Chapter 13 Aldehydes and Ketones

Multiple Choice
1. Which compounds are named correctly? (Sec. 13.3)

OH

CH3

O
CH

CH

HO O
CH3CHCOH

o-hydroxybenzaldehyde
I

2-hydroxypropanoic acid
III

2-methylbenzaldehyde
II

H
O

C O

benzophenone
V

cinnamaldehyde
VI

I, II, III
IV, V, VI
II, IV, V
III, IV, VI

2. Which is the correct structure for 2-hydroxybenzophenone? (Sec. 13.3)

OH
a)

CH3CH

CH

b)

C
OH
O

O
c)

CH3

CH

d)
OH

OH

3. How many chiral ketones are there that have the molecular formula C6H12O? (Sec. 13.2)
a)
b)
c)
d)

C
CH3

1,3-butanedione
IV

a)
b)
c)
d)

CCH3

CH3CCH2CH

1
2
3
4
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4. Which compounds are acetals? (Sec. 13.7)

CH3

II

a)
b)
c)
d)

OH

OCH3

III
CH3

CH3

CH3

IV

VI

CH3

I, II, III
IV, V, VI
III, IV, VI
II, IV, V

5. Which is the product of the following reaction? (Sec. 13.7)

H3O
H2O

O
a) CH3CH2CH +
O

O
b) HOCH2CH2CH2OH + HCH

CH3OH

c) CH3CCH2CH2CH2CH

d) HCCH2CH + CH3OH

6. Which compound reacts with aqueous acid to give an aldehyde? (Sec. 13.7)

HO

H3C
a)

b)

OCH3

CH3
O

c)

d)

CH3
OCH3

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Chapter 13 Aldehydes and Ketones

7. A Grignard reagent is prepared by reacting cyclopentanol with first thionyl chloride and then magnesium
in ether. The Grignard reagent is then reacted with acetaldehyde (ethanal) and the reaction mixture
acidified. What is the major final product of this series of reactions? (Sec. 13.6)

OH

OH

CHCH3

a)

b)

CH2CH2OH

c)

d)

CH2CH3
8. Which is the major product of the reaction of ethyl Grignard and propiophenone (ethyl phenyl ketone)?
(Sec. 13.6)

CH2CH3
a)

CH2CH3
b)

CCH2CH3

CCH3

OH

OH

CH3

CH3

c)

CCH2CH3

CCH3

d)

OH

OH

9. Which is the major product of the following reaction? (Sec. 13.11)

O
O

NaBH4
H2O

Mg
ether

HCl

OH

OH
b)

a)

HO

OH
c)

d)

10. Which reaction does not lead to 3-methyl-3-hexanol? (Sec. 13.6)

a)
b)
c)
d)

2-butanone + propylmagnesium bromide

3-hexanone + methyl magnesium bromide
2-pentanone + ethylmagnesium bromide
3-pentanone + ethylmagnesium bromide

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CH2OCH3

Chapter 13 Aldehydes and Ketones

11. Which is the major product of the following reaction? (Sec. 13.6)

MgBr +

a)

CH3CH2ND2

b)

ether

c)

ND2

d)

NDCH2CH3

12. Which is the major product of the following reaction? (Sec. 13.6)

O
ether

CCH3 + CH3MgBr

OH
a)

CCH3

H3O

OH
b)

CH2CHCH3

CH3
OH
c)

CHCH2OH d)

CHCH2CH3

CH3
13. Which is the major product of the reaction of cyclopentylamine and benzaldehyde followed by nickel
and hydrogen? (Sec. 13.8)

a)

CH2NH

b)

NH

c)

NHCH2

d)

CH2NHCH2

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Chapter 13 Aldehydes and Ketones

14. The following product can be made from the reductive amination of which combination of
compounds? (Sec. 13.8)

NH2
CH

a)
b)
c)
d)

benzaldehyde and benzylamine

benzaldehyde and aniline
benzophenone and ammonia
acetophenone and ammonia

15. Which is the major product of the following reaction? (Sec. 13.11)

O
CH

NaBH4
H2O

O
a)

COH

b)

CH2OH

d)

CH2OH

O
c)

CH

16. 1-Hexene was treated with dilute sulfuric acid. The product of that reaction was reacted with
potassium dichromate in sulfuric acid. This product was then treated with methanol in hydrochloric acid.
What is the major product of this series of reactions? (Sec. 13.7, 13.10)

OCH3
a) CH3CH2CH2CH2CH2CH

OCH3
b) CH3CH2CH2CH2CCH3

OCH3

OCH3

c) CH3CH2CH2CH2CH2COCH3 d) CH3CH2CH2CH2CH2CCH3

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Chapter 13 Aldehydes and Ketones

17. Which oxidation conditions are used in the industrial transformation of cyclohexanone to adipic acid?
(Sec. 13.10)

a) K 2Cr2O 7 / H2SO 4
b) KMnO 4
c) HNO 3
d) AgNO 3 / NH3
18. Which is the best procedure for the following preparation? (Sec. 13.6, 13.10, 13.11)

CH2CH

CH

a)

CH3MgBr
H2SO4

K2Cr2O7
H2SO4

b)

Ag(NH3)2
NH3/H2O

CH3MgBr
H2SO4

c)

NaBH4
H2O

HCl

d)

