ketone reactants where one of the reactants has no a-hydrogens will lead to a single aldol product. 46) What product (including stereochemistry) is formed in the following intermolecular reaction?

A) I B) II C) III D) IV

47) What product (including stereochemistry) is formed in the following intermolecular reaction?

A) I B) II C) III D) IV 48) Which of the following bicyclic ring systems can be prepared by an intermolecular Robinson annulation?

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV 50) What is the major product of the following reaction?

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV

3) Which of the following statements about Aldol reactions with either aldehydes or ketones is true? A) Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones. B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones. C) Equilibrium favors the products with both aldehydes and ketones. D) Equilibrium favors the starting materials with both aldehydes and ketones. Answer: A Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 4) What reaction type is an Aldol reaction? A) Nucleophilic substitution B) Electrophilic substitution C) Electrophilic addition D) Nucleophilic addition Answer: D Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

5) What is the Aldol addition product formed from reaction of the following compound with itself?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 6) What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with itself?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

7) What is the Aldol addition product formed from the reaction of acetone, (CH3)2CO, with itself?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 8) Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

A) I B) II C) III D) None of the choices Answer: C Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

9) Which of the following carbonyl compounds does not undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 10) Why is the Aldol reaction often called an Aldol condensation? A) The initially formed b-hydroxy carbonyl compound loses a hydroxyl group. B) The initially formed b-hydroxy carbonyl compound loses an oxygen atom. C) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom. D) The initially formed b-hydroxy carbonyl compound loses water. Answer: D Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

11) What is the general name for the class of products formed in an Aldol condensation reaction? A) b,g-Unsaturated carbonyl compound B) a,b-Unsaturated carbonyl compound C) a,g-Unsaturated carbonyl compound D) b-Hydroxy carbonyl compound Answer: B Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 12) Which is the unsaturated carbonyl compound formed by the dehydration of the following bhydroxy carbonyl compound?

A) I B) II C) I and II D) None of the choices Answer: B Difficulty: 2 Medium Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

13) Which is the unsaturated carbonyl compound formed in the dehydration of the following bhydroxy carbonyl compound?

A) I B) II C) I and II D) None of the choices Answer: A Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

14) What aldehyde or ketone is needed to prepare the following compound by an Aldol reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 22.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 15) What is the name given to an Aldol reaction between two different carbonyl compounds? A) Multiple Aldol reaction B) Crossed Aldol reaction C) Differential Aldol reaction D) Versatile Aldol reaction Answer: B Difficulty: 1 Easy Section: 22.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

16) When is a crossed Aldol reaction said to be synthetically useful? A) When both carbonyl compounds have a hydrogens B) When both carbonyl compounds have no a hydrogens C) When one carbonyl compound has no a hydrogens D) When one carbonyl compound has no b hydrogens Answer: C Difficulty: 1 Easy Section: 22.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 17) In what situation can the yield of a single crossed Aldol product be increased? A) The electrophilic carbonyl component is relatively unhindered and is used in excess. B) The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount. C) The nucleophilic carbonyl component is relatively unhindered and is used in excess. D) The nucleophilic carbonyl component is relatively hindered and is used in limited amount. Answer: A Difficulty: 1 Easy Section: 22.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

18) What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 22.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

19) What cyclic product is formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 22.04 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 20) What is the general name for the reaction product formed in a Claisen reaction? A) b-Hydroxy ester B) b-Keto ester C) a-Keto ester D) g-Hydroxy ester Answer: B Difficulty: 1 Easy Section: 22.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

21) What reaction type is a Claisen reaction? A) Electrophilic addition B) Electrophilic substitution C) Nucleophilic addition D) Nucleophilic substitution Answer: D Difficulty: 1 Easy Section: 22.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 22) What type of esters can undergo Claisen reactions? A) All esters can undergo Claisen reactions. B) Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions. C) Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions. D) Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions. Answer: D Difficulty: 1 Easy Section: 22.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

23) What is the product of the following Claisen reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 22.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

24) What is the product of the following Claisen reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 22.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 25) What is the name given to the Claisen reaction between two different esters? A) Multiple Claisen reaction B) Differential Claisen reaction C) Crossed Claisen reaction D) Versatile Claisen reaction Answer: C Difficulty: 1 Easy Section: 22.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

26) When is a crossed Claisen reaction between two different esters synthetically useful? A) When only one of the esters has a hydrogen atoms B) When both esters have a hydrogen atoms C) When only one of the esters has b hydrogen atoms D) When both esters lack a hydrogen atoms Answer: A Difficulty: 1 Easy Section: 22.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 27) What is the general name of the product of a crossed Claisen reaction between a ketone and an ester? A) b-Keto ester B) a,b-Dicarbonyl compound C) g-Dicarbonyl compound D) b-Dicarbonyl compound Answer: D Difficulty: 1 Easy Section: 22.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 28) In the correct order, what are the three general steps in the mechanism of a Claisen reaction? A) Enolate formation, elimination, nucleophilic addition B) Enolate formation, nucleophilic addition, elimination C) Elimination, enolate formation, nucleophilic addition D) Nucleophilic addition, enolate formation, elimination Answer: B Difficulty: 1 Easy Section: 22.06 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

29) What is an intramolecular Claisen reaction called? A) Michael reaction B) Robinson reaction C) Hoffman reaction D) Dieckmann reaction Answer: D Difficulty: 1 Easy Section: 22.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 30) In a Michael reaction, what is the name given to the a,b-unsaturated carbonyl component? A) Michael donor B) Michael enolate C) Michael nucleophile D) Michael acceptor Answer: D Difficulty: 1 Easy Section: 22.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 31) In a Michael reaction, where does the nucleophile attack the a,b-unsaturated carbonyl component? A) a-Carbon B) b-Carbon C) Carbonyl carbon D) Carbonyl carbon and b-carbon Answer: B Difficulty: 1 Easy Section: 22.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

32) Which of the following compounds cannot serve as a Michael acceptor?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 22.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 33) What are the two starting materials for a Robinson annulation? A) an a,b-Unsaturated carbonyl compound and an enolate B) a b-Ketoester and an enolate C) a 1,5-Dicarbonyl compound and an enolate D) a 1,3-Dicarbonyl compound and an enolate Answer: A Difficulty: 1 Easy Section: 22.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

34) What are the names for the two parts of the mechanism in a Robinson annulation? A) Michael addition and intramolecular Claisen reaction B) Michael addition and intramolecular aldol reaction C) Claisen reaction and intramolecular aldol reaction D) Aldol reaction and intramolecular Claisen reaction Answer: B Difficulty: 1 Easy Section: 22.09 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 35) Which of the following compounds can undergo an Aldol with itself?

A) I B) II C) III D) Both I and II Answer: C Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

36) What is the product of the self-condensation of ethanal (acetaldehyde), shown below?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 37) The following reaction is an example of what type of reaction?

A) Claisen condensation B) Mixed Aldol reaction C) Robinson annulation D) Dieckmann condensation Answer: D Difficulty: 2 Medium Section: 22.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

38) The following reaction is an example of what type of reaction?

A) Michael reaction B) Aldol self-condensation C) Dieckmann condensation D) Robinson annulation Answer: A Difficulty: 2 Medium Section: 22.08 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 39) The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result? A) It undergoes elimination, since water is a good leaving group. B) The hydroxy group is oxidized to a carbonyl. C) The hydroxy group reacts with the carbonyl to form a ketal. D) Hydroxide is eliminated via an enolate intermediate. Answer: D Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

40) Under basic conditions, the Aldol reaction is reversible, but dehydration is not. What is the reason for this difference in reactivity? A) The initial Aldol product is an alkoxide, so the reaction is not energetically downhill in either direction. B) The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the product. C) The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the starting materials. D) Water is a stable molecule. Answer: A Difficulty: 2 Medium Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 41) Would this crossed Aldol reaction work well? Why or why not?

42) Of the carbonyl compounds; (1) benzaldehyde, (2) acetophenone and (3) dicyclohexyl ketone, which compound has noa-hydrogens? A) Benzaldehyde B) Acetophenone C) Acetone D) All of these compounds contain a-hydrogens. Answer: A Difficulty: 1 Easy Section: 22.01 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 43) Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that A) the Aldol reaction involves substitution while the Claisen reaction involves addition. B) the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. C) the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. D) the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed. Answer: C Difficulty: 2 Medium Section: 22.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

44) If a Claisen condensation reaction is run using methyl propanoate as the reactant, NaOCH3 is the ideal base. Why is it important to use NaOCH3 and not NaOCH2CH3? A) NaOCH3 is a stronger base than NaOCH2CH3, and this reaction requires a stronger base. B) NaOCH3 is a weaker base than NaOCH2CH3, and this reaction requires a weaker base. C) Transesterfication can occur when esters react, and this transesterfication would result in a mixture of products. D) NaOCH3 is more soluble than NaOCH2CH3 in organic solvents, and this reaction requires a full equivalent of base to proceed. A full equivalent of NaOCH2CH3 would not dissolve, so the reaction would not proceed. Answer: C Difficulty: 2 Medium Section: 22.05 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation 45) There are several variations of the Aldol reaction. Which of the following types of reactants leads to only one possible product with the Aldol condensation reaction? A) Two different aldehydes with a-hydrogens are able to form a single aldol condensation product. B) Two different ketones with a-hydrogens are able to form a single aldol condensation product. C) Any aldehyde and ketone mixed together can react to form a single condensation product. D) Any pair of aldehyde or ketone reactants where one of the reactants has no a-hydrogens will lead to a single aldol product. Answer: D Difficulty: 2 Medium Section: 22.02 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22 Accessibility: Keyboard Navigation

46) What product (including stereochemistry) is formed in the following intermolecular reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 22.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

47) What product (including stereochemistry) is formed in the following intermolecular reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 22.05; 22.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

48) Which of the following bicyclic ring systems can be prepared by an intermolecular Robinson annulation?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 22.09 Topic: Aldehydes and Ketones Bloom's: 4. Analyze Chapter: 22

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

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 22.03 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

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

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 22.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

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

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 22.07 Topic: Aldehydes and Ketones Bloom's: 3. Apply Chapter: 22

Organic Chemistry, 6e (Smith) Chapter 23 Amines 1) Which of the following amines are classified as primary (1°) amines?

A) I B) II C) III D) I and II 2) Which of the following amines are classified as secondary (2°) amines?

A) I B) II C) III D) I and II 3) Which of the following amines are classified as tertiary (3°) amines?

A) I B) II C) III D) IV 4) What is the approximate bond angle of the substituents around a nitrogen atom in amines? A) 90° B) 109.5° C) 120° D) 180° 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

5) Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center, the chirality of the amine nitrogen is often ignored. Why is that? A) Because four bonds are needed to define a stereogenic center B) Because chirality only exists with the tetrahedral carbon atoms C) Because there is usually slow interconversion between the two isomeric forms at room temperature D) Because there is usually rapid interconversion between the two isomeric forms at room temperature 6) Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored? A) Because there is rapid interconversion between the two isomeric forms at room temperature B) Because interconversion cannot occur between the two isomeric forms at room temperature C) Because the compound would be a meso compound D) Because the compound would be a racemic mixture 7) What is the common name of the following compound?

A) Isopropylamine B) Sec-butylamine C) 2-Methyl-1-propanamine D) Isobutylamine 8) What is the common name of the following compound?

A) isopropylamine B) sec-butylamine C) isobutylamine D) tert-butylamine

9) What is the common name of the following compound?

A) isopropylamine B) 2-methyl-2-propanamine C) tert-butylamine D) isobutylamine 10) What is the common name of the following compound?

A) diisopropylamine B) dipropylamine C) diisopropanamine D) dibutylamine 11) What is the common name of the following compound?

A) dimethylisobutylamine B) butyldimethylamine C) N,N-dimethylbutanamine D) sec-butyldimethylamine 12) What is the IUPAC name of the following compound?

A) N-propylhexanamine B) N-propylaniline C) N-ethylcyclohexylamine D) N-propylcyclohexanamine 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) N-ethyl-N-methylpentylamine B) N-ethyl-N-methyl-1-pentanamine C) N-methyl-3-octanamine D) N-ethyl-2-heptanamine 14) What is the IUPAC name of the following compound?

A) 3-methyl-1-hexanamine B) 4-methyl-1-hexylamine C) 4-methyl-1-hexanamine D) 3-methyl-6-hexylamine 15) What is the IUPAC name of the following compound?

A) N-ethyl-N-methylcyclopentanamine B) N-cyclopentyl-N-methylethanamine C) N-methyl-N-ethylcyclopentylamine D) N-ethyl-N-methylpentanamine 16) What is the IUPAC name of the following compound?

A) 1-methyl-N-propyl-1-propanamine B) 4-methyl-4-heptanamine C) 2-propyl-3-hexanamine D) N-propyl-2-pentanamine

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

A) (S)-methyl-4-hexanamine B) (S)-5-methyl-3-hexanamine C) (R)-2-methyl-4-hexanamine D) (R)-5-methyl-3-hexanamine 18) What is the IUPAC name of the following compound?

A) (Z)-4-hexen-1-amine B) (E)-4-hexen-1-amine C) (E)-2-hexen-6-amine D) (Z)-2-hexen-6-amine 19) What is the correct assignment of the names of the following aromatic amines?

A) I = pyrrolidine; II = pyrimidine; III = aniline B) I = pyrrole; II = pyrimidine; III = anisole C) I = pyrrolidine; II = pyridine; III =aniline D) I = pyrrole; II = pyridine; III = aniline 20) Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > II > III B) I > III > II C) III > I > II D) III > II > I 5 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

21) Arrange the following compounds in order of increasing boiling point, putting the compound with the least boiling point first.

A) I < II < III B) II < I < III C) I < III < II D) II < III < I 22) Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first.

A) I > II > III B) II > I > III C) III > I > II D) II > III > I 23) The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion. What does this tell you about the amine? A) The amine is a primary amine. B) The amine is a secondary amine. C) The amine contains an even number of N atoms. D) The amine contains an odd number of N atoms. 24) What is a typical characteristic absorption in the IR spectrum of a primary amine? A) Two N-H absorptions at 2500-2600 cm-1 B) One N-H absorption at 2500-2600 cm-1 C) Two N-H absorptions at 3300-3500 cm-1 D) One N-H absorption at 3300-3500 cm-1

25) A compound with molecular formula C6H15N exhibits a singlet at d 0.9 (1H), a triplet at d 1.10 (3H), a singlet at d1.15 (9H), and a quartet at d 2.6 (2H) in its 1HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the structure of this compound?

A) I B) II C) III D) IV 26) What is the name given to naturally occurring amines derived from plant sources? A) Enamines B) Imines C) Alkaloids D) Alkamines 27) Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method for preparing primary amines? A) NH3 is not a nucleophile. B) Elimination will occur. C) NH3 is too bulky to act as a nucleophile. D) Polyalkylation of the amine will result in multiple products. 28) In the preparation of primary amines, how can direct nucleophilic substitution between NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a 1:1 ratio? A) Use a large excess of NH3. B) Use a large excess of alkyl halide. C) Use a limited amount of NH3. D) Make the alkyl halide sterically hindered. 29) Why is the N-H bond of an imide especially acidic? A) The conjugate base is stabilized by electron-donating inductive effect. B) The conjugate base is stabilized by resonance. C) The conjugate acid is stabilized by resonance. D) The conjugate base is stabilized by intramolecular hydrogen bonding.

A) I B) II C) III D) None of the choices 32) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV

33) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV 34) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV

35) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV 36) Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)? A) Because of the electron-withdrawing inductive effect of the alkyl groups B) Because of the steric hindrance of the alkyl groups C) Because of the resonance delocalization of the alkyl groups D) Because of electron-donating inductive effect of the alkyl groups 37) Why are alkylamines more basic than arylamines? A) The lone pair electrons are localized in alkylamines and delocalized in arylamines. B) The lone pair electrons are delocalized in alkylamines and localized in arylamines. C) The lone pair electrons are less readily available in alkylamines. D) The lone pair electrons are more readily available in arylamines. 38) Rank the following compounds in order of increasing basicity, putting the least basic compound first.

A) III < II < IV < I B) II < III < IV < I C) I < IV < II < III D) III < I < II < IV

39) Rank the following compounds in order of decreasing basicity, putting the most basic compound first.

A) II > I > III > IV B) I > II > III > IV C) I > III > II > IV D) IV > II > III > I 40) Rank the following compounds in order of increasing basicity, putting the least basic first.

A) II < III < IV < I B) I < II < III < IV C) IV < III < II < I D) II < I < III < IV 41) Rank the following compounds in order of decreasing basicity, putting the most basic first.

A) I > II > III > IV B) I > III > II > IV C) IV > III > I > II D) II > I > III > IV 42) Why is pyrrole much less basic than pyridine? A) The lone pair of electrons in pyrrole is located on an sp2 orbital. B) The lone pair of electrons in pyrrole is part of the aromatic p system. C) The lone pair of electrons in pyrrole is not part of the aromatic p system. D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine.

43) Why is piperidine a stronger base than pyridine? A) The lone pair of electrons in pyridine is part of the delocalized p system. B) Aromatic compounds are always less basic than non-aromatic compounds. C) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital. D) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp2 hybrid orbital. 44) Rank the following compounds in increasing order of basicity, putting the least basic first.

A) II < I < IV < III B) I < III < II < IV C) IV < II < III < I D) I < II < III < IV 45) Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity, putting the most basic nitrogen atom first.

A) N1 > N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2

46) Histamine, a vasodilator, is responsible for a wide variety of physiological effects. Rank the three nitrogen atoms in histamine in increasing order of basicity, putting least basic nitrogen atom first.

A) N2 < N1 < N3 B) N1 < N2 < N3 C) N3 < N1 < N2 D) N3 < N2 < N1 47) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV

48) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV 49) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV

50) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV 51) Predict the major product of the following reaction.

A) I B) II C) III D) IV

52) Predict the major product of the following reaction.

A) I B) II C) III D) IV 53) Select the reagent(s) required for the following transformation.

A) NaI B) (1) NaNO2, HCl; (2) NaI C) (1) NaNO2, HCl; (2) I2 D) I2 54) Select the reagent(s) required for the following transformation.

A) NaF B) (1) NaNO2, HCl; (2) F2 C) (1) NaNO2, HCl; (2) HBF4 D) F2

55) Select the reagent(s) required for the following transformation.

A) (1) NaNO2, HCl; (2) H2 B) (1) NaNO2, HCl; (2) H2O C) (1) NaNO2, HCl; (2) H3PO4 D) (1) NaNO2, HCl; (2) H3PO2 56) Predict the major product of the following reaction.

A) I B) II C) III D) IV

57) Predict the major product of the following reaction.

A) I B) II C) III D) IV 58) What starting materials are required to synthesize the following azo compound?

A) I B) II C) III D) IV

59) Consider the following multistep synthesis.

What is the structure of intermediate A?

A) I B) II C) III D) IV 60) Consider the following multistep synthesis.

What is the structure of intermediate B?

A) I B) II C) III D) IV

61) Consider the following multistep synthesis.

What is the structure of intermediate C?

A) I B) II C) III D) IV 62) What is the IUPAC name for the following compound?

A) (E,R)-4-chloro-3-penten-2-amine B) (E,S)-4-chloro-3-penten-2-amine C) (Z,R)-4-chloro-3-penten-2-amine D) (Z,S)-4-chloro-3-penten-2-amine 63) What is the IUPAC name for the following compound?

A) (E,R)-4-chloro-3-penten-2-amine B) (E,S)-4-chloro-3-penten-2-amine C) (Z,R)-4-chloro-3-penten-2-amine D) (Z,S)-4-chloro-3-penten-2-amine 20 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 23 Amines 1) Which of the following amines are classified as primary (1°) amines?

A) I B) II C) III D) I and II Answer: D Difficulty: 1 Easy Section: 23.01 Topic: Amines Bloom's: 3. Apply Chapter: 23 2) Which of the following amines are classified as secondary (2°) amines?

A) I B) II C) III D) I and II Answer: C Difficulty: 1 Easy Section: 23.01 Topic: Amines Bloom's: 3. Apply Chapter: 23

3) Which of the following amines are classified as tertiary (3°) amines?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 23.01 Topic: Amines Bloom's: 3. Apply Chapter: 23 4) What is the approximate bond angle of the substituents around a nitrogen atom in amines? A) 90° B) 109.5° C) 120° D) 180° Answer: B Difficulty: 1 Easy Section: 23.02 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation

5) Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center, the chirality of the amine nitrogen is often ignored. Why is that? A) Because four bonds are needed to define a stereogenic center B) Because chirality only exists with the tetrahedral carbon atoms C) Because there is usually slow interconversion between the two isomeric forms at room temperature D) Because there is usually rapid interconversion between the two isomeric forms at room temperature Answer: D Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 6) Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored? A) Because there is rapid interconversion between the two isomeric forms at room temperature B) Because interconversion cannot occur between the two isomeric forms at room temperature C) Because the compound would be a meso compound D) Because the compound would be a racemic mixture Answer: B Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation

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

A) Isopropylamine B) Sec-butylamine C) 2-Methyl-1-propanamine D) Isobutylamine Answer: D Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 8) What is the common name of the following compound?

A) isopropylamine B) sec-butylamine C) isobutylamine D) tert-butylamine Answer: B Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

9) What is the common name of the following compound?

A) isopropylamine B) 2-methyl-2-propanamine C) tert-butylamine D) isobutylamine Answer: C Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 10) What is the common name of the following compound?

A) diisopropylamine B) dipropylamine C) diisopropanamine D) dibutylamine Answer: A Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

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

A) dimethylisobutylamine B) butyldimethylamine C) N,N-dimethylbutanamine D) sec-butyldimethylamine Answer: D Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 12) What is the IUPAC name of the following compound?

A) N-propylhexanamine B) N-propylaniline C) N-ethylcyclohexylamine D) N-propylcyclohexanamine Answer: D Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

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

A) N-ethyl-N-methylpentylamine B) N-ethyl-N-methyl-1-pentanamine C) N-methyl-3-octanamine D) N-ethyl-2-heptanamine Answer: B Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 14) What is the IUPAC name of the following compound?

A) 3-methyl-1-hexanamine B) 4-methyl-1-hexylamine C) 4-methyl-1-hexanamine D) 3-methyl-6-hexylamine Answer: C Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

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

A) N-ethyl-N-methylcyclopentanamine B) N-cyclopentyl-N-methylethanamine C) N-methyl-N-ethylcyclopentylamine D) N-ethyl-N-methylpentanamine Answer: A Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 16) What is the IUPAC name of the following compound?

A) 1-methyl-N-propyl-1-propanamine B) 4-methyl-4-heptanamine C) 2-propyl-3-hexanamine D) N-propyl-2-pentanamine Answer: D Difficulty: 1 Easy Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

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

A) (S)-methyl-4-hexanamine B) (S)-5-methyl-3-hexanamine C) (R)-2-methyl-4-hexanamine D) (R)-5-methyl-3-hexanamine Answer: B Difficulty: 2 Medium Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 18) What is the IUPAC name of the following compound?

A) (Z)-4-hexen-1-amine B) (E)-4-hexen-1-amine C) (E)-2-hexen-6-amine D) (Z)-2-hexen-6-amine Answer: B Difficulty: 2 Medium Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

19) What is the correct assignment of the names of the following aromatic amines?

A) I = pyrrolidine; II = pyrimidine; III = aniline B) I = pyrrole; II = pyrimidine; III = anisole C) I = pyrrolidine; II = pyridine; III =aniline D) I = pyrrole; II = pyridine; III = aniline Answer: D Difficulty: 2 Medium Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 20) Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > II > III B) I > III > II C) III > I > II D) III > II > I Answer: C Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23

21) Arrange the following compounds in order of increasing boiling point, putting the compound with the least boiling point first.

