HAPTER 16ALDEHYDES AND KETONES

MULTIPLE CHOICE
1. What is the IUPAC name of the following compound?

a.
b.
c.
d.

3-methyl-3-phenylpropanol
3-phenylbutanal
3-phenyl-1-butanone
3-phenylbutanoic acid

ANS: B
2. What is the IUPAC name of the following compound?

a.
b.
c.
d.

4-phenyl-3-hexanone
3-phenyl-4-hexanone
1,2-diethyl-2-phenylethanal
1-methyl-1-phenyl-2-butanone

ANS: A
3. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(E)-4-methyl-4-hepten-3-one
(Z)-4-methyl-4-hepten-3-one
(E)-4-methyl-3-hepten-5-one
(Z)-4-methyl-3-hepten-5-one

ANS: A

Brown Organic Chemistry 6e

Test Bank

4. What is the IUPAC name of the following compound?

a.
b.
c.
d.

4,4-diethyl-3-buten-2-one
4-ethyl-3-hexen-2-one
(Z)-4-ethyl-3-hexen-2-one
3-ethyl-4-hexen-5-one

ANS: B
5. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(2S,4R)-dimethylpentanal
(2S,4S)-dimethylpentanal
(R)-2,4-dimethylpentanal
(S)-2,4-dimethylpentanal

ANS: D
6. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(S)-3,4,4-trimethylpentanal
(R)-3,4,4-trimethylpentanal
(R)-3-tert-butyl-3-methylpropanal
(R)-3-tert-butylbutanal

ANS: B
7. What is the correct assignment of the names of the following ketones?

Brown Organic Chemistry 6e

Test Bank

a.
b.
c.
d.

1 = acetone; 2 = phenol; 3 = benzaldehyde

1 = acetone; 2 = acetophenone; 3 = benzophenone
1 = formaldehyde; 2 = benzaldehyde; 3 = acetophenone
1 = acetaldehyde; 2 = acetophenone; 3 = benzaldehyde

ANS: B
8. What is the correct assignment of the names of the following aldehydes and ketones?

a.
b.
c.
d.

1 = acetone; 2 = acetaldehyde; 3 = formaldehyde

1 = acetaldehyde; 2 = acetophenone; 3 = benzophenone
1 = formaldehyde; 2 = acetaldehyde; 3 = acetone
1 = acetaldehyde; 2 = acetone; 3 = acetophenone

ANS: C
9. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2,3-dimethyl-3-heptanol
2,4-dimethyl-4-heptanol
3,5-dimethyl-4-heptanol
3,5-dimethyl-3-heptanol

ANS: B
10. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2,3-dimethyl-3-heptanol
2,4-dimethyl-4-heptanol
2,5-dimethyl-4-heptanol
2,5-dimethyl-3-heptanol

ANS: C

Brown Organic Chemistry 6e

Test Bank

11. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-phenyl-2-butanol
3-phenyl-2-butanol
3-phenylbutanone
propiophenone, PhCOCH2CH3

ANS: A
12. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1-phenyl-1-butanol
1-phenyl-2-butanol
2-phenyl-1-butanol
butyrophenone, PhCOCH2CH2CH3

ANS: A
13. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following
product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl
compound?

Brown Organic Chemistry 6e

Test Bank

a.
b.
c.
d.

only 1
only 3
only 1 and 4
only 2 and 3

ANS: D
14. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following
product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl
compound?

a.
b.
c.
d.

only 1
only 3
only 1 and 3
only 2 and 4

ANS: B
15. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following
product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl
compound?

Brown Organic Chemistry 6e

Test Bank

a.
b.
c.
d.

only 1 and 2
only 3 and 4
only 2 and 3
only 1, 2 and 3

ANS: D
16. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following
product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl
compound?

a.
b.
c.
d.

only 1 and 2
only 3 and 4
only 2 and 3
only 1, 2 and 3

ANS: A
17. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

Brown Organic Chemistry 6e

Test Bank

ANS: B
18. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: A
19. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
20. What is the major organic product obtained from the following reaction?

Brown Organic Chemistry 6e

Test Bank

a.
b.
c.
d.

1
2
3
4

ANS: A
21. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1-butene
2-butene
2-methylpropene
2-methyl-1-propanol

ANS: C
22. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-methyl-2-heptene
3-ethyl-2-pentene
(Z) 2-methyl-3-heptene
(E) 2-methyl-3-heptene

ANS: B
23. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

(E)-3-methyl-2-pentene
(Z)-3-methyl-2-pentene
2-methyl-2-pentene
4-methyl-1-pentene

ANS: C

Brown Organic Chemistry 6e

Test Bank

24. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

(E)-3-methyl-2-pentene
(Z)-3-methyl-2-pentene
2-methyl-2-pentene
4-methyl-1-pentene

ANS: C
25. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following
product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

a.
b.
c.
d.

