ch16 TEST BANK SOLOMONS

Package Title: Solomons Test Bank
Course Title: Solomons 11e

Chapter Number: 16
Question type: Multiple Choice
1) What is the correct IUPAC name for the following compound?
a) 2-Methyl-5-heptanone
b) 7-Methyl-4-octanone
c) 6-Isopropyl-4-octanone
d) Isobutyl propyl ketone
e) 1,1-Dimethyl-4-heptanone
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
2) What is the correct structure for 7-methyl-4-octanone?

O
O O III
I II O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
1
Section: 16.2
a) 5,5-Dimethyl-2-heptanone
b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
c) 5-Ethyl-5-methyl- 2-hexanone
d) 5,5-Dimethyl-2-octanone
e) 3,3-Dimethyl-6-heptanone
Answer: A
Topic: Nomenclature
Section: 16.2
4) What is the correct structure for 5,5-dimethyl-2-heptanone?

O
O O
I O II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 16.2
2
5) A correct name for the following compound would be which of those below?
O
H
a) 2,5-Dimethyl-6-hexanal
b) 2,5-Dimethylhexanal
c) 2-Aldehydoisohexane
d) 3,5-Dimethylheptanone
e) 1-Hydro-2,5-dimethyl-1-hexanone
Answer: B
Topic: Nomenclature
Section: 16.2
6) What is the correct structure for 2,5-dimethylhexanal?

O O
I
II O III
O O
H H
IV
V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 16.2
3
O
a) 5,5-Dimethyl-2-heptanone
b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
c) 5,5-Dimethylcycloheptanone
d) 4,4-Dimethylcycloheptanone
e) 3,3-Dimethylcycloheptanone
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium

O
a) 2,4-dimethyl-2-pentenone
b) 2,5-dimethylcyclopenten-3-one
c) 2,4-dimethylcyclopent-2-enone
d) 3,5-dimethylcyclopent-2-enone
e) 2-methyl-5-methylcyclopent-2-enone
Answer: C
Topic: Nomenclature
Section: 16.2
4
a) 1,1,2-Trimethyl-1,3-hexenone
b) 1,2-Dimethyl-1,3-hexenone
c) 2,3-Dimethyl-1,3-heptenone
d) 2,3-Dimethyl-2-hepten-4-one
e) 5,6-Dimethyl-5-hepten-4-one
Answer: D
Topic: Nomenclature
Section: 16.2
10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

O
O O
I II
III
IV O
V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
11) A correct name for C6H5CH2CH2CH is?
a) 3-Benzylpropanone
5
b) 3-Phenylpropanal
c) 3-Benzylpropanal
d) Nonanone
e) Nonanal
Answer: B
Topic: Nomenclature
Section: 16.2
12) What is the correct structure for 3-phenylpropanal?

O O
II III
I
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?
6
O Ph O OH O
Ph OH OH III Ph
II
I
Ph OH OH O
IV O V Ph
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature
Section: 16.2
14) Which is the proper name for the structure shown?
CHO
Cl
CH3
a) 2-Chloro-5-aldehydotoluene
b) 6-Chloro-3-aldehydotoluene
c) 2-Methyl-4-aldehydochlorobenzene
d) 4-Chloro-3-methylbenzaldehyde
e) 4-Methyl-5-chloro-2-benzaldehyde
Answer: D
Topic: Nomenclature
Section: 16.2
15) What is the correct structure for 4-chloro-3-methylbenzaldehyde?
7
O
O O
H
H H
Cl
I II
Cl III
Cl
O
H
H
O
Cl
Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?
8
O NO2
O
O2N NO2
I II
NO2 O
NO2
O
O2N
O2N H
H
NO2
III IV
O2N H
O
NO2
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 16.2
17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?
9
O
O
Cl
I Cl
II
O
O
H
H
Cl
IV
Cl III
Cl O
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 16.2
18) What is the correct structure for 7-bromo-1-octyn-4-one?

Br
Br Br
O
O O
I II III
Br
Br
O
IV V O
10
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
Br
O
a)2-Methyl-2-bromobutanone
b)(S)-2-Bromo-2-methylcyclobutanone
c)(R)-2-Bromo-2-methylcyclobutanone
d) (S)-1-Bromo-1-methyl-2-cyclobutanone
e)(R)-1-Bromo-1-methyl-2-cyclobutanone
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
a)2-Bromobutanone
b)(S)-2-Bromo-cyclobutanone
c)(R)-2-Bromo-cyclobutanone
d) (S)-1-Bromo-2-cyclobutanone
e)(R)-1-Bromo-2-cyclobutanone
Answer:C
11
Topic: Nomenclature
Section: 16.2
O
Cl H
a) (S)-3-chloro-1-hexanone
b) (S)-1-chloro-3-hexanone
c) (R)-3-chlorocyclohexanone
d) (S)-3-chlorocyclohexanone
e) (S)-1-chloro-3-cyclohexanone
Answer: D
Topic: Nomenclature
Section: 16.2
a) (S)-3-chloro-1-hexanone
b) (S)-1-chloro-3-hexanone
c) (R)-3-chlorocyclohexanone
d) (S)-3-chlorocyclohexanone
e) (S)-1-chloro-3-cyclohexanone
Answer:C
Topic: Nomenclature
Section: 16.2
12
a) (1S, 4R)-bicyclo[2.2.1]hexan-2-one
b) (1S, 4R)-bicyclo[2.1.2]heptan-2-one
c) (1S, 4R)-bicyclo[2.2.1]heptan-2-one
d) (1R, 4S)-bicyclo[2.1.1]heptan-2-one
e) (1S, 4S)-bicyclo[2.1.2]heptan-2-one
Answer:C
Topic: Nomenclature
Section: 16.2
a) bicyclo[1.1.0]butan-2-one
b) bicyclo[1.0.1]butan-2-one
c) bicyclo[1.1.0]pentan-2-one
d) bicyclo[0.1.1]butan-2-one
e) bicyclo[1.0.1]pentan-2-one
Answer:A
Topic: Nomenclature
Section: 16.2
13
a) bicyclo[1.1.1]pentan-2-one
b) bicyclo[1.1.0]pentan-2-one
c) cyclopentanone
d) methylenepentan-2-one
e) bicyclo[1.0.1]pentan-2-one
Answer:B
Topic: Nomenclature
Section: 16.2
CH3 CH CH2 C CH CH3
26) What is the IUPAC name for OH C6 H5 ?
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
Answer: B
Topic: Nomenclature
Section: 16.2