A) I < II < III B) II < I < III C) I < III < II D) II < III < I Answer: D Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23 22) Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first.

A) I > II > III B) II > I > III C) III > I > II D) II > III > I Answer: B Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23

23) The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion. What does this tell you about the amine? A) The amine is a primary amine. B) The amine is a secondary amine. C) The amine contains an even number of N atoms. D) The amine contains an odd number of N atoms. Answer: D Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 24) What is a typical characteristic absorption in the IR spectrum of a primary amine? A) Two N-H absorptions at 2500-2600 cm-1 B) One N-H absorption at 2500-2600 cm-1 C) Two N-H absorptions at 3300-3500 cm-1 D) One N-H absorption at 3300-3500 cm-1 Answer: C Difficulty: 1 Easy Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 23.04 Topic: Amines Bloom's: 3. Apply Chapter: 23 26) What is the name given to naturally occurring amines derived from plant sources? A) Enamines B) Imines C) Alkaloids D) Alkamines Answer: C Difficulty: 1 Easy Section: 23.05 Topic: Amines Bloom's: 1. Remember Chapter: 23 Accessibility: Keyboard Navigation

27) Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method for preparing primary amines? A) NH3 is not a nucleophile. B) Elimination will occur. C) NH3 is too bulky to act as a nucleophile. D) Polyalkylation of the amine will result in multiple products. Answer: D Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 28) In the preparation of primary amines, how can direct nucleophilic substitution between NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a 1:1 ratio? A) Use a large excess of NH3. B) Use a large excess of alkyl halide. C) Use a limited amount of NH3. D) Make the alkyl halide sterically hindered. Answer: A Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 29) Why is the N-H bond of an imide especially acidic? A) The conjugate base is stabilized by electron-donating inductive effect. B) The conjugate base is stabilized by resonance. C) The conjugate acid is stabilized by resonance. D) The conjugate base is stabilized by intramolecular hydrogen bonding. Answer: B Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation

30) Which of the following alkyl halides cannot be used to prepare primary amines by the Gabriel synthesis? A) 2-Bromo-2-methylbutane B) 1-Bromo-2-methylbutane C) 2-Bromo-3-methylbutane D) 1-Bromo-3-methylbutane Answer: A Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 31) Predict the product(s) of the following reaction.

A) I B) II C) III D) None of the choices Answer: B Difficulty: 2 Medium Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

32) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

33) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

34) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

35) What is the major organic product obtained in the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23 36) Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)? A) Because of the electron-withdrawing inductive effect of the alkyl groups B) Because of the steric hindrance of the alkyl groups C) Because of the resonance delocalization of the alkyl groups D) Because of electron-donating inductive effect of the alkyl groups Answer: D Difficulty: 1 Easy Section: 23.08 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation

37) Why are alkylamines more basic than arylamines? A) The lone pair electrons are localized in alkylamines and delocalized in arylamines. B) The lone pair electrons are delocalized in alkylamines and localized in arylamines. C) The lone pair electrons are less readily available in alkylamines. D) The lone pair electrons are more readily available in arylamines. Answer: A Difficulty: 1 Easy Section: 23.08 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 38) Rank the following compounds in order of increasing basicity, putting the least basic compound first.

A) III < II < IV < I B) II < III < IV < I C) I < IV < II < III D) III < I < II < IV Answer: A Difficulty: 2 Medium Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23

39) Rank the following compounds in order of decreasing basicity, putting the most basic compound first.

A) II > I > III > IV B) I > II > III > IV C) I > III > II > IV D) IV > II > III > I Answer: C Difficulty: 2 Medium Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23 40) Rank the following compounds in order of increasing basicity, putting the least basic first.

A) II < III < IV < I B) I < II < III < IV C) IV < III < II < I D) II < I < III < IV Answer: B Difficulty: 2 Medium Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23

41) Rank the following compounds in order of decreasing basicity, putting the most basic first.

A) I > II > III > IV B) I > III > II > IV C) IV > III > I > II D) II > I > III > IV Answer: D Difficulty: 2 Medium Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23 42) Why is pyrrole much less basic than pyridine? A) The lone pair of electrons in pyrrole is located on an sp2 orbital. B) The lone pair of electrons in pyrrole is part of the aromatic p system. C) The lone pair of electrons in pyrrole is not part of the aromatic p system. D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine. Answer: B Difficulty: 1 Easy Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation

43) Why is piperidine a stronger base than pyridine? A) The lone pair of electrons in pyridine is part of the delocalized p system. B) Aromatic compounds are always less basic than non-aromatic compounds. C) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital. D) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp2 hybrid orbital. Answer: D Difficulty: 2 Medium Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23 Accessibility: Keyboard Navigation 44) Rank the following compounds in increasing order of basicity, putting the least basic first.

A) II < I < IV < III B) I < III < II < IV C) IV < II < III < I D) I < II < III < IV Answer: B Difficulty: 2 Medium Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23

45) Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity, putting the most basic nitrogen atom first.

A) N1 > N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2 Answer: C Difficulty: 3 Hard Section: 23.09 Topic: Amines Bloom's: 3. Apply Chapter: 23

A) N2 < N1 < N3 B) N1 < N2 < N3 C) N3 < N1 < N2 D) N3 < N2 < N1 Answer: A Difficulty: 3 Hard Section: 23.08 Topic: Amines Bloom's: 3. Apply Chapter: 23

47) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 23.11 Topic: Amines Bloom's: 3. Apply Chapter: 23 48) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 23.11 Topic: Amines Bloom's: 3. Apply Chapter: 23 26 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

49) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 23.11 Topic: Amines Bloom's: 3. Apply Chapter: 23

50) Predict the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 23.12 Topic: Amines Bloom's: 3. Apply Chapter: 23 51) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 23.12 Topic: Amines Bloom's: 3. Apply Chapter: 23 28 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

52) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 23.12 Topic: Amines Bloom's: 3. Apply Chapter: 23 53) Select the reagent(s) required for the following transformation.

A) NaI B) (1) NaNO2, HCl; (2) NaI C) (1) NaNO2, HCl; (2) I2 D) I2 Answer: B Difficulty: 1 Easy Section: 23.07 Topic: Amines Bloom's: 3. Apply Chapter: 23

54) Select the reagent(s) required for the following transformation.

A) NaF B) (1) NaNO2, HCl; (2) F2 C) (1) NaNO2, HCl; (2) HBF4 D) F2 Answer: C Difficulty: 1 Easy Section: 23.07 Topic: Amines Bloom's: 3. Apply Chapter: 23 55) Select the reagent(s) required for the following transformation.

A) (1) NaNO2, HCl; (2) H2 B) (1) NaNO2, HCl; (2) H2O C) (1) NaNO2, HCl; (2) H3PO4 D) (1) NaNO2, HCl; (2) H3PO2 Answer: D Difficulty: 1 Easy Section: 23.12 Topic: Amines Bloom's: 3. Apply Chapter: 23

56) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 23.12 Topic: Amines Bloom's: 3. Apply Chapter: 23

57) Predict the major product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 23.13 Topic: Amines Bloom's: 3. Apply Chapter: 23

58) What starting materials are required to synthesize the following azo compound?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 23.13 Topic: Amines Bloom's: 3. Apply Chapter: 23

59) Consider the following multistep synthesis.

What is the structure of intermediate A?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 23.07 Topic: Amines Bloom's: 3. Apply Chapter: 23

60) Consider the following multistep synthesis.

What is the structure of intermediate B?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

61) Consider the following multistep synthesis.

What is the structure of intermediate C?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 23.07 Topic: Amines Bloom's: 3. Apply Chapter: 23

62) What is the IUPAC name for the following compound?

A) (E,R)-4-chloro-3-penten-2-amine B) (E,S)-4-chloro-3-penten-2-amine C) (Z,R)-4-chloro-3-penten-2-amine D) (Z,S)-4-chloro-3-penten-2-amine Answer: C Difficulty: 2 Medium Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23 63) What is the IUPAC name for the following compound?

A) (E,R)-4-chloro-3-penten-2-amine B) (E,S)-4-chloro-3-penten-2-amine C) (Z,R)-4-chloro-3-penten-2-amine D) (Z,S)-4-chloro-3-penten-2-amine Answer: B Difficulty: 2 Medium Section: 23.03 Topic: Amines Bloom's: 3. Apply Chapter: 23

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

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

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

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 23.06 Topic: Amines Bloom's: 3. Apply Chapter: 23

Organic Chemistry, 6e (Smith) Chapter 24 Carbon-Carbon Bond-Forming Reactions in Organic Synthesis 1) Organocuprate reagents (R2CuLi) react with several compounds. Which listed reaction is not correct? A) Acid chlorides react with organocuprate reagents to form ketones. B) Epoxides react with organocuprate reagents to form alcohols. C) Alkyl halides react with organocuprate reagents to form coupling products containing a new carbon-carbon bond. D) Carbon dioxide reacts with organocuprate reagents to form carboxylic acids. 2) Which class of compounds listed below does not react with organocuprate reagents to form a coupling product that contains a new carbon-carbon bond? A) 1° Alkyl halides B) 3° Alkyl halides C) Vinyl halides D) Aryl halides 3) Which statement below best explains what is meant by the statement, "An organocuprate reaction with a vinyl halide is stereospecific"? A) The reaction of a specific stereoisomer with the R2CuLi reagent will yield that particular stereoisomer as the product. B) The reaction of a vinyl halide with the R2CuLi reagent will only yield the cis product. C) The reaction of a vinyl halide with the R2CuLi reagent will only yield the trans product. D) The reaction of a vinyl halide with the R2CuLi reagent will only yield one enantiomer product—either R or S configuration. 4) Coupling reactions with vinyl halides are stereospecific. Which choice below best describes the expected product when trans-1-bromo-1-hexene reacts with (CH3)2CuLi? A) The reaction will only yield a trans-alkene. B) The reaction will only yield a cis-alkene. C) The reaction will only yield one enantiomeric product with R configuration. D) The reaction will only yield one enantiomeric product with S configuration.

5) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 6) What is the major organic product of the following reaction?

A) I B) II C) III D) IV

7) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 8) What is the missing reactant in the following reaction?

A) I B) II C) III D) IV

9) Identify the products of the following reaction.

A) A B) B C) C D) D 10) Identify the products of the following reaction.

A) I B) II C) III D) IV

11) Which of the reactions listed below is not stereospecific? A) Suzuki reaction B) Organocuprate coupling reaction C) Heck reaction D) Simmons-Smith reaction 12) Choose the statement below that is not true about the Suzuki reaction. A) The product of the Suzuki reaction is completely stereospecific. B) The Suzuki reaction involves both an organoborane reagent and an organopalladium catalyst. C) The Suzuki reaction forms more highly substituted alkenes. D) The Suzuki reaction involves an oxidative addition followed by a reductive elimination. 13) Which of the following is not a step in the Suzuki reaction? A) Oxidative addition of R-X to the palladium catalyst B) Substitution of the R group to the palladium catalyst C) Transfer of the alkyl group from the organoborane to palladium D) Reductive elimination of R-R, forming the new C-C bond 14) What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have in common when they react with an alkyl halide? A) All reactions form new carbon-carbon bonds. B) They all use palladium as a catalyst in one step of the reaction. C) They are all stereospecific reactions. D) They all require harsh conditions. 15) Which of the following statements is not true about the Simmons-Smith reaction? A) The Simmons-Smith reaction involves the formation of a free carbene. B) The Simmons-Smith reaction uses the reagents zinc-copper couple. C) The Simmons-Smith reaction is stereospecific. D) The Simmons-Smith reaction involves CH2I2 reacting with a copper-activated zinc reagent. 16) Which of the following is true about the use of the Grubbs catalyst? A) The Grubbs catalyst is used in carbon-carbon coupling reactions. B) The Grubbs catalyst is used in alkene metathesis. C) The Grubbs catalyst is used in carbene formation. D) The Grubbs catalyst is used with palladium as a co-catalyst. 17) What products are formed when diazomethane is heated? A) Methane gas and nitrogen gas B) Propene gas and nitrogen gas C) Methyl radical and nitrogen gas D) Methylene and nitrogen gas

18) Which of the following descriptions does not apply to methylene? A) Methylene is sp2 hybridized. B) Methylene is a neutral, reactive intermediate. C) Methylene is a radical intermediate. D) The formula of methylene is :CH2. 19) Which of the following statements is not true about a carbene? A) A carbene is a neutral reactive intermediate. B) A carbene contains a divalent carbon. C) A carbene is sp3 hybridized. D) A carbene is surrounded by six electrons. 20) Which of the following correctly describes a reaction yielding a dichorocarbene? A) The reaction of chloroform with KOC(CH3)3 B) The reaction of chloroform with Zn(Cu) C) The reaction of chloroform with (CH3)2CuLi D) The reaction of diazomethane with KOC(CH3)3 21) Dichlorocarbene reacts with an alkene to form a cyclopropane derivative. In this reaction the dichlorocarbene acts as a(n) A) Lewis base. B) electrophile. C) nucleophile. D) Brønsted-Lowry base. 22) Why is the Grubbs catalyst synthetically important? A) Because it only requires dilute concentrations of the reactants B) Because it produces only stereospecific products C) Because it produces only stereoselective products D) Because it provides a synthetic pathway for ring-closing metathesis reactions

23) What would be the starting material for the following product that was made via a Grubbs catalyst?

A) I B) II C) III D) IV 24) Identify the starting material that would be used to form the following product in a ringclosing metathesis reaction utilizing a Grubbs catalyst?

A) I B) II C) III D) IV

25) Identify the major organic product of the following reaction.

A) I B) II C) III D) IV 26) What would be the major organic product of the following Heck reaction?

A) I B) II C) III D) IV

27) Identify the major organic product of the following reaction.

A) I B) II C) III D) IV 28) Identify the major organic product of the following reaction.

A) I B) II C) III D) IV

29) Identify the structure of the organic product Y formed in the following reaction sequence.

A) I B) II C) III D) IV 30) What is the name for the type of intermediate X formed in the reaction sequence below?

A) A carbocation B) A carbanion C) A free radical D) A carbene 31) As shown below, when cis-2-butene reacts with dichlorocarbene, only the cis-1,1-dichloro2,3-dimethylcyclopropane is formed. What can we conclude about the nature of the reaction mechanism?

A) The mechanism is an SN1 mechanism. B) The mechanism is a concerted. C) The mechanism proceeds through a radical intermediate. D) The mechanism is an E2 mechanism.

32) What is the major organic product of the following reaction?

A) I B) II C) III D) IV 33) What is the major organic product of the following reaction?

A) I B) II C) III D) None of the choices is correct.

34) Identify the structure of the organic product Y formed in the following reaction sequence.

A) I B) II C) III D) IV 35) Many of the reactions studied in this chapter are stereospecific. Why are stereospecific reactions important? A) When a reaction produces a mixture of enantiomers, it is often very difficult to separate them. A mixture of products is often not useful. B) Often stereoisomers of a particular compound will have very different biological effects on an organism. Only one isomer is biologically helpful, and the other may be harmful. C) Often only one stereoisomer is biologically active, and coupling reactions are often used for the production of biological materials. D) All of the choices are true. 36) What starting material could yield the following compound if Simmons-Smith conditions were used?

A) I B) II C) III D) IV

37) What starting material could yield the following compound if Simmons-Smith conditions were used?

A) I B) II C) III D) IV 38) Identify the structure of the major organic product that results from the following reaction.

A) I B) II C) III D) IV

39) Compound X can be synthesized via a ring-closing metathesis reaction when treated with a Grubbs' catalyst. What is a possible structure of the starting material for this reaction?

A) I B) II C) III D) IV 40) What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?

41) What is the appropriate sequence of starting material and reagents that will produce the target molecule shown below?

A) I B) II C) III D) IV

42) Identify the structure of the major organic product that results from the following reaction.

A) I B) II C) III D) IV 43) Identify the structure of the major organic product that results from the following reaction.

A) I B) II C) III D) IV

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

A) I B) II C) III D) IV 45) What reactant would be necessary to produce the product indicated in the following reaction?

A) I B) II C) III D) IV

46) Starting with chloroform, what reactions order and reagents are necessary to produce the following product and its enantiomer?

A) [1] KOC(CH3)3,[2] trans-2-butene B) [1] KOC(CH3)3,[2] cis-2-butene C) [1] trans-2-butene, [2] KOC(CH3)3 D) [1] cis-2-butene, [2] KOC(CH3)3 47) Starting with chloroform, what reactions order and reagents are necessary to produce the following product?

A) [1] KOC(CH3)3,[2] trans-2-butene B) [1] KOC(CH3)3,[2] cis-2-butene C) [1] trans-2-butene, [2] KOC(CH3)3 D) [1] cis-2-butene, [2] KOC(CH3)3

3) Which statement below best explains what is meant by the statement, "An organocuprate reaction with a vinyl halide is stereospecific"? A) The reaction of a specific stereoisomer with the R2CuLi reagent will yield that particular stereoisomer as the product. B) The reaction of a vinyl halide with the R2CuLi reagent will only yield the cis product. C) The reaction of a vinyl halide with the R2CuLi reagent will only yield the trans product. D) The reaction of a vinyl halide with the R2CuLi reagent will only yield one enantiomer product—either R or S configuration. Answer: A Difficulty: 1 Easy Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation 4) Coupling reactions with vinyl halides are stereospecific. Which choice below best describes the expected product when trans-1-bromo-1-hexene reacts with (CH3)2CuLi? A) The reaction will only yield a trans-alkene. B) The reaction will only yield a cis-alkene. C) The reaction will only yield one enantiomeric product with R configuration. D) The reaction will only yield one enantiomeric product with S configuration. Answer: A Difficulty: 1 Easy Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation

5) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

6) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

7) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

8) What is the missing reactant in the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

9) Identify the products of the following reaction.

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

10) Identify the products of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 24.1 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 11) Which of the reactions listed below is not stereospecific? A) Suzuki reaction B) Organocuprate coupling reaction C) Heck reaction D) Simmons-Smith reaction Answer: C Difficulty: 2 Medium Section: 24.1; 24.2; 24.5; 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation

12) Choose the statement below that is not true about the Suzuki reaction. A) The product of the Suzuki reaction is completely stereospecific. B) The Suzuki reaction involves both an organoborane reagent and an organopalladium catalyst. C) The Suzuki reaction forms more highly substituted alkenes. D) The Suzuki reaction involves an oxidative addition followed by a reductive elimination. Answer: C Difficulty: 1 Easy Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation 13) Which of the following is not a step in the Suzuki reaction? A) Oxidative addition of R-X to the palladium catalyst B) Substitution of the R group to the palladium catalyst C) Transfer of the alkyl group from the organoborane to palladium D) Reductive elimination of R-R, forming the new C-C bond Answer: B Difficulty: 1 Easy Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 1. Remember Chapter: 24 Accessibility: Keyboard Navigation 14) What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have in common when they react with an alkyl halide? A) All reactions form new carbon-carbon bonds. B) They all use palladium as a catalyst in one step of the reaction. C) They are all stereospecific reactions. D) They all require harsh conditions. Answer: A Difficulty: 1 Easy Section: 24.2; 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation

15) Which of the following statements is not true about the Simmons-Smith reaction? A) The Simmons-Smith reaction involves the formation of a free carbene. B) The Simmons-Smith reaction uses the reagents zinc-copper couple. C) The Simmons-Smith reaction is stereospecific. D) The Simmons-Smith reaction involves CH2I2 reacting with a copper-activated zinc reagent. Answer: A Difficulty: 1 Easy Section: 24.5 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation 16) Which of the following is true about the use of the Grubbs catalyst? A) The Grubbs catalyst is used in carbon-carbon coupling reactions. B) The Grubbs catalyst is used in alkene metathesis. C) The Grubbs catalyst is used in carbene formation. D) The Grubbs catalyst is used with palladium as a co-catalyst. Answer: B Difficulty: 1 Easy Section: 24.6 Topic: Organometallics (C-C bond transformations) Bloom's: 1. Remember Chapter: 24 Accessibility: Keyboard Navigation 17) What products are formed when diazomethane is heated? A) Methane gas and nitrogen gas B) Propene gas and nitrogen gas C) Methyl radical and nitrogen gas D) Methylene and nitrogen gas Answer: D Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 1. Remember Chapter: 24 Accessibility: Keyboard Navigation

18) Which of the following descriptions does not apply to methylene? A) Methylene is sp2 hybridized. B) Methylene is a neutral, reactive intermediate. C) Methylene is a radical intermediate. D) The formula of methylene is :CH2. Answer: C Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation 19) Which of the following statements is not true about a carbene? A) A carbene is a neutral reactive intermediate. B) A carbene contains a divalent carbon. C) A carbene is sp3 hybridized. D) A carbene is surrounded by six electrons. Answer: C Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation 20) Which of the following correctly describes a reaction yielding a dichorocarbene? A) The reaction of chloroform with KOC(CH3)3 B) The reaction of chloroform with Zn(Cu) C) The reaction of chloroform with (CH3)2CuLi D) The reaction of diazomethane with KOC(CH3)3 Answer: A Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation

21) Dichlorocarbene reacts with an alkene to form a cyclopropane derivative. In this reaction the dichlorocarbene acts as a(n) A) Lewis base. B) electrophile. C) nucleophile. D) Brønsted-Lowry base. Answer: B Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation 22) Why is the Grubbs catalyst synthetically important? A) Because it only requires dilute concentrations of the reactants B) Because it produces only stereospecific products C) Because it produces only stereoselective products D) Because it provides a synthetic pathway for ring-closing metathesis reactions Answer: D Difficulty: 1 Easy Section: 24.6 Topic: Organometallics (C-C bond transformations) Bloom's: 2. Understand Chapter: 24 Accessibility: Keyboard Navigation

23) What would be the starting material for the following product that was made via a Grubbs catalyst?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 24.6 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

24) Identify the starting material that would be used to form the following product in a ringclosing metathesis reaction utilizing a Grubbs catalyst?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 24.6 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

25) Identify the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

26) What would be the major organic product of the following Heck reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

27) Identify the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

28) Identify the major organic product of the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

29) Identify the structure of the organic product Y formed in the following reaction sequence.

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 30) What is the name for the type of intermediate X formed in the reaction sequence below?

A) A carbocation B) A carbanion C) A free radical D) A carbene Answer: D Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

31) As shown below, when cis-2-butene reacts with dichlorocarbene, only the cis-1,1-dichloro2,3-dimethylcyclopropane is formed. What can we conclude about the nature of the reaction mechanism?

A) The mechanism is an SN1 mechanism. B) The mechanism is a concerted. C) The mechanism proceeds through a radical intermediate. D) The mechanism is an E2 mechanism. Answer: B Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 32) What is the major organic product of the following reaction?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 24.5 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 20 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

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

A) I B) II C) III D) None of the choices is correct. Answer: A Difficulty: 2 Medium Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

34) Identify the structure of the organic product Y formed in the following reaction sequence.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 24.1; 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 35) Many of the reactions studied in this chapter are stereospecific. Why are stereospecific reactions important? A) When a reaction produces a mixture of enantiomers, it is often very difficult to separate them. A mixture of products is often not useful. B) Often stereoisomers of a particular compound will have very different biological effects on an organism. Only one isomer is biologically helpful, and the other may be harmful. C) Often only one stereoisomer is biologically active, and coupling reactions are often used for the production of biological materials. D) All of the choices are true. Answer: D Difficulty: 1 Easy Section: 24.1; 24.2; 24.5; 24.6; 24.4; 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 Accessibility: Keyboard Navigation

36) What starting material could yield the following compound if Simmons-Smith conditions were used?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: 24.5 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 37) What starting material could yield the following compound if Simmons-Smith conditions were used?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 24.5 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24 23 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

38) Identify the structure of the major organic product that results from the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

39) Compound X can be synthesized via a ring-closing metathesis reaction when treated with a Grubbs' catalyst. What is a possible structure of the starting material for this reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 24.6 Topic: Organometallics (C-C bond transformations) Bloom's: 4. Analyze Chapter: 24

40) What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?

