Free Printable CH 19 Aldehydes and Ketones

1.

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

a)

I

b)

II

c)

III

d)

IV

e)

V

2.

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

a)

ethanol

b)

2-butanone

c)

acetone

d)

formaldehyde

e)

diethyl ether

3.

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

a)

ethanol

b)

2-butanone

c)

acetone

d)

formaldehyde

e)

diethyl ether

4.

What is the IUPAC name for the following compound?

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

5.

What is the IUPAC name for the following compound?

a)

2,5-dimethyl-6-hexanal

b)

2,5-dimethylhexanal

c)

1,4-dimethylpentanal

d)

1,4-dimethylhexanal

e)

none of these

6.

What is the IUPAC name for the following compound?

a)

5,5-dimethyl-2-heptanone

b)

5,5-dimethylcycloheptanone

c)

5,5-dimethylcycloheptanone

d)

3,3-dimethylcycloheptanone

e)

1,1-dimethyl-4-cycloheptanone

7.

What is the IUPAC name for the following compound?

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

8.

What is the IUPAC name for the following compound?

a)

4-benzylbutanal

b)

3-phenylpropanal

c)

3-benzylpropanal

d)

4-phenylbutanal

e)

2-benzylethanal

9.

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

a)

I

b)

II

c)

III

d)

IV

e)

V

10.

What is the IUPAC name for the following compound?

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

11.

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

a)

I

b)

II

c)

III

d)

IV

e)

V

12.

Provide the structure for 7-bromo-1-octyn-4-one.

a)

I

b)

II

c)

III

d)

IV

e)

none of these

13.

What is the IUPAC name for the following compound?

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

14.

What is the IUPAC name for the following compound?

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

15.

What is the IUPAC name for the following compound?

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

16.

Predict the product for the following reaction.

a)

hexanal

b)

hexanoic acid

c)

2-hexanone

d)

2-chlorohexane

e)

1-hexanol

17.

Predict the product for the following reaction.

a)

hexanal

b)

hexanoic acid

c)

2-hexanone

d)

2-chlorohexane

e)

1-hexanol

18.

Predict the product for the following reaction.

a)

hexanal

b)

hexanoic acid

c)

2-hexanone

d)

2-chlorohexane

e)

1-hexanol

19.

Predict the product for the following reaction.

a)

hexanal

b)

hexanoic acid

c)

2-hexanone

d)

2-chlorohexane

e)

1-hexanol

20.

Predict the product for the following reaction.

a)

hexanal

b)

hexanoic acid

c)

2-hexanone

d)

2-chlorohexane

e)

1-hexanol

21.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

22.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

23.

Predict the product for the following reaction.

a)

3-methyloctanone

b)

3-methyloctanal

c)

2-methyloctanone

d)

2-methyloctanal

e)

2-methyloctanoic acid

24.

Predict the product for the following reaction.

a)

3-methyloctanone

b)

3-methyloctanal

c)

2-methyloctanone

d)

2-methyloctanal

e)

2-methyloctanoic acid

25.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

26.

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

27.

Compound A on ozonolysis yields the following two products What is the structure of compound A?

a)

I

b)

II

c)

III

d)

IV

e)

None of these

28.

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

29.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

30.

Predict the product for the following reaction.

a)

cyclopentene

b)

cyclopentanol

c)

cyclopentanal

d)

cyclopentanone

e)

none of these

31.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

32.

Predict the major product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

None of these

33.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

34.

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

a)

I

b)

II

c)

III

d)

IV

e)

All of these

35.

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

a)

I

b)

II

c)

III

d)

IV

e)

V

36.

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

a)

I

b)

II

c)

III

d)

IV

e)

V

37.

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

38.

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

39.

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

40.

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

41.

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

42.

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

43.

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

44.

Which of the following compounds can be classified as an acetal?

a)

I

b)

II

c)

III

d)

IV

e)

none of these

45.

