Klein, Organic Chemistry 3e
Chapter 19
1.
Name the aldehyde or ketone that is found in nail polish remover.
A.
B.
C.
D.
E.
ethanol
2-butanone
acetone
formaldehyde
diethyl ether
Answer: C
Learning Objective: 19.1 Compare the structures of an aldehyde and a ketone
Difficulty: Easy
2.
Name the aldehyde or ketone that is used as a preservative.
A.
B.
C.
D.
E.
ethanol
2-butanone
acetone
formaldehyde
diethyl ether
Answer: D
Learning Objective: 19.1 Compare the structures of an aldehyde and a ketone
Difficulty: Easy
3.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
2-methyl-5-heptanone
7-methyl-4-octanone
6-isopropyl-4-octanone
isobutyl propyl ketone
1,1-dimethyl-4-heptanone
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
4.
What is the correct structure for 5-methyl-4-octanone?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
5.
What is the IUPAC name for the following compound?
Answer: 5,5-dimethyl-2-heptanone
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
6.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
2,5-dimethyl-6-hexanal
2,5-dimethylhexanal
1,4-dimethylpentanal
1,4-dimethylhexanal
none of these
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
7.
Provide the structure for 4-methylbenzaldehyde.
Answer:
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
8.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
5,5-dimethyl-2-heptanone
5,5-dimethylcycloheptanone
4,4-dimethylcycloheptanone
3,3-dimethylcycloheptanone
1,1-dimethyl-4-cycloheptanone
Answer: C
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
9.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
2,4-dimethyl-2-pentenone
2,5-dimethylcyclopenten-3-one
2,4-dimethylcyclopent-2-enone
3,5-dimethylcyclopent-2-enone
2-methyl-5-methylcyclopent-2-enone
Answer: C
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
10.
Provide the structure for 2,3-dimethyl-2-octen-4-one.
Answer:
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
11.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
4-benzylbutanal
3-phenylpropanal
3-benzylpropanal
4-phenylbutanal
2-benzylethanal
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
12.
What is the structure for 5-hydroxy-2-phenyl-3-hexanone?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
13.
What is the IUPAC name for the following compound?
Answer: 4-chloro-3-methylbenzaldehyde
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
14.
Provide the structure for m-nitroacetophenone.
Answer:
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
15.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
(S)-2-methyl-2-bromobutanone
(S)-2-bromo-2-methylcyclobutanone
(R)-2-bromo-2-methylcyclobutanone
(S)-1-bromo-1-methyl-2-cyclobutanone
(R)-1-bromo-1-methyl-2-cyclobutanone
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
16.
Provide the structure for (S)-3-chlorocyclohexanone.
Answer:
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
17.
What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?
A.
B.
C.
I
II
III
D.
E.
IV
V
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
18.
Provide the structure for 7-bromo-1-octyn-4-one.
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
19.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
4-oxo-5-phenyl-2-hexanol
5-hydroxy-2-phenyl-3-hexanone
2-hydroxy-5-phenyl-4-hexanone
2-hydroxypropyl-1-phenylethyl ketone
5-hydroxy-3-keto-2-phenylhexane
Answer: B
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
20.
What is the IUPAC name for the following compound?
Answer: (2S,3R)-2-isopropyl-3-methylcyclohexanone
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
21.
What is the IUPAC name for the following compound?
A.
(R)-6-bromo-2-heptanal
B.
C.
D.
E.
(S)-6-bromo-2-heptanal
(R)-6-bromo-2-heptanone
(S)-6-bromo-2-heptanone
(R)-2-bromo-6-heptanone
Answer: C
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
22.
What is the IUPAC name for the following compound?
A.
B.
C.
D.
E.
5-cyclohexyl-2-hexanal
5-cyclohexyl-2-hexanone
5-cyclohexyl-5-methyl-2-pentanone
5-(1-methylcyclohexyl)-2-pentanone
4-(1-methylcyclohexyl)-2-butanone
Answer: E
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
23.
Provide the structure for benzophenone.
Answer:
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
24.
What is the IUPAC name for the following compound?
Answer: (2R,4R)-2,4-dimethylpentanedial
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
25.
What is the IUPAC name for the following compound?
Answer: (3R,5R)-3,5-dimethyl-2,6-heptanedione
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Hard
26.