O2 N
O
NO2
a) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal
b) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
c) 3-Methyl-5-(2,5-dinitrophenyl)pentanal
d) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde
e) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde
Answer: C
Topic: Nomenclature
14
Section: 16.2
O
Cl
a) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
b) 3-Methyl-5-(4-chlorophenyl)hexanol
c) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
d) 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde
e) 3-Methyl-5-(4-chlorophenyl)hexanal
Answer: E
Topic: Nomenclature
Section: 16.2
29) Which is the proper name for the structure shown below?
Br
O
a) 7-Bromo-1,4-octynal
b) 7-Bromo-1,4-octynone
c) 2-Bromo-5,7-octynal
d) 7-Bromo-7-methyl-1-heptyne-3-ketone
e) 7-Bromo-1-octyn-4-one
Answer: E
Topic: Nomenclature
Section: 16.2
30) What is the correct structure for (R)-7-bromo-1-octyn-4-one?
15
Br
Br
Br
O
O O
I II III
Br
Br
O
IV V O
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
31) What is the correct structure for (S)-7-bromo-1-octyn-4-one?

Br
Br
Br
O
O O
I II III
Br
Br
O
IV V O
a) I
b) II
c) III
d) IV
e) V
Answer: C
16
Topic: Nomenclature
Section: 16.2
32) Which is the IUPAC name for the structure shown below?
Br H
a) (R)-5-Bromo-2-heptanal
b) (S)-5-Bromo-2-heptanal
c) (R)-5-Bromo-2-heptanone
d) (S)-5-Bromo-2-heptanone
e) (R)-3-Bromopentyl methyl ketone
Answer: C
Topic: Nomenclature
Section: 16.2
H Br
a) (R)-5-Bromo-2-heptanal
b) (S)-5-Bromo-2-heptanal
c) (R)-5-Bromo-2-heptanone
d) (S)-5-Bromo-2-heptanone
e) (R)-3-Bromopentyl methyl ketone
Answer: D
Topic: Nomenclature
Section: 16.2
34) What is the correct structure for (R)-5-bromo-2-heptanone?
17
O
Br H Br H
Br H
H
O O
I II III
H Br
H
H Br O O
V
IV
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 16.2
35) What is the correct structure for (S)-5-bromo-2-heptanone?

O
Br H Br H
Br H
H
O O
I II III
H Br
H
H Br O O
V
IV
18
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
a) 5-Cyclohexyl-2-hexanal
b) 5-Cyclohexyl-2-hexanone
c) 5-Cyclohexyl-5-methyl-2-pentanone
d) 5-(1-Methylcyclohexyl)-2-pentanone
e) 4-(1-Methylcyclohexyl)-2-butanone
Answer: E
Topic: Nomenclature
Section: 16.2
37) What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?
O
II O III O
I
O
O V
IV
a) I
b) II
c) III
d) IV
19
e) V
Answer: D
Topic: Nomenclature
Section: 16.2
38) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?
O
II O III O
I
O
O V
IV
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature
Section: 16.2
39) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?
a) I
b) II
20
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
40) 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
Answer: B
Topic: Physical Properties, Relationships, Stereochemistry

Section: 16.3
41) 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
Answer: A

Section: 16.8
42) Stereoisomers can exist in the case of which of the following?
a) The hydrazoneof benzophenone

b) The oxime of 2-methylcyclopentanone
21
c) The phenylhydrazone of 4-methylcyclohexanone
d) The imine of cyclopentanone
e) Two of these choices.
Answer: B

Section: 16.8
43) In which of the following reactions is the final product expected to be formed as a racemic
mixture?
a) C6H5MgBr + C6H5C O
O
b) HCN + CH3CCH3
c)
O
H
+ HCN
d) CH3C O + xs CH3OH + HCl

O
CH3CHCH2COC2H5 + (i-Bu)2AlH
e) CH3
Answer: C

Section: 16.9
44)Acetals are unstable in the presence of an aqueous solution of which of these?
a) HCl
b) NaOH
c) KHCO3
d) Na2CO3
e) NaCl
22
Answer: A
Topic: Reagents
Section: 16.7
45) 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.
Answer: C
Topic: Reagents
Section: 16.4
46) 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
Answer: C
Topic: Reagents
Section: 16.4
47) Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group
of an aldehyde or ketone?
a) I-
b) H3O+
23
c) AlCl3
d) BF3
e) ZnCl2
Answer: A
Topic: Reagents
Section: 16.6
48) Which reagent(s) could be used to carry out the following transformation?
O
?
a) Zn(Hg), HCl, reflux

b) LiAlH4, ether
c) HSCH2CH2SH, BF3; then Raney Ni (H2)
d) All of these choices.
Answer: E
Topic: Reagents
Section: 16.7
49) The following reduction can be carried out with which reagent(s)?
?
O
a) Zn(Hg), HCl
b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
c) H2NNH2, KOH
d) None of these choices.
e) All of these choices.
Answer:E
Topic: Reagents
Section: 16.7
24
50) The following reduction can be carried out with which reagent(s)?
?
O
a) Zn(Hg), HCl
b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
c) NaBH4, CH3OH
d) Zn(Hg), HCl and i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
e) Zn(Hg), HCl and NaBH4, CH3OH
Answer: D
Topic: Reagents
Section: 16.7
51) Which reagent will not differentiate between 3-butenal and 2-butanone?
a) Br2/CCl4
b) Ag2O,OH-
c) H2NNHC6H5
d) KMnO4,OH-
e) None of these choices.
Answer: C
Topic: Reagents
Section: 16.8
H H
52) The compound C6H5C N N CC6H5 is produced by the reaction of an excess of

benzaldehyde with which compound?
a) Ammonia
b) Hydrazine
c) Nitrogen
d) Phenylhydrazine
e) Hydroxylamine
25
Answer: B
Topic: Reagents
Section: 16.8
53) The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the
Baeyer-Villiger oxidation is:
a) H >Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl

b) Ph- > H>3° alkyl>2° alkyl>1° alkyl>methyl
c) 3° alkyl > 2° alkyl > 1° alkyl > methyl>H >Ph-
d) 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph->H
e) H > 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph-
Answer:A
Topic: Mechanisms
Section: 16.12
54) Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound?
OH
a) C6H5CHOCH3
O
b) C6H5COCH3
c) C6H5C(OCH3)3
OH O
d) C6H5CHOCH3 and C6H5COCH3

