Ch19 Verified Test Bank Aldehydes And Ketones

Organic Chemistry, 4e (Klein)

Chapter 19 Aldehydes and Ketones

1) Name the aldehyde or ketone that is found in nail polish remover.

A) ethanol

B) 2-butanone

C) acetone

D) formaldehyde

E) diethyl ether

Diff: 1

Learning Objective: 19.1 Compare the structures of an aldehyde and a ketone

2) Name the aldehyde or ketone that is used as a preservative.

A) ethanol

B) 2-butanone

C) acetone

D) formaldehyde

E) diethyl ether

Diff: 1

Learning Objective: 19.1 Compare the structures of an aldehyde and a ketone

3) What is the IUPAC name for the compound shown?

A) 2-methyl-5-heptanone

B) 7-methyl-4-octanone

C) 6-isopropyl-4-octanone

D) isobutyl propyl ketone

E) 1,1-dimethyl-4-heptanone

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

4) What is the correct structure for 5-methyl-4-octanone?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

5) What is the IUPAC name for the compound shown?

A) 3,3,-dimethyl-6-heptanone

B) 3,3-methyl-6-heptanone

C) 3-dimethyl-6-heptanone

D) 5,5-dimethyl-2-heptanone

E) 5,5-methyl-2-heptanone

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

6) What is the IUPAC name for the compound shown?

A) 2,5-dimethyl-6-hexanal

B) 2,5-dimethylhexanal

C) 1,4-dimethylpentanal

D) 1,4-dimethylhexanal

E) none of these

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

7) What is the structure of 4-methylbenzaldehyde?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

8) What is the IUPAC name for the compound shown?

A) 5,5-dimethyl-2-heptanone

B) 5,5-dimethylcycloheptanone

C) 4,4-dimethylcycloheptanone

D) 3,3-dimethylcycloheptanone

E) 1,1-dimethyl-4-cycloheptanone

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

9) What is the IUPAC name for the compound shown?

A) 2,4-dimethyl-2-pentenone

B) 2,5-dimethylcyclopenten-3-one

C) 2,4-dimethylcyclopent-2-enone

D) 3,5-dimethylcyclopent-2-enone

E) 2-methyl-5-methylcyclopent-2-enone

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

10) What is the structure of 2,3-dimethyl-2-octen-4-one?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

11) What is the IUPAC name for the compound shown?

A) 4-benzylbutanal

B) 3-phenylpropanal

C) 3-benzylpropanal

D) 4-phenylbutanal

E) 2-benzylethanal

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

12) What is the structure for 5-hydroxy-2-phenyl-3-hexanone?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

13) What is the IUPAC name for the compound shown?

A) 4-chloro-3-methylbenzaldehyde

B) 4-chloro-3-methylcyclohexan-1-one

C) 1-chloro-2-methyl-4-benzaldehyde

D) 1-chloro-2-methylbenzaldehyde

E) 4-chloro-3-methylcyclahexanone

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

14) What is the structure of m-nitroacetophenone?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

15) What is the IUPAC name for the compound shown?

A) (S)-2-methyl-2-bromobutanone

B) (S)-2-bromo-2-methylcyclobutanone

C) (R)-2-bromo-2-methylcyclobutanone

D) (S)-1-bromo-1-methyl-2-cyclobutanone

E) (R)-1-bromo-1-methyl-2-cyclobutanone

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

16) What is the structure of (S)-3-chlorocyclohexanone?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

18) What is the structure of 7-bromo-1-octyn-4-one?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

19) What is the IUPAC name for the compound shown?

A) 4-oxo-5-phenyl-2-hexanol

B) 5-hydroxy-2-phenyl-3-hexanone

C) 2-hydroxy-5-phenyl-4-hexanone

D) 2-hydroxypropyl-1-phenylethyl ketone

E) 5-hydroxy-3-keto-2-phenylhexane

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

20) What is the IUPAC name for the compound shown?