What is the IUPAC name for the following compound?
Answer: 1,2-cyclohexanedione
Learning Objective: 19.2 Assign a name for an aldehyde or ketone using the IUPAC
system of nomenclature
Difficulty: Medium
27.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
hexanal
hexanoic acid
2-hexanone
2-chlorohexane
1-hexanol
Answer: A
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
28.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
hexanal
hexanoic acid
2-hexanone
2-chlorohexane
1-hexanol
Answer: A
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
29.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
hexanal
hexanoic acid
2-hexanone
2-chlorohexane
1-hexanol
Answer: A
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
30.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
hexanal
hexanoic acid
2-hexanone
2-chlorohexane
1-hexanol
Answer: C
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
31.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
hexanal
hexanoic acid
2-hexanone
2-chlorohexane
1-hexanol
Answer: C
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
32.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
33.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
34.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
3-methyloctanone
3-methyloctanal
2-methyloctanone
2-methyloctanal
2-methyloctanoic acid
Answer: B
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
35.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
3-methyloctanone
3-methyloctanal
2-methyloctanone
2-methyloctanal
2-methyloctanoic acid
Answer: B
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
36.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
3-methyloctanone
3-methyloctanal
2-methyloctanone
2-methyloctanal
2-methyloctanoic acid
Answer: B
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
37.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
38.
Compound A on ozonolysis yields acetophenone and propanal. What is the
structure of compound A?
A.
B.
C.
D.
2-phenyl-2-pentene
1-phenyl-1-hexene
1-phenyl-2-pentene
2-phenyl-2-hexene
Answer: A
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
39.
Compound A on ozonolysis yields the following two products What is the
structure of compound A?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
40.
Compound A on ozonolysis yields 2,6-heptanedione. What is the structure of
compound A?
A.
B.
C.
D.
E.
1,2-dimethylcyclohexene
2,6-dimethylcyclohexene
1,5-dimethylcyclopentene
1,2-dimethylcyclopentene
2-methyl-1-cyclopentene
Answer: D
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
41.
Predict the product for the following reaction.
A.
B.
C.
I
II
III
D.
E.
IV
V
Answer: E
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
42.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
cyclopentene
cyclopentanol
cyclopentanal
cyclopentanone
none of these
Answer: D
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
43.
Provide the reagents necessary to carry out the following conversion.
Answer:
1. H2/Ni2B or Na/NH3
2. O3
3. (CH3)2S
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
44.
Predict the product for the following reaction.
Answer:
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
45.
Provide the reagents necessary to carry out the following conversion.
Answer:
9-BBN
H2O2/NaOH/H2O
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
46.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
47.
Predict the product for the following reaction.
Answer:
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
48.
Provide the reagents necessary to carry out the following conversion.
A.
B.
C.
D.
E.
1.
H2O/ H2SO4,
2.
PCC/CH2Cl2
PCC/ CH2Cl2
1.
9-BBN,
2.
H2O2/NaOH/H2O
1.
O3,
2.
Zn/acetic acid
1.
9-BBN
2.
H2O2/NaOH/H2O
3.
CrO3/H2SO4/H2O
Answer: C
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
49.
Provide the reagents necessary to carry out the following conversion.
Answer:
1. BH3
2. H2O2/NaOH/H2O
3. CrO3/H2SO4/H2O OR PCC/CH2Cl2
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
50.
Predict the major product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: C
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
51.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
52.
Provide the reagents necessary to carry out the following conversion.
Answer:
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
53.
Predict the major product for the following reaction.
Answer:
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Medium
54.
Which of the following reactions will produce acetophenone as a major product?
A.
B.
C.
D.
E.
I
II
III
IV
all of these
Answer: E
Learning Objective: 19.3 Describe three methods for synthesizing aldehydes and four
methods for synthesizing ketones
Difficulty: Hard
55.
Which of the following compounds is most reactive towards a nucleophilic
addition reaction?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
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
Difficulty: Easy
56.
Which of the following compounds is least reactive towards a nucleophilic
addition reaction?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: E
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
Difficulty: Easy
57.
Which of the following compounds is least reactive towards a nucleophilic
addition reaction?
A.
B.
C.
D.
E.
I
II
III
IV
Both I & IV
Answer: A
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
Difficulty: Easy
58.