only 1 and 2
only 2 and 4
only 2 and 3
only 1, 2 and 3

ANS: B

Brown Organic Chemistry 6e

Test Bank

26. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following
product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

a.
b.
c.
d.

only 1 and 2
only 1 and 3
only 2 and 4
only 1, 2 and 3

ANS: A
27. Which of the following is not true about the Wittig reaction?
a. triphenylphosphine reacts with 2 alkyl bromides by an SN2 reaction to give an
alkyltriphenylphosphonium bromide
b. alkyltriphenylphosphonium bromides are deprotonated by strong bases to give a
phosphonium ylide
c. phosphonium ylids are nucleophilic
d. the product of the Wittig reaction is an alkyne
ANS: D
28. Which of the following is the best description of the overall transformation involved in a Wittig
reaction?
a. addition
b. substitution
c. elimination
d. rearrangement
ANS: B

Brown Organic Chemistry 6e

Test Bank

10

29. What is the correct assignment of the names of the following functional groups?

a.
b.
c.
d.

1 = enol; 2 = hydrate; 3 = acetal; 4 = hemiacetal

1 = acetal; 2 = hydrate; 3 = enol; 4 = hemiacetal
1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol
1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol

ANS: C
30. What is the correct assignment of the names of the following functional groups?

a.
b.
c.
d.

1 = acetal; 2 = hydrate; 3 = acetal; 4 = hemiacetal

1 = acetal; 2 = enol; 3 = hydrate; 4 = hemiacetal
1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol
1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol

ANS: B
31. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D

Brown Organic Chemistry 6e

Test Bank

11

32. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
33. Which ketone-diol undergoes cyclization to form the following acetal?

a.
b.
c.
d.

1
2
3
4

ANS: A

Brown Organic Chemistry 6e

Test Bank

12

34. Which ketone-diol undergoes cyclization to form the following acetal?

a.
b.
c.
d.

1
2
3
4

ANS: D
35. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: B

Brown Organic Chemistry 6e

Test Bank

13

36. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C
37. What is the correct assignment of the names of the following functional groups?

a.
b.
c.
d.

1 = imine; 2 = amine; 3 = hydrazone; 4 = oxime

1 = hydrazone; 2 = amine; 3 = imine; 4 = oxime
1 = oxime; 2 = imine; 3 = amine; 4 = hydrazone
1 = imine; 2 = hydrazone; 3 = oxime; 4 = amine

ANS: B
38. What is the correct assignment of the names of the following functional groups?

a.
b.
c.
d.

1 = imine; 2 = amine; 3 = hydrazone; 4 = oxime

1 = hydrazone; 2 = amine; 3 = imine; 4 = oxime
1 = oxime; 2 = imine; 3 = amine; 4 = hydrazone
1 = imine; 2 = hydrazone; 3 = oxime; 4 = amine

ANS: C

Brown Organic Chemistry 6e

Test Bank

14

39. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
40. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D
41. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A

Brown Organic Chemistry 6e

Test Bank

15

42. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C
43. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: B

Brown Organic Chemistry 6e

Test Bank

16

44. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C
45. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
46. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

Brown Organic Chemistry 6e

Test Bank

17

ANS: B
47. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C
48. Which combination(s) of amine and carbonyl compound can be used to prepare the following product
by reductive amination?

a.
b.
c.
d.

only 1 and 2
only 2 and 4
only 2 and 3
only 1, 2 and 3

ANS: A

Brown Organic Chemistry 6e

Test Bank

18

49. Which combination(s) of amine and carbonyl compound can be used to prepare the following product
by reductive amination?

a.
b.
c.
d.

only 1
only 3
only 1 and 3
only 1, 2 and 4

ANS: B
50. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: B
51. What is the major organic product obtained from the following reaction?

Brown Organic Chemistry 6e

Test Bank

19

a.
b.
c.
d.

1
2
3
4

ANS: D
52. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-pentanol
pentane
1-pentene
(E) 2-pentene

ANS: A
53. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-methypentane
4-methyl-2-pentanol
4-methyl-1-pentene
(E) 4-methyl-2-pentene

ANS: B
54. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-pentanone
(E)-3-penten-2-ol
2-pentanol
4-hydroxy-2-pentanone

ANS: B

Brown Organic Chemistry 6e

Test Bank

20

55. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-pentanone
(E)-3-penten-2-ol
2-pentanol
4-hydroxy-2-pentanone

ANS: A
56. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-pentanone
(E)-3-penten-2-ol
2-pentanol
4-hydroxy-2-pentanone

ANS: C
57. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: C

Brown Organic Chemistry 6e

Test Bank

21

58. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D
59. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: A

Brown Organic Chemistry 6e

Test Bank

22

60. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: C
61. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: A

Brown Organic Chemistry 6e

Test Bank

23

62. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: C
63. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: B