A) (2R,3R)-2-isopropyl-3-methylcyclohexanone

B) (2S,3S)-2-isopropyl-3-methylcyclohexanone

C) (2S,3R)-2-isopropyl-3-methylcyclohexanone

D) (2R,3S)-2-isopropyl-3-methylcyclohexanone

E) (2R)-2-isopropyl-3-methylcyclohexanone

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

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

A) (R)-6-bromo-2-heptanal

B) (S)-6-bromo-2-heptanal

C) (R)-6-bromo-2-heptanone

D) (S)-6-bromo-2-heptanone

E) (R)-2-bromo-6-heptanone

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

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

A) 5-cyclohexyl-2-hexanal

B) 5-cyclohexyl-2-hexanone

C) 5-cyclohexyl-5-methyl-2-pentanone

D) 5-(1-methylcyclohexyl)-2-pentanone

E) 4-(1-methylcyclohexyl)-2-butanone

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

23) What is the structure of benzophenone?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

24) What is the IUPAC name for the compound shown?

A) (2R,4S)-2,4-methylpentanedial

B) (2S,4R)-2,4-dimethylpentanedial

C) (2R,4S)-2,4-dimethylpentanedial

D) (2S,4S)-2,4-dimethylpentanedial

E) (2R,4R)-2,4-dimethylpentanedial

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

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

A) (3R,5R)-3,5-dimethyl-2,6-heptanone

B) (3S,5S)-3,5-dimethyl-2,6-heptanone

C) (3S,5R)-3,5-dimethyl-2,6-heptanedione

D) (3R,5S)-3,5-dimethyl-2,6-heptanedione

E) (3R,5R)-3,5-dimethyl-2,6-heptanedione

Diff: 3

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

26) What is the IUPAC name for the compound shown?

A) 1,2-cyclohexanediol

B) 1,2-hexanodione

C) 1,2-cyclohexanone

D) 1,2-cyclodihexanone

E) 1,2-cyclohexanedione

Diff: 2

Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC system of nomenclature

27) What is the predicted product of the reaction shown?

A) hexanal

B) hexanoic acid

C) 2-hexanone

D) 2-chlorohexane

E) 1-hexanol

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

28) What is the predicted product of the reaction shown?

A) hexanal

B) hexanoic acid

C) 2-hexanone

D) 2-chlorohexane

E) 1-hexanol

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

29) What is the predicted product of the reaction shown?

A) hexanal

B) hexanoic acid

C) 2-hexanone

D) 2-chlorohexane

E) 1-hexanol

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

30) What is the predicted product of the reaction shown?

A) hexanal

B) hexanoic acid

C) 2-hexanone

D) 2-chlorohexane

E) 1-hexanol

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

31) What is the predicted product for the reaction shown?

A) hexanal

B) hexanoic acid

C) 2-hexanone

D) 2-chlorohexane

E) 1-hexanol

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

32) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

33) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

34) What is the predicted product for the reaction shown?

A) 3-methyloctanone

B) 3-methyloctanal

C) 2-methyloctanone

D) 2-methyloctanal

E) 2-methyloctanoic acid

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

35) What is the predicted product for the reaction shown?

A) 3-methyloctanone

B) 3-methyloctanal

C) 2-methyloctanone

D) 2-methyloctanal

E) 2-methyloctanoic acid

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

36) What is the predicted product of the reaction shown?

A) 3-methyloctanone

B) 3-methyloctanal

C) 2-methyloctanone

D) 2-methyloctanal

E) 2-methyloctanoic acid

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

37) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

38) Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?

A) 2-phenyl-2-pentene

B) 1-phenyl-1-hexene

C) 1-phenyl-2-pentene

D) 2-phenyl-2-hexene

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

39) Compound A on ozonolysis yields the two products shown. What is the structure of compound A?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

40) Compound A on ozonolysis yields 2,6-heptanedione. What is the structure of compound A?