A) (1) HBr, H2O2; (2) KOC(CH3)3 ; (3) MCPBA; (4) CH2=CPh2 B) (1) NBS, hn ; (2) KOC(CH3)3 ; (3) CHBr3, KO(CH3)3 ; (4) a. LiCuPh2, b. H2O C) (1) H2SO4(aq.), D ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) CH2=CPh2 D) (1) Br2, FeBr3 ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) Ph2COCl Answer: B Difficulty: 2 Medium Section: 24.5 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

41) What is the appropriate sequence of starting material and reagents that will produce the target molecule shown below?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

42) Identify the structure of the major organic product that results from the following reaction.

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 24.2 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

43) Identify the structure of the major organic product that results from the following reaction.

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

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

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

45) What reactant would be necessary to produce the product indicated in the following reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 24.3 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

46) Starting with chloroform, what reactions order and reagents are necessary to produce the following product and its enantiomer?

A) [1] KOC(CH3)3,[2] trans-2-butene B) [1] KOC(CH3)3,[2] cis-2-butene C) [1] trans-2-butene, [2] KOC(CH3)3 D) [1] cis-2-butene, [2] KOC(CH3)3 Answer: A Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

47) Starting with chloroform, what reactions order and reagents are necessary to produce the following product?

A) [1] KOC(CH3)3,[2] trans-2-butene B) [1] KOC(CH3)3,[2] cis-2-butene C) [1] trans-2-butene, [2] KOC(CH3)3 D) [1] cis-2-butene, [2] KOC(CH3)3 Answer: B Difficulty: 1 Easy Section: 24.4 Topic: Organometallics (C-C bond transformations) Bloom's: 3. Apply Chapter: 24

Organic Chemistry, 6e (Smith) Chapter 25 Pericyclic Reactions 1) Which of the following statements about pericyclic reactions is true? A) Pericyclic reactions occur by way of ionic intermediates. B) Pericyclic reactions occur by way of radical intermediates. C) Pericyclic reactions involve multiple steps. D) Reactive intermediates are not formed in pericyclic reactions. 2) Which of the following statements about pericyclic reactions is true? A) In pericyclic reactions, bonds are broken and formed in multiple steps. B) In pericyclic reactions, all bonds are broken and formed in a single step. C) One intermediate has been identified in pericyclic reactions. D) The transition state in a pericyclic reaction is acyclic. 3) Which of the following statements about pericyclic reactions is not true? A) Pericyclic reactions are concerted reactions. B) Pericyclic reactions proceed through a cyclic transition state. C) Pericyclic reactions are not stereospecific. D) Pericyclic reactions require light or heat. 4) Which of the following is a type of pericyclic reaction? A) electrocyclic reactions B) acyclic reactions C) cycloelimination reactions D) electrophilic reactions 5) Which of the following is not a type of pericyclic reactions? A) cycloadditions B) nucleophilic reactions C) electrocyclic reactions D) sigmatropic rearrangements 6) Which of the following statements about electrocyclic ring closure is not true? A) It is an intramolecular reaction. B) It requires heat or light. C) The cyclic product contains one more s bond and one fewer p bond than the reactants. D) The cyclic product contains one more p bond and one fewer s bond than the reactants. 7) Which of the following statements about an electrocyclic ring-opening reaction is not true? A) An electrocyclic ring-opening reaction is an intramolecular reaction. B) An electrocyclic ring-opening reaction requires a source of energy (heat or light). C) The product of an electrocyclic ring-opening reaction contains one fewer p bond than the reactant. D) The product of an electrocyclic ring-opening reaction contains one more p bond than the reactant. 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

8) What is the organic product of the following electrocyclic reaction?

A) I B) II C) III D) IV 9) Which of the following statements about cycloaddition reactions is true? A) Cycloaddition reactions occur only intermolecularly. B) Cycloaddition reactions occur only intramolecularly. C) Cycloaddition reactions form a cyclic product with two new p bonds. D) Cycloaddition reactions can be intramolecular or intermolecular. 10) Which of the following statements about sigmatropic reactions is true? A) The reactants contain one more p bond than the product. B) The product contains one more p bond than the reactant. C) A p bond is broken in the reactant. D) A s bond is broken in the reactant. 11) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrocyclic reaction C) Electrophilic reaction D) Sigmatropic reaction

12) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrocyclic reaction C) Electrophilic reaction D) Sigmatropic reaction 13) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrophilic reaction C) Electrocyclic reaction D) Sigmatropic reaction 14) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrophilic reaction C) Electrocyclic reaction D) Sigmatropic reaction 15) Which of the following statements about porbitals is true? A) p orbitals are formed by the linear combination of two sp3 orbitals. B) p orbitals are formed by the linear combination of two sp2 orbitals. C) p orbitals are formed by the linear combination of two sp orbitals. D) p orbitals are formed by the linear combination of two p orbitals.

16) Which of the following statements about molecular orbitals is true? A) The number of molecular orbitals formed is different from the number of atomic orbitals used. B) The number of molecular orbitals formed is equal to the number of atomic orbitals used. C) The number of molecular orbitals formed is equal to twice the number of atomic orbitals used. D) The number of molecular orbitals formed is equal to half the number of atomic orbitals used. 17) Which of the following statements about a p-bonding molecular orbital is true? A) A p-bonding molecular orbital is formed when two p orbitals of similar phase overlap. B) A p-bonding molecular orbital is lower in energy than a s-bonding molecular orbital. C) A p-bonding molecular orbital is formed when two p orbitals of opposite phase overlap. D) Both the statements a p-bonding molecular orbital is formed when two p orbitals of similar phase overlap and a p-bonding molecular orbital is lower in energy than a s-bonding molecular orbital are true. 18) Which of the following statements about a p* antibonding molecular orbital is true? A) A p* antibonding molecular orbital is formed when two p orbitals of similar phase overlap. B) A p* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap. C) A p* antibonding molecular orbital is a higher-energy molecular orbital than a p bonding molecular orbital. D) Both the statements a p* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap and a p* antibonding molecular orbital is a higher-energy molecular orbital than a p bonding molecular orbital are true. 19) How many p molecular orbitals are present in 1,3,5-hexatriene? A) 3 B) 4 C) 5 D) 6 20) How many bonding molecular orbitals are present in 1,3,5-hexatriene? A) 3 B) 4 C) 5 D) 6 21) How many p molecular orbitals are present in 1,3,5,7,9-decapentaene? A) 4 B) 5 C) 10 D) 12

22) How many bonding molecular orbitals are present in 1,3,5,7,9-decapentaene? A) 4 B) 5 C) 10 D) 12 23) How many nodes are present in Y5 of 1,3,5,7,9-decapentaene? A) 2 B) 3 C) 4 D) 5 24) Which of the following statements about electrocyclic reactions is true? A) An electrocyclic reaction is generally irreversible. B) Generally, an acyclic triene is favored over a six-membered ring at equilibrium. C) Generally, a four-membered ring is favored over an acyclic diene at equilibrium. D) An electrocyclic reaction is generally reversible. 25) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II

26) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II 27) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II

28) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II 29) Which of the following statements about thermal electrocyclic reactions is not true? A) The number of s bonds in the conjugated polyene determines whether rotation is conrotatory or disrotatory. B) Thermal electrocyclic reactions occur in a disrotatory fashion for a conjugated polyene with an odd number of p bonds. C) Thermal electrocyclic reactions occur in a conrotatory fashion for a conjugated polyene with an even number of p bonds. D) In thermal reactions, we consider the orbitals of the HOMO of the ground state electronic configuration to determine the course of the reaction. 30) Which of the following statements about photochemical electrocyclic reactions is not true? A) In photochemical reactions, we consider the orbitals of the HOMO of the excited state to determine the course of the reaction. B) Photochemical electrocyclic reactions occur in a conrotatory fashion for a conjugated polyene with an odd number of p bonds. C) Photochemical electrocyclic reactions occur in a disrotatory fashion for a conjugated polyene with an even number of p bonds. D) In photochemical reactions, we consider the orbitals of the LUMO of the excited state to determine the course of the reaction. 31) Which of the following statements about cycloaddition reactions is not true? A) Cycloaddition reactions form a cyclic product with two new s bonds. B) The course of the reaction is determined by the symmetry of the molecular orbitals of the products. C) Cycloaddition reactions are concerted. D) Cycloaddition reactions are stereospecific.

32) Which of the following statements about cycloaddition reactions is true? A) Cycloaddition reactions can be initiated by heat only. B) Cycloaddition reactions can be initiated by light only. C) Cycloaddition reactions can be initiated by heat or light. D) Cycloaddition reactions are identified by the number of p electrons in the two products. 33) Why is the Diels-Alder reaction called a thermal [4+2] cycloaddition? A) Because the reaction is initiated by heat; the diene has four p electrons and the dienophile has two p electrons. B) Because the reaction is initiated by light; the diene has four p electrons and the dienophile has two p electrons. C) Because the reaction is initiated by heat; the dienophile has four p electrons and the diene has two p electrons. D) Because the reaction is initiated by light; the dienophile has four p electrons and the diene has two p electrons. 34) Which of the following statements about [2+2] cycloaddition reactions between two alkenes is true? A) The reaction is initiated by heat. B) The reaction is initiated by light. C) The product is a cyclopentane derivative. D) Each reactant contains two s electrons that participate in the formation of new bonds. 35) What type of cycloaddition reaction is shown below?

A) [2+2] B) [4+2] C) [4+4] D) [0+2] 36) What type of cycloaddition reaction is shown in the following equation?

A) [2+2] B) [4+2] C) [4+4] D) [0+2]

37) What are the two modes of bond formation in cycloaddition reactions? A) Suprafacial and antarafacial bond formations B) Superfacial and antifacial bond formations C) Suprafacial and synfacial bond formations D) Synfacial and antifacial bond formations 38) Which of the following statements about orbital symmetry and cycloaddition reactions is true? A) Thermal cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. B) Thermal cycloadditions involving an odd number of p bonds proceed by a suprafacial pathway. C) Photochemical cycloadditions involving an odd number of p bonds proceed by a suprafacial pathway. D) Photochemical sycloadditions involving an even number of p bonds proceed by an antarafacial pathway. 39) Which of the following statements about orbital symmetry and cycloaddition reactions is true? A) Thermal cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. B) Thermal cycloadditions involving an odd number of p bonds proceed by an antarafacial pathway. C) Photochemical cycloadditions involving an even number of p bonds proceed by an antarafacial pathway. D) Photochemical cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. 40) Which of the following statements about sigmatropic reactions is not true? A) A sigmatropic reaction is an intramolecular pericyclic reaction. B) In a sigmatropic reaction, s bond is broken in one of the reactants. C) The p bonds rearrange in a sigmatropic reaction. D) The number of p bonds in the reactants and product differs in a sigmatropic reaction. 41) Which of the following is not a correct designation for a sigmatropic rearrangement? A) [1,3] B) [1,5] C) [3,3] D) [3,1]

42) What type of sigmatropic rearrangement is illustrated below?

A) [1,3] B) [1,4] C) [3,3] D) [1,5] 43) What type of sigmatropic rearrangement is illustrated below?

A) [1,3] B) [1,4] C) [3,3] D) [1,5] 44) What type of sigmatropic rearrangement is illustrated below?

A) [1,3] B) [1,4] C) [3,3] D) [1,5] 45) Which of the following statements about sigmatropic rearrangements and orbital symmetry is not true? A) Reactions involving six atoms or fewer must take place by suprafacial pathways. B) In a suprafacial rearrangement, the new s bond forms on the opposite side of the p system as the broken s bond. C) In an antarafacial rearrangement, the new s bond forms on the opposite side of the p system as the broken s bond. D) In a suprafacial rearrangement, the new s bond forms on the same side of the p system as the broken s bond.

46) Which of the following statements about the Cope rearrangement is not true? A) The Cope rearrangement involves the rearrangement of a 1,5-diene to an isomeric 1,5-diene. B) The Cope rearrangement takes place readily in a suprafacial pathway under photochemical conditions. C) The Cope rearrangement involves three electron pairs; two in p bonds and one in a s bond. D) The Cope rearrangement takes place readily in a suprafacial pathway, when heated. 47) Which of the following statements about the Claisen rearrangement is true? A) The Claisen rearrangement occurs readily in a suprafacial pathway under photochemical conditions. B) The Claisen rearrangement occurs readily in an antarafacial pathway under thermal conditions. C) The Claisen rearrangement involves three electron pairs; two in p bonds and one in a s bond. D) The Claisen rearrangement involves the rearrangement of an unsaturated ether to a b,gunsaturated carbonyl compound. 48) What is the major organic product of the following Cope rearrangement?

A) I B) II C) III D) IV

49) What is the major organic product of the following oxy-Cope rearrangement?

A) I B) II C) III D) IV 50) What is the major organic product of the following Claisen rearrangement?

A) I B) II C) III D) IV

51) What is the major organic product of the following Claisen rearrangement?

A) I B) II C) III D) IV 52) Which of the following statements about a thermal reaction involving an even number of electron pairs is true? A) A thermal reaction involving an even number of electron pairs is conrotatory or antarafacial. B) A thermal reaction involving an even number of electron pairs is disrotatory or suprafacial. C) A thermal reaction involving an even number of electron pairs is conrotatory or suprafacial. D) A thermal reaction involving an even number of electron pairs is disrotatory or antarafacial. 53) Consider the following reaction sequence. What is the correct classification of the first reaction in the sequence?

A) [1,3] Sigmatropic rearrangement B) [1,5] Sigmatropic rearrangement C) [3,3] Sigmatropic rearrangement D) [5,5] Sigmatropic rearrangement

54) Consider the following reaction sequence. What is the correct classification of the second reaction in the sequence?

A) [2 + 2] Cycloaddition B) [6 + 4] Cycloaddition C) [4 + 4] Cycloaddition D) [4 + 2] Cycloaddition 55) How many pi electrons are in the ground state HOMO for buta-1,3-diene? A) 0 B) 2 C) 4 D) 6 56) How many pi electrons are in the ground state LUMO for buta-1,3-diene? A) 0 B) 2 C) 4 D) 6 57) How many pi electrons are in the excited state HOMO for buta-1,3-diene? A) 0 B) 1 C) 2 D) 3 58) How many pi electrons are in the excited state LUMO for buta-1,3-diene? A) 0 B) 1 C) 2 D) 3 59) How many pi electrons are in the ground state HOMO for hexa-1,3,5-triene? A) 0 B) 2 C) 4 D) 6

60) How many pi electrons are in the ground state LUMO for hexa-1,3,5-triene? A) 0 B) 2 C) 4 D) 6 61) How many pi electrons are in the excited state HOMO for hexa-1,3,5-triene? A) 0 B) 1 C) 2 D) 3 62) How many pi electrons are in the excited state LUMO for hexa-1,3,5-triene? A) 0 B) 1 C) 2 D) 3

4) Which of the following is a type of pericyclic reaction? A) electrocyclic reactions B) acyclic reactions C) cycloelimination reactions D) electrophilic reactions Answer: A Difficulty: 1 Easy Section: 25.01 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 1. Remember Chapter: 25 Accessibility: Keyboard Navigation 5) Which of the following is not a type of pericyclic reactions? A) cycloadditions B) nucleophilic reactions C) electrocyclic reactions D) sigmatropic rearrangements Answer: B Difficulty: 1 Easy Section: 25.01 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 1. Remember Chapter: 25 Accessibility: Keyboard Navigation 6) Which of the following statements about electrocyclic ring closure is not true? A) It is an intramolecular reaction. B) It requires heat or light. C) The cyclic product contains one more s bond and one fewer p bond than the reactants. D) The cyclic product contains one more p bond and one fewer s bond than the reactants. Answer: D Difficulty: 1 Easy Section: 25.01 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 1. Remember Chapter: 25 Accessibility: Keyboard Navigation

7) Which of the following statements about an electrocyclic ring-opening reaction is not true? A) An electrocyclic ring-opening reaction is an intramolecular reaction. B) An electrocyclic ring-opening reaction requires a source of energy (heat or light). C) The product of an electrocyclic ring-opening reaction contains one fewer p bond than the reactant. D) The product of an electrocyclic ring-opening reaction contains one more p bond than the reactant. Answer: C Difficulty: 1 Easy Section: 25.01 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 8) What is the organic product of the following electrocyclic reaction?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25

9) Which of the following statements about cycloaddition reactions is true? A) Cycloaddition reactions occur only intermolecularly. B) Cycloaddition reactions occur only intramolecularly. C) Cycloaddition reactions form a cyclic product with two new p bonds. D) Cycloaddition reactions can be intramolecular or intermolecular. Answer: D Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 10) Which of the following statements about sigmatropic reactions is true? A) The reactants contain one more p bond than the product. B) The product contains one more p bond than the reactant. C) A p bond is broken in the reactant. D) A s bond is broken in the reactant. Answer: D Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 11) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrocyclic reaction C) Electrophilic reaction D) Sigmatropic reaction Answer: B Difficulty: 1 Easy Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25

12) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrocyclic reaction C) Electrophilic reaction D) Sigmatropic reaction Answer: A Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 13) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrophilic reaction C) Electrocyclic reaction D) Sigmatropic reaction Answer: C Difficulty: 1 Easy Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25

14) What is the correct classification of the following reaction?

A) Cycloaddition reaction B) Electrophilic reaction C) Electrocyclic reaction D) Sigmatropic reaction Answer: D Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 15) Which of the following statements about porbitals is true? A) p orbitals are formed by the linear combination of two sp3 orbitals. B) p orbitals are formed by the linear combination of two sp2 orbitals. C) p orbitals are formed by the linear combination of two sp orbitals. D) p orbitals are formed by the linear combination of two p orbitals. Answer: D Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 16) Which of the following statements about molecular orbitals is true? A) The number of molecular orbitals formed is different from the number of atomic orbitals used. B) The number of molecular orbitals formed is equal to the number of atomic orbitals used. C) The number of molecular orbitals formed is equal to twice the number of atomic orbitals used. D) The number of molecular orbitals formed is equal to half the number of atomic orbitals used. Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 6 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

17) Which of the following statements about a p-bonding molecular orbital is true? A) A p-bonding molecular orbital is formed when two p orbitals of similar phase overlap. B) A p-bonding molecular orbital is lower in energy than a s-bonding molecular orbital. C) A p-bonding molecular orbital is formed when two p orbitals of opposite phase overlap. D) Both the statements a p-bonding molecular orbital is formed when two p orbitals of similar phase overlap and a p-bonding molecular orbital is lower in energy than a s-bonding molecular orbital are true. Answer: D Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 18) Which of the following statements about a p* antibonding molecular orbital is true? A) A p* antibonding molecular orbital is formed when two p orbitals of similar phase overlap. B) A p* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap. C) A p* antibonding molecular orbital is a higher-energy molecular orbital than a p bonding molecular orbital. D) Both the statements a p* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap and a p* antibonding molecular orbital is a higher-energy molecular orbital than a p bonding molecular orbital are true. Answer: D Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 19) How many p molecular orbitals are present in 1,3,5-hexatriene? A) 3 B) 4 C) 5 D) 6 Answer: D Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 7 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

20) How many bonding molecular orbitals are present in 1,3,5-hexatriene? A) 3 B) 4 C) 5 D) 6 Answer: A Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 21) How many p molecular orbitals are present in 1,3,5,7,9-decapentaene? A) 4 B) 5 C) 10 D) 12 Answer: C Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 22) How many bonding molecular orbitals are present in 1,3,5,7,9-decapentaene? A) 4 B) 5 C) 10 D) 12 Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation

23) How many nodes are present in Y5 of 1,3,5,7,9-decapentaene? A) 2 B) 3 C) 4 D) 5 Answer: C Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 24) Which of the following statements about electrocyclic reactions is true? A) An electrocyclic reaction is generally irreversible. B) Generally, an acyclic triene is favored over a six-membered ring at equilibrium. C) Generally, a four-membered ring is favored over an acyclic diene at equilibrium. D) An electrocyclic reaction is generally reversible. Answer: D Difficulty: 1 Easy Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 Accessibility: Keyboard Navigation

25) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II Answer: B Difficulty: 2 Medium Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25

26) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II Answer: A Difficulty: 2 Medium Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25

27) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II Answer: D Difficulty: 2 Medium Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25

28) Predict the major organic product(s) of the following electrocyclic reaction.

A) Only I B) Only II C) Only III D) Only I and II Answer: C Difficulty: 2 Medium Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 29) Which of the following statements about thermal electrocyclic reactions is not true? A) The number of s bonds in the conjugated polyene determines whether rotation is conrotatory or disrotatory. B) Thermal electrocyclic reactions occur in a disrotatory fashion for a conjugated polyene with an odd number of p bonds. C) Thermal electrocyclic reactions occur in a conrotatory fashion for a conjugated polyene with an even number of p bonds. D) In thermal reactions, we consider the orbitals of the HOMO of the ground state electronic configuration to determine the course of the reaction. Answer: A Difficulty: 1 Easy Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 Accessibility: Keyboard Navigation

30) Which of the following statements about photochemical electrocyclic reactions is not true? A) In photochemical reactions, we consider the orbitals of the HOMO of the excited state to determine the course of the reaction. B) Photochemical electrocyclic reactions occur in a conrotatory fashion for a conjugated polyene with an odd number of p bonds. C) Photochemical electrocyclic reactions occur in a disrotatory fashion for a conjugated polyene with an even number of p bonds. D) In photochemical reactions, we consider the orbitals of the LUMO of the excited state to determine the course of the reaction. Answer: D Difficulty: 1 Easy Section: 25.03 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 Accessibility: Keyboard Navigation 31) Which of the following statements about cycloaddition reactions is not true? A) Cycloaddition reactions form a cyclic product with two new s bonds. B) The course of the reaction is determined by the symmetry of the molecular orbitals of the products. C) Cycloaddition reactions are concerted. D) Cycloaddition reactions are stereospecific. Answer: B Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 32) Which of the following statements about cycloaddition reactions is true? A) Cycloaddition reactions can be initiated by heat only. B) Cycloaddition reactions can be initiated by light only. C) Cycloaddition reactions can be initiated by heat or light. D) Cycloaddition reactions are identified by the number of p electrons in the two products. Answer: C Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 14 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

33) Why is the Diels-Alder reaction called a thermal [4+2] cycloaddition? A) Because the reaction is initiated by heat; the diene has four p electrons and the dienophile has two p electrons. B) Because the reaction is initiated by light; the diene has four p electrons and the dienophile has two p electrons. C) Because the reaction is initiated by heat; the dienophile has four p electrons and the diene has two p electrons. D) Because the reaction is initiated by light; the dienophile has four p electrons and the diene has two p electrons. Answer: A Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 34) Which of the following statements about [2+2] cycloaddition reactions between two alkenes is true? A) The reaction is initiated by heat. B) The reaction is initiated by light. C) The product is a cyclopentane derivative. D) Each reactant contains two s electrons that participate in the formation of new bonds. Answer: B Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation

35) What type of cycloaddition reaction is shown below?

A) [2+2] B) [4+2] C) [4+4] D) [0+2] Answer: A Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 36) What type of cycloaddition reaction is shown in the following equation?

