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Chapter Sixteen

MULTIPLE CHOICE QUESTIONS


Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
1. What is the correct IUPAC name for the following compound?

A)
B)
C)
D)
E)
Ans:

2-Methyl-5-heptanone
7-Methyl-4-octanone
6-Isopropyl-4-octanone
Isobutyl propyl ketone
1,1-Dimethyl-4-heptanone
B

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
2. What is the correct structure for 7-methyl-4-octanone?
O

II

O
O

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

162

III

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
3. What is the correct IUPAC name for the following compound?

A)
B)
C)
D)
E)
Ans:

5,5-Dimethyl-2-heptanone
5-Ethyl-5,5-dimethyl-Methyl-2-octanone
5-Ethyl-5-methyl- 2-hexanone
5,5-Dimethyl-2-octanone
3,3-Dimethyl-6-heptanone
A

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
4. What is the correct structure for 5,5-dimethyl-2-heptanone?
O

II

III

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
B

163

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
5. A correct name for the following compound would be which of those below?
O
H

A)
B)
C)
D)
E)
Ans:

2,5-Dimethyl-6-hexanal
2,5-Dimethylhexanal
2-Aldehydoisohexane
3,5-Dimethylheptanone
1-Hydro-2,5-dimethyl-1-hexanone
B

Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
6. What is the correct structure for 2,5-dimethylhexanal?
O

II

III

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

164

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
7. What is the correct IUPAC name for the following compound?
O

A)
B)
C)
D)
E)
Ans:

5,5-Dimethyl-2-heptanone
5-Ethyl-5,5-dimethyl-Methyl-2-octanone
5,5-Dimethylcycloheptanone
4,4-Dimethylcycloheptanone
3,3-Dimethylcycloheptanone
D

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
8. What is the correct IUPAC name for the following compound?
O

A)
B)
C)
D)
E)
Ans:

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
C

165

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
9. What is the correct IUPAC name for the following compound?

A)
B)
C)
D)
E)
Ans:

1,1,2-Trimethyl-1,3-hexenone
1,2-Dimethyl-1,3-hexenone
2,3-Dimethyl-1,3-heptenone
2,3-Dimethyl-2-hepten-4-one
5,6-Dimethyl-5-hepten-4-one
D

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
10. What is the correct structure for 2,3-dimethyl-2-hepten-4-one?
O

II

III

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
E

166

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
O

11.

A correct name for C 6 H 5 C H 2 C H 2 C H is?


A) 3-Benzylpropanone
B) 3-Phenylpropanal
C) 3-Benzylpropanal
D) Nonanone
E)
Nonanal
Ans: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
12. What is the correct structure for 3-phenylpropanal?
O

O
H

II

III
O

H
O

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
E

167

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
13. What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?
O

Ph

Ph

OH
Ph

OH

OH

III

OH

II

OH

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
14. Which is the proper name for the structure shown?
C H O
C l
C H

A)
B)
C)
D)
E)
Ans:

2-Chloro-5-aldehydotoluene
6-Chloro-3-aldehydotoluene
2-Methyl-4-aldehydochlorobenzene
4-Chloro-3-methylbenzaldehyde
4-Methyl-5-chloro-2-benzaldehyde
D

168

Ph

Ph

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
15. What is the correct structure for 4-chloro-3-methylbenzaldehyde?
O

Cl

II

Cl

Cl
O

H
H
O
Cl

Cl

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
A

169

III

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
16. What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?
NO2

O2N

NO2

II

NO2

NO2

O2N
H

O2N
H
NO2

III

IV

O2N

O
NO2

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
B

170

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
17. What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?
O

Cl

Cl

II
O

Cl

Cl

IV

III
Cl

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

171

Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
18. What is the correct structure for 7-bromo-1-octyn-4-one?
Br

Br

Br

II

III

Br
Br

IV

A)
B)
C)
D)
E)
Ans:

V O

I
II
III
IV
V
A

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
19. What is the correct IUPAC name for the following compound?
Br

A)
B)
C)
D)
E)
Ans:

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
B

172

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
20. What is the correct IUPAC name for the following compound?
O

Cl

A)
B)
C)
D)
E)
Ans:

(S)-3-chloro-1-hexanone
(S)-1-chloro-3-hexanone
(R)-3-chlorocyclohexanone
(S)-3-chlorocyclohexanone
(S)-1-chloro-3-cyclohexanone
D

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
O

21.
C H

C H

C H

O H
What is the IUPAC name for
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
Ans: B

173

C H
C 6H

C H
5

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
22. Which is the proper name for the structure shown?
O2 N

O
NO2

A)
B)
C)
D)
E)
Ans:

3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal
3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
3-Methyl-5-(2,5-dinitrophenyl)pentanal
3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde
3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde
C

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
23. Which is the proper name for the structure shown?
O
Cl

A)
B)
C)
D)
E)
Ans:

3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
3-Methyl-5-(4-chlorophenyl)hexanol
3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
3-Methyl-5-(4-chlorophenyl)-hexanaldehyde
3-Methyl-5-(4-chlorophenyl)hexanal
E

174

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
24. Which is the proper name for the structure shown below?
Br
O

A)
B)
C)
D)
E)
Ans:

7-Bromo-1,4-octynal
7-Bromo-1,4-octynone
2-Bromo-5,7-octynal
7-Bromo-7-methyl-1-heptyne-3-ketone
7-Bromo-1-octyn-4-one
E

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
25. What is the correct structure for (R)-7-bromo-1-octyn-4-one?
Br

Br

Br
O

II

III

Br
Br

IV

A)
B)
C)
D)
E)
Ans:

V O

I
II
III
IV
V
A

175

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
26. What is the correct structure for (S)-7-bromo-1-octyn-4-one?
Br

Br

Br
O

II

III

Br
Br

IV

A)
B)
C)
D)
E)
Ans:

V O

I
II
III
IV
V
C

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
27. Which is the IUPAC name for the structure shown below?
Br

A)
B)
C)
D)
E)
Ans:

(R)-5-Bromo-2-heptanal
(S)-5-Bromo-2-heptanal
(R)-5-Bromo-2-heptanone
(S)-5-Bromo-2-heptanone
(R)-3-Bromopentyl methyl ketone
C

176

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
28. Which is the IUPAC name for the structure shown below?
H

Br

A)
B)
C)
D)
E)
Ans:

(R)-5-Bromo-2-heptanal
(S)-5-Bromo-2-heptanal
(R)-5-Bromo-2-heptanone
(S)-5-Bromo-2-heptanone
(R)-3-Bromopentyl methyl ketone
D

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
29. What is the correct structure for (R)-5-bromo-2-heptanone?
Br

Br

Br

II

III

Br

Br

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
B

177

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
30. What is the correct structure for (S)-5-bromo-2-heptanone?
Br

Br

Br

II

III

Br

Br

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
E

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
31. Which is the IUPAC name for the structure shown below?