O
e) C6H5COCH3 andC6H5C(OCH3)3
Answer: A
Topic: Reaction Products

Section: 16.7
55) Select the structure of the major product in the following reaction.
26
i) BH3
?
ii) H2O2,OH-, H2O
a) Ethylbenzene
b) 1-Phenylethanol
c) Acetophenone
d) 2-Phenylethanal
e) Vinylbenzene
Answer: D

Section: 16.4
a) I
b) II
c) III
d) IV
e) V
27
Answer:D

Section: 16.12
O
CH3COOOH
a) I
b) II
c) III
d) IV
e) V
Answer:C

Section: 16.12
28
a) I
b) II
c) III
d) IV
e) V
Answer:A

Section: 16.12
29
a) I
b) II
c) III
d) IV
e) V
Answer:B

Section: 16.12
30
a) I
b) II
c) III
d) IV
e) V
Answer:C

Section: 16.12
31
a) I
b) II
c) III
d) IV
e) V
Answer:C

Section: 16.12
32
a) I
b) II
c) III
d) IV
e) V
Answer:C

Section: 16.12
i) BH3
?
ii) H2O2,OH-, H2O
33
OH O
OH
I II III
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 16.4
64) What is the final product, Z, of the following synthesis?
1. LiAlH(O-t-Bu)3
1. KMnO4, OH-, heat SOCl2 ether, -78 oC
CH3 X Y Z
2. H3O+ 2. H2O
O O O O O
COAl(t-Bu)2 COCH3 CH COLi COH
I II III IV V
a) I
b) II
c) III
d) IV
e) V
34
Answer: C

Section: 16.4
H2SO4
?
HgSO4, H2O
a) Ethylbenzene
b) 1-Phenylethanol
c) Acetophenone
d) 2-Phenylethanal
e) Vinylbenzene
Answer: C

Section: 16.5
H2SO4
?
HgSO4, H2O
OH O
I II III
IV V
a) I
b) II
35
c) III
d) IV
e) V
Answer: C

Section: 16.5
i.) KMnO4, OH-, hot
?
ii) H3O+
OH OH
I II III
OH O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 16.5
i.) KMnO4, OH-, hot
?
ii) H3O+
a) cyclopentanol
36
b) 1-cyclopentylcyclopentane
c) cyclopentanone
d) cyclopentene
e) 1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane
Answer: C

Section: 16.5
69) What would be the product of the following reaction sequence?

O
1. DIBAL-H, -78oC.
O
2. H2O
?
O
OH O
O
I II III
O O OH O
H OH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer:C

Section: 16.4
37
70) The product, K, of the following sequence of reactions
CH3
CH3CHCOCl CH3CH2MgBr H3O+

Benzene I J K
AlCl3 ether would be:
OH OH O
HO
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 16.5 and 16.6
71) The product, K, of the following sequence of reactions would be:
38
MgBr
AlCl3 H3O+
I J K
ether heat
Cl
(-H2O)
O
O
HO
III
I II
OH
V
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D

72)The product, J, of the following sequence of reactions would be:
39
a) I
b) II
c) III
d) IV
Answer:B

73) The product, E, of the following sequence of reactions
would be:
40
O OH
I II III
Cl
V
IV
a) I
b) II
c) III
d) IV
e) V
Answer: C

would be:
41
a) I
b) II
c) III
d) IV
Answer:B

OH SH
PCl5 AlCl3 HS Raney Ni
A B D E
BF3 H2
O
+
C (discard)
would be:
42
O
I II III
Cl
V
IV
a) I
b) II
c) III
d) IV
e) V
Answer: C

76) The product, C, of the following reaction sequence,

O
HCN H2O
CH3CCH3 + CN C4H7NO C
H2SO4
heat would be:
CH3
a) CH2 CCOOH
b) CH3CH2COOCH3
CH3CHCH3
c) CN
d) CH3CH=CHCOOH
Answer: A
43
Section: 16.9
77) The product, D, of the following reaction sequence,

O
-
CN HCl
C4H7NO D
HCN H2 O
heat would be:
CH3
a) CH2 CCOOH
b) CH3CH2COOCH3
CH3CHCH3
c) CN
d) CH3CH=CHCOOH
HO COOH
e)
Answer: E

Section: 16.9
78) What is the major product of the following reaction sequence?
44
HCN LiAlH4 H3O+
O ?
OH OH
CN NH2
CN
OH
II III IV
I
OH
COOH
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 16.9
45
HCN HCl
O
H2O
heat
OH OH
OH
CN NH2
CN
OH
II III IV
I
OH
COOH
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 16.9
HCN H2SO4
O
H2O
heat
CN H
NOSO3H COH CN OSO3H CNH2
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
46
Answer: B

Section: 16.9
81) The product, H, of the following reaction sequence,

O
C6H5Li C6H5CCH3
C6H5CH2Br + (C6H5)3P F G H
ether
would be:
CH3
C6H5CH2CC6H5
a) OH
O
b) C6H5CH2CC6H5
C6H5CH CHCC6H5
c) O
d) C6H5CH2CH=CHC6H5
C6H5CH CCH3
e) C6H5
Answer: E

Section: 16.10
82) What would be the final product?

O
(C6H5)3P C6H5Li C6H5CCH3

CH3I ?
ether
C6H5C CH2
a) CH3
47
C 6 H5
C6H5CCH3
b) CH3
c) C6H5CH=CHCH3
OH
C6H5CCH3
d) CH3
C6H5CH CC6H5
e) CH3
Answer: A

Section: 16.10
83) What would be the final product?