Rank the following compounds in decreasing order (most to least) of reactivity
towards a nucleophilic addition reaction.
A.
B.
C.
D.
E.
I > II > III > IV > V
II > IV > V > III > I
III > I > V > IV > II
I > III > II > IV > V
V > IV > II > III > I
Answer: D
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
Difficulty: Medium
59.
Aldehydes are more reactive than ketones towards nucleophilic addition
reactions. Explain why.
Answer: Steric effect: the carbonyl group of the aldehyde is connected to only one alkyl
group which results in a less sterically hindered transition state compared to the ketone.
Electronic effect: the carbonyl carbon of the aldehyde is more electrophilic than that of
the ketone, because the + on the carbonyl carbon is less stabilized via the inductive
effect of only one alkyl group compared to the stabilization by two alkyl groups in a
ketone.
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
Difficulty: Medium
60.
Benzaldehyde is less reactive than ethanal towards nucleophilic addition
reactions. Explain why using words as well as structural drawings.
Answer: 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.
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
Difficulty: Medium
61.
Which of the following statements is consistent with the mechanism for the
nucleophilic addition of aldehydes/ketones under basic conditions?
A.
B.
C.
D.
a proton transfer followed by a nucleophilic attack
a nucleophilic attack followed by a proton transfer
nucleophilic attack is the only step
proton transfer is not required
Answer: B
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
Difficulty: Medium
62.
Which of the following statements is consistent with the mechanism for the
nucleophilic addition of aldehydes/ketones under acidic conditions?
A.
B.
C.
D.
a proton transfer followed by a nucleophilic attack
a nucleophilic attack followed by a proton transfer
nucleophilic attack is the only step
proton transfer is not required
Answer: A
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
Difficulty: Medium
63.
A compound with two OH groups attached to the same carbon is known as
______.
A.
B.
C.
D.
E.
an acetal
a hemiacetal
a hydrate
a vicinal hydrate
none of these
Answer: C
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
Difficulty: Easy
64.
A compound with an OH and an OR group attached to the same carbon is known
as ______.
A.
B.
C.
D.
E.
an acetal
a hemiacetal
a hydrate
a vicinal hydrate
none of these
Answer: B
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
Difficulty: Easy
65.
A compound with two OR groups attached to the same carbon is known as
______.
A.
B.
C.
D.
E.
an acetal
a hemiacetal
a hydrate
a vicinal hydrate
none of these
Answer: A
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
Difficulty: Easy
66.
Which of the following compounds can be classified as an acetal?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: D
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
Difficulty: Easy
67.
Which of the following compounds can be classified as a hemiacetal?
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
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
Difficulty: Easy
68.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: A
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
Difficulty: Medium
69.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: C
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
Difficulty: Medium
70.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
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
Difficulty: Medium
71.
Provide the structure of the product, when cyclohexanecarbaldehyde reacts with
excess 2-propanol in the presence of sulfuric acid.
A.
B.
I
II
C.
D.
E.
III
IV
V
Answer: E
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
Difficulty: Hard
72.
Provide the reagents necessary to carry out the following conversion.
Answer:
1 mol
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
Difficulty: Medium
73.
Predict the product for the following conversion.
Answer:
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
Difficulty: Hard
74.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
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
Difficulty: Hard
75.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
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
Difficulty: Medium
76.
Predict the product(s) for the following reaction.
Answer:
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
Difficulty: Hard
77.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
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
Difficulty: Hard
78.
Which one of the following pairs of compounds will yield the following product in
the presence of sulfuric acid?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
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
Difficulty: Hard
79.
Predict the product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
Answer:
Mechanism
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
Difficulty: Hard
80.
Provide the reagents necessary to carry out the following conversion.
Answer:
1. HOCH2CH2OH/H2SO4
2. CH3CH2MgBr (2 eq)
3. H3O+
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
Difficulty: Hard
81.
Provide the reagents necessary to carry out the following conversion.
Answer:
1. HOCH2CH2OH/H2SO4
2. LiAlH4
3. H3O+
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
Difficulty: Hard
82.
Predict the product when pentanal reacts with CH3NH2 in the presence of an acid
catalyst.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
83.
Predict the product, when 4-methyl-2-hexanone reacts with hydrazine in the
presence of an acid catalyst.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
84.