A)
B)
C)
D)
E)
Ans:

5-Cyclohexyl-2-hexanal
5-Cyclohexyl-2-hexanone
5-Cyclohexyl-5-methyl-2-pentanone
5-(1-Methylcyclohexyl)-2-pentanone
4-(1-Methylcyclohexyl)-2-butanone
E

178

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
32. What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

II

IV

A)
B)
C)
D)
E)
Ans:

III

III

I
II
III
IV
V
D

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
33. What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

II

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

179

Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
34. What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

II

IV

A)
B)
C)
D)
E)
Ans:

III

I
II
III
IV
V
E

Topic: Physical Properties, Relationships, Stereochemistry


Section: 16.3
Difficulty Level: Easy
35. Which of the compounds listed below would you expect to have the highest boiling
point? (They all have approximately the same molecular weight.)
A) Pentane
B) 1-Butanol
C) Butanal
D) 1-Fluorobutane
E)
Diethylether
Ans: B

180

Topic: Reagents
Section: 16.4
Difficulty Level: Easy
36. LiAlH4 (LAH) cannot be used to convert carboxylic acids to the corresponding
aldehydes because:
A) LAH is not sufficiently reactive.
B) RCOOH is converted into RCOOLi.
C) RCOOH is reduced to RCH2OH.
D) RCOOH is reduced to RCH3.
E)
RCOOH is converted into R2C=O.
Ans: C
Topic: Reagents
Section: 16.4
Difficulty Level: Easy
37. Identify the reagent(s) that would bring about the following reaction:
CH3CH2CH2COCl
CH3CH2CH2CHO
A) H2/Ni
B) Li/liq.NH3
C) LiAlH[OC(CH3)3]3, ether
D) NaBH4, CH3OH
E)
LiAlH4, ether
Ans: C

181

Topic: Reaction Products


Section: 16.4 and previous chapters
Difficulty Level: Medium
38. Select the structure of the major product in the following reaction.
i) BH3
?
ii) H2O2,OH-, H2O
A)
B)
C)
D)
E)
Ans:

Ethylbenzene
1-Phenylethanol
Acetophenone
2-Phenylethanal
Vinylbenzene
D

182

Topic: Reaction Products


Section: 16.4 and previous chapters
Difficulty Level: Medium
39. Select the structure of the major product in the following reaction.

i) BH3
ii) H2O2,OH-, H2O

?
OH

OH

II

III

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

183

Topic: Reaction Products


Section: 16.4
Difficulty Level: Medium
40. What is the final product, Z, of the following synthesis?

C H

1 . K M n O 4, O H

2 . H 3O

heat

C O A l ( t- B u ) 2

C O C H

A)
B)
C)
D)
E)
Ans:

-,

S O C l2

II

III

I
II
III
IV
V
C

184

1 . L iA lH ( O - t- B u ) 3
e th e r, -7 8 oC
2 . H 2O

C H

C O Li

C O H

IV

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
41. Which of the following procedures would not yield 3-pentanone as a major product?
C H 3C H 2M g B r
A)
H 3O +
C H 3C H 2C N
e th e r
1. O3
B)
2. Zn/H+

C)

C H 3C H 2L i

C H 3C H 2C N

D)

H 3O

e th e r
H

CH3CH2MgBr
ether

C H 3C H 2C O 2H

PCC

H3O+

CH2Cl2

E)

C H 3C H 2M g B r
e th e r

Ans: E

185

H 3O

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
42. A good synthesis of
H
O

w o u ld b e :
H

H 2O , H 2S O

H2O, H2SO4

H gSO

HgSO4

1 . S ia 2B H

II

2 . H 2O 2, N aO H
H

1. DIBAL-H/-78oC

CN

1. O

II

III

2. H2O

2. Zn, H O A c
H

IV
III

O H

1. K M nO 4, N aO H , heat
2 . H 3 O 1.+ O3
2. Zn/H+

OH

IV

A)
B)
C)
D)
E)
Ans:

1. KMnO4, NaOH, heat


2. H3O+

I
II
III
IV
All of these are equally useful.
B

186

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
43. A good synthesis of
H
O

w o u ld b e :
H

H 2O , H 2S O

H g S HO 24O, H2SO4

HgSO4

1 . S ia 2B H

II

2 . H 2O 2, N aO H
H

III

1. DIBAL-H/-78oC

COOCH3

1. O

II

IV

2. H2O

2. Zn, H O A c
O H

1 . K MH n O 4 , N a O H , h e a t
2 . H 3O

III

1. O3
2. Zn/H+

OH

IV

A)
B)
C)
D)
E)
Ans:

1. KMnO4, NaOH, heat


2. H3O+

I
II
III
IV
All of these are equally useful.
B

187

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
44. A good synthesis of
H
O

w o u ld b e :
H

H 2O , H 2S O

H2SO4
H g S HO 2O,
4

HgSO4

1 . S ia 2B H

II

2 . H 2O 2, N aO H
H

1. O

II

III

IV

1. O3

2. Zn/H+

2. Zn, H O A c
O H

1. K M nO 4, N aO H , heat
2 . H 3O

COCl

III

A)
B)
C)
D)
E)
Ans:

1. LiAl(OC(CH3)3)3H
2. H3O+

OH

IV

1. KMnO4, NaOH, heat


2. H3O+

I
II
III
IV
All of these are equally useful.
C

188

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
45. A good synthesis of
H
O

w o u ld b e :
H

I
I

H 2O , H 2S O
H gSO

4H2O, H2SO4

1 . S ia 2B H

II

HgSO4

2 . H 2 O H2 , N a O H
H

1. O

III I I

IV

III

1. O3

2 . Z n , H O 2.A Zn/H
c +
O H

1. K M nO 4, N aO H , heat
2 . H 3O

PCC
CH2Cl2

OH

OH

IV

A)
B)
C)
D)
E)
Ans:

1. KMnO4, NaOH, heat


2. H3O+

I
II
III
IV
All of these are equally useful.
C

189

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
46. A good synthesis of
H
O

w o u ld b e :
H

H 2O , H 2S O
H gSO

2.H2O2, NaOH

2 . H 2O 2, N aO H
H

III

1. DIBAL-H/-78oC

CN

1. O

II

III

A)
B)
C)
D)
E)
Ans:

2. H2O

2. Zn, H O A c
O H

1 . COOCH
K M n O 4 ,1.N DIBAL-H/-78
a O H , h e a t oC
3

2 . H 3O

COCl

IV

4 1. BH3

1 . S ia 2B H

II

IV

2. H2O

1. LiAl(OC(CH3)3)3H
2. H3O+

I
II
III
IV
All of these are equally useful.
E

190

Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
47. Which synthesis or syntheses would yield propanal?
PC C
A)
C H 3C H 2C H 2O H
C H 2 C l2
O
B)
L iA lH [O C (C H 3 )3 ]3
C H 3C H 2C C l

C)