O
NaH
CH3I + P(OEt)3 ?
C6H5C CH2
a) CH3
C 6 H5
C6H5CCH3
b) CH3
c) C6H5CH=CHCH3
OH
C6H5CCH3
d) CH3
C6H5CH CC6H5
e) CH3
Answer: A
48
Section: 16.10
84) What is the reactant W in the synthesis given below?
C6H5Li
Wittig
Ph3P + W reagent
a) Cyclopentanone
b) Cyclopentene
c) Cyclopentanol
d) Bromocyclopentane
e) Triphenylphosphine oxide
Answer: D

Section: 16.10
85) Predict the major organic product of the following reaction:
H Ag(NH3)2+
O
?
H2O
O H
O O OH
O H O
O O H 3C
HO2C H3C H3C O
I II III IV V
a) I
b) II
49
c) III
d) IV
e) V
Answer:B

Section: 16.12
86) The product, H, of the following reaction sequence,

O
Br NaH
+ P(OEt)3 F G H
would be:
CH3
C6H5CH2CC6H5
a) OH
O
b) C6H5CH2CC6H5
C6H5CH CHCC6H5
c) O
d) C6H5CH2CH=CHC6H5
C6H5CH CCH3
e) C6H5
Answer: E

Section: 16.10
50
OH i) SOCl2
ii) C6H6, AlCl3 ?
O
iii) HSCH2CH2SH, BF3
iv) Raney Ni (H2)
O O OH
OH
I II III
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

OH i) PCl3
ii) C6H6, AlCl3 ?
O
iii) HSCH2CH2SH, BF3
iv) Raney Ni (H2)
O OH
I II III
OH
IV V
51
a) I
b) II
c) III
d) IV
e) V
Answer: B


OH i) PCl3
ii) C6H6, AlCl3 ?
O
iii) Zn(Hg), HCl, heat
O O OH
OH
I II III
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

52
OH i) PCl3
?
O ii) C6H 6, AlCl 3
iii) H 2NNH2, KOH
O O OH
OH
I II III
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E


OH i) PCl5
ii) C6H6, AlCl3 ?
O
O O OH
OH
I II III
IV V
53
a) I
b) II
c) III
d) IV
e) V
Answer: E

a) I
b) II
c) III
d) IV
e) V
Answer: E

54
OH i) SOCl2
ii) C6H6, AlCl3 ?
O
O O OH
OH
I II III
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

55
a) I
b) II
c) III
d) IV
e) V
Answer: E

OH i) PCl3
?
O ii) C6H6, AlCl3
iii) NaBH4, H2O
O OH
I II III
OH
OH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 16.5
56
OH i) PCl3
ii) C6H6, AlCl3 ?
O
iii) LiAlH4
iv) H2O
O OH
I II III
OH
OH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 16.5
OH i) PCl3
ii) C6H6, AlCl3 ?
O
O OH
I II III
OH
OH
IV V
57
a) I
b) II
c) III
d) IV
e) V
Answer: A

a) I
b) II
c) III
d) IV
e) V
Answer: A

58
99) The product, E, of the following reaction sequence,
PCl5 C6H6 NaBH4
CH3CH2COOH C D E
AlCl3 CH3OH would be:
O OH O
CH2CH2CH3 COCH2CH3 CHCH2CH3 CCH2CH3 CH(CH3)2
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 16.5
100) The product, D, of the following sequence of reactions
O
SOCl2 toluene Zn(Hg)
CH3CH2COH A B D
AlCl3 HCl
+
C (discard)
would be:
O O
CH3 CH2CH2CH3 CH3CH2CCH2 CH3 CH2CH2CCl
I II III
CH3
CH3 CH2CH2CH2Cl CH3 CH
CH3
IV V
a) I
b) II
c) III
59
d) IV
e) V
Answer: A

101) The product, D, of the following sequence of reactions
would be:
O O
I II III
CH3
CH3
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

102)The product, D, of the following sequence of reactions
60
would be:
O O
I II III
CH3
CH3
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

103) The product, E, of the following reaction sequence,

OH
PCl5 C6H6 LAH
C D E
AlCl3
O would
be:
O OH O
CH2CH2CH3 COCH2CH3 CHCH2CH3 CCH2CH3 CH(CH3)2
I II III IV V
a) I
b) II
c) III
d) IV
61
e) V
Answer: C

Section: 16.5
104) What is the final product of this synthetic sequence?
Br2 Mg 1. C6H5CHO H2Cr2O4

Benzene ?
FeCl3 ether 2. H3O+ acetone
a) C6H5CC6H5
b) p-BrC6H4CH2C6H5
c) C6H5CH2COOH
O
d) C6H5CH2CC6H5
e) C6H5CH2C6H5
Answer: A

Section: 16.5
i) H2, Lindlar catalyst

?
ii) O3
iii)Zn, CH3CO2H
a) 4-Methylhexanal
b) 4-Methyl-1-hexanol
c) 3-Methylhexanal
d) 4,10-Dimethyldodecane-6,7-dione
e) 4,10-Dimethyldodecane-6,7-diol
Answer: A
62
Section: 16.4
i) H2, P-2
?
ii) O3
iii)Zn, CH3CO2H
a) 4-Methylhexanal
c) 3-Methylhexanal
Answer: A

Section: 16.4
i) H2, Ni2B
?
ii) O3
iii)Zn, CH3CO2H
a) 4-Methylhexanal
c) 3-Methylhexanal
Answer: A

Section: 16.4
63
i) Li, NH3(l)
?
ii) O3
iii)Zn, CH3CO2H
a) 3-Methylhexanal
c) 4-Methylhexanal
Answer: C

Section: 16.4
109) 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
Answer: B

Section: 16.7
64
HCN H2SO4 LiAlH4 H3O+
O ?
H2 O
heat
OH OH
CN NH2
CN
OH
II III IV
I
OH
COOH
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 16.9
HCN HCl LiAlH4 H3O+

O ?
H2O
heat
OH OH
OH
CN NH2
CN
OH
II III IV
I
OH
COOH
65
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 16.9
i) H2, Lindlar catalyst