A) 1,2-dimethylcyclohexene

B) 2,6-dimethylcyclohexene

C) 1,5-dimethylcyclopentene

D) 1,2-dimethylcyclopentene

E) 2-methyl-1-cyclopentene

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

41) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

42) What is the predicted product of the reaction shown?

A) cyclopentene

B) cyclopentanol

C) cyclopentanal

D) cyclopentanone

E) none of these

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

43) Provide the reagents necessary to carry out the conversion shown.

A) 1. H2O; 2. O3; 3. (CH3)2S

B) 1. LiAlH3; 2. H3O+; 3. (CH3)2S

C) 1. H2/Ni2B or Na/NH3; 2. O3

D) 1. H2/Ni2B; 2. (CH3)2S

E) 1. H2/Ni2B or Na/NH3; 2. O3; 3. (CH3)2S

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

44) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

45) Provide the reagents necessary to carry out the conversion shown.

A) 9-BBN; H2O2/NaOH/H2O

B) H3O+; LiAlH3; H2O

C) PdCl2; O2, H2O

D) 9-BBN; O3, H2O

E) H2/Ni2B; H2/Pd; H3O+

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

46) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

47) Predict the product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

48) Provide the reagents necessary to carry out the conversion shown.

A) 1. H2O/ H2SO4,

2. PCC/CH2Cl2

B) PCC/ CH2Cl2

C) 1. 9-BBN,

2. H2O2/NaOH/H2O

D) 1. O3,

2. Zn/acetic acid

E) 1. 9-BBN

2. H2O2/NaOH/H2O

3. CrO3/H2SO4/H2O

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

49) What reagents are necessary to carry out the conversion shown?

A) 1. BH3; 2. H2O2/NaOH/H2O; 3. CrO3/H2SO4/H2O or PCC/CH2Cl2

B) 2. H2/Pt; 2. H2O2; 3. H2O

C) 1. H2O2/NaOH/H2O; 2. PCC/CH2Cl2

D) 1. BH3; 2. PCC/CH2Cl2

E) 1. O3; 2. H2O2/NaOH/H2O; 3. H3O+

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

50) Predict the major product for the reaction shown.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

51) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

52) What reagents are necessary to carry out the conversion shown?

A) /H3O+

B) /AlCl3

C) /AlCl3

D) , AlCl3

E) , H3O+

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

53) What is the predicted major product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

54) Which of the following reactions will produce acetophenone as a major product?

A) I

B) II

C) III

D) IV

E) all of these

Diff: 3

Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four methods for synthesizing ketones

55) Which of the following compounds is most reactive towards a nucleophilic addition reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

56) Which of the following compounds is least reactive towards a nucleophilic addition reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

57) Which of the following compounds is least reactive towards a nucleophilic addition reaction?

A) I

B) II

C) III

D) IV

E) Both I & IV

Diff: 1

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

58) Rank the following compounds in decreasing order (most to least) of reactivity towards a nucleophilic addition reaction.

A) I > II > III > IV > V

B) II > IV > V > III > I

C) III > I > V > IV > II

D) I > III > II > IV > V

E) V > IV > II > III > I

Diff: 2

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

59) Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.

A) There is a steric effect in which the carbonyl group of the aldehyde produces a more sterically hindered transition state and an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic.

B) There is a steric effect in which the carbonyl group of the aldehyde produces a less sterically hindered transition state and an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic.

C) There is a steric effect in which the carbonyl group of the aldehyde produces a less sterically hindered transition state and an electronic effect because the carbonyl carbon of the aldehyde is less electrophilic.

D) There is a steric effect in which the carbonyl group of the aldehyde produces a less sterically hindered transition state, but this is counteracted by an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic.

E) There is a steric effect in which the carbonyl group of the aldehyde produces a more sterically hindered transition state, but this is counteracted by an electronic effect because the carbonyl carbon of the aldehyde is more electrophilic.

