chapter 16

Brown Organic Chemistry 6e Test Bank 1

HAPTER 16ALDEHYDES AND KETONES

MULTIPLE CHOICE

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

a. 3-methyl-3-phenylpropanol

b. 3-phenylbutanal

c. 3-phenyl-1-butanone

d. 3-phenylbutanoic acid

ANS: B


a. 4-phenyl-3-hexanone

b. 3-phenyl-4-hexanone

c. 1,2-diethyl-2-phenylethanal

d. 1-methyl-1-phenyl-2-butanone

ANS: A


a. (E)-4-methyl-4-hepten-3-one

b. (Z)-4-methyl-4-hepten-3-one

c. (E)-4-methyl-3-hepten-5-one

d. (Z)-4-methyl-3-hepten-5-one

ANS: A



a. 4,4-diethyl-3-buten-2-one

b. 4-ethyl-3-hexen-2-one

c. (Z)-4-ethyl-3-hexen-2-one

d. 3-ethyl-4-hexen-5-one

ANS: B


a. (2S,4R)-dimethylpentanal

b. (2S,4S)-dimethylpentanal

c. (R)-2,4-dimethylpentanal

d. (S)-2,4-dimethylpentanal

ANS: D


a. (S)-3,4,4-trimethylpentanal

b. (R)-3,4,4-trimethylpentanal

c. (R)-3-tert-butyl-3-methylpropanal

d. (R)-3-tert-butylbutanal

ANS: B

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


a. 1 = acetone; 2 = phenol; 3 = benzaldehyde

b. 1 = acetone; 2 = acetophenone; 3 = benzophenone

c. 1 = formaldehyde; 2 = benzaldehyde; 3 = acetophenone

d. 1 = acetaldehyde; 2 = acetophenone; 3 = benzaldehyde

ANS: B

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

a. 1 = acetone; 2 = acetaldehyde; 3 = formaldehyde

b. 1 = acetaldehyde; 2 = acetophenone; 3 = benzophenone

c. 1 = formaldehyde; 2 = acetaldehyde; 3 = acetone

d. 1 = acetaldehyde; 2 = acetone; 3 = acetophenone

ANS: C

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

a. 2,3-dimethyl-3-heptanol

b. 2,4-dimethyl-4-heptanol

c. 3,5-dimethyl-4-heptanol

d. 3,5-dimethyl-3-heptanol

ANS: B


a. 2,3-dimethyl-3-heptanol

b. 2,4-dimethyl-4-heptanol

c. 2,5-dimethyl-4-heptanol

d. 2,5-dimethyl-3-heptanol

ANS: C



a. 2-phenyl-2-butanol

b. 3-phenyl-2-butanol

c. 3-phenylbutanone

d. propiophenone, PhCOCH2CH3

ANS: A


a. 1-phenyl-1-butanol

b. 1-phenyl-2-butanol

c. 2-phenyl-1-butanol

d. 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?


a. only 1

b. only 3

c. only 1 and 4

d. only 2 and 3

ANS: D



compound?

a. only 1

b. only 3

c. only 1 and 3

d. only 2 and 4

ANS: B



compound?


a. only 1 and 2

b. only 3 and 4

c. only 2 and 3

d. only 1, 2 and 3

ANS: D



compound?