A) [2+2] B) [4+2] C) [4+4] D) [0+2] Answer: B Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25

39) Which of the following statements about orbital symmetry and cycloaddition reactions is true? A) Thermal cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. B) Thermal cycloadditions involving an odd number of p bonds proceed by an antarafacial pathway. C) Photochemical cycloadditions involving an even number of p bonds proceed by an antarafacial pathway. D) Photochemical cycloadditions involving an even number of p bonds proceed by a suprafacial pathway. Answer: D Difficulty: 1 Easy Section: 25.04 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 40) Which of the following statements about sigmatropic reactions is not true? A) A sigmatropic reaction is an intramolecular pericyclic reaction. B) In a sigmatropic reaction, s bond is broken in one of the reactants. C) The p bonds rearrange in a sigmatropic reaction. D) The number of p bonds in the reactants and product differs in a sigmatropic reaction. Answer: D Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 41) Which of the following is not a correct designation for a sigmatropic rearrangement? A) [1,3] B) [1,5] C) [3,3] D) [3,1] Answer: D Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 18 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) What type of sigmatropic rearrangement is illustrated below?

A) [1,3] B) [1,4] C) [3,3] D) [1,5] Answer: D Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 43) What type of sigmatropic rearrangement is illustrated below?

A) [1,3] B) [1,4] C) [3,3] D) [1,5] Answer: C Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25

44) What type of sigmatropic rearrangement is illustrated below?

A) [1,3] B) [1,4] C) [3,3] D) [1,5] Answer: A Difficulty: 2 Medium Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 45) Which of the following statements about sigmatropic rearrangements and orbital symmetry is not true? A) Reactions involving six atoms or fewer must take place by suprafacial pathways. B) In a suprafacial rearrangement, the new s bond forms on the opposite side of the p system as the broken s bond. C) In an antarafacial rearrangement, the new s bond forms on the opposite side of the p system as the broken s bond. D) In a suprafacial rearrangement, the new s bond forms on the same side of the p system as the broken s bond. Answer: B Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 Accessibility: Keyboard Navigation

46) Which of the following statements about the Cope rearrangement is not true? A) The Cope rearrangement involves the rearrangement of a 1,5-diene to an isomeric 1,5-diene. B) The Cope rearrangement takes place readily in a suprafacial pathway under photochemical conditions. C) The Cope rearrangement involves three electron pairs; two in p bonds and one in a s bond. D) The Cope rearrangement takes place readily in a suprafacial pathway, when heated. Answer: B Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 47) Which of the following statements about the Claisen rearrangement is true? A) The Claisen rearrangement occurs readily in a suprafacial pathway under photochemical conditions. B) The Claisen rearrangement occurs readily in an antarafacial pathway under thermal conditions. C) The Claisen rearrangement involves three electron pairs; two in p bonds and one in a s bond. D) The Claisen rearrangement involves the rearrangement of an unsaturated ether to a b,gunsaturated carbonyl compound. Answer: C Difficulty: 1 Easy Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 Accessibility: Keyboard Navigation

48) What is the major organic product of the following Cope rearrangement?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 49) What is the major organic product of the following oxy-Cope rearrangement?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

50) What is the major organic product of the following Claisen rearrangement?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25

51) What is the major organic product of the following Claisen rearrangement?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 3. Apply Chapter: 25 52) Which of the following statements about a thermal reaction involving an even number of electron pairs is true? A) A thermal reaction involving an even number of electron pairs is conrotatory or antarafacial. B) A thermal reaction involving an even number of electron pairs is disrotatory or suprafacial. C) A thermal reaction involving an even number of electron pairs is conrotatory or suprafacial. D) A thermal reaction involving an even number of electron pairs is disrotatory or antarafacial. Answer: A Difficulty: 2 Medium Section: 25.06 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation

53) Consider the following reaction sequence. What is the correct classification of the first reaction in the sequence?

A) [1,3] Sigmatropic rearrangement B) [1,5] Sigmatropic rearrangement C) [3,3] Sigmatropic rearrangement D) [5,5] Sigmatropic rearrangement Answer: B Difficulty: 3 Hard Section: 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 25 54) Consider the following reaction sequence. What is the correct classification of the second reaction in the sequence?

A) [2 + 2] Cycloaddition B) [6 + 4] Cycloaddition C) [4 + 4] Cycloaddition D) [4 + 2] Cycloaddition Answer: D Difficulty: 3 Hard Section: 25.04; 25.05 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 4. Analyze Chapter: 25

55) How many pi electrons are in the ground state HOMO for buta-1,3-diene? A) 0 B) 2 C) 4 D) 6 Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 56) How many pi electrons are in the ground state LUMO for buta-1,3-diene? A) 0 B) 2 C) 4 D) 6 Answer: A Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 57) How many pi electrons are in the excited state HOMO for buta-1,3-diene? A) 0 B) 1 C) 2 D) 3 Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation

58) How many pi electrons are in the excited state LUMO for buta-1,3-diene? A) 0 B) 1 C) 2 D) 3 Answer: A Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 59) How many pi electrons are in the ground state HOMO for hexa-1,3,5-triene? A) 0 B) 2 C) 4 D) 6 Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 60) How many pi electrons are in the ground state LUMO for hexa-1,3,5-triene? A) 0 B) 2 C) 4 D) 6 Answer: A Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation

61) How many pi electrons are in the excited state HOMO for hexa-1,3,5-triene? A) 0 B) 1 C) 2 D) 3 Answer: B Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation 62) How many pi electrons are in the excited state LUMO for hexa-1,3,5-triene? A) 0 B) 1 C) 2 D) 3 Answer: A Difficulty: 1 Easy Section: 25.02 Topic: Conjugated Dienes and Pericyclic Reactions Bloom's: 2. Understand Chapter: 25 Accessibility: Keyboard Navigation

Organic Chemistry, 6e (Smith) Chapter 26 Carbohydrates 1) Which of the following compounds is an aldose?

A) A B) B C) C D) D 2) How many carbons does a pentose sugar have? A) 2 B) 3 C) 4 D) 5 3) How many possible stereoisomers are there of the following heptose?

A) 16 B) 21 C) 32 D) 64

4) Is the following carbohydrate D or L? Provide an explanation for your answer.

A) It is D because the OH group on C2 is on the right. B) It is L because the OH group on C4 is on the left. C) It is L because the OH group on C3 is on the left. D) It is D because the sugar is not symmetric. 5) Which of the following compounds is a b anomer?

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

6) Which is the correct Haworth projection for the aanomer of allose?

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

7) Which is the correct Haworth projection for the banomer of D-glucose?

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

8) Which is the correct Fischer projection for the open-chain form of the carbohydrate shown below?

A) A B) B C) C D) D 9) Does a monosaccharide prefer to exist in the open-chain or closed-ring form? A) Open B) Closed C) Both forms exist in equal ratios. 10) What is the process called for the interconversion of one anomer to the other? A) Racemization B) Mutarotation C) Epimerization D) Enolization

11) What is the correct chair form for the aanomer of D-mannose?

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

12) What is the correct chair form for the banomer of D-glucose?

A) A B) B C) C D) D 13) Which of the following reagents would convert glucose into ethyl glucopyranoside? A) EtBr, aq. HCl B) EtOH, aq. HCl C) EtOH, NaOH D) Ag2O in NH4OH 14) Which of the following is a reducing sugar?

15) Which of the following reagents will selectively oxidize an aldose to an aldonic acid? A) PCC B) Ag2O in NH4OH C) FeCl3 D) HNO3 16) Which of the following pairs of carbohydrates will afford the same product from a Wohl degradation? A) Xylose/glucose B) Ribose/arabinose C) Fructose/mannose D) Lyxose/threose 17) What are the products of the following reaction?

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

18) Which of the following compounds is not a valid representation for D-glucose?

A) A B) B C) C D) D E) E 19) Cellulose is a polysaccharide with ________ linkages. A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) b-1,6'-glycosidic D) a-1,6'-glycosidic 20) Amylose is a polysaccharide with ________ linkages. A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) b-1,6'-glycosidic D) a-1,6'-glycosidic 21) The branching units in amylopectin, a polysaccharide, which enable this molecule to be water soluble are connected with ________ linkages. A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) a-1,6'-glycosidic D) b-1,6'-glycosidic 22) What is the composition of lactose? A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage 9 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

23) What is the composition of sucrose? A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage 24) What is the composition of maltose? A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage 25) From the sugars shown below, which one is a non-reducing sugar?

A) A B) B C) C D) D 26) From the disaccharides listed below, which one will not undergo mutarotation? A) Sucrose B) Maltose C) Lactose D) Xylobiose

27) Upon hydrolysis of cellulose, what sugar is formed? A) Sucrose B) Maltose C) Lactose D) Glucose 28) Upon hydrolysis of amylose, what sugar is formed? A) Sucrose B) Maltose C) Lactose D) Glucose 29) Upon hydrolysis of amylopectin, what sugar is formed? A) Sucrose B) Maltose C) Lactose D) Glucose 30) From the sugars shown below, which one will not give a positive test with Tollens reagent?

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

31) What is the best description of the product formed in the following reaction sequence?

A) The product is an optically active aldonic acid. B) The product is an optically inactive aldonic acid. C) The product is an optically active aldaric acid. D) The product is an optically inactive aldaric acid. 32) The following reaction is an example of a base-catalyzed epimerization reaction in which a ketose is converted to a pair of aldoses. What are the products from this reaction?

A) D-glucose and D-mannose B) D-galactose and D-talose C) D-talose and D-idose D) D-glucose and D-idose 33) Which sugar is represented by the line angle structure below?

A) D-fructose B) D-sorbose C) L-psicose D) L-tagatose 12 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

34) Oxidation of a D-hexose with nitric acid forms an optically active aldaric acid. A Wohl degradation of the same D-hexose followed by oxidation with nitric acid forms an optically active aldaric acid. What are the three possible D-hexoses that fit this data? A) D-allose, D-altrose and D-glucose B) D-glucose, D- mannose and D-talose C) D-glucose, D-idose and D-altrose D) D-galactose, D-talose and D-mannose 35) After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was isolated from the reaction mixture. The following experimental data was obtained. What is the structure of this unknown sugar? Data: - Molecular formula: C6H12O6 - Reacts with phenylhydrazine to give an osazone, mp 178°C. - Reacts with HNO3 to give an optically active aldaric acid. - Wohl degradation followed by HNO3 oxidation gives an optically inactive aldaric acid. - Two Wohl degradations followed by HNO3 oxidation give a meso-tartaric acid.

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

36) Which of the following sugars can be classified as an aldohexose?

A) A B) B C) C D) D 37) Which of the following sugars can be classified as a ketohexose?

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

38) Which of the following sugars can be classified as a ketotetrose?

A) A B) B C) C D) D 39) Which of the following sugars can be classified as a ketopentose?

A) A B) B C) C D) D 40) Which of the following best describes the relationship between D-glucose and D-fructose? A) Enantiomers B) Epimers C) Anomers D) Constitutional isomers 41) What is the classification of pyranose forms of monosaccharides? A) 5-Membered cyclic hemiacetals B) 6-Membered cyclic acetals C) 5-Membered cyclic acetals D) 6-Membered cyclic hemiacetals

42) What is the Fischer projection of the monosaccharide from which the following glycoside was prepared?

A) I B) II C) III D) IV 43) What is the Fischer projection of the monosaccharide from which the following glycoside was prepared?

A) I B) II C) III D) IV

44) What is the Haworth projection of the α anomer of a monosaccharide epimeric with Dglucose at C3?

A) I B) II C) III D) IV 45) Which of the following is D-fructose?

A) I B) II C) III D) IV

46) Which of the following is D-sorbose?

A) I B) II C) III D) IV 47) Which of the following is D-glucose?

A) I B) II C) III D) IV

48) Which of the following is D-galactose?

A) I B) II C) III D) IV 49) Which of the following is a disaccharide? A) Maltose B) Lactose C) Sucrose D) All of these choices are correct 50) Which of the following is a polysaccharide? A) Cellulose B) Starch C) Glycogen D) All of these choices are correct

Organic Chemistry, 6e (Smith) Chapter 26 Carbohydrates 1) Which of the following compounds is an aldose?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 26.02 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 2) How many carbons does a pentose sugar have? A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: 26.03 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

3) How many possible stereoisomers are there of the following heptose?

A) 16 B) 21 C) 32 D) 64 Answer: C Difficulty: 2 Medium Section: 26.03 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

4) Is the following carbohydrate D or L? Provide an explanation for your answer.

5) Which of the following compounds is a b anomer?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

6) Which is the correct Haworth projection for the aanomer of allose?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

7) Which is the correct Haworth projection for the banomer of D-glucose?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

8) Which is the correct Fischer projection for the open-chain form of the carbohydrate shown below?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 9) Does a monosaccharide prefer to exist in the open-chain or closed-ring form? A) Open B) Closed C) Both forms exist in equal ratios. Answer: B Difficulty: 1 Easy Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

10) What is the process called for the interconversion of one anomer to the other? A) Racemization B) Mutarotation C) Epimerization D) Enolization Answer: B Difficulty: 1 Easy Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 11) What is the correct chair form for the aanomer of D-mannose?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

12) What is the correct chair form for the banomer of D-glucose?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

13) Which of the following reagents would convert glucose into ethyl glucopyranoside? A) EtBr, aq. HCl B) EtOH, aq. HCl C) EtOH, NaOH D) Ag2O in NH4OH Answer: B Difficulty: 1 Easy Section: 26.08 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 14) Which of the following is a reducing sugar?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 26.09 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

15) Which of the following reagents will selectively oxidize an aldose to an aldonic acid? A) PCC B) Ag2O in NH4OH C) FeCl3 D) HNO3 Answer: B Difficulty: 1 Easy Section: 26.09 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 16) Which of the following pairs of carbohydrates will afford the same product from a Wohl degradation? A) Xylose/glucose B) Ribose/arabinose C) Fructose/mannose D) Lyxose/threose Answer: B Difficulty: 2 Medium Section: 26.09 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

17) What are the products of the following reaction?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 26.09 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

18) Which of the following compounds is not a valid representation for D-glucose?

A) A B) B C) C D) D E) E Answer: E Difficulty: 1 Easy Section: 26.02 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 19) Cellulose is a polysaccharide with ________ linkages. A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) b-1,6'-glycosidic D) a-1,6'-glycosidic Answer: A Difficulty: 1 Easy Section: 26.11 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

20) Amylose is a polysaccharide with ________ linkages. A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) b-1,6'-glycosidic D) a-1,6'-glycosidic Answer: B Difficulty: 2 Medium Section: 26.12 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 21) The branching units in amylopectin, a polysaccharide, which enable this molecule to be water soluble are connected with ________ linkages. A) b-1,4'-glycosidic B) a-1,4'-glycosidic C) a-1,6'-glycosidic D) b-1,6'-glycosidic Answer: C Difficulty: 2 Medium Section: 26.12 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 22) What is the composition of lactose? A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage Answer: C Difficulty: 1 Easy Section: 26.11 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

23) What is the composition of sucrose? A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage Answer: B Difficulty: 1 Easy Section: 26.11 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 24) What is the composition of maltose? A) Two glucose units with a a-1,4'-glycoside bond B) One glucose and one fructose unit with a a-glycosidic bond to the 2' carbon of a fructofuranose ring C) One galactose and one glucose unit with a b-1,4'-glycoside bond D) Repeating unit of glucose units joined in a b-1,4'-glycosidic linkage Answer: A Difficulty: 2 Medium Section: 26.12 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

25) From the sugars shown below, which one is a non-reducing sugar?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 26.09 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 26) From the disaccharides listed below, which one will not undergo mutarotation? A) Sucrose B) Maltose C) Lactose D) Xylobiose Answer: A Difficulty: 2 Medium Section: 26.11 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

27) Upon hydrolysis of cellulose, what sugar is formed? A) Sucrose B) Maltose C) Lactose D) Glucose Answer: D Difficulty: 2 Medium Section: 26.12 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 28) Upon hydrolysis of amylose, what sugar is formed? A) Sucrose B) Maltose C) Lactose D) Glucose Answer: D Difficulty: 2 Medium Section: 26.12 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 29) Upon hydrolysis of amylopectin, what sugar is formed? A) Sucrose B) Maltose C) Lactose D) Glucose Answer: D Difficulty: 2 Medium Section: 26.12 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

30) From the sugars shown below, which one will not give a positive test with Tollens reagent?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 26.10 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

31) What is the best description of the product formed in the following reaction sequence?

A) The product is an optically active aldonic acid. B) The product is an optically inactive aldonic acid. C) The product is an optically active aldaric acid. D) The product is an optically inactive aldaric acid. Answer: D Difficulty: 2 Medium Section: 26.10 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 32) The following reaction is an example of a base-catalyzed epimerization reaction in which a ketose is converted to a pair of aldoses. What are the products from this reaction?

A) D-glucose and D-mannose B) D-galactose and D-talose C) D-talose and D-idose D) D-glucose and D-idose Answer: B Difficulty: 2 Medium Section: 26.10 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 19 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

33) Which sugar is represented by the line angle structure below?

A) D-fructose B) D-sorbose C) L-psicose D) L-tagatose Answer: C Difficulty: 1 Easy Section: 26.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 34) Oxidation of a D-hexose with nitric acid forms an optically active aldaric acid. A Wohl degradation of the same D-hexose followed by oxidation with nitric acid forms an optically active aldaric acid. What are the three possible D-hexoses that fit this data? A) D-allose, D-altrose and D-glucose B) D-glucose, D- mannose and D-talose C) D-glucose, D-idose and D-altrose D) D-galactose, D-talose and D-mannose Answer: B Difficulty: 2 Medium Section: 26.10 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

35) After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was isolated from the reaction mixture. The following experimental data was obtained. What is the structure of this unknown sugar? Data: - Molecular formula: C6H12O6 - Reacts with phenylhydrazine to give an osazone, mp 178°C. - Reacts with HNO3 to give an optically active aldaric acid. - Wohl degradation followed by HNO3 oxidation gives an optically inactive aldaric acid. - Two Wohl degradations followed by HNO3 oxidation give a meso-tartaric acid.

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 26.10 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

36) Which of the following sugars can be classified as an aldohexose?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 26.03 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 37) Which of the following sugars can be classified as a ketohexose?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 26.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

38) Which of the following sugars can be classified as a ketotetrose?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 26.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 39) Which of the following sugars can be classified as a ketopentose?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 26.04 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 23 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

40) Which of the following best describes the relationship between D-glucose and D-fructose? A) Enantiomers B) Epimers C) Anomers D) Constitutional isomers Answer: D Difficulty: 1 Easy Section: 26.05 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation 41) What is the classification of pyranose forms of monosaccharides? A) 5-Membered cyclic hemiacetals B) 6-Membered cyclic acetals C) 5-Membered cyclic acetals D) 6-Membered cyclic hemiacetals Answer: D Difficulty: 1 Easy Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26 Accessibility: Keyboard Navigation

42) What is the Fischer projection of the monosaccharide from which the following glycoside was prepared?

A) I B) II C) III D) IV Answer: B Difficulty: 3 Hard Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

43) What is the Fischer projection of the monosaccharide from which the following glycoside was prepared?

A) I B) II C) III D) IV Answer: C Difficulty: 3 Hard Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

44) What is the Haworth projection of the α anomer of a monosaccharide epimeric with Dglucose at C3?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 26.06 Topic: Carbohydrates Bloom's: 3. Apply Chapter: 26

45) Which of the following is D-fructose?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 26.04 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 26

46) Which of the following is D-sorbose?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 26.04 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 26

47) Which of the following is D-glucose?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 26.03 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 26

48) Which of the following is D-galactose?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 26.03 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 26 49) Which of the following is a disaccharide? A) Maltose B) Lactose C) Sucrose D) All of these choices are correct Answer: D Difficulty: 1 Easy Section: 26.11 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 26 Accessibility: Keyboard Navigation

50) Which of the following is a polysaccharide? A) Cellulose B) Starch C) Glycogen D) All of these choices are correct Answer: D Difficulty: 1 Easy Section: 26.12 Topic: Carbohydrates Bloom's: 1. Remember Chapter: 26 Accessibility: Keyboard Navigation

Organic Chemistry, 6e (Smith) Chapter 27 Amino Acids and Proteins 1) Which of the following compounds is not an amino acid?

A) A B) B C) C D) D 2) What is the configuration of naturally occurring amino acids? A) D B) S C) L D) R 3) Which is the correct structure for serine?

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

4) Which is the correct structure for the amino acid proline?

A) A B) B C) C D) D 5) Which is the correct structure for the amino acid cysteine?

A) A B) B C) C D) D 6) Which is the correct structure for the amino acid valine?

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

7) Which of the following is the correct structure for alanine at pH = 7?

A) A B) B C) C D) D 8) Which of the following is the correct structure for aspartic acid at pH = 1?

A) A B) B C) C D) D 9) Which of the following aldehydes would be a good starting material in the Strecker synthesis of phenylalanine?

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

10) What reagents would you use to convert acetaldehyde into alanine? A) NH3 B) HCN C) NaCN, NH4Cl D) NaNH2 11) What is the separation of a racemic mixture into its component enantiomers called? A) Diastereomers B) Meso C) Resolution D) Neutralization 12) Why does the formation of salts of a racemic mixture of N-acetyl valine with a single enantiomer of a-methylbenzylamine enable the separation of the two enantiomers of N-acetyl valine? A) They form amides. B) They form diastereomers. C) They form salts. D) They form meso compounds. 13) Why can glycine not be resolved into two enantiomers? A) It has no stereogenic centers. B) It has no nitrogen atoms. C) It has no aromatic rings. D) It cannot be converted into a salt. 14) What amino acid is at the N-terminus of the following peptide?

A) Valine B) Serine C) Alanine D) Proline

15) What amino acid is at the C-terminus of the following peptide?

A) Valine B) Serine C) Alanine D) Proline 16) Why is the s-trans form of an amide bond more stable? A) There is no s-cis form in an amide bond. B) The oxygen is hydrogen-bonded with the nitrogen atom. C) The nitrogen is able to be sp2-hybridized. D) The more sterically bulky groups are farther apart. 17) Why do amide bonds exist as reasonably stable s-cis or s-trans isomers at room temperature? A) These amide bonds are not stable. B) There is partial double bond character between the carbonyl carbon and the nitrogen atom. C) The oxygen atom is hydrogen-bonded with the nitrogen atom. D) The side-chains can form hydrogen bonds. 18) Which of the following is the major advantage of the Merrifield synthesis of peptides? A) It allows for the formation of absolutely no by-products. B) Impurities can be easily washed away. C) Excess reagent can be used. D) It prevents hydrogenation. 19) What are the basic steps in the Merrifield peptide synthesis? A) Coupling and hydrolysis B) Hydrolysis and deprotection C) Deprotection and hydrogenation D) Coupling and deprotection

20) Which of the following is the structure of the amino acid lysine?

A) A B) B C) C D) D 21) What is (are) the missing reagent(s) in the reaction below?

A) NH3 B) HCN C) NaCN, NH4Cl D) NaNH2

22) What is the major organic product for the following reaction?

A) A B) B C) C D) D 23) What is the IUPAC or common name for the following compound?