C H 3C

CH

e th e r, -7 8 o C
1 . S ia 2 B H
2 . H 2O 2, O H

D) All of these
E)
None of these
Ans: D
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
48. Select the structure of the major product in the following reaction.

i) H2, Lindlar catalyst


ii) O3
iii)Zn, CH3CO2H
A)
B)
C)
D)
E)
Ans:

4-Methylhexanal
4-Methyl-1-hexanol
3-Methylhexanal
4,10-Dimethyldodecane-6,7-dione
4,10-Dimethyldodecane-6,7-diol
A

191

Topic: Reaction Products


Section: 16.4
Difficulty Level: Hard
49. Select the structure of the major product in the following reaction.
i) H2, P-2
ii) O3
iii)Zn, CH3CO2H

A)
B)
C)
D)
E)
Ans:

4-Methylhexanal
4-Methyl-1-hexanol
3-Methylhexanal
4,10-Dimethyldodecane-6,7-dione
4,10-Dimethyldodecane-6,7-diol
A

Topic: Reaction Products


Section: 16.4
Difficulty Level: Hard
50. Select the structure of the major product in the following reaction.
i) H2, Ni2B
ii) O3
iii)Zn, CH3CO2H

A)
B)
C)
D)
E)
Ans:

4-Methylhexanal
4-Methyl-1-hexanol
3-Methylhexanal
4,10-Dimethyldodecane-6,7-dione
4,10-Dimethyldodecane-6,7-diol
A

192

Topic: Reaction Products


Section: 16.4
Difficulty Level: Hard
51. Select the structure of the major product in the following reaction.
i) Li, NH3(l)
ii) O3
iii)Zn, CH3CO2H

A)
B)
C)
D)
E)
Ans:

3-Methylhexanal
4-Methyl-1-hexanol
4-Methylhexanal
4,10-Dimethyldodecane-6,7-dione
4,10-Dimethyldodecane-6,7-diol
C

193

Topic: Reaction Products


Section: 16.4
Difficulty Level: Hard
52. Select the structure of the major product in the following reaction.

i) H2, Lindlar catalyst


ii) O3
iii)Zn, CH3CO2H
O

?
O

OH

III

II
OH

OH

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
A

194

Topic: Synthesis
Section: 16.4
Difficulty Level: Hard
53. A good synthesis of
H
O

w o u ld b e :
H

H 2O , H 2S O
H gSO

1 . S ia 2B H

II

2 . H 2O 2, N aO H
H

1. O

III

IV
A)
B)
C)
D)
E)
Ans:

2. Zn, H O A c
O H

1. K M nO 4, N aO H , heat
2 . H 3O

I
II
III
IV
All of these are equally useful.
B

195

Topic: Reaction Products


Section: 16.5 and previous chapters
Difficulty Level: Medium
54. Select the structure of the major product in the following reaction.
H2SO4
?
HgSO4, H2O
A)
B)
C)
D)
E)
Ans:

Ethylbenzene
1-Phenylethanol
Acetophenone
2-Phenylethanal
Vinylbenzene
C

Topic: Reaction Products


Section: 16.5 and previous chapters
Difficulty Level: Medium
55. Select the structure of the major product in the following reaction.

H2SO4
HgSO4, H2O

?
OH

II

III

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

196

Topic: Reaction Products


Section: 16.5
Difficulty Level: Medium
56. Select the structure of the major product in the following reaction.
i.) KMnO4, OH-, hot
?

ii) H3O+

OH

OH

II

III

OH

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
E

Topic: Reaction Products


Section: 16.5
Difficulty Level: Medium
57. Select the structure of the major product in the following reaction.
i.) KMnO4, OH-, hot
+

ii) H3O

A)
B)
C)
D)
E)
Ans:

cyclopentanol
1-cyclopentylcyclopentane
cyclopentanone
cyclopentene
1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane
C

197

Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
58. Which of the reactions listed below would serve as a synthesis of acetophenone,
O
C 6H 5C C H

A)

OH

PCC
CH2Cl2

B)
C)

C 6H

C H 3C O C l

C 6H 5C N + C H 3L i
D) Answers A) and B) only
E)
Answers A), B), and C)
Ans: E

A lC l3
e th e r

H 3O

Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
59. Which of the following would yield 3-pentanone as the major product?
e th e r
A)
H 3O +
C H 3C H 2C N + C H 3C H 2L i
P ro d u ct
ether
B)
H3O+
CN

C)

MgBr

PCC
OH

CH2Cl2

D) Two of these
E)
All of these
Ans: E

198

Product

Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
60. Which of the following is not a synthesis of benzophenone,
O
C 6H 5C C 6H

A)
C 6H
B)
C)

C 6H 5C C l

(C 6H 5)2C H O H
(C 6H 5)2C H = C H

D)

A lC l3

H 2C rO

a c e to n e
1. O 3
2

2. Zn, H O A c

PCC
Ph2CHOH

CH2Cl2

E)
All of the above will give benzophenone.
Ans: E
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
61. Which of the following is a synthesis of 3-heptanone?
A)
PCC
1 . C H 3C H 2M g B r
C H 3C H 2C H 2C H 2C H 2O H
C H 2C l2
2 . H 3O +
+
C H 3(C H 2)2C H 2L i
B)
H 3O
C H 3C H 2C N
e th e r
P B r3
C H 3C H 2M g B r
C)
N aC N
C H 3C H 2C H 2C H 2O H
e th e r
e th e r
1. O3
D)
2. Zn/H+

E)
All of the above are syntheses of 3-heptanone.
Ans: E

199

H 2C r2O
a c e to n e

H 3O

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
62. What would be the product of the following reaction sequence?
OH
i) PCl3
?
ii) C6H6, AlCl3
O
iii) Zn(Hg), HCl, heat

OH
OH

A)
B)
C)
D)
E)
Ans:

II

I
II
III
IV
V
E

IV

III

200

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
63. What would be the product of the following reaction sequence?
OH
i) PCl5
?
ii) C6H6, AlCl3
O
iii) Zn(Hg), HCl, heat

OH

O
OH

II

IV
A)
B)
C)
D)
E)
Ans:

III

I
II
III
IV
V
E

201

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
64. What would be the product of the following reaction sequence?
OH
i) SOCl2
?
ii) C6H6, AlCl3
O
iii) Zn(Hg), HCl, heat

OH

O
OH

II

IV
A)
B)
C)
D)
E)
Ans:

III

I
II
III
IV
V
E

202

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
65. What would be the product of the following reaction sequence?
OH
O

i) PCl3
ii) C6H6, AlCl3
iii) NaBH4, H2O

OH

II

III

OH
OH

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

IV

203

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
66. What would be the product of the following reaction sequence?
OH
O

i) PCl3
ii) C6H6, AlCl3
iii) LiAlH4
iv) H2O

OH

II

III

OH
OH

IV
A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

204

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
67. What would be the product of the following reaction sequence?
OH
O

i) PCl3
ii) C6H6, AlCl3
iii) Zn(Hg), HCl, heat

OH

II

III

OH
OH

IV
A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
A

205

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
68. The product, E, of the following reaction sequence,
P C l5
C 6H 6
C H 3C H 2C O O H
C
D
A lC l3

