Chapter 16 - Test Bank Chem 200

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
II
III
O
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
1
Section: 16.2
O
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
II
III
IV
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
II
III
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 16.2
3
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
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
II
III
IV
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
O
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
H
II
III
O
H
O
IV
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?
Ph
Ph
OH
II
I
Ph
OH
III
OH
OH
OH
IV
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
Ph
Cl
II
III
Cl
Cl
O
H
H
O
Cl
IV
Cl
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?
NO2
O2N
NO2
II
NO2
NO2
O
O2N
H
O2N
H
NO2
III
IV
O2N
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?
Cl
Cl
II
O
Cl
IV
III
Cl
Cl
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
II
III
Br
Br
IV
V O
10
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
Br
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
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
O
CH3
26) What is the IUPAC name for
CH
CH2
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
CH
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
CH3
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
II
III
Br
Br
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
II
III
Br
Br
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
O
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
Br
Br
Br
II
III
Br
Br
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?
Br
Br
Br
II
III
Br
Br
IV
18
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
O
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?
IV
III
II
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?
IV
III
II
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?
H
a) C6H5MgBr + C6H5C
b) HCN +
c)
CH3CCH3
HCN
d) CH3C
+ xs CH3OH + HCl
O
O
CH3CHCH2COC2H5
e)
+ (i-Bu)2AlH
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) Ib) 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,OHc) H2NNHC6H5
d) KMnO4,OHe) None of these choices.
Answer: C
Topic: Reagents
Section: 16.8
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 >Phd) 3 alkyl > 2 alkyl > 1 alkyl > methyl>Ph->H
e) H > 3 alkyl > 2 alkyl > 1 alkyl > methyl>PhAnswer: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
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
OH
II
III
IV
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. KMnO4,
CH3
OH-,
heat
2. H3O+
SOCl2
1. LiAlH(O-t-Bu)3
ether, -78 oC
2. H2O
COAl(t-Bu)2
COCH3
CH
COLi
COH
II
III
a) I
b) II
c) III
d) IV
e) V
34
IV
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
II
III
IV
a) I
b) II
35
c) III
d) IV
e) V
Answer: C
Section: 16.5
i.) KMnO4, OH-, hot
?
ii) H3O+
OH
OH
II
III
OH
IV
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.
2. H2O
O
OH
O
H
II
I
O
III
OH
IV
OH
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
Benzene
AlCl3
OH
CH3CH2MgBr
ether
H3O+
K
would be:
OH
HO
II
III
IV
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+
heat
ether
Cl
(-H2O)
O
O
HO
III
II
OH
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
e) None of these choices.
Answer:B
73) The product, E, of the following sequence of reactions
would be:
40
OH
III
II
I
O
Cl
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
A
AlCl3
HS
B
BF3
+
C (discard)
would be:
42
Raney Ni
H2
III
II
I
O
Cl
IV
a) I
b) II
c) III
d) IV
e) V
Answer: C
76) The product, C, of the following reaction sequence,
O
CH3CCH3
CN
HCN
C4H7NO
CH3
a) CH2 CCOOH
b) CH3CH2COOCH3
CH3CHCH3
CN
c)
d) CH3CH=CHCOOH
Answer: A
43
H2O
H2SO4
heat
would be:
Section: 16.9
77) The product, D, of the following reaction sequence,
O
-
CN
HCN
HCl
C4H7NO
H2 O
heat
CH3
a) CH2 CCOOH
b) CH3CH2COOCH3
CH3CHCH3
CN
c)
d) CH3CH=CHCOOH
HO
COOH
e)
Answer: E
Section: 16.9
78) What is the major product of the following reaction sequence?
44
would be:
HCN
H3O+
LiAlH4
OH
OH
CN
NH2
CN
OH
III
II
OH
COOH
a) I
b) II
c) III
d) IV
e) V
Answer: C
Section: 16.9
45
IV
HCN
HCl
H2O
heat
OH
OH
OH
CN
NH2
CN
OH
III
II
IV
OH
COOH
a) I
b) II
c) III
d) IV
e) V
Answer: E
Section: 16.9
O
HCN
H2SO4
H2O
heat
CN
NOSO3H
OSO3H
CN
COH
H
CNH2
II
III
IV
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
C6H5CH2Br + (C6H5)3P
C6H5Li
ether
would be:
CH3
C6H5CH2CC6H5
a)
OH
O
b) C6H5CH2CC6H5
C6H5CH
CHCC6H5
O
c)
d) C6H5CH2CH=CHC6H5
C6H5CH
e)
CCH3
C6H5
Answer: E
Section: 16.10
82) What would be the final product?
O
(C6H5)3P
CH3I
C6H5CCH3
ether
C6H5C
a)
C6H5Li
CH2
CH3
47
C6H5CCH3
C 6 H5
C6H5CCH3
CH3
b)
c) C6H5CH=CHCH3
OH
C6H5CCH3
d)
CH3
C6H5CH
CC6H5
CH3
e)
Answer: A