Diff: 2

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

60) Benzaldehyde is less reactive than ethanal towards nucleophilic addition reactions. Explain why using words as well as structural drawings.

A) The carbonyl carbon of bezaldehyde is more electrophilic than the ethanal because of the delocalization of the positive charge on the carbonyl carbon via resonance.

B) The carbonyl carbon of bezaldehyde is less electrophilic than the ethanal, because of the localization of the positive charge on the carbonyl carbon via resonance.

C) The carbonyl carbon of bezaldehyde is less electrophilic than the ethanal because of the delocalization of the negative charge on the carbonyl carbon via resonance.

D) The carbonyl carbon of bezaldehyde is more electrophilic than the ethanal, because of the delocalization of the negative charge on the carbonyl carbon via resonance.

E) The carbonyl carbon of bezaldehyde is less electrophilic than the ethanal because of the delocalization of the positive charge on the carbonyl carbon via resonance.

Diff: 2

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

61) Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under basic conditions?

A) a proton transfer followed by a nucleophilic attack

B) a nucleophilic attack followed by a proton transfer

C) nucleophilic attack is the only step

D) proton transfer is not required

Diff: 2

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

62) Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under acidic conditions?

A) a proton transfer followed by a nucleophilic attack

B) a nucleophilic attack followed by a proton transfer

C) nucleophilic attack is the only step

D) proton transfer is not required

Diff: 2

Learning Objective: 19.4 Explain why the carbon of a carbonyl group is susceptible to nucleophilic attack, why aldehydes are more reactive than ketones, and describe mechanisms for nucleophilic addition under basic and acidic conditions

63) A compound with two OH groups attached to the same carbon is known as ________.

A) an acetal

B) a hemiacetal

C) a hydrate

D) a vicinal hydrate

E) none of these

Diff: 1

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

64) A compound with an OH and an OR group attached to the same carbon is known as ________.

A) an acetal

B) a hemiacetal

C) a hydrate

D) a vicinal hydrate

E) none of these

Diff: 1

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

65) A compound with two OR groups attached to the same carbon is known as ________.

A) an acetal

B) a hemiacetal

C) a hydrate

D) a vicinal hydrate

E) none of these

Diff: 1

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

66) Which of the compounds shown can be classified as an acetal?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

67) Which of the compounds shown can be classified as a hemiacetal?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

68) What is the predicted product of the following reaction?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

69) What is the predicted product of the following reaction?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

70) What is the predicted product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

71) What is the predicted product formed when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

72) What reagents are needed to carry out the conversion shown?

A) 1 mole

B) 2 moles

C) CH3CH2CH2CH2CH2CH2OH and H2SO4

D) CH3CH2CH2CH2CH2OH and H2SO4

E) /H2SO4

Diff: 2

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

73) What is the predicted product of the conversion shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

74) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

75) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

76) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

77) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

78) Which one of the following pairs of compounds will yield the product shown in the presence of sulfuric acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

79) Predict the product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

80) What reagents are needed to carry out the conversion shown?

A) 1. HOCH2CH2OH, H2SO4; 2. CH3CH2AlCl3 (2 eq.); 3. H3O+

B) 1 HOCH2CH2CH2OH, H2SO4; 2. CH3MgBr (4 eq.)

C) 1. HOCH2CH2CH2CH2CH2CH2OH, H2SO4; 2. H3O+

D) 1. HOCH2CH2OH, H2SO4; 2. CH3CH2MgBr (2 eq.); 3. H3O+

E) 1. HOCH2CH2CO3H; 2. H3O+

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

81) What reagents are needed to carry out the conversion shown?