A) Cysteinylalanine B) Alanylcysteine C) Serinylalanine D) Alanylserine 24) Amino acid synthesis is possible by all except one of the pathways listed. Which is not a synthetic pathway for amino acids? A) Amination of malonic ester followed by hydrolysis and decarboxylation B) Nucleophilic addition of NH3 to an aldehyde followed by addition of cyanide to the imine, and, finally, hydrolysis C) SN2 reaction using an a-halo carboxylic acid with ammonia as the nucleophile D) Reaction of NH4Cl and NaCN with an aldehyde followed by an acidic work-up

25) Which of the following correctly describes a protein? A) a dipeptide; two amino acids joined together by one amide bond B) a tripeptide; three amino acids joined together by two amide bonds C) a polymer of more than 40 amino acids joined together by amide bonds D) a polypeptide of any number of amino acids joined together by amide bonds 26) Which of the following correctly describes a peptide bond? A) a bond between sp3-hybridized atoms only B) a bond usually found in the s-cis conformation C) an amide bond D) the result of the formation of the carbonyl group of one amino acid with a R-group from the other amino acid 27) Which of the following correctly describes the Merrifield synthesis? A) It uses a solid phase technique for the synthesis of peptides. B) It uses DCC (dicyclohexylcarbodiimide) to form the amide bond in a peptide synthesis. C) It uses BOC (tert-butoxycarbonyl) as a protecting group for peptide synthesis. D) It uses aqueous phase techniques for the synthesis of large polypeptides. 28) Which of the following correctly describes the tertiary structure of a peptide? A) the three-dimensional conformations of localized regions of a protein B) the particular sequence of amino acids that are joined together by peptide bonds C) the structure is defined by the b-pleated sheet form D) the three-dimensional shape adopted by the entire peptide 29) What are the only covalent bonds that stabilize the tertiary structure of a peptide? A) Hydrogen bonds B) Disulfide bonds C) Van der Waal bonds D) Ionic bonds 30) Which of the following is (are) globular protein(s)? A) Hemoglobin B) Keratins C) Collagens D) Elastins 31) Which of the following is (are) fibrous protein(s)? A) Keratins B) Hormones C) Enzymes D) Antibodies

32) What is the appropriate sequence of reaction conditions used to synthesize valine from acetamidomalonic ester?

A) (1) NaOH; (2) (CH3)2CHBr; (3) Cl2, H2O, heat B) (1) NaOCH2CH3; (2) (CH3)2CH2CHBr; (3) HCl, H2O, heat C) (1) NaOCH2CH3; (2) (CH3)2CHBr; (3) HCl, H2O, heat D) (1) NaOH; (2) CH3CH2CH2Br; (3) HCl, H2O, heat 33) Below is a 2D chromatogram that shows the separation of five amino acids. In this technique, the amino acid mixture is first separated by chromatography using a polar solvent system. Then the plate is rotated 90°, and the amino acids are further separated by electrophoresis. Identify the spots obtained from a mixture of Trp, Glu, Lys, Ile and Thr. A table with isoelectric points is included to aid in solving this problem.

34) Below is a proposed method for resolving a racemic mixture of (R)- and (S)-phenylalanine. Upon separation of the products, will this method produce (R)- or (S)-phenylalanine?

A) (R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of L-amino acids. B) (S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of L-amino acids. C) (R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of D-amino acids. D) (S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of D-amino acids. 35) Give the order (1st to last) in which the following amino acids would be eluted with a buffer of pH = 4 from a column containing a cationic-exchange resin (Dowex 50): Arg (pI = 10.8), Ser (pI = 5.7), Asp (pI = 2.8) and His (pI = 7.6). A) His, Ser, Asp, Arg B) Arg, His, Ser, Asp C) His, Ser, Arg, Asp D) Asp, Ser, His, Arg 36) Reaction of a polypeptide, composed of 12 amino acids, with carboxypeptidase A releases Met (C-terminal amino acid). The polypeptide undergoes partial hydrolysis to give 12 groups of peptides. Use the groups of overlapping amino acids to determine the proper sequence of this polypeptide. Note: Since these lists of peptides are separated by commas, they are not necessarily in the proper sequence. Ser, Lys, Trp-5. Met, Ala, Gly- 9. Lys, Ser Gly, His, Ala-6. Ser, Lys, Val -10. Glu, His, Val Glu, Val, Ser-7. Glu, His-11. Trp, Leu, Glu Leu, Glu, Ser-8. Leu, Lys, Trp-12. Ala, Met A) Met-Ala-Gly-His-Glu-Val-Ser-Lys-Trp-Leu-Glu-Ser B) Met-Ala-Gly-Glu-His-Ser-Val-Lys-Trp-Leu-Glu-Ser C) Ser-Glu-Leu-Trp-Lys-Ser-Val-Glu-His-Gly-Ala-Met D) Ser-Lys-Leu-Trp-Lys-Ser-Val-His-Glu-Gly-Ala-Met 37) What is formed by the combination of four amino acids? A) A protein B) A polypeptide C) A tripeptide D) A tetrapeptide

38) Which of the following amino acids is achiral? A) Phenylalanine B) Glycine C) Valine D) Alanine 39) Which of the following amino acids does not have an L-isomer? A) Alanine B) Valine C) Glycine D) Leucine 40) Which one of the following naturally occurring amino acids does not have an S configuration? A) Cysteine B) Alanine C) Tyrosine D) Isoleucine 41) What is the name given to the pH at which the concentration of the zwitterionic form of an amino acid is at a maximum concentration? A) Electric point B) Dipolar point C) Neutral point D) Isoelectric point 42) What is the major organic product for the following reaction?

A) I B) II C) III D) IV

43) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV

44) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV

45) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV

46) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV

Organic Chemistry, 6e (Smith) Chapter 27 Amino Acids and Proteins 1) Which of the following compounds is not an amino acid?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 2. Understand Chapter: 27 2) What is the configuration of naturally occurring amino acids? A) D B) S C) L D) R Answer: C Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27 Accessibility: Keyboard Navigation

3) Which is the correct structure for serine?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27 4) Which is the correct structure for the amino acid proline?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27

5) Which is the correct structure for the amino acid cysteine?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27 6) Which is the correct structure for the amino acid valine?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27

7) Which of the following is the correct structure for alanine at pH = 7?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 8) Which of the following is the correct structure for aspartic acid at pH = 1?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

9) Which of the following aldehydes would be a good starting material in the Strecker synthesis of phenylalanine?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 10) What reagents would you use to convert acetaldehyde into alanine? A) NH3 B) HCN C) NaCN, NH4Cl D) NaNH2 Answer: C Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

11) What is the separation of a racemic mixture into its component enantiomers called? A) Diastereomers B) Meso C) Resolution D) Neutralization Answer: C Difficulty: 1 Easy Section: 27.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 12) Why does the formation of salts of a racemic mixture of N-acetyl valine with a single enantiomer of a-methylbenzylamine enable the separation of the two enantiomers of N-acetyl valine? A) They form amides. B) They form diastereomers. C) They form salts. D) They form meso compounds. Answer: B Difficulty: 2 Medium Section: 27.04 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 13) Why can glycine not be resolved into two enantiomers? A) It has no stereogenic centers. B) It has no nitrogen atoms. C) It has no aromatic rings. D) It cannot be converted into a salt. Answer: A Difficulty: 2 Medium Section: 27.04 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

14) What amino acid is at the N-terminus of the following peptide?

A) Valine B) Serine C) Alanine D) Proline Answer: A Difficulty: 1 Easy Section: 27.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 15) What amino acid is at the C-terminus of the following peptide?

A) Valine B) Serine C) Alanine D) Proline Answer: C Difficulty: 1 Easy Section: 27.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

16) Why is the s-trans form of an amide bond more stable? A) There is no s-cis form in an amide bond. B) The oxygen is hydrogen-bonded with the nitrogen atom. C) The nitrogen is able to be sp2-hybridized. D) The more sterically bulky groups are farther apart. Answer: D Difficulty: 1 Easy Section: 27.06 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 17) Why do amide bonds exist as reasonably stable s-cis or s-trans isomers at room temperature? A) These amide bonds are not stable. B) There is partial double bond character between the carbonyl carbon and the nitrogen atom. C) The oxygen atom is hydrogen-bonded with the nitrogen atom. D) The side-chains can form hydrogen bonds. Answer: B Difficulty: 1 Easy Section: 27.06 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 18) Which of the following is the major advantage of the Merrifield synthesis of peptides? A) It allows for the formation of absolutely no by-products. B) Impurities can be easily washed away. C) Excess reagent can be used. D) It prevents hydrogenation. Answer: B Difficulty: 1 Easy Section: 27.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

19) What are the basic steps in the Merrifield peptide synthesis? A) Coupling and hydrolysis B) Hydrolysis and deprotection C) Deprotection and hydrogenation D) Coupling and deprotection Answer: D Difficulty: 1 Easy Section: 27.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 20) Which of the following is the structure of the amino acid lysine?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

21) What is (are) the missing reagent(s) in the reaction below?

A) NH3 B) HCN C) NaCN, NH4Cl D) NaNH2 Answer: C Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

22) What is the major organic product for the following reaction?

A) A B) B C) C D) D Answer: A Difficulty: 3 Hard Section: 27.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

23) What is the IUPAC or common name for the following compound?

A) Cysteinylalanine B) Alanylcysteine C) Serinylalanine D) Alanylserine Answer: B Difficulty: 1 Easy Section: 27.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 24) Amino acid synthesis is possible by all except one of the pathways listed. Which is not a synthetic pathway for amino acids? A) Amination of malonic ester followed by hydrolysis and decarboxylation B) Nucleophilic addition of NH3 to an aldehyde followed by addition of cyanide to the imine, and, finally, hydrolysis C) SN2 reaction using an a-halo carboxylic acid with ammonia as the nucleophile D) Reaction of NH4Cl and NaCN with an aldehyde followed by an acidic work-up Answer: A Difficulty: 2 Medium Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

25) Which of the following correctly describes a protein? A) a dipeptide; two amino acids joined together by one amide bond B) a tripeptide; three amino acids joined together by two amide bonds C) a polymer of more than 40 amino acids joined together by amide bonds D) a polypeptide of any number of amino acids joined together by amide bonds Answer: C Difficulty: 1 Easy Section: 27.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 26) Which of the following correctly describes a peptide bond? A) a bond between sp3-hybridized atoms only B) a bond usually found in the s-cis conformation C) an amide bond D) the result of the formation of the carbonyl group of one amino acid with a R-group from the other amino acid Answer: C Difficulty: 1 Easy Section: 27.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 27) Which of the following correctly describes the Merrifield synthesis? A) It uses a solid phase technique for the synthesis of peptides. B) It uses DCC (dicyclohexylcarbodiimide) to form the amide bond in a peptide synthesis. C) It uses BOC (tert-butoxycarbonyl) as a protecting group for peptide synthesis. D) It uses aqueous phase techniques for the synthesis of large polypeptides. Answer: A Difficulty: 2 Medium Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

28) Which of the following correctly describes the tertiary structure of a peptide? A) the three-dimensional conformations of localized regions of a protein B) the particular sequence of amino acids that are joined together by peptide bonds C) the structure is defined by the b-pleated sheet form D) the three-dimensional shape adopted by the entire peptide Answer: D Difficulty: 1 Easy Section: 27.05 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 29) What are the only covalent bonds that stabilize the tertiary structure of a peptide? A) Hydrogen bonds B) Disulfide bonds C) Van der Waal bonds D) Ionic bonds Answer: B Difficulty: 1 Easy Section: 27.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 30) Which of the following is (are) globular protein(s)? A) Hemoglobin B) Keratins C) Collagens D) Elastins Answer: A Difficulty: 1 Easy Section: 27.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27 Accessibility: Keyboard Navigation

31) Which of the following is (are) fibrous protein(s)? A) Keratins B) Hormones C) Enzymes D) Antibodies Answer: A Difficulty: 1 Easy Section: 27.10 Topic: Amino Acids, Peptides, and Proteins Bloom's: 1. Remember Chapter: 27 Accessibility: Keyboard Navigation 32) What is the appropriate sequence of reaction conditions used to synthesize valine from acetamidomalonic ester?

A) (1) NaOH; (2) (CH3)2CHBr; (3) Cl2, H2O, heat B) (1) NaOCH2CH3; (2) (CH3)2CH2CHBr; (3) HCl, H2O, heat C) (1) NaOCH2CH3; (2) (CH3)2CHBr; (3) HCl, H2O, heat D) (1) NaOH; (2) CH3CH2CH2Br; (3) HCl, H2O, heat Answer: C Difficulty: 2 Medium Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

33) Below is a 2D chromatogram that shows the separation of five amino acids. In this technique, the amino acid mixture is first separated by chromatography using a polar solvent system. Then the plate is rotated 90°, and the amino acids are further separated by electrophoresis. Identify the spots obtained from a mixture of Trp, Glu, Lys, Ile and Thr. A table with isoelectric points is included to aid in solving this problem.

amino acid-pI value Trp-5.9 Glu-3.2 Lys-9.7 Ile-6.0 Thr-5.6 A) 1=Lys, 2=Thr, 3=Glu, 4=Trp, 5=Ile B) 1=Glu, 2=Thr, 3=Lys, 4=Trp, 5=Ile C) 1=Lys, 2=Ile, 3=Glu, 4=Trp, 5=Thr D) 1=Glu, 2=Ile, 3=Lys, 4=Trp, 5=Thr Answer: A Difficulty: 3 Hard Section: 27.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

34) Below is a proposed method for resolving a racemic mixture of (R)- and (S)-phenylalanine. Upon separation of the products, will this method produce (R)- or (S)-phenylalanine?

36) Reaction of a polypeptide, composed of 12 amino acids, with carboxypeptidase A releases Met (C-terminal amino acid). The polypeptide undergoes partial hydrolysis to give 12 groups of peptides. Use the groups of overlapping amino acids to determine the proper sequence of this polypeptide. Note: Since these lists of peptides are separated by commas, they are not necessarily in the proper sequence. Ser, Lys, Trp-5. Met, Ala, Gly- 9. Lys, Ser Gly, His, Ala-6. Ser, Lys, Val -10. Glu, His, Val Glu, Val, Ser-7. Glu, His-11. Trp, Leu, Glu Leu, Glu, Ser-8. Leu, Lys, Trp-12. Ala, Met A) Met-Ala-Gly-His-Glu-Val-Ser-Lys-Trp-Leu-Glu-Ser B) Met-Ala-Gly-Glu-His-Ser-Val-Lys-Trp-Leu-Glu-Ser C) Ser-Glu-Leu-Trp-Lys-Ser-Val-Glu-His-Gly-Ala-Met D) Ser-Lys-Leu-Trp-Lys-Ser-Val-His-Glu-Gly-Ala-Met Answer: C Difficulty: 3 Hard Section: 27.03 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 37) What is formed by the combination of four amino acids? A) A protein B) A polypeptide C) A tripeptide D) A tetrapeptide Answer: D Difficulty: 1 Easy Section: 27.06 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

38) Which of the following amino acids is achiral? A) Phenylalanine B) Glycine C) Valine D) Alanine Answer: B Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 39) Which of the following amino acids does not have an L-isomer? A) Alanine B) Valine C) Glycine D) Leucine Answer: C Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 40) Which one of the following naturally occurring amino acids does not have an S configuration? A) Cysteine B) Alanine C) Tyrosine D) Isoleucine Answer: A Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation

41) What is the name given to the pH at which the concentration of the zwitterionic form of an amino acid is at a maximum concentration? A) Electric point B) Dipolar point C) Neutral point D) Isoelectric point Answer: D Difficulty: 1 Easy Section: 27.01 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27 Accessibility: Keyboard Navigation 42) What is the major organic product for the following reaction?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: 27.07 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

43) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

44) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

45) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

46) What is the product of the following reaction? (Assume workup to neutralize.)

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: 27.02 Topic: Amino Acids, Peptides, and Proteins Bloom's: 3. Apply Chapter: 27

Organic Chemistry, 6e (Smith) Chapter 28 Synthetic Polymers 1) Which of the following monomers yields the polymer shown below?

A) A B) B C) C D) D 2) Which of the following is the repeating unit in polyvinyl chloride (PVC)?

A) A B) B C) C D) D 3) Which of the following is (are) addition polymer(s)? I. polypropylene II. Teflon III. nylon A) Only I B) Only II C) Only III D) Both I and II

4) Which of the following is (are) condensation polymer(s)? I. polypropylene II. Teflon III. nylon A) Only I B) Only II C) Only III D) Both II and III 5) 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 6) 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 7) In which type of polymer are the chains packed less tightly together, resulting in lower melting points and a softer texture? A) Isotactic polymers B) Syndiotactic polymers C) Atactic polymers D) Cross-linked polymers 8) Which of the following best describes the polymer chain shown below?

A) Atactic polypropylene B) Isotactic polypropylene C) Syndiotactic polypropylene D) Cross-linked polypropylene

9) Which of the following is used to make Teflon? A) Fluoroethene B) 1,1,4,4-Tetrafluorobutadiene C) 1,2-Difluoroethene D) Tetrafluoroethylene 10) Which of the following best describes the polymer chain shown below?

A) Atactic polypropylene B) Isotactic polypropylene C) Syndiotactic polypropylene D) Cross-linked polypropylene 11) The monomer used to make superglue is shown below. Which of the following methods of polymerization is most suitable for this type of monomer?

A) Free-radical chain-growth B) Cationic chain-growth C) Anionic chain-growth D) Acid-catalyzed step-growth 12) Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an initiator? A) Free-radical chain-growth B) Cationic chain-growth C) Anionic chain-growth D) Acid-catalyzed step-growth

13) Which of the following is the monomer that gives the polymer shown below?

A) A B) B C) C D) D 14) What modification occurs when a small amount of p-divinylbenzene is added to the polymerization reaction of styrene to form polystyrene? (Recall that 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 15) Identify the repeating unit in the polymer formed from the following reaction sequence.

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

16) The acid-catalyzed dimerization of isobutylene gives a mixture of two isomeric alkenes, A and B. Hydrogenation of this mixture gives a single C8H18 hydrocarbon. What is the structure of this hydrocarbon?

A) 2,2,4-Trimethylpentane B) 2,3,4-Trimethylpentane C) 2,4-Dimethylhexane D) 2,5-Dimethyhexane 17) 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 18) Which of the following monomers is used to make the polymer carbowax, shown below?

19) Which of the following initiators can be used for anionic chain-growth polymerization? A) Benzoyl peroxide B) CH3CH2CH2CH2Li C) BF3 D) Al(CH2CH3)3, TiCl4 20) Which 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 21) Which of the following initiators is used to make isotactic polypropylene? A) Benzoyl peroxide B) CH3CH2CH2CH2Li C) BF3 D) Al(CH2CH3)3, TiCl4 22) The repeating unit of a polymer is shown below. This polymer is formed by

A) addition of ethylene. B) addition of trans-2-butene. C) 1,2 addition of butadiene. D) 1,4 addition of butadiene. 23) Vulcanization is the process of cross-linking polymer chains in rubber using what chemical? A) Sulfur B) Formaldehyde C) Benzoyl peroxide D) Ethylene glycol

24) What monomer(s) would be used to make the polyester shown below?

A) Butanedioic acid B) 4-Hydroxybutanal C) 4-Hydroxybutanoic acid D) Butanedioic acid and 1,4-butanediol 25) Which of the following is the repeating unit of the polymer formed in the polymerization of p-hydroxybenzoic acid?

A) A B) B C) C D) D 26) Identify the monomer(s) needed to make the following polyester.

A) 3-Hydroxybutanoic acid B) Butanedioic acid C) Butanedioic acid and ethylene glycol D) Butanedioic acid and ethanol

27) Which of the following is (are) repeating unit(s) of step-growth polymers?

A) Only I B) Only II C) Only III D) I and II 28) 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 29) What is the purpose of plasticizers? A) To harden plastics B) To soften plastics C) To initiate polymerizations D) To cross-link polymer chains

30) 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 31) What is the name given to polymers that soften when heated and harden when cooled? A) Cross-linked polymers B) Copolymers C) Thermosetting polymers D) Thermoplastics 32) What is the structure of the polymer which results when styrene is reacted with BF3 and H2O?

33) Rank the following monomers (X, Y and Z) in order of increasing ability to undergo anionic polymerization, starting with the least reactive monomer.

A) Y< X < Z B) Z < Y < X C) X < Y < Z D) Y < Z < X 34) Melamine and formaldehyde combine to form the polymer, Melmac®. How is Melmac® classified, and what physical characteristics are consistent with its structure?

A) Polycarbonate, transparent B) Polyurethane, elastic C) Thermosetting, rigid D) Thermoplastic, can be melted and molded into new shapes

35) Which monomer and which type of initiator would you use to synthesize the following polymer?

A) A B) B C) C D) D E) E 36) Which of the following sets of products results if nylon 66 is treated with sulfuric acid?

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

37) What is the classification of the following polymer in which X and Y represent repeating units?

A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer 38) What is the classification of the following polymer in which X and Y represent repeating units?

A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer 39) What is the classification of the following polymer in which X and Y represent repeating units?

A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer 40) What is the name given to polymers with single monomers? A) Homopolymers B) Copolymers C) Block polymers D) Random polymers 41) What is the name given to polymers with two or more different monomers? A) Homopolymers B) Copolymers C) Block polymers D) Random polymers 12 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) What are the structures of the three monomers needed to synthesize the following polymer?

A) I B) II C) III D) IV 43) What type of polymer is Lexan? A) Epoxy B) Polyurethane C) Polycarbonate D) Polyamide 44) What type of polymer is Nylon? A) Epoxy B) Polyurethane C) Polycarbonate D) Polyamide 45) What type of polymer is Spandex? A) HDPE B) Polyurethane C) Polycarbonate D) Polyamide

Organic Chemistry, 6e (Smith) Chapter 28 Synthetic Polymers 1) Which of the following monomers yields the polymer shown below?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 28.01 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 2) Which of the following is the repeating unit in polyvinyl chloride (PVC)?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 28.01 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

3) Which of the following is (are) addition polymer(s)? 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: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation 4) Which of the following is (are) condensation polymer(s)? 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: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation

5) 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: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation 6) 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: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation 7) In which type of polymer are the chains packed less tightly together, resulting in lower melting points and a softer texture? A) Isotactic polymers B) Syndiotactic polymers C) Atactic polymers D) Cross-linked polymers Answer: C Difficulty: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation

8) Which 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: 28.04 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 9) Which of the following is used to make Teflon? A) Fluoroethene B) 1,1,4,4-Tetrafluorobutadiene C) 1,2-Difluoroethene D) Tetrafluoroethylene Answer: D Difficulty: 1 Easy Section: 28.05 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation

10) Which 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: 2 Medium Section: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 11) The monomer used to make superglue is shown below. Which of the following methods of polymerization is most suitable for this type of monomer?

A) Free-radical chain-growth B) Cationic chain-growth C) Anionic chain-growth D) Acid-catalyzed step-growth Answer: C Difficulty: 1 Easy Section: 28.04 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

12) Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an initiator? A) Free-radical chain-growth B) Cationic chain-growth C) Anionic chain-growth D) Acid-catalyzed step-growth Answer: A Difficulty: 1 Easy Section: 28.04 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation 13) Which of the following is the monomer that gives the polymer shown below?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 28.06 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

14) What modification occurs when a small amount of p-divinylbenzene is added to the polymerization reaction of styrene to form polystyrene? (Recall that 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: 2 Medium Section: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 Accessibility: Keyboard Navigation 15) Identify the repeating unit in the polymer formed from the following reaction sequence.

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

A) 2,2,4-Trimethylpentane B) 2,3,4-Trimethylpentane C) 2,4-Dimethylhexane D) 2,5-Dimethyhexane Answer: A Difficulty: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 17) 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: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

18) Which of the following monomers is used to make the polymer carbowax, shown below?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 19) Which 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: 28.02 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28 Accessibility: Keyboard Navigation

20) Which 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: 28.02 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28 Accessibility: Keyboard Navigation 21) Which 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: 28.02 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28 Accessibility: Keyboard Navigation

22) The repeating unit of a polymer is shown below. This polymer is formed by

A) addition of ethylene. B) addition of trans-2-butene. C) 1,2 addition of butadiene. D) 1,4 addition of butadiene. Answer: D Difficulty: 2 Medium Section: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 23) Vulcanization is the process of cross-linking polymer chains in rubber using what chemical? A) Sulfur B) Formaldehyde C) Benzoyl peroxide D) Ethylene glycol Answer: A Difficulty: 1 Easy Section: 28.05 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation

24) What monomer(s) would be used to make the polyester shown below?