Section: 16.10
83) What would be the final product?
O
CH3I
C6H5C
a)
P(OEt)3
NaH
CH2
CH3
C 6 H5
C6H5CCH3
CH3
b)
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?
Ph3P +
C6H5Li
Wittig
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+
H2O
O
O
O
HO2C
O
O
H3C
II
OH
O
H
H 3C
H3C
III
IV
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
P(OEt)3
NaH
would be:
CH3
C6H5CH2CC6H5
a)
OH
O
b) C6H5CH2CC6H5
C6H5CH
CHCC6H5
O
c)
d) C6H5CH2CH=CHC6H5
C6H5CH
e)
CCH3
C6H5
Answer: E
Section: 16.10
50
OH
i) SOCl2
ii) C6H6, AlCl3
iii) HSCH2CH2SH, BF3
iv) Raney Ni (H2)
OH
O
OH
II
III
IV
a) I
b) II
c) III
d) IV
e) V
Answer: E
OH
O
i) PCl3
ii) C6H6, AlCl3
iii) HSCH2CH2SH, BF3
iv) Raney Ni (H2)
OH
II
III
OH
IV
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
OH
OH
II
IV
III
a) I
b) II
c) III
d) IV
e) V
Answer: E
52
OH
O
i) PCl3
ii) C6H 6, AlCl 3
iii) H 2NNH2, KOH
OH
O
OH
II
III
IV
a) I
b) II
c) III
d) IV
e) V
Answer: E
OH
i) PCl5
?
ii) C6H6, AlCl3
O
OH
O
OH
II
IV
III
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
O
i) SOCl2
ii) C6H6, AlCl3
OH
O
OH
II
IV
III
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
O
i) PCl3
ii) C6H6, AlCl3
iii) NaBH4, H2O
OH
II
III
OH
OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D
Section: 16.5
56
OH
O
i) PCl3
ii) C6H6, AlCl3
iii) LiAlH4
iv) H2O
OH
II
III
OH
OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D
Section: 16.5
OH
O
i) PCl3
ii) C6H6, AlCl3
OH
II
III
OH
OH
IV
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
AlCl3
CH3OH
CH2CH2CH3
would be:
OH
COCH2CH3
CHCH2CH3
CCH2CH3
CH(CH3)2
IV
II
III
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
CH3CH2COH
toluene
AlCl3
Zn(Hg)
HCl
C (discard)
would be:
O
CH3
CH2CH2CH3
CH3CH2CCH2
CH3
O
CH3
II
CH2CH2CH2Cl
CH2CH2CCl
III
CH3
CH
CH3
CH3
IV
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
CH3
CH2CH2CH3
CH3CH2CCH2
CH3
O
CH3
II
CH2CH2CH2Cl
CH2CH2CCl
III
CH3
CH
CH3
CH3
IV
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
CH3
CH3CH2CCH2
CH2CH2CH3
CH3
CH2CH2CCl
II
CH3
III
CH2CH2CH2Cl
CH3
CH
CH3
CH3
IV
a) I
b) II
c) III
d) IV
e) V
Answer: A
103) The product, E, of the following reaction sequence,
OH
PCl5
C6H6
C
AlCl3
LAH
would
be:
CH2CH2CH3
OH
COCH2CH3
CHCH2CH3
CCH2CH3
CH(CH3)2
IV
II
III
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?
Benzene
Br2
Mg
FeCl3
ether
1. C6H5CHO
H2Cr2O4
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
H2SO4
HCN
H3O+
LiAlH4
H2 O
heat
OH
OH
CN
NH2
CN
OH
III
II
IV
OH
COOH
a) I
b) II
c) III
d) IV
e) V
Answer: D
Section: 16.9
HCN
LiAlH4
HCl
H3O+
H2O
heat
OH
OH
OH
CN
NH2
CN
OH
III
II
IV
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
?
O
OH
III
II
OH
OH
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
heat
H3O+
a)
b) C6H5CH(OCH3)2
1. LiAlH4, ether
C6H5COOH
2. H2O
c)
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?
a)
b)
H3O+
CH3CH2MgBr
CH3CH2CN
ether
1. O3
2. Zn/H+
c)
d)
CH3CH2CN
H
H3O+
CH3CH2Li
ether
CH3CH2MgBr
H3O+
ether
CH2Cl2
e)
CH3CH2CO2H
PCC
CH3CH2MgBr
H3O+
ether
Answer: E
Topic: Synthesis
Section: 16.4
115) A good synthesis of
67
H
O
would be:
H
H2O, H2SO4
HgSO4
1. DIBAL-H/-78oC
CN
II
2. H2O
1. O3
III
2. Zn/H+
OH
IV
1. KMnO4, NaOH, heat

