ch16 Problems

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
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
A)
B)
C)
D)
E)
Ans:
5-Ethyl-5,5-dimethyl-Methyl-2-octanone
5-Ethyl-5-methyl- 2-hexanone
5,5-Dimethyl-2-octanone
A
Topic: Nomenclature
Section: 16.2
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
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
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
O
A)
B)
C)
D)
E)
Ans:
5-Ethyl-5,5-dimethyl-Methyl-2-octanone
5,5-Dimethylcycloheptanone
D
Topic: Nomenclature
Section: 16.2
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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

i) BH3
ii) H2O2,OH-, H2O
?
OH
OH
II
III
IV
A)
B)
C)
D)
E)
Ans:
I
II
III
IV
V
D
183

Section: 16.4
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
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
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
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:

2. H3O+
I
II
III
IV
B
187
Topic: Synthesis
Section: 16.4
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
2 . H 3O
COCl
III
A)
B)
C)
D)
E)
Ans:
1. LiAl(OC(CH3)3)3H
2. H3O+
OH
IV

2. H3O+
I
II
III
IV
C
188
Topic: Synthesis
Section: 16.4
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
2 . H 3O
PCC
CH2Cl2
OH
OH
IV
A)
B)
C)
D)
E)
Ans:

2. H3O+
I
II
III
IV
C
189
Topic: Synthesis
Section: 16.4
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
E
190
Topic: Synthesis
Section: 16.4
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
Section: 16.4
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

Section: 16.4
i) H2, P-2
ii) O3
iii)Zn, CH3CO2H
A)
B)
C)
D)
E)
Ans:
4-Methylhexanal
4-Methyl-1-hexanol
3-Methylhexanal
A

Section: 16.4
i) H2, Ni2B
ii) O3
iii)Zn, CH3CO2H
A)
B)
C)
D)
E)
Ans:
4-Methylhexanal
4-Methyl-1-hexanol
3-Methylhexanal
A
192

Section: 16.4
i) Li, NH3(l)
ii) O3
iii)Zn, CH3CO2H
A)
B)
C)
D)
E)
Ans:
3-Methylhexanal
4-Methyl-1-hexanol
4-Methylhexanal
C
193

Section: 16.4
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
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
2 . H 3O
I
II
III
IV
B
195

H2SO4
?
HgSO4, H2O
A)
B)
C)
D)
E)
Ans:
Ethylbenzene
1-Phenylethanol
Acetophenone
2-Phenylethanal
Vinylbenzene
C

H2SO4
HgSO4, H2O
?
OH
II
III
IV
A)
B)
C)
D)
E)
Ans:
I
II
III
IV
V
C
196

Section: 16.5
i.) KMnO4, OH-, hot
?
ii) H3O+
OH
OH
II
III
OH
IV
A)
B)
C)
D)
E)
Ans:
I
II
III
IV
V
E

Section: 16.5
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
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
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
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
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

Section: 16.5
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

Section: 16.5
OH
i) PCl5
?
ii) C6H6, AlCl3
O
OH
O
OH
II
IV
A)
B)
C)
D)
E)
Ans:
III
I
II
III
IV
V
E
201

Section: 16.5
OH
i) SOCl2
?
ii) C6H6, AlCl3
O
OH
O
OH
II
IV
A)
B)
C)
D)
E)
Ans:
III
I
II
III
IV
V
E
202

Section: 16.5
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

Section: 16.5
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

Section: 16.5
OH
O
i) PCl3
ii) C6H6, AlCl3
OH
II
III
OH
OH
IV
A)
B)
C)
D)
E)
Ans:
I
II
III
IV
V
A
205

Section: 16.5
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

Section: 16.5
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

Section: 16.5
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

Section: 16.5
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
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
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

Section: 16.6
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

Section: 16.5 and 16.6
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

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

Section: 16.7
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
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

Section: 16.7
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'

Section: 16.7
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

Section: 16.7
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
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
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
Section: 16.7
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

Section: 16.7
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
Section: 16.7
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
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
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

Section: 16.7
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
Section: 16.7
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

Section: 16.7
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
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
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

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

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

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

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
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
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

Section: 16.8
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
Section: 16.8
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
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

Section: 16.8
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

Section: 16.8
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

Section: 16.8
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

Section: 16.9
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:

Section: 16.9
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:

Section: 16.9
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

Section: 16.9
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

Section: 16.9
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

Section: 16.9
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

Section: 16.9
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

Section: 16.9
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

Section: 16.10
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

Section: 16.10
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

Section: 16.10
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

Section: 16.10
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
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
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

Section: 16.10
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

Section: 16.12
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
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
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
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
125. The 1H NMR spectrum of a compound with formula C7H14O gives two signals. Which
A) 2-Heptanone
B) 3-Heptanone
E)
Two of the above
Ans: C
Topic: Spectroscopy
Section: 16.13
126. The 13C NMR spectrum of a compound with formula C7H14O gives three signals. Which
A) 2-Heptanone
B) 3-Heptanone
E)
Two of the above
Ans: D
Topic: Spectroscopy
Section: 16.13
127. The 13C NMR spectrum of a compound with formula C7H14O gives five signals. Which
A) 2-Heptanone
B) 3-Heptanone
E)
Two of the above
Ans: C
246
Topic: Spectroscopy
Section: 16.13
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
E)
Two of the above
Ans: B
247
SHORT ANSWER QUESTIONS

Topic: Synthetic Strategy
Section: 16.4
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
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

Section: 16.5
131. Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-bromobutane.
i. C2H5Li, Et2O
Ans:
NaCN
CN
Br
ii. H3O+

Section: 16.5
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:
Section: 16.5
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

Section: 16.5
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

Section: 16.5
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

Section: 16.5
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

Section: 16.5
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
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
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
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
141. A compound with two OR groups attached to the same carbon is known as a(n)
_________.
Ans: acetal
Section: 16.7
142.
Complete the following reaction sequence, giving structural details of all significant
O
H+
OH
Ans:
O
OH
H
H+
O
OH
252

Section: 16.7
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

Section: 16.7
144.
intermediates.
O
H
1. OsO4
2. NaHSO3
?
+
Ans:
O
OH
1. OsO4
2. NaHSO3
OH
H+
253

Section: 16.7
145.
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
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
147. A compound containing a C=N double bond is known as a(n) __________.
Ans: imine
Section: 16.8
148. Oximes are formed when aldehydes and ketones react with _______________.
Ans: hydroxylamine, NH2OH
254
Topic: Cyanohydrins
Section: 16.9
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
150. The reaction between a phosphorus ylide and an aldehyde or ketone is called the
___________ reaction.
Ans: Wittig
Topic: Wittig Reaction
Section: 16.10
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
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
153. The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example
of a ______________reaction.
Ans: stereospecific
255

Section: 16.10
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
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
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

Section: 16.12
157. The Tollens test, used in conjunction with 2,4-DNP, can distinguish between
______________ and _______________.
Ans: aldehydes and ketones
Section: 16.12
158. What reagent would help you distinguish between acetophenone and 2methylbenzaldehyde?
Ans: Tollens Reagent
258
CH3
+
H
Topic: Spectroscopy
Section: 16.13
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
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
C5H10O
IR: 1720 cm1
1
H NMR: 1.1 (triplet, 3H), 2.4 (quartet, 2H)
Ans:
Topic: Spectroscopy
Section: 16.13
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
C7H6O
IR: 1703 cm1
1
H NMR: 7-8 (complex multiplet, 5H), 10.0 (singlet, 1H)

O
Ans:
Topic: Spectroscopy
Section: 16.13
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
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
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
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
C6H12O
IR: 1708 cm1
DEPT Experiments show: signals at 24.61, 26.42 as CH3
Ans:
263
Topic: Spectroscopy
Section: 16.13
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
C5H10O
IR: 1728 cm1
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
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

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Chapter Sixteen

MULTIPLE CHOICE QUESTIONS

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

Topic: Physical Properties, Relationships, Stereochemistry

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

i) H2, Lindlar catalyst

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

i) H2, Lindlar catalyst

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Carbonyl Reactivity

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: New Functional Groups

Topic: New Functional Groups

Topic: New Functional Groups

Topic: New Functional Groups

Topic: Reaction Products

iii) H2O, H3O

2CH3MgBr, then NH4+

Zn(Hg), HCl, reflux

Topic: Carbonyl Reactivity

Topic: Reaction Products

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

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

is produced by the reaction of an excess of

Topic: Physical Properties, Relationships, Stereochemistry

Topic: Reactions of Aldehydes and Ketones

Topic: Reactions of Aldehydes and Ketones

Topic: Reactions of Aldehydes and Ketones

Topic: Reactions of Aldehydes and Ketones

Topic: Reaction Products

Topic: Reaction Products