A) Butanedioic acid B) 4-Hydroxybutanal C) 4-Hydroxybutanoic acid D) Butanedioic acid and 1,4-butanediol Answer: C Difficulty: 2 Medium Section: 28.06 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28 25) Which of the following is the repeating unit of the polymer formed in the polymerization of p-hydroxybenzoic acid?

A) A B) B C) C D) D Answer: A Difficulty: 1 Easy Section: 28.06 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

26) Identify the monomer(s) needed to make the following polyester.

A) 3-Hydroxybutanoic acid B) Butanedioic acid C) Butanedioic acid and ethylene glycol D) Butanedioic acid and ethanol Answer: C Difficulty: 2 Medium Section: 28.06 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 27) Which of the following is (are) repeating unit(s) of step-growth polymers?

A) Only I B) Only II C) Only III D) I and II Answer: D Difficulty: 2 Medium Section: 28.06 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

28) 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: 2 Medium Section: 28.07 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 29) What is the purpose of plasticizers? A) To harden plastics B) To soften plastics C) To initiate polymerizations D) To cross-link polymer chains Answer: B Difficulty: 1 Easy Section: 28.07 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation

30) 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: 2 Medium Section: 28.03 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28 31) What is the name given to polymers that soften when heated and harden when cooled? A) Cross-linked polymers B) Copolymers C) Thermosetting polymers D) Thermoplastics Answer: D Difficulty: 1 Easy Section: 28.07 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation

32) What is the structure of the polymer which results when styrene is reacted with BF3 and H2O?

A) A B) B C) C D) D Answer: B Difficulty: 2 Medium Section: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

33) Rank the following monomers (X, Y and Z) in order of increasing ability to undergo anionic polymerization, starting with the least reactive monomer.

A) Y< X < Z B) Z < Y < X C) X < Y < Z D) Y < Z < X Answer: D Difficulty: 2 Medium Section: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

34) Melamine and formaldehyde combine to form the polymer, Melmac®. How is Melmac® classified, and what physical characteristics are consistent with its structure?

A) Polycarbonate, transparent B) Polyurethane, elastic C) Thermosetting, rigid D) Thermoplastic, can be melted and molded into new shapes Answer: C Difficulty: 2 Medium Section: 28.07 Topic: Synthetic Polymers Bloom's: 4. Analyze Chapter: 28

35) Which monomer and which type of initiator would you use to synthesize the following polymer?

A) A B) B C) C D) D E) E Answer: A Difficulty: 2 Medium Section: 28.02 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

36) Which of the following sets of products results if nylon 66 is treated with sulfuric acid?

A) A B) B C) C D) D Answer: D Difficulty: 2 Medium Section: 28.06 Topic: Synthetic Polymers Bloom's: 3. Apply Chapter: 28

37) What is the classification of the following polymer in which X and Y represent repeating units?

A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer Answer: A Difficulty: 1 Easy Section: 28.02 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28 38) What is the classification of the following polymer in which X and Y represent repeating units?

A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer Answer: C Difficulty: 1 Easy Section: 28.02 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28

39) What is the classification of the following polymer in which X and Y represent repeating units?

A) Block copolymer B) Homopolymer C) Alternating copolymer D) Random copolymer Answer: D Difficulty: 1 Easy Section: 28.02 Topic: Synthetic Polymers Bloom's: 2. Understand Chapter: 28 40) What is the name given to polymers with single monomers? A) Homopolymers B) Copolymers C) Block polymers D) Random polymers Answer: A Difficulty: 1 Easy Section: 28.02 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation 41) What is the name given to polymers with two or more different monomers? A) Homopolymers B) Copolymers C) Block polymers D) Random polymers Answer: B Difficulty: 1 Easy Section: 28.02 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

42) What are the structures of the three monomers needed to synthesize the following polymer?

A) I B) II C) III D) IV Answer: A Difficulty: 3 Hard Section: 28.06 Topic: Synthetic Polymers Bloom's: 4. Analyze Chapter: 28 43) What type of polymer is Lexan? A) Epoxy B) Polyurethane C) Polycarbonate D) Polyamide Answer: C Difficulty: 1 Easy Section: 28.06 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation 23 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

44) What type of polymer is Nylon? A) Epoxy B) Polyurethane C) Polycarbonate D) Polyamide Answer: D Section: 28.06 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation 45) What type of polymer is Spandex? A) HDPE B) Polyurethane C) Polycarbonate D) Polyamide Answer: B Difficulty: 1 Easy Section: 28.06 Topic: Synthetic Polymers Bloom's: 1. Remember Chapter: 28 Accessibility: Keyboard Navigation

A) A B) B C) C D) D 3) Which of the following compounds is not a hydrolyzable lipid?

4) Evaluate the following statement: The terpene structure shown is a hydrolysable lipid.

A) True, because it contains an alcohol functional group. B) False, because alcohol and aldehyde moieties are not hydrolysable. C) True, because there are three polar groups and only 12 total carbon atoms. D) False, because there is too much steric repulsion from the alcohol and aldehyde moieties. 5) What happens to the melting point in fatty acids as the unsaturation increases? A) It increases B) It decreases. C) There is no direct correlation between unsaturation and melting point. D) The melting point stays the same. 6) Solid fats are generally from what source? A) Vegetables B) Starches C) Legumes D) Animals 7) Liquid oils usually have a higher percentage of what component compared to solid fats? A) Oxygen B) Hydrogen C) Unsaturation D) Aromatic rings 8) How can an unsaturated fatty acid be converted into a saturated fatty acid? A) Hydrogenation B) Hydration C) Ozonolysis D) Hydrolysis 9) What chemical process causes an oil (such as soybean oil) to become rancid? A) Hydrogenation with hydrogen B) Hydration with water C) Oxidation with molecular oxygen D) Bromination with bromine

10) What is the main cellular function of a triacylglycerol? A) Signal transduction B) Form cell membranes C) Nerve cell transferal D) Energy storage 11) Which of the following is a phospholipid?

A) A B) B C) C D) D 12) What is the purpose of vitamin K? A) Energy storage B) Blood clotting C) Photosynthesis D) Hydrogenation 13) Eicosanoids are derived from what compound? A) Arachidonic acid B) Cyclohexane C) Cholesterol D) Triacylglycerols 14) What is the first key enzyme required for the synthesis of prostaglandins from arachidonic acid? A) Protein Kinase C B) Synthase C) Transferase D) COX (cyclic oxygenase)

15) What is (are) the basic subunits of terpenes? A) Cyclohexane B) Triacylglycerols C) Isoprene D) Carbonyls 16) How many isoprene units are in the following molecule?

A) 1 B) 2 C) 3 D) 4 17) How many isoprene units are contained in the following molecule?

A) 5 B) 4 C) 3 D) 2

18) Which of the following compounds is a steroid?

A) A B) B C) C D) D 19) What is (are) the biological precursor(s) for the formation of the steroid skeleton found in cholesterol? A) Cyclohexane B) Squalene C) Triacylglycerols D) Arachadonic acid 20) Which structure represents the lowest energy conformation of a trans-decalin?

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

21) Which of the following sequences shows a reasonable series of 1,2-rearrangements as might be found in the biosynthesis of a steroid?

A) A B) B C) C D) D 22) Which of the following is not one of the three main categories of hydrolyzable lipids? A) Waxes B) Steroids C) Triacylglycerols D) Phospholipids 23) Which of the following classes of molecules is not a nonhydrolyzable lipid? A) Steroids B) Terpenes C) Phospholipids D) Eicosanoids

24) All except one of the statements below are true about the molecule given. Which statement is not correct?

A) This molecule is a phospholipid and is generally found in fruits, vegetables, fish, liver, and dairy products. B) This molecule is a phospholipid that composes the main fabric of the insoluble barrier that protects the cell. C) This molecule contains two fatty acids and has at least one stereogenic center. D) This molecule is a phospholipid and belongs to the general category of lecithins. 25) From the statements below, pick out the one that is not correct for fat-soluble vitamins. A) Fat-soluble vitamins are classified as lipids. B) Fat-soluble vitamins are a group of biologically active compounds containing 20 carbon atoms. C) Fat-soluble vitamins are required in small quantities for normal metabolism. D) Fat-soluble vitamins are stored in fat cells for use when they are needed. 26) What is the result of the oxidation of arachidonic acid with O2 by cyclooxygenase? A) It results in the synthesis of prostaglandins, thromboxanes, and prostacyclins. B) It results in the synthesis of fat-soluble vitamins from sphingomyelins. C) It results in the synthesis of phosphoacylglycerols. D) It is an important step in the synthesis of lipids that form the lipid bilayer.

27) Triacylglycerol A yields compound B when treated with excess H2, Pd-C. Ozonolysis of A affords three molecules of compound C and one molecule of compound D. What is the structure of A?

Choices for Triglycerol A:

A) A B) B C) C D) D 28) Patchouli alcohol is an example of a terpene. How is this molecule classified?

A) Monoterpene B) Diterpene C) Triterpene D) Sesquiterpene

29) The stereoselective introduction of the C15 OH group on the w side chain of prostaglandins has presented a challenge for synthetic chemists. Recently, Mulzer and co-workers demonstrated a new route in which the w side chain is synthesized independently and then attached to the bicyclic counterpart. What is the appropriate sequence of reagents for the following synthesis?

A) (1) PBr3; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3 B) (1) PCC; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X C) (1) PBr3; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X D) (1) TsCl, pyridine; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3 30) Norethindrone is a synthetic steroid that is better than progesterone in suppressing ovulation. What reagents (1-3) are required to convert norethindrone to the derivatives shown below?

A) (1) H2, Pd-C; (2) (CH3)2CHCH2NH2, NaBH3CN; (3) a. O3, b. Zn, DMS B) (1) H2, Pd-C; (2) (CH3)2CHCH2NH2, mild acid; (3) a. O3, b. Zn, DMS C) (1) a. LiAlH4, b. H2O; (2) (CH3)2CHCH2NH2, NaBH3CN; (3) a. OsO4, b. NaHSO3 D) (1) a. LiAlH4, b. H2O; (2) (CH3)2CHCH2NH2, mild acid; (3) a. OsO4, b. NaHSO3

31) Sphingomyelins are a major component of the myelin sheath. Damage to the myelin sheath results in such diseases as multiple sclerosis. Which compound below corresponds to a sphingomyelin?

A) A B) B C) C D) D 32) Which of the following are complex lipids? A) Steroids B) Terpenes C) Waxes D) Protaglandins 33) Which of the following are simple lipids? A) Steroids B) Terpenes C) Waxes D) Prostaglandins 34) Which of the following correctly describes waxes? A) Long chain alcohols B) Long chain esters C) Long chain ethers D) Long chain fatty acids

35) What is the correct classification of the following compound? CH3(CH2)15COOH A) Saturated triglyceride B) Simple lipid C) Wax D) Saturated fatty acid 36) Which of the following fatty acids has the highest melting point? A) Palmitic acid B) Arachidic acid C) Stearic acid D) Lauric acid 37) Which of the following fatty acids has the lowest melting point? A) Palmitic acid B) Arachidic acid C) Stearic acid D) Lauric acid 38) Which of the following fatty acids has the highest melting point? A) Linoleic acid B) Oleic acid C) Arachidonic acid D) Palmitoleic acid 39) Which of the following fatty acids has the lowest melting point? A) Linoleic acid B) Oleic acid C) Arachidonic acid D) Palmitoleic acid 40) Which of the following fatty acids is not present in natural fats and oils? A) Hexadecanoic acid B) Heptadecanoic acid C) Octadecanoic acid D) None of the choices 41) What is the name of the reaction of triglycerides with a base? A) Esterification B) Transesterification C) Ozonolysis D) Saponification

42) What is the structure of a cortisone derivative that has a C=C between C6 and C7, methyl group at C8 and chlorine at C12? The configuration of C8 is S and the configuration at C12 is R.

A) I B) II C) III D) IV 43) How many isoprene units can be found in the following compound?

A) 1 B) 4 C) 8 D) 9 44) Which state about waxes is not true? A) Waxes are esters B) Waxes are formed from a high molecular weight alcohol and a fatty acid C) Waxes are water soluble D) Waxes are the simplest hydrolysable lipid 45) Which of the following is a fat soluble vitamin? A) Vitamin A B) Vitamin D3 C) Vitamin K D) All of these choices are correct

Organic Chemistry, 6e (Smith) Chapter 29 Lipids 1) Provide a definition of the term lipid. A) A compound with a carbonyl group B) A compound with an aromatic ring C) A hydrophobic biomolecule D) A water-soluble compound Answer: C Difficulty: 1 Easy Section: 29.01 Topic: Lipids Bloom's: 2. Understand Chapter: 29 Accessibility: Keyboard Navigation 2) Which of the following compounds is not a lipid?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 29.01 Topic: Lipids Bloom's: 2. Understand Chapter: 29

3) Which of the following compounds is not a hydrolyzable lipid?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 29.01 Topic: Lipids Bloom's: 3. Apply Chapter: 29 4) Evaluate the following statement: The terpene structure shown is a hydrolysable lipid.

5) What happens to the melting point in fatty acids as the unsaturation increases? A) It increases B) It decreases. C) There is no direct correlation between unsaturation and melting point. D) The melting point stays the same. Answer: B Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 6) Solid fats are generally from what source? A) Vegetables B) Starches C) Legumes D) Animals Answer: D Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 7) Liquid oils usually have a higher percentage of what component compared to solid fats? A) Oxygen B) Hydrogen C) Unsaturation D) Aromatic rings Answer: C Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

8) How can an unsaturated fatty acid be converted into a saturated fatty acid? A) Hydrogenation B) Hydration C) Ozonolysis D) Hydrolysis Answer: A Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 9) What chemical process causes an oil (such as soybean oil) to become rancid? A) Hydrogenation with hydrogen B) Hydration with water C) Oxidation with molecular oxygen D) Bromination with bromine Answer: C Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 10) What is the main cellular function of a triacylglycerol? A) Signal transduction B) Form cell membranes C) Nerve cell transferal D) Energy storage Answer: D Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

11) Which of the following is a phospholipid?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: 29.04 Topic: Lipids Bloom's: 3. Apply Chapter: 29 12) What is the purpose of vitamin K? A) Energy storage B) Blood clotting C) Photosynthesis D) Hydrogenation Answer: B Difficulty: 1 Easy Section: 29.05 Topic: Lipids Bloom's: 2. Understand Chapter: 29 Accessibility: Keyboard Navigation

13) Eicosanoids are derived from what compound? A) Arachidonic acid B) Cyclohexane C) Cholesterol D) Triacylglycerols Answer: A Difficulty: 1 Easy Section: 29.05 Topic: Lipids Bloom's: 2. Understand Chapter: 29 Accessibility: Keyboard Navigation 14) What is the first key enzyme required for the synthesis of prostaglandins from arachidonic acid? A) Protein Kinase C B) Synthase C) Transferase D) COX (cyclic oxygenase) Answer: D Difficulty: 1 Easy Section: 29.05 Topic: Lipids Bloom's: 1. Remember Chapter: 29 Accessibility: Keyboard Navigation 15) What is (are) the basic subunits of terpenes? A) Cyclohexane B) Triacylglycerols C) Isoprene D) Carbonyls Answer: C Difficulty: 1 Easy Section: 29.07 Topic: Lipids Bloom's: 1. Remember Chapter: 29 Accessibility: Keyboard Navigation

16) How many isoprene units are in the following molecule?

A) 1 B) 2 C) 3 D) 4 Answer: D Difficulty: 1 Easy Section: 29.07 Topic: Lipids Bloom's: 3. Apply Chapter: 29

17) How many isoprene units are contained in the following molecule?

A) 5 B) 4 C) 3 D) 2 Answer: B Difficulty: 2 Medium Section: 29.07 Topic: Lipids Bloom's: 3. Apply Chapter: 29

18) Which of the following compounds is a steroid?

A) A B) B C) C D) D Answer: C Difficulty: 1 Easy Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 19) What is (are) the biological precursor(s) for the formation of the steroid skeleton found in cholesterol? A) Cyclohexane B) Squalene C) Triacylglycerols D) Arachadonic acid Answer: B Difficulty: 1 Easy Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

20) Which structure represents the lowest energy conformation of a trans-decalin?

A) A B) B C) C D) D Answer: D Difficulty: 1 Easy Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 21) Which of the following sequences shows a reasonable series of 1,2-rearrangements as might be found in the biosynthesis of a steroid?

A) A B) B C) C D) D Answer: A Difficulty: 2 Medium Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 10 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

22) Which of the following is not one of the three main categories of hydrolyzable lipids? A) Waxes B) Steroids C) Triacylglycerols D) Phospholipids Answer: B Difficulty: 1 Easy Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 23) Which of the following classes of molecules is not a nonhydrolyzable lipid? A) Steroids B) Terpenes C) Phospholipids D) Eicosanoids Answer: C Difficulty: 1 Easy Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

24) All except one of the statements below are true about the molecule given. Which statement is not correct?

A) This molecule is a phospholipid and is generally found in fruits, vegetables, fish, liver, and dairy products. B) This molecule is a phospholipid that composes the main fabric of the insoluble barrier that protects the cell. C) This molecule contains two fatty acids and has at least one stereogenic center. D) This molecule is a phospholipid and belongs to the general category of lecithins. Answer: A Difficulty: 2 Medium Section: 29.01 Topic: Lipids Bloom's: 3. Apply Chapter: 29 25) From the statements below, pick out the one that is not correct for fat-soluble vitamins. A) Fat-soluble vitamins are classified as lipids. B) Fat-soluble vitamins are a group of biologically active compounds containing 20 carbon atoms. C) Fat-soluble vitamins are required in small quantities for normal metabolism. D) Fat-soluble vitamins are stored in fat cells for use when they are needed. Answer: B Difficulty: 1 Easy Section: 29.05 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

26) What is the result of the oxidation of arachidonic acid with O2 by cyclooxygenase? A) It results in the synthesis of prostaglandins, thromboxanes, and prostacyclins. B) It results in the synthesis of fat-soluble vitamins from sphingomyelins. C) It results in the synthesis of phosphoacylglycerols. D) It is an important step in the synthesis of lipids that form the lipid bilayer. Answer: A Difficulty: 2 Medium Section: 29.05 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 27) Triacylglycerol A yields compound B when treated with excess H2, Pd-C. Ozonolysis of A affords three molecules of compound C and one molecule of compound D. What is the structure of A?

Choices for Triglycerol A:

A) A B) B C) C D) D Answer: C Difficulty: 3 Hard Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

28) Patchouli alcohol is an example of a terpene. How is this molecule classified?

A) Monoterpene B) Diterpene C) Triterpene D) Sesquiterpene Answer: D Difficulty: 2 Medium Section: 29.07 Topic: Lipids Bloom's: 3. Apply Chapter: 29

A) (1) PBr3; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3 B) (1) PCC; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X C) (1) PBr3; (2) Ph3P=CH2; (3) Grubbs' catalyst, Reagent X D) (1) TsCl, pyridine; (2) Grubbs' catalyst, Reagent X; (3) KOC(CH3)3 Answer: B Difficulty: 2 Medium Section: 29.04 Topic: Lipids Bloom's: 3. Apply Chapter: 29

30) Norethindrone is a synthetic steroid that is better than progesterone in suppressing ovulation. What reagents (1-3) are required to convert norethindrone to the derivatives shown below?

31) Sphingomyelins are a major component of the myelin sheath. Damage to the myelin sheath results in such diseases as multiple sclerosis. Which compound below corresponds to a sphingomyelin?

A) A B) B C) C D) D Answer: C Difficulty: 2 Medium Section: 29.04 Topic: Lipids Bloom's: 3. Apply Chapter: 29 32) Which of the following are complex lipids? A) Steroids B) Terpenes C) Waxes D) Protaglandins Answer: C Difficulty: 1 Easy Section: 29.02 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

33) Which of the following are simple lipids? A) Steroids B) Terpenes C) Waxes D) Prostaglandins Answer: A Difficulty: 1 Easy Section: 29.07 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 34) Which of the following correctly describes waxes? A) Long chain alcohols B) Long chain esters C) Long chain ethers D) Long chain fatty acids Answer: B Difficulty: 1 Easy Section: 29.02 Topic: Lipids Bloom's: 2. Understand Chapter: 29 Accessibility: Keyboard Navigation 35) What is the correct classification of the following compound? CH3(CH2)15COOH A) Saturated triglyceride B) Simple lipid C) Wax D) Saturated fatty acid Answer: D Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

36) Which of the following fatty acids has the highest melting point? A) Palmitic acid B) Arachidic acid C) Stearic acid D) Lauric acid Answer: B Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 37) Which of the following fatty acids has the lowest melting point? A) Palmitic acid B) Arachidic acid C) Stearic acid D) Lauric acid Answer: D Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 38) Which of the following fatty acids has the highest melting point? A) Linoleic acid B) Oleic acid C) Arachidonic acid D) Palmitoleic acid Answer: B Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

39) Which of the following fatty acids has the lowest melting point? A) Linoleic acid B) Oleic acid C) Arachidonic acid D) Palmitoleic acid Answer: C Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 40) Which of the following fatty acids is not present in natural fats and oils? A) Hexadecanoic acid B) Heptadecanoic acid C) Octadecanoic acid D) None of the choices Answer: B Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation 41) What is the name of the reaction of triglycerides with a base? A) Esterification B) Transesterification C) Ozonolysis D) Saponification Answer: D Difficulty: 1 Easy Section: 29.03 Topic: Lipids Bloom's: 3. Apply Chapter: 29 Accessibility: Keyboard Navigation

42) What is the structure of a cortisone derivative that has a C=C between C6 and C7, methyl group at C8 and chlorine at C12? The configuration of C8 is S and the configuration at C12 is R.

A) I B) II C) III D) IV Answer: C Difficulty: 3 Hard Section: 29.08 Topic: Lipids Bloom's: 3. Apply Chapter: 29 43) How many isoprene units can be found in the following compound?

A) 1 B) 4 C) 8 D) 9 Answer: B Difficulty: 2 Medium Section: 29.07 Topic: Lipids Bloom's: 3. Apply Chapter: 29

44) Which state about waxes is not true? A) Waxes are esters B) Waxes are formed from a high molecular weight alcohol and a fatty acid C) Waxes are water soluble D) Waxes are the simplest hydrolysable lipid Answer: C Difficulty: 1 Easy Section: 29.02 Topic: Lipids Bloom's: 2. Understand Chapter: 29 Accessibility: Keyboard Navigation 45) Which of the following is a fat soluble vitamin? A) Vitamin A B) Vitamin D3 C) Vitamin K D) All of these choices are correct Answer: D Difficulty: 1 Easy Section: 29.05 Topic: Lipids Bloom's: 2. Understand Chapter: 29 Accessibility: Keyboard Navigation

Organic Chemistry, 6e (Smith) Spectroscopy A Mass Spectrometry 1) In electron impact mass spectrometry (EIMS), what is being detected? A) The molecular mass of the compound B) The molecular formula of the compound C) The mass to charge ratio of any ionic species D) The mass to charge ratio of any neutral species 2) What type of feature will be observed in the EI mass spectrum of chlorobenzene? A) An absorption at 3100 cm–1 B) A signal at 113 C) A signal at 112 and a signal at 114 in a ratio of 3:1 D) A signal at 112 and a signal at 114 in a ratio of 1:1 3) You observe a compound that exhibits a mass spectrum with peak at 160 and a peak at 162, both of equal intensity. This compound contains A) two chlorine atoms. B) one iodine atom. C) one bromine atom. D) two bromine atoms. 4) A compound X has a molecular ion peak in its mass spectrum at m/z 136. What information does this tell us about X? A) X has a molecular mass of 136. B) The molecular formula for X is C8H8O2. C) The empirical formula for X is C4H4O. D) Both A (X has a molecular mass of 136) and B (The molecular formula for X is C8H8O2) are true. E) Statements (X has a molecular mass of 136), (The molecular formula for X is C8H8O2), and (The empirical formula for X is C4H4O) are all true. 5) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?