a. only 1 and 2

b. only 3 and 4

c. only 2 and 3

d. only 1, 2 and 3

ANS: A


a. 1 b. 2 c. 3 d. 4


ANS: B

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

a. 1 b. 2 c. 3 d. 4

ANS: A


a. 1 b. 2 c. 3 d. 4

ANS: A



a. 1 b. 2 c. 3 d. 4

ANS: A


a. 1-butene

b. 2-butene

c. 2-methylpropene

d. 2-methyl-1-propanol

ANS: C


a. 2-methyl-2-heptene

b. 3-ethyl-2-pentene

c. (Z) 2-methyl-3-heptene

d. (E) 2-methyl-3-heptene

ANS: B


a. (E)-3-methyl-2-pentene

b. (Z)-3-methyl-2-pentene

c. 2-methyl-2-pentene

d. 4-methyl-1-pentene

ANS: C



a. (E)-3-methyl-2-pentene

b. (Z)-3-methyl-2-pentene


d. 4-methyl-1-pentene

ANS: C


product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

a. only 1 and 2

b. only 2 and 4

c. only 2 and 3

d. only 1, 2 and 3

ANS: B



product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

a. only 1 and 2

b. only 1 and 3

c. only 2 and 4

d. 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


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

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

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

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

d. 1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol

ANS: C


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

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

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

d. 1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol

ANS: B


a. 1 b. 2 c. 3 d. 4

ANS: D



a. 1 b. 2 c. 3 d. 4

ANS: A

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

a. 1 b. 2 c. 3 d. 4

ANS: A


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

a. 1 b. 2 c. 3 d. 4

ANS: D


a. 1 b. 2 c. 3 d. 4

ANS: B



a. 1 b. 2 c. 3 d. 4

ANS: C


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

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

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

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

ANS: B


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

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

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

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

ANS: C



a. 1 b. 2 c. 3 d. 4

ANS: A


a. 1 b. 2 c. 3 d. 4

ANS: D


a. 1 b. 2 c. 3 d. 4

ANS: A



a. 1 b. 2 c. 3 d. 4

ANS: C


a. 1 b. 2 c. 3 d. 4

ANS: B



a. 1 b. 2 c. 3 d. 4

ANS: C


a. 1 b. 2 c. 3 d. 4

ANS: A


a. 1 b. 2 c. 3 d. 4


ANS: B


a. 1 b. 2 c. 3 d. 4

ANS: C

48. Which combination(s) of amine and carbonyl compound can be used to prepare the following product

by reductive amination?

a. only 1 and 2

b. only 2 and 4

c. only 2 and 3

d. only 1, 2 and 3

ANS: A


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

by reductive amination?

a. only 1

b. only 3

c. only 1 and 3

d. only 1, 2 and 4

ANS: B


a. 1 b. 2 c. 3 d. 4

ANS: B



a. 1 b. 2 c. 3 d. 4

ANS: D


a. 2-pentanol

b. pentane

c. 1-pentene

d. (E) 2-pentene

ANS: A


a. 2-methypentane

b. 4-methyl-2-pentanol


d. (E) 4-methyl-2-pentene

ANS: B


a. 2-pentanone

b. (E)-3-penten-2-ol

c. 2-pentanol

d. 4-hydroxy-2-pentanone

ANS: B



a. 2-pentanone


c. 2-pentanol


ANS: A


a. 2-pentanone


c. 2-pentanol


ANS: C


a. 1 b. 2 c. 3 d. 4

ANS: C



a. 1 b. 2 c. 3 d. 4

ANS: D


a. 1 b. 2 c. 3 d. 4

ANS: A



a. 1 b. 2 c. 3 d. 4

ANS: C


a. 1 b. 2 c. 3 d. 4

ANS: A



a. 1 b. 2 c. 3 d. 4

ANS: C


a. 1 b. 2 c. 3 d. 4

ANS: B



a. 1 b. 2 c. 3 d. 4

ANS: A

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

a. tautomers

b. constitutional isomers, but not tautomers

c. resonance structures

d. stereoisomers

ANS: A


a. tautomers



d. stereoisomers

ANS: C



a. tautomers



d. stereoisomers

ANS: A

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

a. 1 b. 2 c. 3 d. 4

ANS: C

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

a. 1 b. 2 c. 3 d. 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


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 sp

2 hybridization

ANS: D


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


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-phenyl-

2-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?


a. acid

b. base

c. nucleophile

d. electrophile

ANS: D

PROBLEM


ANS:

(S)-2-chloropentanal


ANS:

(S)-3-methyl-2-pentanone


ANS:



ANS:


ANS:


ANS:


ANS:




ANS:


ANS:


ANS:



ANS:

chapter 16

Documents

following compound

following product

heptanol ans

acetophenone ans

following reaction

dimethylpentanal ans

following ketones

following aldehydes