O
C H 2C H 2C H

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

N aB H

C H C H 2C H

II

III

206

C H 3O H

O H

C O C H 2C H

would be:

O
3

C C H 2C H

IV

C H (C H 3)2

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
69. The product, D, of the following sequence of reactions
O

S O C l2

C H 3C H 2C O H

to lu e n e
A lC l3

Z n (H g )

H C l

+
C

(d is c a rd )

would be:
O
C H

C H 2C H 2C H

C H 3C H 2C C H

C H

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
A

O
C H

II

C H 2C H 2C H 2C l

III

C H

IV

C H
C H
C H

207

C H 2C H 2C C l

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
70. The product, E, of the following reaction sequence,
OH

C6H6

PCl5

LAH

AlCl3

would be:
O
C H 2C H 2C H

A)
B)
C)
D)
E)
Ans:

O H

C O C H 2C H

C H C H 2C H

II

I
II
III
IV
V
C

III

O
3

C C H 2C H

C H (C H 3)2

IV

Topic: Reaction Products


Section: 16.5
Difficulty Level: Hard
71. What is the final product of this synthetic sequence?

B enzene
A)

B r2

M g

F e C l3

e th e r

O
C 6H 5C C 6H

B)
C)
D)

1 . C 6H 5C H O
2. H 3O

p-BrC6H4CH2C6H5
C6H5CH2COOH
O
C 6H 5C H 2C C 6H

E)
C6H5CH2C6H5
Ans: A

208

H 2C r2O
a c e to n e

Topic: Reagents
Section: 16.6
Difficulty Level: Easy
72. Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl
group of an aldehyde or ketone?
A) IB) H3O+
C) AlCl3
D) BF3
E)
ZnCl2
Ans: A
Topic: Carbonyl Reactivity
Section: 16.6
Difficulty Level: Medium
73. What, in general, is the order of decreasing reactivity of these carbonyl compounds
towards nucleophilic reagents?
H

O
C H 3C C H

I
A)
B)
C)
D)
E)
Ans:

C H 3C

O
O

II
I > III > IV > II > V
IV > II > I > III > V
V > III > I > II > IV
I > IV > II > III > V
III > V > IV > II > I
B

(C H 3)3C C C H

III

209

HC

IV

(C H 3)3C C C (C H 3)3

Topic: Carbonyl Reactivity


Section: 16.6
Difficulty Level: Medium
74. What, in general, is the order of increasing reactivity of these carbonyl compounds
towards nucleophilic reagents?
H

O
C H 3C C H

I
A)
B)
C)
D)
E)
Ans:

C H 3C

O
O

(C H 3)3C C C H

II
I < III < V < II < IV
IV < II < I < III < V
V< III < I < II < IV
II< I < V < III < IV
III < V < IV < II < I
C

HC

III

(C H 3)3C C C (C H 3)3

IV

Topic: Reaction Products


Section: 16.5 and 16.6
Difficulty Level: Medium
75. The product, K, of the following sequence of reactions
C H

B enzene

C H 3C H C O C l

A lC l3
O H

C H 3C H 2M g B r
e th e r

H 3O

K
would be:

O H

H O

A)
B)
C)
D)
E)
Ans:

I
I
II
III
IV
V
B

II

III

210

IV

Topic: Reaction Products


Section: 16.5 and 16.6
Difficulty Level: Medium
76. The product, K, of the following sequence of reactions would be:
MgBr

AlCl3

I
Cl

H3O+

heat

ether

(-H2O)

O
O

HO

III

II

OH

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

211

Topic: Reaction Products


Section: 16.7
Difficulty Level: Easy
77. Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what
compound?
O H
A)
B)

C 6H 5C H O C H
O
C 6H 5C O C H

C)
D)
E)
Ans:

C6H5C(OCH3)3
Answers A) and B)
Answers B) and C)
A

Topic: New Functional Groups


Section: 16.7
Difficulty Level: Easy
78. Which of the following compounds is an acetal?
O

O
OCH3

A)
B)
C)
D)
E)
Ans:

I
I
II
III
IV
None of these
C

OH

II

III

212

IV

Topic: New Functional Groups


Section: 16.7
Difficulty Level: Easy
79. Which is the general formula for a thioacetal?
H
A)
B)

R C
S
R C H SR '

C)

O H
RC HSR'

D)

SH
R C H SR '

E)

SR '
R CHO R '

Ans: D

SR'

Topic: New Functional Groups


Section: 16.7
Difficulty Level: Easy
80. Which compound is an acetal?
O

I
A)
B)
C)
D)
E)
Ans:

OH

II

OCH3

OH

III

I
II
III
IV
All of the above
B

213

IV

Topic: New Functional Groups


Section: 16.7
Difficulty Level: Easy
81. Which compound is a hemiacetal?
O

OH

II

I
A)
B)
C)
D)
E)
Ans:

OCH3

OH

III

IV

I
II
III
IV
All of the above
A

Topic: Synthesis
Section: 16.7
Difficulty Level: Easy
82. Which of the following reactions would yield benzaldehyde?
O H A)
C 6H 5C H 2C l
H 2O
heat
B)
H 3O +
C 6H 5C H (O C H 3)2
C)
1 . L iA lH 4 , e th e r
C 6H 5C O O H
2 . H 2O
D) Answers A) and B)
E)
Answers A), B), and C)
Ans: B

214

Topic: Reagents
Section: 16.7
Difficulty Level: Easy
83. Acetals are unstable in the presence of an aqueous solution of which of these?
A) HCl
B) NaOH
C) KHCO3
D) Na2CO3
E)
NaCl
Ans: A
Topic: Reaction Products
Section: 16.7
Difficulty Level: Medium
84. What new compound will eventually be formed when HCl is added to a solution of
pentanal in methanol?
O
A)
O
O

B)
C)
D)

Cl

OH
O
O

E)
Ans: A

OH

Cl

215

Topic: Reaction Products


Section: 16.7
Difficulty Level: Medium
85. What new compound will be formed when gaseous HCl is added to a solution of
propanal in methanol?
O
A)
C H 3C H 2C O C H
O

B)

C H 3C H 2C O H

C)
D)

CH3CH2CH(OCH3)2
C H 3C H 2C H O C H

O H

E)
None of the above
Ans: C
Topic: Reaction Products
Section: 16.7
Difficulty Level: Medium
86. What is the major product of the following reaction sequence?
OH, HCl
OCH3 i)
HO
?
O
ii) LAH, Et2O
O

iii) H2O, H3O


O

OH

HO

OH
O

HO

III

OH

OH

O
O

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
E

II

IV

216

Topic: Synthesis
Section: 16.7
Difficulty Level: Medium
87. Which sequence of reactions would be utilized to convert
O