A) A signal at 95 amu B) A signal at 94 amu C) Two signals at 95 and 94 amu D) A signal at 106 amu 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

A) I B) II C) III D) IV 10) 2,2-dimethylbutane gives a significant fragment peak at m/z = 57. Which of the following is the most probable structure of the fragment ion?

11) 2,3-dimethylbutane gives a base fragment peak at m/z = 43. Which of the following is the most probable structure of the fragment ion?

A) I B) II C) III D) IV 12) Pentane, C5H12, would have which of the following fragments in its mass spectrum? m/z II

III 43 IV 57 A) I B) II C) III D) All of the choices are correct. 13) Hexane, C6H14, would have which of the following fragments in its mass spectrum? m/z I

III

A) I B) II C) III D) All of the choices are correct.

14) Heptane, C7H16, would have which of the following fragments in its mass spectrum? m/z I

III

A) I B) II C) III D) All of the choices are correct. 15) Butane, C4H10, would have which of the following fragments in its mass spectrum? m/z I

III

A) I B) II C) III D) I and II 16) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66

17) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66 18) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66 19) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66

Organic Chemistry, 6e (Smith) Spectroscopy A Mass Spectrometry 1) In electron impact mass spectrometry (EIMS), what is being detected? A) The molecular mass of the compound B) The molecular formula of the compound C) The mass to charge ratio of any ionic species D) The mass to charge ratio of any neutral species Answer: C Difficulty: 1 Easy Section: A.01 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: Spectroscopy A Accessibility: Keyboard Navigation 2) What type of feature will be observed in the EI mass spectrum of chlorobenzene? A) An absorption at 3100 cm–1 B) A signal at 113 C) A signal at 112 and a signal at 114 in a ratio of 3:1 D) A signal at 112 and a signal at 114 in a ratio of 1:1 Answer: C Difficulty: 1 Easy Section: A.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 3) You observe a compound that exhibits a mass spectrum with peak at 160 and a peak at 162, both of equal intensity. This compound contains A) two chlorine atoms. B) one iodine atom. C) one bromine atom. D) two bromine atoms. Answer: C Difficulty: 1 Easy Section: A.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

4) A compound X has a molecular ion peak in its mass spectrum at m/z 136. What information does this tell us about X? A) X has a molecular mass of 136. B) The molecular formula for X is C8H8O2. C) The empirical formula for X is C4H4O. D) Both A (X has a molecular mass of 136) and B (The molecular formula for X is C8H8O2) are true. E) Statements (X has a molecular mass of 136), (The molecular formula for X is C8H8O2), and (The empirical formula for X is C4H4O) are all true. Answer: A Difficulty: 2 Medium Section: A.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 5) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?

A) A signal at 95 amu B) A signal at 94 amu C) Two signals at 95 and 94 amu D) A signal at 106 amu Answer: A Difficulty: 2 Medium Section: A.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A

6) In a typical mass spectrum, a smaller signal is observed at a mass 1 amu higher than the molecular ion peak. Why? A) Due to small impurities in the sample B) Machine error C) Because a small percentage of the compound will have a carbon that is the isotope 13C instead of 12C D) Because of fragmentation Answer: C Difficulty: 1 Easy Section: A.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 7) Which of the following statements about the base peak of a mass spectrum is always true? A) The base peak corresponds to the molecular ion. B) The base peak corresponds to the most abundant ion. C) The base peak corresponds to the lowest m/z. D) None of these. Answer: B Difficulty: 1 Easy Section: A.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 8) What would be the molecular formula of rose oxide which contains C, H, and O and has two degrees of unsaturation and a molecular ion in its mass spectrum at m/z =154? A) C10H18O B) C9H14O2 C) C10H2O2 D) C8H10O3 Answer: A Difficulty: 2 Medium Section: A.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 3 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

9) Which of the following alkanes gives a significant fragment peak at m/z = 57?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A 10) 2,2-dimethylbutane gives a significant fragment peak at m/z = 57. Which of the following is the most probable structure of the fragment ion?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A

11) 2,3-dimethylbutane gives a base fragment peak at m/z = 43. Which of the following is the most probable structure of the fragment ion?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A 12) Pentane, C5H12, would have which of the following fragments in its mass spectrum? m/z II

III 43 IV 57 A) I B) II C) III D) All of the choices are correct. Answer: D Difficulty: 1 Easy Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation

13) Hexane, C6H14, would have which of the following fragments in its mass spectrum? m/z I

III

A) I B) II C) III D) All of the choices are correct. Answer: D Difficulty: 1 Easy Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 14) Heptane, C7H16, would have which of the following fragments in its mass spectrum? m/z I

III

A) I B) II C) III D) All of the choices are correct. Answer: D Difficulty: 1 Easy Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 6 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

15) Butane, C4H10, would have which of the following fragments in its mass spectrum? m/z I

III

A) I B) II C) III D) I and II Answer: D Difficulty: 1 Easy Section: A.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A Accessibility: Keyboard Navigation 16) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66 Answer: A Difficulty: 1 Easy Section: A.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A

17) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66 Answer: C Difficulty: 1 Easy Section: A.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A 18) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66 Answer: A Difficulty: 1 Easy Section: A.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A

19) What is the molecular ion, m/z, for the following molecule?

A) 72 B) 70 C) 68 D) 66 Answer: B Difficulty: 1 Easy Section: A.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy A

Organic Chemistry, 6e (Smith) Spectroscopy B Infrared Spectroscopy 1) What type(s) of molecular motion is (are) observed using infrared spectroscopy? A) Stretching and bending B) Rotation and excitation C) Spin flipping D) Fragmentation 2) The functional group region of an infrared spectrum is A) where the cations appear. B) greater than or equal to 1500 cm–1. C) less than 1500 cm–1. D) greater than or equal to 2500 cm–1. 3) Stronger bonds will be found where in the infrared spectrum? A) Higher molecular weight B) Lower molecular weight C) Lower wavenumbers D) Higher wavenumbers 4) Compared to a C–H bond, a C–D bond will vibrate where in the infrared spectrum? A) Higher molecular weight B) Lower molecular weight C) Lower wavenumbers D) Higher wavenumbers 5) Why does an alkyne carbon–carbon triple bond vibrate at a higher wavenumber than an alkene carbon–carbon double bond? A) It is stronger. B) It is weaker. C) It has fewer hydrogens. D) It makes a less stable cation. 6) Why is the infrared absorption for the stretching motion of internal alkynes rarely observed? A) They do not form cations. B) They are too strong. C) Stretching in internal alkynes does not involve a change in dipole moment. D) They do not have hydrogens.

7) Consider the three organic compounds drawn below. Which of the following statements is (are) true about the IR spectra of I, II, and III?

A) I shows strong absorptions at 2950 cm–1 and 1700 cm–1. B) II shows strong absorptions at 2950 cm–1 and 2250 cm–1. C) III shows strong absorptions at 2950 cm–1 and 3200–3600 cm–1. D) Statements (I shows strong absorptions at 2950 cm–1 and 1700 cm–1) and (III shows strong absorptions at 2950 cm–1 and 3200–3600 cm–1) are true. 8) In an IR spectrum, which of the indicated C–H bonds exhibits a stretching absorption at the largest wave number?

A) I B) II C) III D) IV 9) Which of the following statements is (are) accurate about the IR spectrum of compounds I, II, and III below?

10) Which of the indicated C–H bonds absorbs at the lowest wave number in the IR spectrum?

A) I B) II C) III D) IV 11) Which of the following statements is (are) true about the IR spectrum of the compound drawn below?

A) It shows absorptions at 3000–3150 cm–1 and 1720 cm–1. B) It shows absorptions at 3000–2850 cm–1 and 2150 cm–1. C) It shows absorptions at 2250 cm–1 and 1650 cm–1. D) It shows absorptions at 2250 cm–1 and 1720 cm–1. E) Both statements (It shows absorptions at 3000–2850 cm–1 and 2250 cm–1) and (It shows absorptions at 2250 cm–1 and 1720 cm–1) are true. 12) A compound X shows a molecular ion peak at m/z 72 in its mass spectrum, and a strong peak at ~1715 cm–1 in its IR spectrum. Which structures are possible for compound X?

A) I B) II C) III D) I and II

13) You are given a bottle of an organic liquid and told it must be either cyclohexane or 1hexene. Which of the following statements is (are) true about these two compounds?

A) The two compounds can be differentiated by their mass spectra because they will have molecular ion peaks at different m/z. B) 1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not. C) Both cyclohexane and 1-hexene will show C–H absorptions at about 2950 cm–1. D) Statements (1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not) and (Both cyclohexane and 1-hexene will show C–H absorptions at about 2950 cm–1) are both true. E) Statements (The two compounds can be differentiated by their mass spectra because they will have molecular ions at different masses), (1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not), and (Both cyclohexane and 1- hexene will show C–H absorptions at about 2950 cm–1) are all true. 14) Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 104 and shows prominent peaks in its IR spectrum at 3200– 2850 cm–1? A) The compound has a molecular mass of 104. B) The compound contains a C=O group and Csp3-H hybridized bonds. C) The compound contains an OH group and Csp3-H hybridized bonds. D) Both (The compound has a molecular mass of 104) and (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements. E) Both (The compound has a molecular mass of 104) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements. 15) An alkyne C–H bond absorbs at higher wave number than an alkene C–H bond. What does this tell you about the strength of these two bonds? A) The alkene C–H bond is stronger. B) The alkyne C–H bond is stronger. C) The alkene C–C bond is stronger. D) The alkyne C–C bond is stronger.

16) Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 94 and shows prominent peaks in its IR spectrum at 3600– 3200 and 1600 cm–1? A) The compound has a molecular mass of 94. B) The compound contains a C=O group and Csp3-H hybridized bonds. C) The compound contains an OH group and a benzene ring. D) Both (The compound has a molecular mass of 94) and (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements. E) Both (The compound has a molecular mass of 94) and (The compound contains an OH group and a benzene ring) are true statements. 17) Which of the following statement(s) is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 69 and shows a prominent peak in its IR spectrum at 2250 cm– 1? A) The compound has a molecular mass of 70. B) The compound contains a C=O group. C) The compound contains a cyano or alkyne group. D) Both (The compound has a molecular mass of 70) and (The compound contains a C=O group) are true statements. E) Both (The compound has a molecular mass of 70) and (The compound contains a cyano or alkyne group) are true statements. 18) Which of the following statements is (are) true about a compound that has molecular ion peaks in its mass spectrum at mass 170 and 172 and shows prominent peaks in its IR spectrum at 3150–3000 and 1600 cm–1? A) The compound is not pure. B) The compound contains a halogen. C) The compound contains an OH group and Csp3-H hybridized bonds. D) Both (The compound is not pure) and (The compound contains a halogen) are true statements. E) Both (The compound is not pure) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements. 19) Which of the following structures is consistent with a compound that displays a molecular ion peak at 103 and infrared signals at 2250 and 1600 cm–1?

20) Which of the following structures is consistent with a compound that displays a molecular ion peak at 56 and infrared signals at 2250 and 3600–3200 cm–1?

A) I B) II C) III D) IV 21) Which of the following structures is consistent with a compound that displays a molecular ion peak at 84 and infrared signals at 3000–2850 cm–1 and no signals between 3000-3300 cm-1?

A) I B) II C) III D) IV 22) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?

A) A signal at 1600 cm–1 B) A signal at 3300 cm–1 C) A single mass peak at 92 amu D) Two mass peaks at 92 and 94 amu

23) What type of signal(s) would you observe in the mass and/or infrared spectrum of the following compound?

A) A signal at 96 amu B) Two signals at 112 and 114 amu C) A signal at 1600 cm–1 D) A signal at 1720 cm–1 24) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?

A) A signal at 95 amu B) A signal at 94 amu C) Two signals at 95 and 94 amu D) A signal at 3600–3200 cm–1

25) Examine the IR below and classify the compound.

A) Alkane B) Carboxylic acid C) Alcohol D) Alkene

26) Examine the IR below and classify the compound.

A) Alcohol B) Aldehyde C) Amine D) Ketone E) Carboxylic acid

27) Examine the IR below and classify the compound.

A) Alcohol B) Arene C) Amine D) Ketone E) Carbocylic acid

28) Examine the IR below and classify the compound.

A) Alcohol B) Aldehyde C) Carboxylic acid D) Ketone

29) Examine the IR below and classify the compound.

A) Alcohol B) Aldehyde C) Amine D) Ketone

30) 13C NMR is a technique in which the total number of signals represents the number of unique carbon atoms in a molecule. Propose a structure that is consistent with the following data. a) The IR includes peaks at 1603 and 1495 cm-1. b) The 13C NMR has a total of 7 signals. c) The compound has one acidic proton.

A) I B) II C) III D) IV 31) The base peak in a mass spectrum corresponds to the most stable fragment. Propose a structure for a compound that is consistent with the following data. a) The molecular ion peak has m/z = 116. b) The base peak is at m/z = 59. c) The compound is composed of C, H and O atoms. d) The IR spectrum shows a strong absorbance at 3257 cm-1.

A) I B) II C) III D) IV

32) An IR spectrum has the following potentially important absorptions: 3091, 3067, 2963, 2921, 2252, 1603, 1499, 1455, 1416, 1078, 1031, 941, 735, and 696 cm-1. Indicate which structure corresponds to the IR data.

A) I B) II C) III D) IV 33) When the phenol shown below is treated with KOH, it forms a product whose IR spectrum does not show an absorption in the 3200-3600 cm-1 region. Propose a structure for the product.

A) I B) II C) III D) IV 34) Which of the following information is primarily obtained from an IR spectrum? A) Conjugated p system present in a compound. B) Functional groups present in a compound. C) Molecular weight of a compound. D) The carbon and hydrogen framework of a compound.

35) Which of the following compounds will have the lowest wavenumber for carbonyl absorption?

A) I B) II C) III D) IV 36) Which of the following π bonds is IR inactive?

A) I B) II C) III D) IV 37) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s IR.

A) 3300 cm-1 B) 3100 cm-1 C) 2250 cm-1 D) 1750 cm-1

38) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s IR.

A) 3300 cm-1 B) 3100 cm-1 C) 2250 cm-1 D) 1750 cm-1 39) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s IR.

A) 3300 cm-1 B) 3100 cm-1 C) 2250 cm-1 D) 1750 cm-1

Organic Chemistry, 6e (Smith) Spectroscopy B Infrared Spectroscopy 1) What type(s) of molecular motion is (are) observed using infrared spectroscopy? A) Stretching and bending B) Rotation and excitation C) Spin flipping D) Fragmentation Answer: A Difficulty: 1 Easy Section: B.02 Topic: Analytical/Spectroscopy Bloom's: 1. Remember Chapter: Spectroscopy B Accessibility: Keyboard Navigation 2) The functional group region of an infrared spectrum is A) where the cations appear. B) greater than or equal to 1500 cm–1. C) less than 1500 cm–1. D) greater than or equal to 2500 cm–1. Answer: B Difficulty: 1 Easy Section: B.02 Topic: Analytical/Spectroscopy Bloom's: 1. Remember Chapter: Spectroscopy B Accessibility: Keyboard Navigation 3) Stronger bonds will be found where in the infrared spectrum? A) Higher molecular weight B) Lower molecular weight C) Lower wavenumbers D) Higher wavenumbers Answer: D Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation

4) Compared to a C–H bond, a C–D bond will vibrate where in the infrared spectrum? A) Higher molecular weight B) Lower molecular weight C) Lower wavenumbers D) Higher wavenumbers Answer: C Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation 5) Why does an alkyne carbon–carbon triple bond vibrate at a higher wavenumber than an alkene carbon–carbon double bond? A) It is stronger. B) It is weaker. C) It has fewer hydrogens. D) It makes a less stable cation. Answer: A Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation 6) Why is the infrared absorption for the stretching motion of internal alkynes rarely observed? A) They do not form cations. B) They are too strong. C) Stretching in internal alkynes does not involve a change in dipole moment. D) They do not have hydrogens. Answer: C Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation

7) Consider the three organic compounds drawn below. Which of the following statements is (are) true about the IR spectra of I, II, and III?

A) I shows strong absorptions at 2950 cm–1 and 1700 cm–1. B) II shows strong absorptions at 2950 cm–1 and 2250 cm–1. C) III shows strong absorptions at 2950 cm–1 and 3200–3600 cm–1. D) Statements (I shows strong absorptions at 2950 cm–1 and 1700 cm–1) and (III shows strong absorptions at 2950 cm–1 and 3200–3600 cm–1) are true. Answer: D Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 8) In an IR spectrum, which of the indicated C–H bonds exhibits a stretching absorption at the largest wave number?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

9) Which of the following statements is (are) accurate about the IR spectrum of compounds I, II, and III below?

A) Compound I shows absorptions at 2950 and 1700 cm–1. B) Compound II shows absorptions at 3200–3600 and 1650 cm–1. C) Compound III shows absorptions at 3200–3600 and 2950 cm–1. D) Both (Compound I shows absorptions at 2950 and 1700 cm–1) and (Compound II shows absorptions at 3200–3600 and 1650 cm–1) are true. Answer: D Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 10) Which of the indicated C–H bonds absorbs at the lowest wave number in the IR spectrum?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

11) Which of the following statements is (are) true about the IR spectrum of the compound drawn below?

A) It shows absorptions at 3000–3150 cm–1 and 1720 cm–1. B) It shows absorptions at 3000–2850 cm–1 and 2150 cm–1. C) It shows absorptions at 2250 cm–1 and 1650 cm–1. D) It shows absorptions at 2250 cm–1 and 1720 cm–1. E) Both statements (It shows absorptions at 3000–2850 cm–1 and 2250 cm–1) and (It shows absorptions at 2250 cm–1 and 1720 cm–1) are true. Answer: E Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 12) A compound X shows a molecular ion peak at m/z 72 in its mass spectrum, and a strong peak at ~1715 cm–1 in its IR spectrum. Which structures are possible for compound X?

A) I B) II C) III D) I and II Answer: A Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

13) You are given a bottle of an organic liquid and told it must be either cyclohexane or 1hexene. Which of the following statements is (are) true about these two compounds?

A) The two compounds can be differentiated by their mass spectra because they will have molecular ion peaks at different m/z. B) 1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not. C) Both cyclohexane and 1-hexene will show C–H absorptions at about 2950 cm–1. D) Statements (1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not) and (Both cyclohexane and 1-hexene will show C–H absorptions at about 2950 cm–1) are both true. E) Statements (The two compounds can be differentiated by their mass spectra because they will have molecular ions at different masses), (1-Hexene will show an absorption at 1650 cm–1 but cyclohexane will not), and (Both cyclohexane and 1- hexene will show C–H absorptions at about 2950 cm–1) are all true. Answer: D Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 14) Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 104 and shows prominent peaks in its IR spectrum at 3200– 2850 cm–1? A) The compound has a molecular mass of 104. B) The compound contains a C=O group and Csp3-H hybridized bonds. C) The compound contains an OH group and Csp3-H hybridized bonds. D) Both (The compound has a molecular mass of 104) and (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements. E) Both (The compound has a molecular mass of 104) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements. Answer: A Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation 6 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

15) An alkyne C–H bond absorbs at higher wave number than an alkene C–H bond. What does this tell you about the strength of these two bonds? A) The alkene C–H bond is stronger. B) The alkyne C–H bond is stronger. C) The alkene C–C bond is stronger. D) The alkyne C–C bond is stronger. Answer: B Difficulty: 2 Medium Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation 16) Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 94 and shows prominent peaks in its IR spectrum at 3600– 3200 and 1600 cm–1? A) The compound has a molecular mass of 94. B) The compound contains a C=O group and Csp3-H hybridized bonds. C) The compound contains an OH group and a benzene ring. D) Both (The compound has a molecular mass of 94) and (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements. E) Both (The compound has a molecular mass of 94) and (The compound contains an OH group and a benzene ring) are true statements. Answer: E Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation

17) Which of the following statement(s) is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 69 and shows a prominent peak in its IR spectrum at 2250 cm– 1? A) The compound has a molecular mass of 70. B) The compound contains a C=O group. C) The compound contains a cyano or alkyne group. D) Both (The compound has a molecular mass of 70) and (The compound contains a C=O group) are true statements. E) Both (The compound has a molecular mass of 70) and (The compound contains a cyano or alkyne group) are true statements. Answer: C Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation 18) Which of the following statements is (are) true about a compound that has molecular ion peaks in its mass spectrum at mass 170 and 172 and shows prominent peaks in its IR spectrum at 3150–3000 and 1600 cm–1? A) The compound is not pure. B) The compound contains a halogen. C) The compound contains an OH group and Csp3-H hybridized bonds. D) Both (The compound is not pure) and (The compound contains a halogen) are true statements. E) Both (The compound is not pure) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements. Answer: B Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B Accessibility: Keyboard Navigation

19) Which of the following structures is consistent with a compound that displays a molecular ion peak at 103 and infrared signals at 2250 and 1600 cm–1?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 20) Which of the following structures is consistent with a compound that displays a molecular ion peak at 56 and infrared signals at 2250 and 3600–3200 cm–1?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

21) Which of the following structures is consistent with a compound that displays a molecular ion peak at 84 and infrared signals at 3000–2850 cm–1 and no signals between 3000-3300 cm-1?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 22) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?

A) A signal at 1600 cm–1 B) A signal at 3300 cm–1 C) A single mass peak at 92 amu D) Two mass peaks at 92 and 94 amu Answer: D Difficulty: 1 Easy Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

23) What type of signal(s) would you observe in the mass and/or infrared spectrum of the following compound?

A) A signal at 96 amu B) Two signals at 112 and 114 amu C) A signal at 1600 cm–1 D) A signal at 1720 cm–1 Answer: D Difficulty: 1 Easy Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 24) What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?

A) A signal at 95 amu B) A signal at 94 amu C) Two signals at 95 and 94 amu D) A signal at 3600–3200 cm–1 Answer: A Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

25) Examine the IR below and classify the compound.

A) Alkane B) Carboxylic acid C) Alcohol D) Alkene Answer: C Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

26) Examine the IR below and classify the compound.

A) Alcohol B) Aldehyde C) Amine D) Ketone E) Carboxylic acid Answer: D Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

27) Examine the IR below and classify the compound.

A) Alcohol B) Arene C) Amine D) Ketone E) Carbocylic acid Answer: B Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

28) Examine the IR below and classify the compound.

A) Alcohol B) Aldehyde C) Carboxylic acid D) Ketone Answer: C Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

29) Examine the IR below and classify the compound.

A) Alcohol B) Aldehyde C) Amine D) Ketone Answer: C Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

31) The base peak in a mass spectrum corresponds to the most stable fragment. Propose a structure for a compound that is consistent with the following data. a) The molecular ion peak has m/z = 116. b) The base peak is at m/z = 59. c) The compound is composed of C, H and O atoms. d) The IR spectrum shows a strong absorbance at 3257 cm-1.

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 33) When the phenol shown below is treated with KOH, it forms a product whose IR spectrum does not show an absorption in the 3200-3600 cm-1 region. Propose a structure for the product.