?
ii) O3
iii)Zn, CH3CO2H
O OH O
H H
III
I II
OH
O
OH
O
V
IV
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 16.4
113) Which of the following reactions would yield benzaldehyde?
66
OH-
C6H5CH2Cl
H2O
a) heat
H3O+
b) C6H5CH(OCH3)2
1. LiAlH4, ether
C6H5COOH
c) 2. H2O
d) Two of these choices.
Answer: B
Topic: Synthesis
Section: 16.7
114) Which of the following procedures would not yield 3-pentanone as a major product?
CH3CH2MgBr H3O+
CH3CH2CN
a) ether
b)
1. O3
2. Zn/H+
CH3CH2Li H3O+
CH3CH2CN
c) ether
d)
H
CH3CH2MgBr H3O+ PCC
ether CH2Cl2
O
CH3CH2MgBr H3O+
CH3CH2CO2H
e) ether
Answer: E
Topic: Synthesis
Section: 16.4
115) A good synthesis of
67
H
O
would be:
H
H2O, H2SO4
I
HgSO4
CN 1. DIBAL-H/-78oC
II 2. H2O
1. O3
III
2. Zn/H+
OH
1. KMnO4, NaOH, heat
IV 2. H3O+
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Answer: B
Topic: Synthesis
Section: 16.4
68
H
O
would be:
H
H2O, H2SO4
I
HgSO4
COOCH3 1. DIBAL-H/-78oC
II 2. H2O
1. O3
III
2. Zn/H+
OH
IV 2. H3O+
a) I
b) II
c) III
d) IV
Answer: B
Topic: Synthesis
Section: 16.4
69
H
O
would be:
H
H2O, H2SO4
I
HgSO4
1. O3
II
2. Zn/H+
COCl 1. LiAl(OC(CH3)3)3H
III
2. H3O+
OH
IV 2. H3O+
a) I
b) II
c) III
d) IV
Answer: C
Topic: Synthesis
Section: 16.4
70
H
O
would be:
H
H2O, H2SO4
I
HgSO4
1. O3
II
2. Zn/H+
PCC
III CH2Cl2
OH
OH
IV 2. H3O+
a) I
b) II
c) III
d) IV
Answer: C
Topic: Synthesis
Section: 16.4
71
H
O
would be:
H
H2O, H2SO4
I
HgSO4
1. O3
II
2. Zn/H+
1. DMSO, (COCl)2
III 2. Et3N
OH
OH
IV 2. H3O+
a) I
b) II
c) III
d) IV
Answer: C
Topic: Synthesis
Section: 16.4
72
H
O
would be:
H
1. BH3
I
2.H2O2, NaOH
CN 1. DIBAL-H/-78oC
II 2. H2O
COOCH3 1. DIBAL-H/-78oC
III 2. H2O
COCl 1. LiAl(OC(CH3)3)3H
IV
2. H3O+
a) I
b) II
c) III
d) IV
Answer: E
Topic: Synthesis
Section: 16.4
121) Which synthesis or syntheses would yield propanal?
PCC
CH3CH2CH2OH
a) CH2Cl2
73
O
LiAlH[OC(CH3)3]3
CH3CH2CCl
b) ether, -78 oC
1. Sia2BH
CH3C CH
c) 2. H2O2, OH-
Answer: D
Topic: Synthesis
Section: 16.4
a)
O
LiAlH[OC(CH3)3]3
CH3CH2CCl
b) ether, -78 oC
1. Sia2BH
CH3C CH
c) 2. H2O2, OH-
Answer: D
Topic: Synthesis
Section: 16.4
PCC
CH3CH2CH2OH
a) CH2Cl2
74
O
LiAlH[OC(CH3)3]3
CH3CH2CCl
b) ether, -78 oC
c)
Answer: D
Topic: Synthesis
Section: 16.4
PCC
CH3CH2CH2OH
a) CH2Cl2
b)
c)
Answer: D
Topic: Synthesis
Section: 16.4
a)
75
b)
c)
Answer: D
Topic: Synthesis
Section: 16.4
126) Which of the reactions listed below would serve as a synthesis of acetophenone,
O
C6H5CCH3 ?
a)
OH
PCC
CH2Cl2
AlCl3
b) C6H6 + CH3COCl
ether H3O+
c) C6H5CN + CH3Li
Answer: E
Topic: Synthesis
Section: 16.5
127) Which of the reactions listed below would serve as a synthesis of acetophenone,
O
C6H5CCH3 ?
76
a)
AlCl3
b) C6H6 + CH3COCl
ether H3O+
c) C6H5CN + CH3Li
Answer: E
Topic: Synthesis
Section: 16.5
128) Which of the following would yield 3-pentanone as the major product?
ether H3O+
a) CH3CH2CN + CH3CH2Li Product
b)
ether H3O+
CN + MgBr Product
c)
PCC
CH2Cl2
OH
Answer: E
Topic: Synthesis
Section: 16.5
129) Which sequence of reactions would be utilized to convert
77
CH3
O CO2CH3 into O C CH3 ?
OH
a) 2CH3MgBr, then NH4+

b) HOCH2CH2OH, H3O+; LiAlH4, ether; 2CH3MgBr, then NH4+
c) HOCH2CH2OH, H3O+; 2CH3MgBr, then NH4+
d) HOCH2CH2OH, H3O+; H2, Pt; CH3OH, NH4+
Answer: C
Topic: Synthesis
Section: 16.7
130) Which of the following procedures would not yield (CH3)2CHCH as a product?
PCC
I OH
CH2Cl2
SOCl2 LiAlH(O-t-Bu)3
II CO2H
ether, -78 oC
O3 Zn
III
HOAc
KMnO4 H3 O +
IV OH
NaOH
O H3 O +
V
O
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Synthesis
78
131) Which of the following procedures would not yield (CH3)2CHCH as a product?
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Synthesis
132) Which reaction sequence would be used to prepare
79
?
1. ether H2
I O + MgBr 2. H3O+ Ni
O 1. ether H2
II + 2 CH3MgBr
H 2. H3O+ Ni
(C6H5)3P C6H5Li cyclopentanone H2

III
Cl Ni
O CH3MgBr H 3O +
IV
ether
a) I
b) II
c) III
d) IV
e) All of these choices would yield the product.
Answer: C
Topic: Synthesis
Section: 16.10
133) Which Wittig reagent would be used to synthesize
CH=P(C6H5)3 P(C6H5)3
CH3CH=P(C6H5)3 CH3CH2CH=P(C6H5)3
I II III IV
a) I
b) II
c) III
d) IV
e) Either I or II could be used.
80
Answer: E
Topic: Synthesis
Section: 16.10
134) Which of the following is not a synthesis of benzophenone,
C6H5CC6H5 ?
O
AlCl3
a) C6H6 + C6H5CCl
H2CrO4
(C6H5)2CHOH
b) acetone
1. O3
(C6H5)2CH=CH2
c) 2. Zn, HOAc
d)
PCC
Ph2CHOH
CH2Cl2
e) All of these choices will give benzophenone.
Answer: E
Topic: Synthesis
Section: 16.5
C6H5CC6H5 ?
O
AlCl3
a) C6H6 + C6H5CCl
H2CrO4
(C6H5)2CHOH
b) acetone
81
1. O3
(C6H5)2CH=CH2
c) 2. Zn, HOAc
d)
Answer: E
Topic: Synthesis
Section: 16.5
C6H5CC6H5 ?
O
AlCl3
a) C6H6 + C6H5CCl
PCC
Ph2CHOH
b) CH2Cl2
1. O3
(C6H5)2CH=CH2
c) 2. Zn, HOAc
d)
Answer: E
Topic: Synthesis
Section: 16.5
82
H
O
would be:
H
H2O, H2SO4
I
HgSO4
H
1. Sia2BH
II
2. H2O2, NaOH
H
1. O3
III
2. Zn, HOAc
OH 1. KMnO4, NaOH, heat