A)
B)
C)
D)
E)
Ans:

C O 2C H

in to

C H 3
C C H

O H

2CH3MgBr, then NH4+


HOCH2CH2OH, H3O+; LiAlH4, ether; 2CH3MgBr, then NH4+
HOCH2CH2OH, H3O+; 2CH3MgBr, then NH4+
HOCH2CH2OH, H3O+; H2, Pt; CH3OH, NH4+
None of the above
C

Topic: Reagents
Section: 16.7
Difficulty Level: Medium
88. Which reagent(s) could be used to carry out the following transformation?
O

?
A)
B)
C)
D)
E)
Ans:

Zn(Hg), HCl, reflux


LiAlH4, ether
HSCH2CH2SH, BF3; then Raney Ni (H2)
All of the above
Two of the above
E

217

Topic: Carbonyl Reactivity


Section: 16.7
Difficulty Level: Medium
89. Which of these gem-diols is expected to be the most stable?
O H
A)
C F 3C C F

B)
C)

O H

CH3CH(OH)2
O H
C H 3C C H

O H

D) C6H5CH(OH)2
E)
ClCH2CH(OH)2
Ans: A
Topic: Carbonyl Reactivity
Section: 16.7
Difficulty Level: Medium
90. Which of these gem-diols is expected to be the least stable?
O H
A)
C F 3C C F

B)
C)

O H

CH3CH(OH)2
O H
C H 3C C H

O H

D) C6H5CH(OH)2
E)
ClCH2CH(OH)2
Ans: C

218

Topic: Reaction Products


Section: 16.7
Difficulty Level: Hard
91. What new compound will eventually be formed when HCl is added to a solution of
pentanal in methanol?
A) 1-Chloro-1-methoxypentane
B) 1,1-Dimethoxypentane
C) 1,1-Dihydroxypentane
D) 1,1-Dichloropentane
E) 1-Chloro-2-methoxypentane
Ans: B
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
92. The following reduction can be carried out with which reagent(s)?

?
A)
B)
C)
D)
E)
Ans:

Zn(Hg), HCl
i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
NaBH4, CH3OH
A&B
A&C
D

219

Topic: Synthesis
Section: 16.4 and 16.7
Difficulty Level: Medium
O

93.

Which of the following procedures would not yield ( C H 3 ) 2 C H C H as a product?


PC C
I
O H
C H 2 C l2
S O C l2

II

C O 2H

A)
B)
C)
D)
E)
Ans:

Zn

H O A c
K M nO

IV

e th e r, -7 8 oC
O

III

L i A l H ( O - t- B u ) 3

O H
O

H 3O

N aO H
H 3O

I
II
III
IV
V
D

220

Topic: Reaction Products


Section: 16.5 and 16.7
Difficulty Level: Medium
94. The product, E, of the following sequence of reactions
OH

SH

PCl5

Raney Ni

HS

H2

BF3

+
C (discard)

would be:
O

OH

III

II

I
O

Cl

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

221

Topic: Reaction Products


Section: 16.5 and 16.7
Difficulty Level: Medium
95. The product, E, of the following sequence of reactions
OH

SH

PCl5

Raney Ni

HS

H2

BF3

+
C (discard)

would be:
O

III

II

I
O

Cl

IV

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

222

Topic: Reaction Products


Section: 16.5 and 16.7
Difficulty Level: Hard
96. What would be the product of the following reaction sequence?
OH
i) SOCl2
?
ii) C6H6, AlCl3
O
iii) HSCH2CH2SH, BF3
iv) Raney Ni (H2)
O

OH
OH

II

IV
A)
B)
C)
D)
E)
Ans:

III

I
II
III
IV
V
E

223

Topic: Reaction Products


Section: 16.5 and 16.7
Difficulty Level: Hard
97. What would be the product of the following reaction sequence?
OH
O

i) PCl3
ii) C6H6, AlCl3
iii) HSCH2CH2SH, BF3
iv) Raney Ni (H2)

OH

II

III

OH

IV
A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
B

Topic: Reagents
Section: 16.8
Difficulty Level: Medium
98. Which reagent will not differentiate between 3-butenal and 2-butanone?
A) Br2/CCl4
B) Ag2O,OHC) H2NNHC6H5
D) KMnO4,OHE)
None of these
Ans: C

224

Topic: Reagents
Section: 16.8
Difficulty Level: Medium
99.

The compound C 6 H 5 C N N C C 6 H
benzaldehyde with which compound?
A) Ammonia
B) Hydrazine
C) Nitrogen
D) Phenylhydrazine
E)
Hydroxylamine
Ans: B

is produced by the reaction of an excess of

Topic: Physical Properties, Relationships, Stereochemistry


Section: 16.8
Difficulty Level: Medium
100. Stereoisomers can exist in the case of which of the following?
A) The hydrazone of butanone
B) The oxime of acetone
C) The phenylhydrazone of cyclohexanone
D) The cyclic acetal formed from propanal and ethane-1,2-diol
E)
The imine of cyclopentanone
Ans: A
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.8
Difficulty Level: Medium
101. Stereoisomers can exist in the case of which of the following?
A) The hydrazone of benzophenone
B) The oxime of 2-methylcyclopentanone
C) The phenylhydrazone of 4-methylcyclohexanone
D) The imine of cyclopentanone
E)
Two of the above
Ans: B

225

Topic: Reactions of Aldehydes and Ketones


Section: 16.8
Difficulty Level: Medium
102. Which of the following is formed when 3-methylcyclopentanone reacts with
hydroxylamine?
N-NH-C6H5

N-NH2

N-OH

II

III
NO2

O
N

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

N
H

NH2

N
H

IV

226

NO2

Topic: Reactions of Aldehydes and Ketones


Section: 16.8
Difficulty Level: Medium
103. Which of the following is formed when 4-methylpentanal reacts with phenylhydrazine?
N-C6H5

N-NH-C6H5

N-NH2

II

III

O
N

IV
A)
B)
C)
D)
E)
Ans:

N
H

N=N-C6H5

NH2

I
II
III
IV
V
A

227

Topic: Reactions of Aldehydes and Ketones


Section: 16.8
Difficulty Level: Medium
104. Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with
hydroxylamine?
N-NH-C6H5

N-NH2

N-OH

III

II

NO2

O
N

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

N
H

NH2

N
H

IV

228

NO2

Topic: Reactions of Aldehydes and Ketones


Section: 16.8
Difficulty Level: Medium
105. Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with
hydrazine?
N-NH-C6H5

N-NH2

N-OH

III

II

NO2

O
N

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
B

N
H

NH2

N
H

IV

229

NO2

Topic: Reaction Products


Section: 16.9
Difficulty Level: Medium
106. The product, C, of the following reaction sequence,
O

C H 3C C H

C H

A)
C H

B)
C)