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
HgSO4
COOCH3
II
1. DIBAL-H/-78oC
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
HgSO4
H
1. O3
II
2. Zn/H+
COCl
III
1. LiAl(OC(CH3)3)3H
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
HgSO4
H
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
HgSO4
H
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
2.H2O2, NaOH
1. DIBAL-H/-78oC
CN
II
2. H2O
COOCH3
III
1. DIBAL-H/-78oC
2. H2O
COCl
IV
1. LiAl(OC(CH3)3)3H
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?
CH3CH2CH2OH
a)
PCC
CH2Cl2
73
O
CH3CH2CCl
LiAlH[OC(CH3)3]3
ether, -78 oC
b)
CH3C
CH
1. Sia2BH
2. H2O2, OHc)
Answer: D
Topic: Synthesis
Section: 16.4
a)
O
CH3CH2CCl
LiAlH[OC(CH3)3]3
ether, -78 oC
b)
CH3C
CH
1. Sia2BH
2. H2O2, OHc)
Answer: D
Topic: Synthesis
Section: 16.4
CH3CH2CH2OH
a)
PCC
CH2Cl2
74
O
CH3CH2CCl
LiAlH[OC(CH3)3]3
b)
ether, -78 oC
c)
Answer: D
Topic: Synthesis
Section: 16.4
CH3CH2CH2OH
a)
PCC
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
b) C6H6 + CH3COCl
c) C6H5CN + CH3Li
AlCl3
ether
H3O+
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
H3O+
ether
c) C6H5CN + CH3Li
Answer: E
Topic: Synthesis
Section: 16.5
128) Which of the following would yield 3-pentanone as the major product?
a) CH3CH2CN + CH3CH2Li
ether
Product
H3O+
b)
ether
CN
Product
MgBr
c)
PCC
CH2Cl2
OH

Answer: E
Topic: Synthesis
Section: 16.5
129) Which sequence of reactions would be utilized to convert
77
H3O+
CO2CH3
into
CH3
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
O
130) Which of the following procedures would not yield (CH3)2CHCH as a product?
PCC
I
OH
CH2Cl2
SOCl2
II
CO2H
ether, -78 oC
O3
III
Zn
HOAc
KMnO4
IV
LiAlH(O-t-Bu)3
OH
H3 O +
NaOH
H3 O +
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Synthesis
78