A) 1. HOCH2CH2OH/H2SO4; 2. LiAlH4; 3. H3O+

B) 1. HOCH2CH2OH/H2SO4; 2. AlCl3; 3. H3O+

C) 1. HOCH2CH2OH; 2. AlCl3; 3. H3O+

D) 1. HOCH2CH2CH2CH2OH; 2. LiAlH4; 3. H2SO4

E) 1. HOCH2CH2CH3/H2SO4; 2. LiAlH4; 3. H3O+

Diff: 3

Learning Objective: 19.5 Describe how a ketone or aldehyde is converted into a hydrate, an acetal, a hemiacetal, or a cyclic acetal, and explain why acetals can function as protecting groups

82) What is the predicted product when pentanal reacts with CH3NH2 in the presence of an acid catalyst?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

83) What is the predicted product when 4-methyl-2-hexanone reacts with hydrazine in the presence of an acid catalyst?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

84) What is the predicted product when 4-methyl-2-hexanone reacts with methylamine in the presence of an acid catalyst?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

85) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

86) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

87) What is the predicted product when cyclopentanecarbaldehyde reacts with phenylhydrazine (PhNHNH2) in the presence of an acid catalyst?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

88) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

89) What is the predicted product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

90) What reagents are needed to carry out the conversion shown?

A) propanone / H2SO4

B) propanal/ H2SO4

C) 1-propanol/H2SO4

D) 2-propanol/ H2SO4

E) ethanal/ H2SO4

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

91) What is the predicted product for the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

92) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

93) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

94) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

95) What are reactants will form the enamine shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

96) What reactants will form the enamine shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

97) Predict the product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

98) What reactant(s) is(are) necessary to prepare the compound shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

99) What is the predicted product for the reaction shown?

A) 3-methylhexane

B) 3-methyl-4-hexanol

C) 4-methyl-2-hexene

D) 3-methyl-4-hexene

E) 3-methyl-3-hexene

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

100) What is the predicted product for the reaction shown?

A) 3-methylhexane

B) 4-methyl-1-hexanol

C) 4-methyl-2-hexene

D) 3-methyl-4-hexene

E) 3-methyl-3-hexene

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

101) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

102) Which of the possible reagent(s) could not be used to carry out the transformation shown?

A) Zn(Hg), HCl

B) LiAlH4, ether

C) HSCH2CH2SH, BF3; then Raney Ni (H2)

D) 1. NH2NH2/H+

2. KOH/H2O/heat

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

103) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

104) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

105) What reagents are needed to carry out the conversion shown?

A) NaBH4/CH3OH

B) 1. NH2NH2/H+ 2. KOH/H2O/heat

C) H2/Ni

D) 1. LiAlH4, 2. H2O

Diff: 3

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

106) What is the major product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.6 Discuss imine formation, including formation of a carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner reduction

107) What is the predicted product(s) for the reaction shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

108) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

109) What are the predicted products of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

110) What are the predicted products for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

111) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

112) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

113) What are the predicted products of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

114) What are the predicted products for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

115) What are the predicted products of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

116) What are the predicted products for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

117) What are the predicted products of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine, and enamine hydrolysis

118) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals

119) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals

120) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals

121) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals

122) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to form thioacetals and cyclic thioacetals

123) Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents

124) What would be the product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents

125) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents

126) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents

127) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents

128) What reagents are necessary to carry out the conversion shown?

A) NaBH4/CH3OH

B) 1. HOCH2CH2OH/H2SO4

2. NaBH4/CH3OH

3. H3O+, Δ

C) 1. HOCH2CH2OH/H2SO4,

2. LiAlH4/ether

3. NaOH, H2O

D) H3O+

E) none of the above

Diff: 3

Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols when treated with hydride reducing agents

129) What is the predicted product of the reaction sequence shown?

A) 6,7-dimethyl-3-nonanol

B) 6,7-dimethyl-3-nonanone

C) 6,7-dimethyl-3-nonanal

D) 3,4-dimethyl-7-nonanol

E) 3,4-dimethyl-7-nonanone

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

130) What is the predicted product of the reaction sequence shown?