C N

H C N

C 4H 7N O

C CO O H

CH3CH2COOCH3
C H 3C H C H

C N

D) CH3CH=CHCOOH
E)
None of these
Ans: A

230

H 2O
H 2S O
heat

C
4

would be:

Topic: Reaction Products


Section: 16.9
Difficulty Level: Medium
107. The product, D, of the following reaction sequence,
O
-

CN

HCN

HCl
C4H7NO

H2 O
heat

C H

A)
C H

C CO O H

B)
C)

CH3CH2COOCH3

D)
E)

CH3CH=CHCOOH

C H 3C H C H

C N

HO

COOH

Ans: E

231

would be:

Topic: Reaction Products


Section: 16.9
Difficulty Level: Medium
108. What is the major product of the following reaction sequence?
HCN

H3O+

LiAlH4

OH

OH
CN

NH2

CN

OH

III

II

OH

COOH

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
C

232

IV

Topic: Reaction Products


Section: 16.9
Difficulty Level: Medium
109. What is the major product of the following reaction sequence?
HCN

HCl

H2O
heat

OH

OH

OH
CN

NH2

CN

OH

III

II

OH

COOH

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
E

233

IV

Topic: Reaction Products


Section: 16.9
Difficulty Level: Medium
110. What is the major product of the following reaction sequence?
O

H C N

H 2S O

H 2O
heat
C N

N O S O 3H

C N

C O H

H
O S O 3H

C N H

A)
B)
C)
D)
E)
Ans:

I
I
II
III
IV
V
B

II

III

234

IV

Topic: Physical Properties, Relationships, Stereochemistry


Section: 16.9
Difficulty Level: Medium
111. In which of the following reactions is the final product expected to be formed as a
racemic mixture?
H
A)
C 6H 5M g B r +

C 6H 5C

B)
H CN

C H 3C C H

C)

HCN

D)

C H 3C

O
O

E)

x s C H 3O H

C H 3C H C H 2C O C 2H
C H

H Cl

+ (i-B u )2 A lH

Ans: C

235

Topic: Reaction Products


Section: 16.9
Difficulty Level: Hard
112. What is the major product of the following reaction sequence?
H2SO4

HCN

LiAlH4

H3O+

H2 O
heat

OH

OH
CN

NH2

CN

OH

III

II

OH

COOH

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

236

IV

Topic: Reaction Products


Section: 16.9
Difficulty Level: Hard
113. What is the major product of the following reaction sequence?
HCN

LiAlH4

HCl

H3O+

H2O
heat

OH

OH

OH
CN

NH2

CN

OH

III

II

OH

COOH

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
D

237

IV

Topic: Reaction Products


Section: 16.10
Difficulty Level: Medium
114. The product, H, of the following reaction sequence,

C 6H 5C H 2B r +

would be:
A)

(C 6H 5)3P
C H

C 6H 5C H 2C C 6H

O H
O

B)
C)

C 6H 5C H 2C C 6H 5
C 6H 5C H
C H C C 6H

D)
E)

C6H5CH2CH=CHC6H5
C 6H 5C H

C CH
C 6H

3
5

Ans: E

238

C 6H 5L i
e th e r

C 6H 5C C H

Topic: Reaction Products


Section: 16.10
Difficulty Level: Medium
115. What would be the final product?
(C 6H 5)3P

C H 3I
A)

C 6H 5C

C H

C 6H 5C C H

C H3
C 6H 5
C 6H 5C C H
CH

C6H5CH=CHCH3
O H
C 6H 5C C H

E)

C 6H 5L i
e th e r

B)

C)
D)

CH
C 6H 5C H

C C 6H
CH

Ans: A

239

Topic: Reaction Products


Section: 16.10
Difficulty Level: Medium
116. What would be the final product?
O

CH3I

A)

C 6H 5C

C H

C 6H 5C C H
CH

C6H5CH=CHCH3
O H
C 6H 5C C H

E)

C H3
C 6H 5

B)

C)
D)

NaH

P(OEt)3

CH
C 6H 5C H

C C 6H
CH

Ans: A

240

Topic: Reaction Products


Section: 16.10
Difficulty Level: Medium
117. What is the reactant W in the synthesis given below?

Ph3P +

A)
B)
C)
D)
E)
Ans:

C6H5Li

Wittig
reagent

Cyclopentanone
Cyclopentene
Cyclopentanol
Bromocyclopentane
Triphenylphosphine oxide
D

241

Topic: Synthesis
Section: 16.10
Difficulty Level: Medium
118. Which reaction sequence would be used to prepare
?

II

III

IV
A)
B)
C)
D)
E)
Ans:

1 . e th e r

M gB r

(C 6H 5)3P

2. H 3O

2 C H 3M gB r

N i

1 . e th e r
2 . H 3O

H
+

C 6H 5L i

N i
c y c lo p e n ta n o n e

C l

N i
O

C H 3M gB r

H 3O

e th e r
I
II
III
IV
All of the above would yield the product.
C

242

Topic: Synthesis
Section: 16.10
Difficulty Level: Medium
119. Which Wittig reagent would be used to synthesize

?
C H = P (C 6H 5)3

C H 3C H = P (C 6H 5)3
A)
B)
C)
D)
E)
Ans:

P (C 6H 5)3

I
II
I
II
III
IV
Either I or II could be used.
E

C H 3C H 2C H = P (C 6H 5)3

III

IV

Topic: Reaction Products


Section: 16.10
Difficulty Level: Hard
120. The product, H, of the following reaction sequence,
O

Br

would be:
A)

C H

C 6H 5C H 2C C 6H

O H
O

B)
C)

P(OEt)3

C 6H 5C H 2C C 6H 5
C 6H 5C H
C H C C 6H

D)
E)

C6H5CH2CH=CHC6H5
C 6H 5C H

C CH
C 6H

3
5

Ans: E

243

NaH

Topic: Reaction Products


Section: 16.12
Difficulty Level: Medium
121. Predict the major organic product of the following reaction:
A g (N H 3)2+

H
O

A)
B)
C)
D)
E)
Ans:

I
II
III
IV
V
B

H O 2C

H 3C

H 2O

II

H 3C

H 3C

III

O H
O

O
O

IV

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
122. A compound with formula C5H10O gives two signals only, both singlets, in the 1H NMR
spectrum. Which of these structures is a possible one for this compound?
O
A)
B)

C H 3C H 2C C H 2C H
O

C)

(C H 3)2C H C C H
H
(C H 3)3C C

D)

C H 3C H 2C H C
C H

E)

(C H 3)2C H C H 2C

Ans: C

244

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
123. A compound with formula C5H10O gives two signals only, one a triplet and the other a
quartet, in the 1H NMR spectrum. Which of these structures is a possible one for this
compound?
O
A)
B)

C H 3C H 2C C H 2C H
O

C)

(C H 3)2C H C C H
H
(C H 3)3C C

D)