Predict the product, when 4-methyl-2-hexanone reacts with methylamine in the
presence of an acid catalyst.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
85.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
86.
Predict the product for the following reaction.
A.
I
B.
C.
D.
E.
II
III
IV
V
Answer: E
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
87.
Predict
the
product,
when
cyclopentanecarbaldehyde
phenylhydrazine (PhNHNH2) in the presence of an acid catalyst.
A.
B.
C.
D.
E.
I
II
III
IV
V
reacts
with
Answer: A
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
88.
Predict the product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
Answer:
Mechanism
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Hard
89.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
90.
Provide the reagents necessary to carry out the following conversion.
A.
B.
C.
D.
E.
propanone / H2SO4
propanal/ H2SO4
1-propanol/H2SO4
2-propanol/ H2SO4
ethanal/ H2SO4
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
91.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
92.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
93.
Predict the product for the following reaction sequence.
Answer:
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
94.
Predict the product for the following reaction.
Answer:
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
95.
Provide the reactants that will form the following enamine.
Answer:
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
96.
Provide the reactants that will form the following enamine.
Answer:
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
97.
Predict the product for the following reaction.
Answer:
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Hard
98.
Provide the reactant(s) necessary to prepare the following compound.
Answer:
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Hard
99.
Provide the product for the following reaction.
A.
B.
C.
D.
E.
3-methylhexane
3-methyl-4-hexanol
4-methyl-2-hexene
3-methyl-4-hexene
3-methyl-3-hexene
Answer: A
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
100.
Provide the product for the following reaction.
A.
B.
C.
D.
E.
3-methylhexane
4-methyl-1-hexanol
4-methyl-2-hexene
3-methyl-4-hexene
3-methyl-3-hexene
Answer: A
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
101.
Provide the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
102.
Which of the following reagent(s) could not be used to carry out the following
transformation?
A.
B.
C.
D.
Zn(Hg), HCl
LiAlH4, ether
HSCH2CH2SH, BF3; then Raney Ni (H2)
1.
NH2NH2/H+
2.
KOH/H2O/heat
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
103.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
104.
Predict the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
105.
Provide the reagents necessary to carry out the following conversion.
A.
B.
C.
D.
NaBH4/CH3OH
1. NH2NH2/H+ 2. KOH/H2O/heat
H2/Ni
1. LiAlH4 , 2. H2O
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Hard
106.
Provide the major product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.6 Discuss imine formation, including formation of a
carbinolamine, a hydrazone, an oxime, and an enamine, and describe Wolff-Kishner
reduction
Difficulty: Medium
107.
Predict the product(s) for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: C
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Hard
108.
Predict the product(s) for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
none of these
Answer: E
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Hard
109.
Predict the product(s) for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Hard
110.
Predict the product(s) for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Hard
111.
Predict the product(s) for the following reaction.
Answer:
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Hard
112.
Predict the product(s) for the following reaction.
Answer: No reaction.
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Hard
113.
Predict the product(s) for the following reaction.
Answer:
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Medium
114.
Predict the product(s) for the following reaction.
Answer:
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Medium
115.
Predict the product(s) for the following reaction.
Answer:
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Medium
116.
Predict the product(s) for the following reaction.
Answer:
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Medium
117.
Predict the product(s) for the following reaction.
Answer:
Learning Objective: 19.7 Describe the conditions for, and mechanism of, acetal, imine,
and enamine hydrolysis
Difficulty: Medium
118.
Provide the product of the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: E
Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to
form thioacetals and cyclic thioacetals
Difficulty: Medium
119.
Provide the product of the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to
form thioacetals and cyclic thioacetals
Difficulty: Medium
120.
Provide the product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to
form thioacetals and cyclic thioacetals
Difficulty: Medium
121.
Predict the product for the following reaction.
Answer:
Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to
form thioacetals and cyclic thioacetals
Difficulty: Medium
122.
Predict the product for the following reaction.
Answer:
Learning Objective: 19.8 Describe the reactions of aldehydes and ketones with thiol to
form thioacetals and cyclic thioacetals
Difficulty: Medium
123.
Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
A.
B.
C.
D.
I
II
III
IV
E.
V
Answer: A
Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols
when treated with hydride reducing agents
Difficulty: Medium
124.
What would be the product of the following reaction?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols
when treated with hydride reducing agents
Difficulty: Medium
125.