A) 6,7-dimethyl-3-nonanol

B) 6,7-dimethyl-3-nonanone

C) 6,7-dimethyl-3-nonanal

D) 3,4-dimethyl-7-nonanol

E) 3,4-dimethyl-7-nonanone

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

131) What reagents are necessary to carry out the conversion shown?

A) 1. MgBr; 2. ; 3. H3O+; 4. PCC/CH2Cl2

B) 1. Mg/ether; 2. ; 3. H3O+; 4. PCC/CH2Cl2

C) 1. LiAlH; 2. H3O+; 3. PCC/CH2Cl2

D) 1. CrO3, H2SO4; 2. ; 3. H3O+

E) 1. Mg/ether; 2. ; 3. H3O+; 4. AlCl3

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

132) What reagents are necessary to carry out the conversion shown?

A) 1. CH3CH2ONa

2. H2O

B) 1. CH3CH2MgBr

2. H2O

C) 1. CH3CH2CH2ONa

2. H2O

D) 1. CH3CH2CH2MgBr

2. H2O

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

133) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

134) Which one of the compounds shown will yield 1-hexanol when treated with butylmagnesium bromide followed by acid workup?

A) 1-hexanol

B) formaldehyde

C) propanal

D) oxirane

E) hexanal

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

135) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

136) What reagents are necessary to carry out the conversion shown?

A) 1. PCC/CH2Cl2; 2. KCN/HCN

B) 1. H2SO4; 2. KCN/HCN

C) 1. CrO3, H2SO4; 2. H2O; 3. KCN/HCN

D) 1. PCC/CH2Cl2; 2. H2O; 3. CH3CH2CN

E) 1. CrO3, H2SO4; 2. H2O; 3. CH3CH2CN

Diff: 2

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

137) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

138) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

139) What are the reagents necessary to carry out the conversion shown?

A) 1. PCC/CH2Cl2; 2. KCN/HCN

B) 1. PCC/CH2Cl2; 2. H3O+

C) 1. CrO3, H2SO4; 2. CH3CH2CN

D) 1. CrO3, H2SO4; 2. H2O; 3. CH3CH2CN

E) 1. KCN/HCN; 2. H3O+

Diff: 1

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

140) Which reactants are the best choice to prepare the alkene shown using the Wittig reaction?

A) ethanal and 2-bromopentane/PPh3/n-BuLi

B) propanal and 2-bromopentane/PPh3/n-BuLi

C) 2-pentanone and 1-bromopropane/PPh3/n-BuLi

D) 2-pentanone and 2-bromopropane/PPh3/n-BuLi

E) butanal and 2-bromopentane/PPh3/n-BuLi

Diff: 2

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

141) What ylide is needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction?

A) Ph3P=CH(CH2CH3)2

B) Ph3P=CHCH2CH3

C) Ph3P=CHCH2CH2CH3

D) Ph3P=CH2

E) Ph3P=CHCH2(CH3)2

Diff: 2

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

142) What is the reactant for the reaction shown?

A) cyclohexanone

B) cyclohexanecarbaldehyde

C) cyclohexylpropanone

D) 3-cyclohexylpropanal

Diff: 2

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

143) What is the predicted product for the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

144) Provide the structures of X, Y and Z in the following reaction sequence.

A) X is III, Y is I, and Z is II

B) X is I, Y is II, and Z is IV

C) X is III, Y is I or II, and Z is IV

D) X is V, Y is III, and Z is I or II

E) X is II, Y is I, and Z is V

Diff: 3

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

145) Provide the structure of the reactants necessary to prepare the following compound using the Wittig reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a Grignard reagent, with hydrogen cyanide, and with a Wittig reagent

146) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation

147) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation

148) Predict the product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation

149) What is the correct order of the migration rate in the Baeyer—Villiger oxidation reaction for the groups shown?