Brown Organic Chemistry 6e

Test Bank

24

64. What is the major organic product obtained from the following sequence of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: A
65. What is the relationship between the following two structures?

a.
b.
c.
d.

tautomers
constitutional isomers, but not tautomers
resonance structures
stereoisomers

ANS: A
66. What is the relationship between the following two structures?

a.
b.
c.
d.

tautomers
constitutional isomers, but not tautomers
resonance structures
stereoisomers

ANS: C

Brown Organic Chemistry 6e

Test Bank

25

67. What is the relationship between the following two structures?

a.
b.
c.
d.

tautomers
constitutional isomers, but not tautomers
resonance structures
stereoisomers

ANS: A
68. Which of the following has the highest Keq for enolization?

a.
b.
c.
d.

1
2
3
4

ANS: C
69. Which of the following has the highest Keq for enolization?

a.
b.
c.
d.

1
2
3
4

ANS: C
70. What type of reaction takes place upon treatment of a ketone with HCN to form a cyanohydrin?
a. nucleophilic addition
b. electrophilic addition
c. nucleophilic substitution
d. electrophilic substitution
ANS: A

Brown Organic Chemistry 6e

Test Bank

26

71. Which of the following is the best description of the mechanism of the reaction between a ketone and
an amine to form an imine?
a. concerted bimolecular substitution
b. nucleophilic addition followed by elimination
c. elimination followed by nucleophilic addition
d. electrophilic addition followed by rearrangement
ANS: B
72. Which of the following statements is not true?
a. The carbon atom of a carbonyl group is electrophilic
b. In general, aldehydes are more electrophilic than ketones
c. Nucleophilic addition to carbonyl groups can be catalyzed by acid or base
d. Addition of a nucleophile to a carbonyl group changes the hybridization of the carbonyl
carbon from sp3 to sp2 hybridization
ANS: D
73. Which of the following statements is not true?
a. Reaction of benzophenone with methanol in the presence of acid gives a acetal
b. Reaction of butanal with ethanol in the presence of base gives an acetal
c. Reaction of benzaldehyde with ethanol in the presence of acid gives an acetal
d. Reaction of acetone with methanol in the presence of base gives a hemiacetal
ANS: B
74. Which of the following statements is not true?
a. The reaction of a ketone with methanol in the presence of acid to give a acetal proceeds
via a resonance stabilized cation
b. Protonation of a ketone increases its electrophilicity
c. The conversion of a hemiacetal to an acetal under acidic conditions proceeds via an SN1
mechanism
d. The conversion of a hemiacetal to an acetal is catalyzed by both acid and base
ANS: D
75. Which of the following is a reactive intermediate in the reaction of acetone with bromine in acetic acid
to form 1-bromo-2-propanone?
a. carbanion
b. enol
c. enolate
d. radical
ANS: B
76. Which of the following is a reactive intermediate in the base-catalyzed racemization of (R)-3-phenyl2-butanone?
a. carbanion
b. enol
c. enolate
d. radical
ANS: C

77. What is the reactivity of Br2 in the acid-catalyzed bromination of acetophenone?

Brown Organic Chemistry 6e

Test Bank

27

a.
b.
c.
d.

acid
base
nucleophile
electrophile

ANS: D
PROBLEM
1. What is the IUPAC name of the following compound?

ANS:
(S)-2-chloropentanal
2. What is the IUPAC name of the following compound?

ANS:
(S)-3-methyl-2-pentanone
3. What is the major organic product obtained from the following reaction?

ANS:

4. What is the major organic product obtained from the following reaction?

Brown Organic Chemistry 6e

Test Bank

28

ANS:

5. What is the major organic product obtained from the following reaction?

ANS:

6. What is the major organic product obtained from the following reaction?

ANS:

7. What is the major organic product obtained from the following reaction?

ANS:

8. What is the major organic product obtained from the following reaction?

Brown Organic Chemistry 6e

Test Bank

29

ANS:

9. What is the major organic product obtained from the following reaction?

ANS:

10. What is the major organic product obtained from the following reaction?

ANS:

11. What is the major organic product obtained from the following reaction?

ANS:

Brown Organic Chemistry 6e

Test Bank

30

12. What is the major organic product obtained from the following reaction?

ANS:

13. What is the major organic product obtained from the following reaction?

ANS:

14. What is the major organic product obtained from the following reaction?

ANS:

15. What is the major organic product obtained from the following reaction?

ANS:

Brown Organic Chemistry 6e

Test Bank

31

16. What is the major organic product obtained from the following sequence of reactions?

ANS:

17. What is the major organic product obtained from the following sequence of reactions?

ANS:

18. What is the major organic product obtained from the following sequence of reactions?

ANS:

Brown Organic Chemistry 6e

Test Bank

32

19. What is the major organic product obtained from the following sequence of reactions?

ANS:

Brown Organic Chemistry 6e

Test Bank

33