What would be the product of the following reaction?
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: A
Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols
when treated with hydride reducing agents
Difficulty: Medium
126.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols
when treated with hydride reducing agents
Difficulty: Hard
127.
Provide the product of the following reaction.
A.
B.
C.
D.
I
II
III
IV
Answer: A
Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols
when treated with hydride reducing agents
Difficulty: Hard
128.
Provide the reagents necessary to carry out the following conversion.
A.
B.
NaBH4/CH3OH
1.
HOCH2CH2OH/H2SO4
2.
NaBH4/CH3OH
3.
H3O+, 
1.
HOCH2CH2OH/H2SO4,
2.
LiAlH4/ether
3.
NaOH, H2O
+
H3O
C.
D.
E.
none of the above
Answer: E
Learning Objective: 19.9 Describe the reduction of aldehydes and ketones to alcohols
when treated with hydride reducing agents
Difficulty: Hard
129.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
6,7-dimethyl-3-nonanol
6,7-dimethyl-3-nonanone
6,7-dimethyl-3-nonanal
3,4-dimethyl-7-nonanol
3,4-dimethyl-7-nonanone
Answer: B
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
130.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
6,7-dimethyl-3-nonanol
6,7-dimethyl-3-nonanone
6,7-dimethyl-3-nonanal
3,4-dimethyl-7-nonanol
3,4-dimethyl-7-nonanone
Answer: B
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
131.
Provide the reagents necessary to carry out the following conversion.
Answer:
1. Mg/ether
2.
3. H3O+
4. PCC/CH2Cl2
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
132.
Provide the reagents necessary to carry out the following conversion.
A.
1.
2.
1.
2.
1.
2.
1.
2.
B.
C.
D.
Answer: B
CH3CH2ONa
H2O
CH3CH2MgBr
H2O
CH3CH2CH2ONa
H2O
CH3CH2CH2MgBr
H2O
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
133.
Provide the product for the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
134.
Provide the reagents necessary for the following conversion.
A.
1.
NaBH4/CH3OH
2.
CH3CH2MgBr
CH3CH2MgBr/ether
1.
H3O+
2.
CH3CH2MgBr/ ether
1.
CH3CH2MgBr/ ether
2.
H3O+,
B.
C.
D.
Answer: B
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Medium
135.
Which one of the following compounds will yield 1-hexanol when treated with
butylmagnesium bromide followed by acid workup?
A.
B.
C.
D.
E.
1-hexanol
formaldehyde
propanal
oxirane
hexanal
Answer: D
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
136.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
137.
Provide the reagents necessary to carry out the following conversion.
Answer:
1. PCC/CH2Cl2
2. KCN/HCN
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Medium
138.
Predict the product of the following reaction sequence,
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
139.
Predict the product of the following reaction sequence,
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
140.
Provide the reagents necessary to carry out the following conversion
Answer:
1. KCN/HCN
2. H3O+
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Easy
141.
Which of the following is the best choice to prepare the following alkene using the
Wittig reaction?
A.
B.
C.
D.
E.
ethanal and 2-bromopentane/PPh3
propanal and 2-bromopentane/PPh3
2-pentanone and 1-bromopropane/PPh3
2-pentanone and 2-bromopropane/PPh3
butanal and 2-bromopentane/PPh3
Answer: C
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Medium
142.
Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3pentanone using a Wittig reaction.
A.
B.
C.
D.
E.
Ph3P=CH(CH2CH3)2
Ph3P=CHCH2CH3
Ph3P=CHCH2CH2CH3
Ph3P=CH2
Ph3P=CHCH2(CH3)2
Answer: C
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Medium
143.
Provide the reactant for the following reaction.
A.
cyclohexanone
B.
C.
D.
cyclohexanecarbaldehyde
cyclohexylpropanone
3-cyclohexylpropanal
Answer: B
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Medium
144.
Predict the product for the following reaction sequence.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: D
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
145.
Provide the structures of X, Y and Z in the following reaction sequence.
Answer:
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Hard
146.
Provide the structure of the reactants necessary to prepare the following
compound using the Wittig reaction.
Answer:
Learning Objective: 19.10 Describe the reactions of aldehydes and ketones with a
Grignard reagent, with hydrogen cyanide, and with a Wittig reagent
Difficulty: Medium
147.