A) phenyl > methyl > t-butyl > H

B) phenyl > t-butyl > methyl > H

C) H > phenyl > methyl > t-butyl

D) H > t-butyl > phenyl > methyl

E) methyl > t-butyl > phenyl > H

Diff: 1

Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the mechanism of Baeyer-Villiger oxidation

150) What is an appropriate stepwise synthesis for 1-pentanol from butanal?

A) 1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4. ; 5. H3O+

B) 1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4. ; 5. H3O+

C) 1. NaBH4/CH3OH; 2. Mg/ether; 3. ; 4. H3O+

D) 1. NaBH4/CH3OH; 2. Mg/ether; 3. ; 4. H3O+

E) 1. NaBH4; 2. PBr3; 3. Mg/ether; 4.

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

151) What is an appropriate stepwise synthesis for pentanal from butanal?

A) 1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4. ; 5. PCC

B) 1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 4. ; 5. H3O+

C) 1. NaBH4/CH3OH; 2. Mg/ether; 3. ; 4. H3O+

D) 1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 3. ; 4. H3O+; 5. PCC

E) 1. NaBH4; 2. PBr3; 3. Mg/ether; 4.

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

152) What is an appropriate stepwise synthesis for 3-phenylpropanal from benzyl alcohol?

A) 1. PBr3; 2. Mg/ether; 3. ; 4. H3O+; 5. PCC

B) 1. PBr3; 2. Mg/ether; 3. ; 4. H3O+

C) 1. PBr3; 2. Mg/ether; 3. ; 4. H3O+

D) 1. NaBH4/CH3OH; 2. PBr3; 3. Mg/ether; 3. ; 4. H3O+; 5. PCC

E) 1. PBr3; 2. Mg/ether; 3. ; 4. H3O+

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

153) What is an appropriate stepwise synthesis for the reaction shown.

A) 1. CrO3/H2O; 2. ; 3. H2O; 4. H2O2/NaOH/H2O

B) 1. CrO3/H2SO4/H2O; 2. ; 3. H2O; 4. 9-BBN; 5. H2O2/NaOH/H2O

C) 1. PCC; 2. ; 3. 9-BBN; 4. H2O2/NaOH/H2O

D) 1. CrO3/H2SO4; 2. ; 3. H2O; 4. 9-BBN; 5. NaOH

E) 1. CrO3/H2SO4/H2O; 2. ; 3. H2O; 4. H2O2

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

154) What is an appropriate stepwise synthesis for 4-methyl-1-pentanamine from 3-methyl-1-butanol?

A) 1. PBr3; 2. NaCN; 3. CrO3/H2O

B) 1. PBr3; 2. NaCN; 3. LiAlH4

C) 1. PBr3; 2. LiAlH4; 3. PCC; 4. ; 5. H2O

D) 1. PBr3; 2. NaCN; 3. NaOH

E) 1. LiAlH4; 2. NaCN; 3. CrO3/H2O

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

155) What is an appropriate stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane?

A) 1. ; 2. 9-BBN; 3. H2O2/NaOH/H2O

B) 1. PBr3; 2. NaCN; 3. LiAlH4

C) 1. PBr3; 2. LiAlH4; 3. PCC; 4. ; 5. H2O

D) 1. ; 2. PBr3; 3. NaOH

E) 1. LiAlH4; 2. NaCN; 3. CrO3/H2O

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

156) What is an appropriate stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane?

A) 1. ; 2. H2O/H2SO4/HgSO4

B) 1. PBr3; 2. ; 3. LiAlH4

C) 1. PBr3; 2. LiAlH4; 3. PCC; 4. ; 5. H2O

D) 1. ; 2. PBr3; 3. NaOH

E) 1. LiAlH4; 2. NaCN; 3. CrO3/H2O

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

157) What is an appropriate stepwise synthesis for the conversion shown?