Which of the following compounds can be classified as a hemiacetal?

a)

I

b)

II

c)

III

d)

IV

e)

none of these

46.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

none of these

47.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

none of these

48.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

49.

Provide the structure of the product, when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid.

a)

I

b)

II

c)

III

d)

IV

e)

V

50.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

51.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

52.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

53.

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

a)

I

b)

II

c)

III

d)

IV

e)

V

54.

Predict the product when pentanal reacts with CH3NH2 in the presence of an acid catalyst.

a)

I

b)

II

c)

III

d)

IV

e)

V

55.

Predict the 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

56.

Predict the 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

57.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

58.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

59.

Predict the product, when cyclopentanecarbaldehyde reacts with phenylhydrazine (PhNHNH2) in the presence of an acid catalyst.

a)

I

b)

II

c)

III

d)

IV

e)

V

60.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

61.

Predict the product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

62.

Predict the product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

63.

Provide the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

64.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

65.

Predict the product for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

66.

Provide the major product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

67.

Predict the product(s) for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

68.

Predict the product(s) for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

none of these

69.

Predict the product(s) for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

70.

Predict the product(s) for the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

71.

Provide the product of the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

72.

Provide the product of the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

73.

Provide the product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

74.

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

75.

What would be the product of the following reaction?

a)

I

b)

II

c)

III

d)

IV

e)

V

76.

What would be the product of the following reaction?

a)

I

b)

II

c)

III

d)

IV

e)

V

77.

Predict the product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

78.

Provide the product of the following reaction.

a)

I

b)

II

c)

III

d)

IV

79.

Provide the reagents necessary to carry out the following conversion.

a)

NaBH₄/CH₃OH

b)

1. HOCH₂CH₂OH/H₂SO₄

2. NaBH₄/CH₃OH

3. H₃O⁺, D

c)

1. HOCH₂CH₂OH/H₂SO_4,

2. LiAlH₄/ether

3. NaOH, H₂O

d)

H₃O⁺

e)

none of the above

80.

Predict the product for the following reaction sequence.

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

81.

Predict the product for the following reaction sequence.

a)

6,7-dimethyl-3-nonanol

b)

6,7-dimethyl-3-nonanol

c)

6,7-dimethyl-3-nonanol

d)

3,4-dimethyl-7-nonanol

e)

3,4-dimethyl-7-nonanone

82.

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

a)

1-hexanol

b)

formaldehyde

c)

propanal

d)

oxirane

e)

hexanal

83.

Predict the product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

84.

Predict the product of the following reaction sequence,

a)

I

b)

II

c)

III

d)

IV

e)

V

85.

Predict the product of the following reaction sequence,

a)

I

b)

II

c)

III

d)

IV

e)

V

86.

Which of the following is the best choice to prepare the following alkene using the Wittig reaction?

a)

ethanal and 2-bromopentane/PPh₃

b)

propanal and 2-bromopentane/PPh3

c)

2-pentanone and 1-bromopropane/PPh3

d)

2-pentanone and 2-bromopropane/PPh3

e)

butanal and 2-bromopentane/PPh₃

87.

Provide the structure of the ylide 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

88.

Provide the reactant for the following reaction.

a)

cyclohexanone

b)

cyclohexanecarbaldehyde

c)

cyclohexylpropanone

d)

3-cyclohexylpropanal

89.

Predict the product for the following reaction sequence.

a)

I

b)

II

c)

III

d)

IV

e)

V

90.

Predict the product of the following reaction.

a)

I

b)

II

c)

III

d)

IV

91.

Predict the product of the following reaction.

a)

I

b)

II

c)

III

d)

IV

e)

V

92.

What is the correct order of the migration rate for the following groups in the Baeyer–Villiger oxidation reaction?

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

93.

A compound with formula C5H10O shows only two singlets, in its 1H NMR spectrum. Which one of the following is a possible structure for this compound?

a)

I

b)

II

c)

III

d)

IV

e)

V

CH 19 Aldehydes and Ketones

Total questions: 93

Worksheet time: 47mins

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