IV
2. H3O+
a) I
b) II
c) III
d) IV
Answer: B
Topic: Synthesis
Section: 16.4
138) Which of the following is a synthesis of 3-heptanone?
a)
CH3(CH2)2CH2Li H3O+
CH3CH2CN
b) ether
PBr3 NaCN CH3CH2MgBr H3O+
CH3CH2CH2CH2OH
c) ether ether
d)
83
1. O3
2. Zn/H+
e) All of these choices are syntheses of 3-heptanone.
Answer: E
Topic: Synthesis
Section: 16.5
139) Which of the following is a synthesis of 3-heptanone?
a)
CH3(CH2)2CH2Li H3 O+
CH3CH2CN
b) ether
PBr3 NaCN CH3CH2MgBr H3O+
CH3CH2CH2CH2OH
c) ether ether
d)
1. O3
2. Zn/H+
e) All of these choices are syntheses of 3-heptanone.
Answer: E
Topic: Synthesis
Section: 16.5
140) What, in general, is the order of decreasing reactivity of these carbonyl compounds towards
nucleophilic reagents?
O H O H O
CH3CCH3 CH3C O (CH3)3CCCH3 HC O (CH3)3CCC(CH3)3
I II III IV V
a) I > III > IV> II > V

b) IV > II > I > III > V
c) V > III > I > II > IV
84
d) I>IV>II>III>V
e) III > V > IV > II > I
Answer: B
Topic: Carbonyl Reactivity

Section: 16.6
141) Which of these gem-diols is expected to be the most stable?
OH
CF3CCF3
a) OH
b) CH3CH(OH)2
OH
CH3CCH3
c) OH
d) C6H5CH(OH)2
e) ClCH2CH(OH)2
Answer: A

Section: 16.7
142) Which of these gem-diols is expected to be the least stable?
OH
CF3CCF3
a) OH
b) CH3CH(OH)2
OH
CH3CCH3
c) OH
d) C6H5CH(OH)2
e) ClCH2CH(OH)2
85
Answer: C

Section: 16.7
143) What, in general, is the order of increasing reactivity of these carbonyl compounds towards
nucleophilic reagents?
O H O H O
CH3CCH3 CH3C O (CH3)3CCCH3 HC O (CH3)3CCC(CH3)3
I II III IV V
a) I < III < V < II < IV

b) IV < II < I < III < V
c) V< III < I < II < IV
d) II< I < V < III < IV
e) III < V < IV < II < I
Answer: C

Section: 16.6
144) Which of the following compounds is an acetal?

O O O O
OCH3 O OH O
O O
I II III IV
a) I
b) II
c) III
d) IV
Answer: C
Topic: New Functional Groups

Section: 16.7
86
145) Which is the general formula for a thioacetal?
a) RC S
RCHSR'
b) OH
RCHSR'
c) SH
RCHSR'
d) SR'
RCHOR'
e) SR'
Answer: D

Section: 16.7
146) Which compound is an acetal?

O
O
OH
O OH O OCH3 O
I II III IV
a) I
b) II
c) III
d) IV
Answer: B

Section: 16.7
147) Which compound is a hemiacetal?

O
O
OH
O OH O OCH3 O
I II III IV
87
a) I
b) II
c) III
d) IV
Answer: A

Section: 16.7
148) Which of the following is formed when 3-methylcyclopentanone reacts with

hydroxylamine?
N-NH-C6H5 N-NH2 N-OH
I II III
NO2
O
N N
N NH2 N
H H NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Reactions of Aldehydes and Ketones

Section: 16.8
149) Which of the following is formed when 4-methylpentanal reacts with phenylhydrazine?
88
N-NH-C6H5 N-C6H5 N-NH2
I II III
O
N N=N-C6H5
N NH2
H
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 16.8
150) Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with

hydroxylamine?
I II III
NO2
O
N N
N NH2 N
H H NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
89
Section: 16.8
151) Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with

hydrazine?
I II III
NO2
O
N N
N NH2 N
H H NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 16.8
152) 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?
a) CH3CH2CCH2CH3
O
b) (CH3)2CHCCH3
H
c) (CH3)3CC O
H
CH3CH2CHC O
d) CH3
90
H
e) (CH3)2CHCH2C O
Answer: C
Topic: Spectroscopy
Section: 16.14
153) 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?
a) CH3CH2CCH2CH3
O
b) (CH3)2CHCCH3
H
c) (CH3)3CC O
H
CH3CH2CHC O
d) CH3
H
e) (CH3)2CHCH2C O
Answer: A
Topic: Spectroscopy
Section: 16.14
154) The1H 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
Answer: D
91
Topic: Spectroscopy
Section: 16.14
155) The1H NMR spectrum of a compound with formula C7H14O gives two signals. Which of
a) 2-Heptanone
b) 3-Heptanone
d)2,2-Dimethyl-3-pentanone
Answer: C
Topic: Spectroscopy
Section: 16.14
156) The13C NMR spectrum of a compound with formula C7H14O gives three signals. Which of
a) 2-Heptanone
b) 3-Heptanone
Answer: D
Topic: Spectroscopy
Section: 16.14
157) The13C NMR spectrum of a compound with formula C7H14O gives five signals. Which of
a) 2-Heptanone
b) 3-Heptanone
92
Answer: C
Topic: Spectroscopy
Section: 16.14
158) The1H 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
Answer: B
Topic: Spectroscopy
Section: 16.14
Question type: Molecular Drawing
159) Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-
bromobutane.
NaCN i. DIBAL-H O
Br CN
Answer: ii. H2O
Topic: Synthetic Strategy

Section: 16.4
160) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-bromobutane.
NaCN i. C2H5Li, Et2O

Br CN
ii. H3O+
Answer: O
93
Section: 16.5
161) Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-
bromobutane.
Answer:
HBr
NaCN i. DIBAL-H O
Br CN
ROOR ii. H2O

Section: 16.5
162) Suggest a synthetic strategy for the synthesis of 6-methyl-3-heptanol from 4-

methylpentanenitrile, (CH3)2CHCH2CH2CN.
i. DIBAL-H
CN
ii. H2O OH
iii. C2H5MgBr, Et2O
iv. H3O+
OR
i. C2H5MgBr, Et2O
CN
ii. H3O+
OH
Answer: iii. NaBH4, H2O

