Organic Chemistry

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
148

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
149
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
150
CH2OCH3
MgBr +
a)
CH3CH2ND2
b)
ether
c)
ND2
d)
NDCH2CH3
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
151
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
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
152
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
153
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
IV
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)
155
4. The starting material that completes the following reaction is,
1)
MgBr
, ether
HO
2) H+, H2O
(Sec. 13.6)
OH
HO
O
H+
(Sec. 13.7)
6. The reagents that complete the following reaction are,
(Sec. 13.8)
NH3
NH2
H2, Ni
(Sec. 13.8)
O
H
OH
(Sec. 13.10)
156
9. The major product that completes the following reaction is,
1) LiAlH4, ether
O
2) H2O
(Sec. 13.11)
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)
157
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)
158

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.
159

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

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Chapter 13 Aldehydes and Ketones

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

Chapter 13 Aldehydes and Ketones

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

Chapter 13 Aldehydes and Ketones

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

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

2-butanone + propylmagnesium bromide

Chapter 13 Aldehydes and Ketones

Chapter 13 Aldehydes and Ketones

benzaldehyde and benzylamine

Chapter 13 Aldehydes and Ketones

Chapter 13 Aldehydes and Ketones

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

II, I, IV, III

II, I, IV, III

Chapter 13 Aldehydes and Ketones

Fill in the Blank

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

Chapter 13 Aldehydes and Ketones

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

6. The reagents that complete the following reaction are,

Chapter 13 Aldehydes and Ketones

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

10. The reagents that complete the following reaction are,

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

4. The enol form of cyclohexanone is,

Chapter 13 Aldehydes and Ketones

Chapter 13 Aldehydes and Ketones

Chapter 13 Aldehydes and Ketones

8. H2CrO4 or Ag+ conditions

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