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: B.05 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

34) Which of the following information is primarily obtained from an IR spectrum? A) Conjugated p system present in a compound. B) Functional groups present in a compound. C) Molecular weight of a compound. D) The carbon and hydrogen framework of a compound. Answer: B Difficulty: 1 Easy Section: B.02 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: Spectroscopy B Accessibility: Keyboard Navigation 35) Which of the following compounds will have the lowest wavenumber for carbonyl absorption?

A) I B) II C) III D) IV Answer: D Difficulty: 1 Easy Section: B.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

36) Which of the following π bonds is IR inactive?

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: B.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 37) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s IR.

A) 3300 cm-1 B) 3100 cm-1 C) 2250 cm-1 D) 1750 cm-1 Answer: A Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

38) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s IR.

A) 3300 cm-1 B) 3100 cm-1 C) 2250 cm-1 D) 1750 cm-1 Answer: D Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B 39) Ignoring sp3 CH stretching, estimate where the major peak be in the following compound’s IR.

A) 3300 cm-1 B) 3100 cm-1 C) 2250 cm-1 D) 1750 cm-1 Answer: C Difficulty: 1 Easy Section: B.04 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy B

Organic Chemistry, 6e (Smith) Spectroscopy C Nuclear Magnetic Resonance Spectroscopy 1) How many unique protons are present in each of the following compounds?

A) I = 6; II = 3; III = 6 B) I = 5; II = 4; III = 6 C) I = 6, II = 4, III = 4 D) I = 6; II = 4; III = 6 2) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 2; II = 6; III = 1 B) I = 3; II = 5; III = 2 C) I = 1; II = 5; III = 1 D) I = 2; II = 6; III = 2 3) Into how many peaks will each of the circled protons be split? (Assume complete resolution of all NMR peaks is possible)

A) I = 3; II = 8; III = 1; IV = 4; V = 3 B) I = 9; II = 8; III = 2; IV = 4; V = 4 C) I = 4; II = 8; III = 2; IV = 4; V = 5 D) I = 4; Ii = 7; III = 2; IV = 4; V = 3 1 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

4) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 8; II = 4; III = 3; IV = 3 B) I = 7; II = 4; III = 3; IV = 4 C) I = 7; II = 3; III = 3; IV = 3 D) I = 7; II = 4; III = 2; IV = 4 5) How many different kinds of protons are present in each of the following molecules?

A) I = 3; II = 5; III = 5; IV = 4; V = 3 B) I = 4; II = 5; III = 4; IV = 4; V = 3 C) I = 4; II = 5; III = 5; IV = 4; V = 3 D) I = 4; II = 5; III = 5; IV = 3; V = 4 6) Into how many peaks will each of the circled protons be split? (Assume complete resolution of all NMR peaks is possible)

A) I = 3; II = 7; III = 4 B) I = 2; II = 7; III = 4 C) I = 2; II = 7; III = 3 D) I = 2; II = 6; III = 4

7) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 6; II = 2; III = 3 B) I = 7; II = 3; III = 3 C) I = 7; II = 1; III = 3 D) I = 7; II = 2; III = 3 8) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 1; II = 4; III = 7 B) I = 3; II = 3; III = 7 C) I = 2; II = 4; III = 7 D) I = 2; II = 4; III = 6 9) How many different kinds of protons are present in each of the following compounds?

A) I = 4; II = 3; III = 1 B) I = 4; II = 4; III = 1 C) I = 4; II = 4; III = 2 D) I = 3; II = 3; III = 1

10) How many different kinds of protons are present in each of the following compounds?

A) I = 2; II = 4; III = 6 B) I = 2; II = 4; III = 4 C) I = 3; II = 3; III = 5 D) I = 2; II = 4; III = 5 11) How many different kinds of protons are present in each of the following compounds?

A) I = 6; II = 5; III = 3 B) I = 7; II = 5; III = 3 C) I = 7; II = 6; III = 3 D) I = 6; II = 6; III = 3 12) How many different kinds of protons are present in each of the following molecules?

A) I = 6; II = 3; III = 4 B) I = 5; II = 3; III = 4 C) I = 6; II = 4; III = 5 D) I = 6; II = 4; III = 4

13) How many different kinds of protons are present in each of the following compounds?

A) I = 2; II = 3; III = 4 B) I = 2; II = 3; III = 3 C) I = 3; II = 3; III = 3 D) I = 3; II = 3; III = 4 14) How many different kinds of protons are present in each of the following compounds?

A) I = 4; II = 4; III = 4 B) I = 4; II = 4; III = 5 C) I = 3; II = 3; III = 5 D) I = 3; II = 4; III = 5 15) Which of the labeled protons absorbs furthest upfield in the 1H NMR spectrum?

A) Ha B) Hb C) Hc D) Hd

16) Which of the following compounds does not show only one signal in its 1H NMR spectrum?

A) I B) II C) III D) IV 17) Which of the indicated protons in the molecules below would absorb furthest downfield in a 1H NMR spectrum?

A) I B) II C) III D) IV 18) Which of the labeled protons would absorb furthest downfield in a 1H NMR spectrum?

A) I B) II C) III D) IV

19) Which of the indicated protons would absorb furthest downfield in a 1H NMR spectrum?

A) I B) II C) III D) IV 20) Which compound does not give four sets of absorptions in its 1H NMR spectrum (i.e., which compound does not have four unique hydrogens)?

A) I B) II C) III D) IV

21) Compound X has a molecular formula C8H10 and gives the 1H NMR spectrum below. What is the structure of X?

A) A B) B C) C D) D 22) How many different kinds of protons are present in each of the following compounds?

A) a: 5; b: 6 B) a: 5; b: 5 C) a: 4; b: 6 D) a: 4; b: 5

23) Into how many peaks will the circled proton be split?

A) 5 B) 6 C) 7 D) 8 24) Which of the indicated protons absorbs furthest downfield?

A) Ha B) Hb C) Hc D) Hd 25) For each of the following compounds, indicate how many 13C NMR signals will be observed.

A) a: 4; b: 4; c: 7; d: 4 B) a: 5; b: 4; c: 7; d: 3 C) a: 4; b: 7; c: 7; d: 3 D) a: 5; b: 4; c: 6; d: 5 9 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

26) For each of the following compounds, indicate how many 13C NMR signals will be seen.

A) a: 3; b: 3; c: 5; d: 3 B) a: 4; b: 3; c: 5; d: 3 C) a: 3; b: 4; c: 5; d: 3 D) a: 4; b: 3; c: 3; d: 3 27) Which of the following compounds would give rise to a 13C spectrum with 6 peaks?

A) I B) II C) III D) IV

28) An unknown compound X has the empirical formula C3H6O and a molecular ion in its mass spectrum at 116. Compound X shows no IR absorption at 3200-3600 cm-1 but shows a peak at 1700 cm-1. The 1H NMR spectral data of X is shown below. What is the structure of compound X?

A) I B) II C) III D) IV 29) What is the relationship between Ha and Hb in the following compound?

A) Homotopic B) Enantiotopic C) Diastereotopic D) Mesotopic

30) What is the relationship between Ha and Hb in the following compound?

A) Homotopic B) Enantiotopic C) Diastereotopic D) Mesotopic 31) An unknown compound X has the molecular formula C6H14O. Compound X shows a strong peak in its IR spectrum at 3000 cm-1. The 1H NMR spectral data of compound X is given below. What is the structure of compound X?

A) I B) II C) III D) IV

32) An unknown compound X has the molecular formula C7H13OBr. Compound X shows a strong peak in its IR spectrum at 1700 cm-1. The 1H NMR spectral data of compound X is given below. What is the structure of compound X?

A) I B) II C) III D) IV 33) An unknown compound X has the molecular formula C6H12O2. Compound X shows a strong peak in its IR spectrum at 1700 cm-1. The 1H NMR spectral data of compound X is given below. What is the structure of compound X?

A) I B) II C) III D) IV

34) An unknown compound X has the molecular formula C6H14O. Compound X shows a peak in its IR spectrum at 3200-3600 cm-1. The 1H NMR spectral data for compound X is given below. What is the structure of compound X?

A) I B) II C) III D) IV 35) An unknown compound X has the molecular formula C10H11O2Br. Compound X shows a strong absorption in its IR spectrum at 1700 cm-1. The 1H NMR spectral data for compound X is given below. What is the structure of compound X?

A) Only I B) Only II C) Only III D) I or II

36) How could spectroscopy be used to distinguish between the following compounds?

A) Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm. B) Compound B has a peak at 3200-3500 cm-1 in its IR spectrum. C) Compound A has a peak in its IR spectrum at 2900 cm-1. D) Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm and compound B has a peak at 3200-3500 cm-1 in its IR spectrum. 37) An unknown compound A has the molecular formula C7H14O2. Compound A absorbs strongly in the IR at 1700 cm-1. The 1H NMR spectral data for compound A are given below. What is the structure of compound A?

A) I B) II C) III D) IV

38) An unknown compound A has the molecular formula C12H16O. Compound A absorbs strongly in the IR at 1700 cm-1. The NMR spectral data for compound A are given below. What is the structure of compound A?

A) I B) II C) III D) IV 39) Which of the following statements about 13C NMR is not true? A) In 13C proton-decoupled NMR spectra, all peaks are singlets. B) 13C NMR spectra display peaks for only carbons that bear hydrogen atoms. C) 13C NMR chemical shifts occur over a greater range than 1H NMR chemical shifts. D) 13C NMR easily differentiates between the different hybridized carbons (sp3, sp2, and sp hybridized carbons). 40) What region of the electromagnetic spectrum does nuclear magnet resonance spectroscopy use? A) Radio frequency B) Microwave frequency C) Infrared frequency D) Visible frequency E) Ultraviolet frequency

41) An unknown compound has the formula of C9H12. The following 1H NMR peaks were observed: Doublet at Δ 1.22 Septet at Δ 2.83 Multiplet at Δ 7.09 From the data above, pick the compound below that fits the spectra data.

A) I B) II C) III D) IV 42) Which of the following statements is true about electromagnetic radiation? A) All molecules absorb electromagnetic radiation at some frequency. B) Frequency is directly proportional to wavelength. C) NMR uses the microwave region of the electromagnetic spectrum. D) The radio frequency region of the electromagnetic spectrum has the largest energy per photon. E) Energy is inversely proportional to frequency. 43) Which of the following spectroscopy methods does not involve the interaction of organic molecules with electromagnetic radiation? A) Nuclear magnetic resonance B) Infrared spectroscopy C) Mass spectrometry D) Ultraviolet spectroscopy 44) What effect does increasing the operating frequency of a 1H NMR spectrum have on the value of chemical shift in Δ? A) Chemical shift in Δ will also increase. B) Chemical shift in Δ will decrease. C) Chemical shift in Δ will remain the same. D) It is not possible to predict the change in chemical shift in Δ. 45) What effect does increasing the operating frequency of a 1H NMR spectrum have on the frequency of an absorption in Hz? A) Frequency of an absorption in Hz will also increase. B) Frequency of an absorption in Hz will decrease. C) Frequency of an absorption in Hz will remain the same. D) It is not possible to predict the change in frequency of an absorption in Hz. 17 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

46) What effect does increasing the operating frequency of a 1H NMR spectrum have on the magnitude of a coupling constant J in Hz? A) Magnitude of coupling constant J in Hz will also increase. B) Magnitude of coupling constant J in Hz will decrease. C) Magnitude of coupling constant J in Hz will remain the same. D) It is not possible to predict the change in the magnitude of coupling constant J in Hz. 47) Which of the indicated protons absorbs further downfield?

A) HA B) HB C) HC D) HD 48) How many different kinds of protons are present in the following molecule?

A) 2 B) 3 C) 4 D) 5

49) How many different kinds of 13C peaks will be seen?

A) 2 B) 3 C) 4 D) 5 50) How many different kinds of protons are present in the following molecule?

A) 2 B) 3 C) 4 D) 5 51) How many different kinds of 13C peaks will be seen?

A) 2 B) 3 C) 4 D) 5

Organic Chemistry, 6e (Smith) Spectroscopy C Nuclear Magnetic Resonance Spectroscopy 1) How many unique protons are present in each of the following compounds?

A) I = 6; II = 3; III = 6 B) I = 5; II = 4; III = 6 C) I = 6, II = 4, III = 4 D) I = 6; II = 4; III = 6 Answer: C Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 2) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 2; II = 6; III = 1 B) I = 3; II = 5; III = 2 C) I = 1; II = 5; III = 1 D) I = 2; II = 6; III = 2 Answer: A Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

3) Into how many peaks will each of the circled protons be split? (Assume complete resolution of all NMR peaks is possible)

A) I = 3; II = 8; III = 1; IV = 4; V = 3 B) I = 9; II = 8; III = 2; IV = 4; V = 4 C) I = 4; II = 8; III = 2; IV = 4; V = 5 D) I = 4; Ii = 7; III = 2; IV = 4; V = 3 Answer: B Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 4) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 8; II = 4; III = 3; IV = 3 B) I = 7; II = 4; III = 3; IV = 4 C) I = 7; II = 3; III = 3; IV = 3 D) I = 7; II = 4; III = 2; IV = 4 Answer: B Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

5) How many different kinds of protons are present in each of the following molecules?

A) I = 3; II = 5; III = 5; IV = 4; V = 3 B) I = 4; II = 5; III = 4; IV = 4; V = 3 C) I = 4; II = 5; III = 5; IV = 4; V = 3 D) I = 4; II = 5; III = 5; IV = 3; V = 4 Answer: C Difficulty: 2 Medium Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 6) Into how many peaks will each of the circled protons be split? (Assume complete resolution of all NMR peaks is possible)

A) I = 3; II = 7; III = 4 B) I = 2; II = 7; III = 4 C) I = 2; II = 7; III = 3 D) I = 2; II = 6; III = 4 Answer: B Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

7) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 6; II = 2; III = 3 B) I = 7; II = 3; III = 3 C) I = 7; II = 1; III = 3 D) I = 7; II = 2; III = 3 Answer: D Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 8) How many peaks would be observed for each of the circled protons in the compounds below?

A) I = 1; II = 4; III = 7 B) I = 3; II = 3; III = 7 C) I = 2; II = 4; III = 7 D) I = 2; II = 4; III = 6 Answer: C Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

9) How many different kinds of protons are present in each of the following compounds?

A) I = 4; II = 3; III = 1 B) I = 4; II = 4; III = 1 C) I = 4; II = 4; III = 2 D) I = 3; II = 3; III = 1 Answer: A Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 10) How many different kinds of protons are present in each of the following compounds?

A) I = 2; II = 4; III = 6 B) I = 2; II = 4; III = 4 C) I = 3; II = 3; III = 5 D) I = 2; II = 4; III = 5 Answer: D Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

11) How many different kinds of protons are present in each of the following compounds?

A) I = 6; II = 5; III = 3 B) I = 7; II = 5; III = 3 C) I = 7; II = 6; III = 3 D) I = 6; II = 6; III = 3 Answer: B Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 12) How many different kinds of protons are present in each of the following molecules?

A) I = 6; II = 3; III = 4 B) I = 5; II = 3; III = 4 C) I = 6; II = 4; III = 5 D) I = 6; II = 4; III = 4 Answer: A Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

13) How many different kinds of protons are present in each of the following compounds?

A) I = 2; II = 3; III = 4 B) I = 2; II = 3; III = 3 C) I = 3; II = 3; III = 3 D) I = 3; II = 3; III = 4 Answer: C Difficulty: 2 Medium Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 14) How many different kinds of protons are present in each of the following compounds?

A) I = 4; II = 4; III = 4 B) I = 4; II = 4; III = 5 C) I = 3; II = 3; III = 5 D) I = 3; II = 4; III = 5 Answer: D Difficulty: 2 Medium Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

15) Which of the labeled protons absorbs furthest upfield in the 1H NMR spectrum?

A) Ha B) Hb C) Hc D) Hd Answer: D Difficulty: 2 Medium Section: C.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 16) Which of the following compounds does not show only one signal in its 1H NMR spectrum?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

17) Which of the indicated protons in the molecules below would absorb furthest downfield in a 1H NMR spectrum?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: C.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 18) Which of the labeled protons would absorb furthest downfield in a 1H NMR spectrum?

A) I B) II C) III D) IV Answer: D Difficulty: 2 Medium Section: C.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

19) Which of the indicated protons would absorb furthest downfield in a 1H NMR spectrum?

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: C.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 20) Which compound does not give four sets of absorptions in its 1H NMR spectrum (i.e., which compound does not have four unique hydrogens)?

A) I B) II C) III D) IV Answer: C Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

21) Compound X has a molecular formula C8H10 and gives the 1H NMR spectrum below. What is the structure of X?

A) A B) B C) C D) D Answer: B Difficulty: 1 Easy Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

22) How many different kinds of protons are present in each of the following compounds?

A) a: 5; b: 6 B) a: 5; b: 5 C) a: 4; b: 6 D) a: 4; b: 5 Answer: C Difficulty: 2 Medium Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 23) Into how many peaks will the circled proton be split?

A) 5 B) 6 C) 7 D) 8 Answer: C Difficulty: 1 Easy Section: C.06 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

24) Which of the indicated protons absorbs furthest downfield?

A) Ha B) Hb C) Hc D) Hd Answer: A Difficulty: 2 Medium Section: C.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 25) For each of the following compounds, indicate how many 13C NMR signals will be observed.

A) a: 4; b: 4; c: 7; d: 4 B) a: 5; b: 4; c: 7; d: 3 C) a: 4; b: 7; c: 7; d: 3 D) a: 5; b: 4; c: 6; d: 5 Answer: B Difficulty: 1 Easy Section: C.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 13 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

26) For each of the following compounds, indicate how many 13C NMR signals will be seen.

A) a: 3; b: 3; c: 5; d: 3 B) a: 4; b: 3; c: 5; d: 3 C) a: 3; b: 4; c: 5; d: 3 D) a: 4; b: 3; c: 3; d: 3 Answer: B Difficulty: 1 Easy Section: C.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 27) Which of the following compounds would give rise to a 13C spectrum with 6 peaks?

A) I B) II C) III D) IV Answer: B Difficulty: 1 Easy Section: C.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

A) I B) II C) III D) IV Answer: A Difficulty: 1 Easy Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

29) What is the relationship between Ha and Hb in the following compound?

A) Homotopic B) Enantiotopic C) Diastereotopic D) Mesotopic Answer: A Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 30) What is the relationship between Ha and Hb in the following compound?

A) Homotopic B) Enantiotopic C) Diastereotopic D) Mesotopic Answer: B Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

31) An unknown compound X has the molecular formula C6H14O. Compound X shows a strong peak in its IR spectrum at 3000 cm-1. The 1H NMR spectral data of compound X is given below. What is the structure of compound X?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

33) An unknown compound X has the molecular formula C6H12O2. Compound X shows a strong peak in its IR spectrum at 1700 cm-1. The 1H NMR spectral data of compound X is given below. What is the structure of compound X?

A) I B) II C) III D) IV Answer: A Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

35) An unknown compound X has the molecular formula C10H11O2Br. Compound X shows a strong absorption in its IR spectrum at 1700 cm-1. The 1H NMR spectral data for compound X is given below. What is the structure of compound X?

A) Only I B) Only II C) Only III D) I or II Answer: D Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

36) How could spectroscopy be used to distinguish between the following compounds?

A) Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm. B) Compound B has a peak at 3200-3500 cm-1 in its IR spectrum. C) Compound A has a peak in its IR spectrum at 2900 cm-1. D) Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm and compound B has a peak at 3200-3500 cm-1 in its IR spectrum. Answer: B Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 37) An unknown compound A has the molecular formula C7H14O2. Compound A absorbs strongly in the IR at 1700 cm-1. The 1H NMR spectral data for compound A are given below. What is the structure of compound A?

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 22 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

A) I B) II C) III D) IV Answer: B Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 39) Which of the following statements about 13C NMR is not true? A) In 13C proton-decoupled NMR spectra, all peaks are singlets. B) 13C NMR spectra display peaks for only carbons that bear hydrogen atoms. C) 13C NMR chemical shifts occur over a greater range than 1H NMR chemical shifts. D) 13C NMR easily differentiates between the different hybridized carbons (sp3, sp2, and sp hybridized carbons). Answer: B Difficulty: 1 Easy Section: C.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C Accessibility: Keyboard Navigation

40) What region of the electromagnetic spectrum does nuclear magnet resonance spectroscopy use? A) Radio frequency B) Microwave frequency C) Infrared frequency D) Visible frequency E) Ultraviolet frequency Answer: A Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 1. Remember Chapter: Spectroscopy C Accessibility: Keyboard Navigation 41) An unknown compound has the formula of C9H12. The following 1H NMR peaks were observed: Doublet at Δ 1.22 Septet at Δ 2.83 Multiplet at Δ 7.09 From the data above, pick the compound below that fits the spectra data.

A) I B) II C) III D) IV Answer: C Difficulty: 2 Medium Section: C.10 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

42) Which of the following statements is true about electromagnetic radiation? A) All molecules absorb electromagnetic radiation at some frequency. B) Frequency is directly proportional to wavelength. C) NMR uses the microwave region of the electromagnetic spectrum. D) The radio frequency region of the electromagnetic spectrum has the largest energy per photon. E) Energy is inversely proportional to frequency. Answer: A Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C Accessibility: Keyboard Navigation 43) Which of the following spectroscopy methods does not involve the interaction of organic molecules with electromagnetic radiation? A) Nuclear magnetic resonance B) Infrared spectroscopy C) Mass spectrometry D) Ultraviolet spectroscopy Answer: C Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C Accessibility: Keyboard Navigation 44) What effect does increasing the operating frequency of a 1H NMR spectrum have on the value of chemical shift in Δ? A) Chemical shift in Δ will also increase. B) Chemical shift in Δ will decrease. C) Chemical shift in Δ will remain the same. D) It is not possible to predict the change in chemical shift in Δ. Answer: C Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: Spectroscopy C Accessibility: Keyboard Navigation 25 Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education.

45) What effect does increasing the operating frequency of a 1H NMR spectrum have on the frequency of an absorption in Hz? A) Frequency of an absorption in Hz will also increase. B) Frequency of an absorption in Hz will decrease. C) Frequency of an absorption in Hz will remain the same. D) It is not possible to predict the change in frequency of an absorption in Hz. Answer: A Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: Spectroscopy C Accessibility: Keyboard Navigation 46) What effect does increasing the operating frequency of a 1H NMR spectrum have on the magnitude of a coupling constant J in Hz? A) Magnitude of coupling constant J in Hz will also increase. B) Magnitude of coupling constant J in Hz will decrease. C) Magnitude of coupling constant J in Hz will remain the same. D) It is not possible to predict the change in the magnitude of coupling constant J in Hz. Answer: C Difficulty: 1 Easy Section: C.01 Topic: Analytical/Spectroscopy Bloom's: 2. Understand Chapter: Spectroscopy C Accessibility: Keyboard Navigation

47) Which of the indicated protons absorbs further downfield?

A) HA B) HB C) HC D) HD Answer: D Difficulty: 2 Medium Section: C.03 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 48) How many different kinds of protons are present in the following molecule?

A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

49) How many different kinds of 13C peaks will be seen?

A) 2 B) 3 C) 4 D) 5 Answer: D Difficulty: 1 Easy Section: C.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C 50) How many different kinds of protons are present in the following molecule?

A) 2 B) 3 C) 4 D) 5 Answer: B Difficulty: 1 Easy Section: C.02 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

51) How many different kinds of 13C peaks will be seen?

A) 2 B) 3 C) 4 D) 5 Answer: B Difficulty: 1 Easy Section: C.11 Topic: Analytical/Spectroscopy Bloom's: 3. Apply Chapter: Spectroscopy C

Organic Chemistry 6th Edition by Janice G Smith. All Chapters 1-29 | TEST BANK