Section: 16.5
163) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene.
Answer:
HBr NaCN i. C2H5Li, Et2O
Br CN ii. H3O+
ROOR O
94
Section: 16.5
164) Cis-stilbene (cis-1,2-diphenylethene) can be prepared in high yield from its trans
diastereomer. Propose a reasonable synthesis.
H H
Ph H
H Ph Ph Ph
multiple steps
trans-stilbene cis-stilbene
Answer:
Ph H O O PPh3 H H
Ph H Ph3P
m-CPBA
Ph Ph Ph Ph
H Ph H Ph
H H

Section: 16.10
165) Complete the following reaction sequence, giving structural details of all significant
intermediates and the final product.
O
H H+
OH
Answer:
O
OH
H H+
O
OH
Topic: Reaction Sequence

Section: 16.7
95
166) 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 / H+
O 1. CH3Li
?
2. H+/H2O
O
Answer:
HO O
O
H / H+ H
O 1. CH3Li
2. H+/H2O
O
O
HO
HO
CH3

Section: 16.7
intermediates.
O
H
1. OsO4
?
2. NaHSO3 H+
Answer:
O
OH H
O
1. OsO4
2. NaHSO3 H+ O
OH

Section: 16.7
96
168) Complete the following reaction sequence, giving structural details of all
significantintermediates and the final product.
O
H+ KMnO4, OH-, heat H+

+ ?
HO H
H2 O
O
Answer:
O
O
H+ KMnO4, OH-, heat
+ HO H
O O H
O
O O
H+
HO OH
O O O H2O

Section: 16.7
intermediates X, Y, and final product Z.
1. LiAlH(O-t-Bu)3
1. KMnO4, OH-, heat SOCl2 ether, -78 oC
CH3 X Y Z
2. H3O+ 2. H2O
COOH COCl CHO
X Y
Z
Answer:

Section: 16.4
intermediates.
97
i. Br2, hν
?
ii. Mg, CH3CH2CN
iii. H3O+
iv. NaBH4
Answer:
O HO
Br2, hν Br i. Mg, CH CH CN
3 2
NaBH4
ii. H3O+

Section: 16.5
intermediates.
i. EtMgBr i. O3 ?
+ ii.Zn, CH3CO2H
ii. H3O , heat
O
i. EtMgBr i. O3 O
ii. H3O+, heat ii.Zn, CH3CO2H

O
O HO
Answer:

Section: 16.5
Br2 Mg 1. C6H5CHO H2Cr2O4
Benzene ?
FeCl3 ether 2. H3O+ acetone
OH O
Br MgBr
Answer:

Section: 16.5
98
Answer:

Question type: Essay
174) Aldehydes are more reactive than ketones towards nucleophilic substitution because of both
steric and electronic factors. Briefly explain.
a) Steric reasons: ___.
b) Electronic reasons: ___.
Answer: a) aldehydes have a small hydrogen substituent on one side, so less steric crowding than
ketones with alkyl groups either side of the carbonyl carbon.
b) aldehydes have only one electron-releasing group to partly neutralize/stabilize the partial
positive charge at the carbonyl carbon while ketones have two
Topic: Relative Reactivity

Section: 16.6
Question type: fill-in-the-blank
175) A compound with an OH and OR group attached to the same carbon is known as a(n) ___.
Answer: hemiacetal
Topic: Hemiacetals
Section: 16.7
99
176) A compound with two OH groups attached to the same carbon is known as a(n) ___.
Answer: hydrate or gem-diol
Topic: Hydrates
Section: 16.7
177) A compound with two OR groups attached to the same carbon is known as a(n) ___.
Answer: acetal
Topic: Acetals
Section: 16.7
178) A compound with an OH and CN group attached to the same carbon is known as a(n) ___.
Answer: cyanohydrin
Topic: Cyanohydrins
Section: 16.9
179) A compound containing a C=N double bond is known as a(n) ___.
Answer: imine
Topic: Imines
Section: 16.8
180) 2,4-DNP is a reagent frequently used for functional group tests; it detects the presence of
___.
Answer: aldehydes and ketones
Topic: Functional Group Tests

Section: 16.8
100
181) Oximes are formed when aldehydes and ketones react with ___.
Answer:hydroxylamine, NH2OH

Section: 16.8
182) The reaction between a phosphorus ylide and an aldehyde or ketone is called the ___
reaction.
Answer: Wittig
Topic: Wittig Reaction

Section: 16.10
183) The driving force for the Wittig reaction is the formation of the very strong ___ bond in
___.
Answer: P-O bond; triphenylphosphine oxide
Topic: Wittig Reaction

Section: 16.10
184) The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example of
a ___ reaction.
Answer: stereospecific
Topic: General
Section: 16.10
185) The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example of
a ___ reaction.
Answer: stereospecific
Topic: General
Section: 16.10
101
Question type: Molecular Drawing
186) Draw a complete mechanism, using arrow convention to indicate electron movement, for
the following transformation:
Answer:
O H+ O H
H H
N N
H
N N
HO N
H2O H
+
~H
-H2O
N
-H+
102
Topic: Mechanisms
Section: 16.8
187) Draw a complete mechanism, using arrow convention to indicate electron movement,for the
following transformation:
O H H
H3C H
+ PPh3 + Ph3P O
H CH3 H3 C CH3
Answer:
O H3C O PPh3
O H
H3C H
+ PPh3
H3C rotation 180o H3C CH3
H CH3 H PPh3 as shown H H
O PPh3 H H
+ Ph3P O
H3C CH3 H3C CH3

H H
Topic: Mechanisms
Section: 16.10
188) Draw a complete mechanism, using arrow convention to indicate electron movement, for
the following transformation:
O H3C H
H H
+ PPh3 + Ph3P O
H3 C CH3 H CH3
Answer:
103
O H3C O PPh3
O H
H H
+ PPh3
H rotation 180o H CH3
H3C CH3 H3C PPh3 as shown CH3 H
O PPh3 H3C H
+ Ph3P O
H CH3 H CH3
CH3 H
Topic: Mechanisms
Section: 16.10
Question type: fill-in-the-blank
189) The Tollens test, used in conjunction with 2,4-DNP, can distinguish between ___ and ___.
Answer: aldehydes and ketones