LiAlH4
H2O

HBr

NaBH4
H2O
Mg
ether

Mg
ether

H2CO

PCC

CO2
H3O+

19. Which is the best procedure for the following preparation? (Sec. 13.8)

HN
a)

HN

NaBH4
H2O

HN

HN
c)

Ni / H2

NaBH4
H2O

b)

d)

Ni / H2

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Chapter 13 Aldehydes and Ketones

20. Which compound is a Schiff base? (Sec. 13.8)

NH2

a)

b) H2N N

c) CH3CH2NH3 CH3

d)

NH

21. Arrange the compounds in order of increasing solubility in water (least first). (Sec. 13.4)

O
CH

O
O

I
a)
b)
c)
d)

CH3CH2CH

II

H3C

CHCH2CH2CH2CH2CCH3
H3C

III

IV

I, II, III, IV
IV, I, II, III
IV, III, II, I
II, II, I, IV

22. Arrange the compounds in order of increasing solubility in water (least first). (Sec. 13.4)

OH

CH3CH2CH2CH

CH3CH2CH2CH2

CH3CH2CH2CH2CH3

II

III

a)
b)
c)
d)

O
CH3CH2

CH2CH3
IV

II, I, IV, III

I, II, IV, III
III, IV, I, II
II, I, IV, III

23. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 13.4)

OH

CH3CH2CH2CH

CH3CH2CH2CH2

CH3CH2CH2CH2CH3

II

III

a)
b)
c)
d)

II, I, IV, III

I, II, IV, III
III, IV, I, II
II, I, IV, III

154

O
CH3CH2

CH2CH3
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Chapter 13 Aldehydes and Ketones

24. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 13.4)

O
CH
O
I
a)
b)
c)
d)

CH3CH2CH

II

H3C

CHCH2CH2CH2CH2CCH3
H3C

III

IV

III, II, I, IV
IV, I, II, III
IV, III, II, I
II, II, I, IV

25. Which structure is the major tautomer of 2-pentanone in aqueous acid? (Sec. 13.9)

OH

OH

a)

OH

b)

c)

OH
d)

Fill in the Blank

1. The IUPAC name of the following structure is ___________________________. (Sec. 13.3)

Br
2. The IUPAC name of the following structure is ___________________________. (Sec. 13.3)

3. The major product that completes the following reaction is,

1)

MgBr
, ether

H
2) H+, H2O
(Sec. 13.6)

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Chapter 13 Aldehydes and Ketones

4. The starting material that completes the following reaction is,

1)

MgBr

, ether

HO

2) H+, H2O
(Sec. 13.6)
5. The starting material that completes the following reaction is,

OH

HO

O
H+

(Sec. 13.7)

6. The reagents that complete the following reaction are,

(Sec. 13.8)
7. The starting material that completes the following reaction is,

NH3

NH2

H2, Ni
(Sec. 13.8)
8. The reagents that complete the following reaction are,

O
H

OH
(Sec. 13.10)

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Chapter 13 Aldehydes and Ketones

9. The major product that completes the following reaction is,

1) LiAlH4, ether
O

2) H2O
(Sec. 13.11)

10. The reagents that complete the following reaction are,

OH
H
(Sec. 13.11)

True-False
1. The name of the following molecule is 1,5-cyclohexanecarbaldehyde. (Sec. 13.3)

O
H

2. The name of the following compound is 3-cyclohexenone. (Sec. 13.3)

3. The order of boiling points for the following functional groups, of similar molecular weights, is,
ether > aldehyde > alcohol > carboxylic acid

(Sec. 13.4)

4. The enol form of cyclohexanone is,

OH

(Sec. 13.9)

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Chapter 13 Aldehydes and Ketones

5. The product of the reaction of acetone (propanone) with bromine and acetic acid is 1-bromo-2propanone. (Sec. 13.9)
6. The product of the reaction of 2-hydroxybutanal with phenyl magnesium bromide is 1-phenyl-1,2butanediol. (Sec. 13.6)
7. The product of the reaction of benzaldehyde with silver ammonium nitrate (Tollens reagent) is benzoic
acid. (Sec. 13.10)
8. The product of the reaction of 3-pentanone with ammonia, hydrogen, and nickel is 3-pentanamine. (Sec.
13.8)
9. The mechanism for the formation of the enol form of propanal under basic conditions (NaOH) is,

O
H

Na+
H

+ H2O

H
-OH

(Sec. 13.9)

10. Two ways to drive the acetal reaction to completion are to use excess alcohol and remove water
produced. (Sec. 13.7)

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Chapter 13 Aldehydes and Ketones

Answers
Multiple Choice
1. a
2. b
3. b
4. c
5. b
6. c
7. a
8. a
9. a
10. d
11. a
12. a
13. c
14. c
15. b
16. b
17. c
18. c
19. c
20. d
21. b
22. c
23. c
24. a
25. c
Fill in the Blank
1. R 4-bromo-5-oxohexanal
2. E 4-nonene-2,8-dione
3.

OH
H

4.

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Chapter 13 Aldehydes and Ketones

5.

O
H
6.

H2N
Ni, H2
7.

O
H

8. H2CrO4 or Ag+ conditions

9.

OH
10. 1) NaBH4, ethanol 2) H2O
True-False
1. F
2. T
3. F
4. F
5. T
6. F
7. T
8. T
9. F
10. T

160