Predict the product of the following reaction.
A.
B.
C.
D.
I
II
III
IV
Answer: C
Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the
mechanism of Baeyer-Villiger oxidation
Difficulty: Medium
148.
Predict the product of the following reaction.
A.
B.
C.
D.
E.
I
II
III
IV
V
Answer: B
Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the
mechanism of Baeyer-Villiger oxidation
Difficulty: Medium
149.
Predict the product of the following reaction.
Answer:
Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the
mechanism of Baeyer-Villiger oxidation
Difficulty: Medium
150.
What is the correct order of the migration rate for the following groups in the
Baeyer–Villiger oxidation reaction?
A.
B.
C.
D.
E.
phenyl > methyl > t-butyl > H
phenyl > t-butyl > methyl > H
H > phenyl > methyl > t-butyl
H > t-butyl > phenyl > methyl
methyl > t-butyl > phenyl > H
Answer: D
Learning Objective: 19.11 Describe the reaction of ketones with peroxy acids and the
mechanism of Baeyer-Villiger oxidation
Difficulty: Easy
151.
Suggest a stepwise synthesis for 1-pentanol from butanal.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
152.
Suggest a stepwise synthesis for pentanal from butanal.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
153.
Suggest a stepwise synthesis for 3-phenylpropanal from benzyl alcohol.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
154.
Suggest a stepwise synthesis for the following.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
155.
Suggest a stepwise synthesis for 4-methyl-1-pentanamine from 3-methyl-1butanol.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
156.
Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
157.
Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1bromobutane.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
158.
Suggest a stepwise synthesis for the following.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
159.
Suggest a stepwise synthesis for the following.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
160.
Provide structures for the intermediates and final product.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
161.
Provide structures for the intermediates and final product.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
162.
Provide structures for the intermediates and final product.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
163.
Suggest a stepwise synthesis for the following.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
164.
Using 1-propanol as your only source of carbon, and using any other reagents as
appropriate, write a complete stepwise synthesis for 3-hexanone.
Answer:
Learning Objective: 19.12 Name the products that can be made from aldehydes and
ketones and the reagents required for the reactions
Difficulty: Hard
165.
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.
B.
C.
D.
E.
I
II
III
IV
V
Answer: C
Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR
spectra of aldehydes and ketones
Difficulty: Medium
166.
The 1H NMR spectrum of a compound with formula C7H14O shows only two
signals. Which one of the following is a possible structure for this compound?
A.
B.
C.
D.
E.
2-heptanone
3-heptanone
2,4-dimethyl-3-pentanone
2,2-dimethyl-3-pentanone
Two of the above
Answer: C
Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR
spectra of aldehydes and ketones
Difficulty: Medium
167.
The 13C NMR spectrum of a compound with formula C7H14O shows five signals.
Which one of the following is a possible structure for this compound?
A.
B.
C.
D.
E.
2-heptanone
3-heptanone
2,2-dimethyl-3-pentanone
2,4-dimethyl-3-pentanone
none of these
Answer: C
Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR
spectra of aldehydes and ketones
Difficulty: Medium
168.
The 1H NMR spectrum of a compound with formula C7H14O shows a singlet at
9.2 ppm. Which one of the following is a possible structure for this compound?
A.
B.
C.
D.
E.
2-methyl-3-hexanone
2-methylhexanal
2,2 -dimethylpentanal
2,2-dimethyl-3-pentanone
B&C
Answer: E
Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR
spectra of aldehydes and ketones
Difficulty: Medium
169.
Provide a structure for the compound with molecular formula C5H10O and with
the following spectroscopic data.
IR: 1720 cm−1
1H NMR: 0.9  (triplet, 3H), 1.7  (sextet, 2H), 2.1  (singlet, 3H), 2.4  (triplet, 2H)
Answer:
Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR
spectra of aldehydes and ketones
Difficulty: Medium
170.
Provide a structure for the compound with molecular formula C9H10O and with
the following spectroscopic data.
IR: 1680 cm−1
1H NMR: 1.25  (triplet, 3H), 3.0  (quartet, 2H), 7-8  (multiplet, 5H)
Answer:
Learning Objective: 19.13 Describe the characteristic signals in the IR and NMR
spectra of aldehydes and ketones
Difficulty: Medium