Section: 16.13
Question type: Essay
190) What reagent would help you distinguish between acetophenone and 2-
methylbenzaldehyde?
Answer: Tollen’s Reagent

Section: 16.13
191) Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde
and acetophenone.
104
Answer: 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
approximateδ ppm approximate δ ppm
doublet (-CH2-) 2.5 singlet (-CH3) 2.0
multiplet (C6H5) 7 multiplet (C6H5) 7.2
triplet(-CHO) 9
Topic: Spectroscopy
Section: 16.14
192) Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1720 cm−1

1
H NMR: 1.9δ (triplet, 3H), 1.7δ (sextet, 2H), 2.1δ (singlet, 3H), 2.4δ (triplet, 2H)
O
CH3CH2CH2CCH3
Answer:
Topic: Spectroscopy
Section: 16.14
C5H10O
IR: 1720 cm−1

1
H NMR: 1.1δ (triplet, 3H), 2.4δ (quartet, 2H)
Answer: O
Topic: Spectroscopy
Section: 16.14
105
C9H10O
IR: 1680 cm−1

1
H NMR: 1.25δ (triplet, 3H), 3.0δ (quartet, 2H), 7-8δ (complexmultiplet, 5H)
O
Answer:
Topic: Spectroscopy
Section: 16.14
C7H6O
IR: 1703 cm−1

1
H NMR: 7-8δ (complexmultiplet, 5H), 10.0δ (singlet, 1H)
O
Answer:
Topic: Spectroscopy
Section: 16.14
C3H6O
IR: 1730 cm−1
106
1
H NMR: 1.1δ (triplet, 3H), 2.5δ (doubletofquartets, 2H), 9.8δ (doublet, 1H)
H
Answer: O
Topic: Spectroscopy
Section: 16.14
C5H10O
IR: 1716 cm−1
Broadband decoupled 13C NMR: 7.93, 35.50, 212.07δ
DEPT Experiments show: signal at 7.93 δ as CH3 and signal at 35.50 δ as CH2
Answer: O
Topic: Spectroscopy
Section: 16.14
C5H10O
IR: 1717 cm−1
Broadband decoupled 13C NMR: 13.70, 17.41, 29.78, 45.71, 208.93δ
DEPT Experiments show: signals at 13.70, 29.78 δ as CH3 and signals at 17.41, 45.71 δ
as CH2
Answer: CH3CH2CH2CCH3
107
Topic: Spectroscopy
Section: 16.14
C4H8O
IR: 1728 cm−1
Broadband decoupled 13C NMR: 13.71, 15.69, 45.82, 202.80δ
DEPT Experiments show: signal at 13.71 δ as CH3 and signals at 15.69, 45.82 δ as CH2
Answer: H
Topic: Spectroscopy
Section: 16.14
C6H12O
IR: 1708 cm−1
Broadband decoupled 13C NMR: 24.61, 26.42, 44.31, 213.81δ
DEPT Experiments show: signals at 24.61, 26.42 δ as CH3
Answer: O
Topic: Spectroscopy
Section: 16.14
108
C4H8O
IR: 1737 cm−1
Broadband decoupled 13C NMR: 15.48, 41.07, 204.86δ
DEPT Experiments show: signal at 41.07 δ as CH and signal at 15.48 δ as CH3
Answer: O
Topic: Spectroscopy
Section: 16.14
C5H10O
IR: 1728 cm−1
Broadband decoupled 13C NMR: 22.59, 23.57, 52.66, 202.71 δ
DEPT Experiments show: signal at 23.57 δ as CH, signal at 22.59 δ as CH3, and signal at
52.66 δ as CH2.
O
Answer: H
Topic: Spectroscopy
Section: 16.14
203) Acetaldehyde is reacted with excess methanol in acid. The product was isolated and gave
the following 1H NMR spectroscopic data:
1.3 δ (doublet, 3H)

3.4 δ (singlet, 6H)
109
4.6 δ (quartet, 1H)
Propose a structure consistent with this information.
Answer:
O
Topic: Spectroscopy
Section: 16.14
110

ch16 TEST BANK SOLOMONS

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Package Title: Solomons Test Bank

Course Title: Solomons 11e

Question type: Multiple Choice

1) What is the correct IUPAC name for the following compound?

2) What is the correct structure for 7-methyl-4-octanone?

3) What is the correct IUPAC name for the following compound?

4) What is the correct structure for 5,5-dimethyl-2-heptanone?

6) What is the correct structure for 2,5-dimethylhexanal?

7) What is the correct IUPAC name for the following compound?

8) What is the correct IUPAC name for the following compound?

9) What is the correct IUPAC name for the following compound?

10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

11) A correct name for C6H5CH2CH2CH is?

12) What is the correct structure for 3-phenylpropanal?

13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?

14) Which is the proper name for the structure shown?

15) What is the correct structure for 4-chloro-3-methylbenzaldehyde?

16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

18) What is the correct structure for 7-bromo-1-octyn-4-one?

CH3 CH CH2 C CH CH3

26) What is the IUPAC name for OH C6 H5 ?

27) Which is the proper name for the structure shown?

28) Which is the proper name for the structure shown?

30) What is the correct structure for (R)-7-bromo-1-octyn-4-one?

31) What is the correct structure for (S)-7-bromo-1-octyn-4-one?

34) What is the correct structure for (R)-5-bromo-2-heptanone?

35) What is the correct structure for (S)-5-bromo-2-heptanone?

37) What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

38) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

39) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

Topic: Physical Properties, Relationships, Stereochemistry

41) Stereoisomers can exist in the case of which of the following?

a) The hydrazone of butanone

Topic: Physical Properties, Relationships, Stereochemistry

42) Stereoisomers can exist in the case of which of the following?

a) The hydrazoneof benzophenone

Topic: Physical Properties, Relationships, Stereochemistry

d) CH3C O + xs CH3OH + HCl

Topic: Physical Properties, Relationships, Stereochemistry

44)Acetals are unstable in the presence of an aqueous solution of which of these?

a) LAH is not sufficiently reactive.

CH3CH2CH2COCl ⎯⎯⎯→ CH3CH2CH2CHO

a) Zn(Hg), HCl, reflux

52) The compound C6H5C N N CC6H5 is produced by the reaction of an excess of

a) H >Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl

d) C6H5CHOCH3 and C6H5COCH3

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

64) What is the final product, Z, of the following synthesis?

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

69) What would be the product of the following reaction sequence?