C H 3C H 2C H C
C H

E)

(C H 3)2C H C H 2C

Ans: A
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
124. The 1H NMR spectrum of a compound with formula C7H14O gives three signals. Which
of these structures is a possible one 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
Ans: D

245

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
125. The 1H NMR spectrum of a compound with formula C7H14O gives two signals. Which
of these structures is a possible one 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
Ans: C
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
126. The 13C NMR spectrum of a compound with formula C7H14O gives three signals. Which
of these structures is a possible one for this compound?
A) 2-Heptanone
B) 3-Heptanone
C) 2,2-Dimethyl-3-pentanone
D) 2,4-Dimethyl-3-pentanone
E)
Two of the above
Ans: D
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
127. The 13C NMR spectrum of a compound with formula C7H14O gives five signals. Which
of these structures is a possible one for this compound?
A) 2-Heptanone
B) 3-Heptanone
C) 2,2-Dimethyl-3-pentanone
D) 2,4-Dimethyl-3-pentanone
E)
Two of the above
Ans: C

246

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
128. The 1H NMR spectrum of a compound with formula C7H14O gives a doublet at 9.2 ppm.
Which of these structures is a possible one for this compound?
A) 2-Methyl-3-hexanone
B) 2-Methylhexanal
C) 2,2 -Dimethylpentanal
D) 2,2-Dimethyl-3-pentanone
E)
Two of the above
Ans: B

247

SHORT ANSWER QUESTIONS


Topic: Synthetic Strategy
Section: 16.4
Difficulty Level: Medium
129. Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1bromobutane.
Ans:
i. DIBAL-H
O
NaCN
CN
Br
ii. H2O
Topic: Reaction Sequence
Section: 16.4
Difficulty Level: Hard
130. Complete the following reaction sequence, giving structural details of all significant
intermediates X, Y, and final product Z.
1 . L iA lH ( O - t- B u ) 3
1 . K M n O 4, O H , h eat
S O C l2
e th e r, -7 8 oC
C H 3
X
Y
2 . H 2O
2 . H 3O +
Ans:

COOH

O
X

C O A l ( t- B u ) 2

COCl

YC O C H

II

Z C H

III

248

CHO

C O Li

IV

C O H

Topic: Synthetic Strategy


Section: 16.5
Difficulty Level: Medium
131. Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-bromobutane.
i. C2H5Li, Et2O
Ans:
NaCN
CN

Br

ii. H3O+

Topic: Synthetic Strategy


Section: 16.5
Difficulty Level: Hard
132. Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1bromobutane.
HBr
i. DIBAL-H
NaCN
CN
Br
ii. H2O
ROOR
Ans:
Topic: Synthetic Strategy
Section: 16.5
Difficulty Level: Hard
133. Suggest a synthetic strategy for the synthesis of 6-methyl-3-heptanol from 4methylpentanenitrile, (CH3)2CHCH2CH2CN.
Ans:
i. DIBAL-H
CN

ii. H2O

OH

iii. C2H5MgBr, Et2O


iv. H3O+
OR

CN

i. C2H5MgBr, Et2O
ii. H3O+

OH

iii. NaBH4, H2O

249

Topic: Synthetic Strategy


Section: 16.5
Difficulty Level: Hard
134. Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene.
Ans:
HBr
i. C2H5Li, Et2O
NaCN
CN ii. H O+
Br
3
ROOR

Topic: Reaction Sequence


Section: 16.5
Difficulty Level: Hard
135. Complete the following reaction sequence, giving structural details of all significant
intermediates.
i. Br2, h
ii. Mg, CH3CH2CN
iii. H3O+
iv. NaBH4

Ans:
O

Br2, h

Br i. Mg, CH CH CN
3
2

ii. H3O+

250

NaBH4

HO

Topic: Reaction Sequence


Section: 16.5
Difficulty Level: Hard
136. Complete the following reaction sequence, giving structural details of all significant
intermediates.
i. O3
i. EtMgBr
?
+
ii.Zn, CH3CO2H
ii. H3O , heat
O

Ans:
O

i. EtMgBr
ii. H3O+, heat

i. O3
ii.Zn, CH3CO2H

HO

O
O

Topic: Reaction Sequence


Section: 16.5
Difficulty Level: Hard
137. Complete the following reaction sequence, giving structural details of all significant
intermediates and the final product.
B r2
M g
1 . C 6H 5C H O
H 2C r2O 4
B enzene
?
F e C l3
e th e r
a c e to n e
2. H 3O +
O
OH
Ans:
Br

MgBr

Topic: Relative Reactivity


Section: 16.6
Difficulty Level: Medium
138. Aldehydes are more reactive than ketones towards nucleophilic substitution because of
both steric and electronic factors. Briefly explain.
a. Steric reasons: ______________.
b. Electronic reasons: __________.
Ans: a. aldehydes have the small hydrogen substituent on one side, so less steric
crowding than ketones
b. aldehydes have only one electron-releasing group to partly neutralize/stabilize
the partial positive charge at the carbonyl carbon while ketones have two

251

Topic: Hemiacetals
Section: 16.7
Difficulty Level: Easy
139. A compound with an OH and OR group attached to the same carbon is known as a(n)
_____________.
Ans: hemiacetal
Topic: Hydrates
Section: 16.7
Difficulty Level: Easy
140. A compound with two OH groups attached to the same carbon is known as a(n)
_________.
Ans: hydrate or gem-diol
Topic: Acetals
Section: 16.7
Difficulty Level: Easy
141. A compound with two OR groups attached to the same carbon is known as a(n)
_________.
Ans: acetal
Topic: Reaction Sequence
Section: 16.7
Difficulty Level: Medium
142.

Complete the following reaction sequence, giving structural details of all significant
intermediates and the final product.
O

H+

OH

Ans:
O
OH
H

H+
O

OH

252

Topic: Reaction Sequence


Section: 16.7
Difficulty Level: Hard
143.

In the total synthesis of the Cecropia juvenile hormone, the following sequence of
reactions were used. Draw the intermediate and final product formed.
HO

/ H+

1. CH3Li

2. H+/H2O
O

Ans:
HO

/ H+

1. CH3Li
2. H+/H2O

HO
H

HO
CH3

Topic: Reaction Sequence


Section: 16.7
Difficulty Level: Hard
144.

Complete the following reaction sequence, giving structural details of all significant
intermediates.
O
H

1. OsO4
2. NaHSO3

?
+

Ans:
O
OH

1. OsO4
2. NaHSO3
OH

H+

253

Topic: Reaction Sequence


Section: 16.7
Difficulty Level: Hard
145.