A) 1. PBr3; 2. PCC; 3. H2O

B) 1. PBr3; 2. H2SO4; 3. PCC; 4. H2O

C) 1. KMnO4; 2. CrO3; 3. H2O

D) 1. KMnO4/NaOH/H2O (hot); 2. H2O

E) 1. KMnO4/NaOH/H2O (cold); 2. CrO3/H2SO4/H2O

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

158) What is an appropriate stepwise synthesis for the conversion shown?

A) 1. Mg/ether; 2. ; 3. H3O+; 4. PCC/CH2Cl2

B) 1. Mg/ether; 2. ; 3. H3O+; 4. PCC/CH2Cl2

C) 1. Mg/ether; 2. ; 3. PCC/CH2Cl2

D) 1. MgBr; 2. H3O+; 3. PCC/CH2Cl2

E) 1. MgBr; 2. H3O+; 3. H2SO4

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

159) In the reaction below, what are the structures for the intermediates and final product?

A) X is I, Y is III, Z is II, and A is V

B) X is II, Y is I, Z is V, and A is III

C) X is III, Y is II, Z is I, and A is IV

D) X is I, Y is II, Z is III, and A is IV

E) X is I, Y is III, Z is I, and A is II

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

160) In the reaction below, what are the structures for the intermediates and final product?

A) X is I, Y is III, Z is II, and A is V

B) X is II, Y is I, Z is V, and A is III

C) X is III, Y is II, Z is I, and A is IV

D) X is I, Y is II, Z is III, and A is IV

E) X is I, Y is III, Z is I, and A is II

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

161) In the reaction below, what are the structures for the intermediates and final product?

A) X is I, Y is III, and Z is II

B) X is II, Y is I, and Z is V

C) X is III, Y is II, and Z is I

D) X is I, Y is II, and Z is III

E) X is I, Y is III, and Z is I

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

162) What is an appropriate stepwise synthesis for the conversion shown?

A) 1. PCC; 2. CH3CH2NH2/H2SO4

B) 1. CrO3; 2. H2O; MgBrCH3; H2O

C) 1. CH3CH2NH2/H2SO4

D) 1. H2SO4; 2. Mg/ether; 3. PCC

E) 1. MgBrCH3 2. H2O

Diff: 3

Learning Objective: 19.12 Name the products that can be made from aldehydes and ketones and the reagents required for the reactions

163) A compound with formula C5H10O shows only two singlets in its 1H NMR spectrum. Which one of the compounds shown could produce this spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones

164) The 1H NMR spectrum of a compound with formula C7H14O shows only two signals. Which one of the choices is a possible structure for this compound?

A) 2-heptanone

B) 3-heptanone

C) 2,4-dimethyl-3-pentanone

D) 2,2-dimethyl-3-pentanone

E) Two of the above

Diff: 2

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones

165) The 13C NMR spectrum of a compound with formula C7H14O shows five signals. Which one of the choices is a possible structure for this compound?

A) 2-heptanone

B) 3-heptanone

C) 2,2-dimethyl-3-pentanone

D) 2,4-dimethyl-3-pentanone

E) none of these

Diff: 2

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones

166) The 1H NMR spectrum of a compound with formula C7H14O shows a singlet at 9.2 ppm. Which one of the choices is a possible structure for this compound?

A) 2-methyl-3-hexanone

B) 2-methylhexanal

C) 2,2 -dimethylpentanal

D) 2,2-dimethyl-3-pentanone

E) B & C

Diff: 2

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones

167) Provide a structure for the compound with molecular formula C5H10O and with the following spectroscopic data.

IR: 1720 cm-1

1H NMR: 0.9 δ (triplet, 3H), 1.7 δ (sextet, 2H), 2.1 δ (singlet, 3H), 2.4 δ (triplet, 2H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones

168) Provide a structure for the compound with molecular formula C9H10O and with the following spectroscopic data.

IR: 1680 cm-1

1H NMR: 1.25 δ (triplet, 3H), 3.0 δ (quartet, 2H), 7-8 δ (multiplet, 5H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR spectra of aldehydes and ketones

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