Complete the following reaction sequence, giving structural details of all significant
intermediates and the final product.
O

KMnO4, OH-, heat

H+

HO

H+

H2 O

Ans:
O

H+
HO

KMnO4, OH-, heat

H
O

H
O

H
O

H2O

HO

OH

Topic: Functional Group Tests


Section: 16.8
Difficulty Level: Easy
146. 2,4-DNP is a reagent frequently used for functional group tests; it detects the presence
of _____________.
Ans: aldehydes and ketones
Topic: Imines
Section: 16.8
Difficulty Level: Easy
147. A compound containing a C=N double bond is known as a(n) __________.
Ans: imine
Topic: Functional Group Tests
Section: 16.8
Difficulty Level: Easy
148. Oximes are formed when aldehydes and ketones react with _______________.
Ans: hydroxylamine, NH2OH

254

Topic: Cyanohydrins
Section: 16.9
Difficulty Level: Easy
149. A compound with an OH and CN group attached to the same carbon is known as a(n)
_____________.
Ans: cyanohydrin
Topic: Wittig Reaction
Section: 16.10
Difficulty Level: Easy
150. The reaction between a phosphorus ylide and an aldehyde or ketone is called the
___________ reaction.
Ans: Wittig
Topic: Wittig Reaction
Section: 16.10
Difficulty Level: Easy
151. The driving force for the Wittig reaction is the formation of the very strong
_______________ bond in _______________.
Ans: P-O bond; triphenylphosphine oxide
Topic: General
Section: 16.10
Difficulty Level: Hard
152. The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example
of a ______________reaction.
Ans: stereospecific
Topic: General
Section: 16.10
Difficulty Level: Hard
153. The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example
of a ______________reaction.
Ans: stereospecific

255

Topic: Synthetic Strategy


Section: 16.10
Difficulty Level: Hard
154. Cis-stilbene (cis-1,2-diphenylethene) can be prepared in high yield from its trans
diastereomer. Propose a reasonable synthesis.
Ph

Ph

Ph

Ph

multiple steps
cis-stilbene

trans-stilbene

Ans:
Ph

m-CPBA
H

Ph

Ph

Ph

256

PPh3

Ph3P
Ph

Ph

Ph

Ph

Topic: Mechanisms
Section: 16.10
Difficulty Level: Hard
155. Draw a complete mechanism, using arrow convention to indicate electron movement,
for the following transformation:
O
H3C

PPh3

CH3

H3C

Ph3P

CH3

Ans:

O
H3C
H

O H3C
H

PPh3

PPh3
H3C

CH3

PPh3

PPh3

rotation 180o
as shown

CH3
H

H3C

257

CH3

+
H3C

H3C

CH3

Ph3P

Topic: Mechanisms
Section: 16.10
Difficulty Level: Hard
156. Draw a complete mechanism, using arrow convention to indicate electron movement,
for the following transformation:
O
H

H3C

PPh3

CH3

H3C

Ph3P

CH3

Ans:

O
H
H3C

O H3C
H

PPh3

CH3

PPh3
H
H3C

CH3

PPh3

H3C

PPh3

rotation 180o
as shown

CH3
CH3

Ph3P

CH3

Topic: Functional Group Tests


Section: 16.12
Difficulty Level: Easy
157. The Tollens test, used in conjunction with 2,4-DNP, can distinguish between
______________ and _______________.
Ans: aldehydes and ketones
Topic: Functional Group Tests
Section: 16.12
Difficulty Level: Easy
158. What reagent would help you distinguish between acetophenone and 2methylbenzaldehyde?
Ans: Tollens Reagent

258

CH3

+
H

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
159. Explain clearly how you might use 1H NMR to distinguish between
2-phenylacetaldehyde and acetophenone.
Ans: A quick inspection of 1H NMR of the two substances would allow easy
identification and distinction between them: the expected 1H NMR spectra of the
two substances are described below.
2-Phenylacetaldehyde
Acetophenone
C6H5CH2CHO
and
C6H5COCH3
3 signals
2 signals
approximate ppm approximate ppm
doublet (-CH2-) 2.5
singlet (-CH3) 2.0
multiplet (C6H5) 7
multiplet (C6H5) 7.2
triplet(-CHO) 9
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
160. Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1720 cm1
1

H NMR: 1.9 (triplet, 3H), 1.7 (sextet, 2H), 2.1 (singlet, 3H), 2.4 (triplet, 2H)
O
CH3CH2CH2CCH3

Ans:

259

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
161. Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1720 cm1
1

H NMR: 1.1 (triplet, 3H), 2.4 (quartet, 2H)

Ans:

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
162. Propose a structure that fits the following spectroscopic data:
C9H10O
IR: 1680 cm1
1

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

Ans:

260

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
163. Propose a structure that fits the following spectroscopic data:
C7H6O
IR: 1703 cm1
1

H NMR: 7-8 (complex multiplet, 5H), 10.0 (singlet, 1H)


O

Ans:
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
164. Propose a structure that fits the following spectroscopic data:
C3H6O
IR: 1730 cm1
1

H NMR: 1.1 (triplet, 3H), 2.5 (doublet of quartets, 2H), 9.8 (doublet, 1H)
H

Ans:

261

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
165. Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1716 cm1
Broadband decoupled 13C NMR: 7.93, 35.50, 212.07
DEPT Experiments show: signal at 7.93 as CH3 and signal at 35.50 as CH2

Ans:

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
166. Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1717 cm1
Broadband decoupled 13C NMR: 13.70, 17.41, 29.78, 45.71, 208.93
DEPT Experiments show: signals at 13.70, 29.78 as CH3 and signals at 17.41, 45.71
as CH2
O
CH3CH2CH2CCH3

Ans:

262

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
167. Propose a structure that fits the following spectroscopic data:
C4H8O
IR: 1728 cm1
Broadband decoupled 13C NMR: 13.71, 15.69, 45.82, 202.80
DEPT Experiments show: signal at 13.71 as CH3 and signals at 15.69, 45.82 as CH2
O

Ans:

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
168. Propose a structure that fits the following spectroscopic data:
C6H12O
IR: 1708 cm1
Broadband decoupled 13C NMR: 24.61, 26.42, 44.31, 213.81
DEPT Experiments show: signals at 24.61, 26.42 as CH3

Ans:

263

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
169. Propose a structure that fits the following spectroscopic data:
C4H8O
IR: 1737 cm1
Broadband decoupled 13C NMR: 15.48, 41.07, 204.86
DEPT Experiments show: signal at 41.07 as CH and signal at 15.48 as CH3

Ans:

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
170. Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1728 cm1
Broadband decoupled 13C NMR: 22.59, 23.57, 52.66, 202.71
DEPT Experiments show: signal at 23.57 as CH, signal at 22.59 as CH3, and signal at
52.66 as CH2.
O

Ans:

264

Topic: Spectroscopy
Section: 16.13
Difficulty Level: Hard
171. Acetaldehyde is reacted with excess methanol in acid. The product was isolated and
gave the following 1H NMR spectroscopic data:
1.3 (doublet, 3H)
3.4 (singlet, 6H)
4.6 (quartet, 1H)
Propose a structure consistent with this information.
Ans:
O

265