O
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
II
III
MgBr
+ 2 CH3MgBr
(C6H5)3P
1. ether
H2
2. H3O+
Ni
1. ether
H2
2. H3O+
Ni
C6H5Li
cyclopentanone
Ni
Cl
IV
H2
H 3O +
CH3MgBr
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
?
CH3CH=P(C6H5)3
CH=P(C6H5)3
P(C6H5)3
II
III
a) I
b) II
c) III
d) IV
e) Either I or II could be used.
80
CH3CH2CH=P(C6H5)3
IV
Answer: E
Topic: Synthesis
Section: 16.10
134) Which of the following is not a synthesis of benzophenone,
O
C6H5CC6H5
?
O
a) C6H6 + C6H5CCl
b)
c)
d)
(C6H5)2CHOH
(C6H5)2CH=CH2
AlCl3
H2CrO4
acetone
1. O3
2. Zn, HOAc
PCC
Ph2CHOH
CH2Cl2
e) All of these choices will give benzophenone.

Answer: E
Topic: Synthesis
Section: 16.5
O
C6H5CC6H5
?
O
a) C6H6 + C6H5CCl
b)
(C6H5)2CHOH
AlCl3
H2CrO4
acetone
81
c)
d)
(C6H5)2CH=CH2
1. O3
2. Zn, HOAc

Answer: E
Topic: Synthesis
Section: 16.5
O
C6H5CC6H5
?
O
AlCl3
a) C6H6 + C6H5CCl
PCC
b)
c)
d)
Ph2CHOH
CH2Cl2
(C6H5)2CH=CH2
1. O3
2. Zn, HOAc

Answer: E
Topic: Synthesis
Section: 16.5
82
H
O
would be:
H
H2O, H2SO4
HgSO4
H
1. Sia2BH
II
2. H2O2, NaOH
H
1. O3
III
2. Zn, HOAc
OH
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)
CH3CH2CN
CH3(CH2)2CH2Li
b)
CH3CH2CH2CH2OH
c)
d)
ether
PBr3
H3O+
NaCN
ether
CH3CH2MgBr
ether
83
H3O+
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)
CH3CH2CN
H3 O+
CH3(CH2)2CH2Li
b)
CH3CH2CH2CH2OH
ether
PBr3
NaCN
CH3CH2MgBr
ether
c)
d)
H3O+
ether
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
CH3CCH3
H
CH3C
II
O
O
HC
(CH3)3CCCH3
III
IV
a) I > III > IV> II > V

b) IV > II > I > III > V
c) V > III > I > II > IV
84
O
O
(CH3)3CCC(CH3)3
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
OH
a)
b) CH3CH(OH)2
OH
CH3CCH3
OH
c)
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
OH
a)
b) CH3CH(OH)2
OH
CH3CCH3
OH
c)
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?
H
O
CH3CCH3
CH3C
II
HC
(CH3)3CCCH3
III
IV
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
OCH3
OH
II
IV
III
a) I
b) II
c) III
d) IV
Answer: C
Topic: New Functional Groups
Section: 16.7
86
O
O
(CH3)3CCC(CH3)3
145) Which is the general formula for a thioacetal?

H
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
O
OH
OCH3
II
OH
III
IV
a) I
b) II
c) III
d) IV
Answer: B
Section: 16.7
147) Which compound is a hemiacetal?
O
O
O
OH
II
OCH3
OH
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
II
III
NO2
O
N
IV
N
H
NH2
N
H
NO2
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-C6H5
N-NH-C6H5
N-NH2
II
III
O
N
IV
N
H
N=N-C6H5
NH2
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?
N-NH-C6H5
N-NH2
N-OH
III
II
NO2
O
N
IV
N
H
NH2
N
H
NO2
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?
N-NH-C6H5
N-NH2
N-OH
III
II
NO2
O
N
N
H
NH2
IV
N
H
NO2
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?
O
a) CH3CH2CCH2CH3
O
b) (CH3)2CHCCH3
H
c) (CH3)3CC
O
H
CH3CH2CHC
d)
CH3
90
e) (CH3)2CHCH2C
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?
O
a) CH3CH2CCH2CH3
O
b) (CH3)2CHCCH3
H
c) (CH3)3CC
O
H
CH3CH2CHC
d)
CH3
e) (CH3)2CHCH2C
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-1bromobutane.
Answer:
Br
NaCN
CN
i. DIBAL-H
ii. H2O
Topic: Synthetic Strategy

Section: 16.4
160) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-bromobutane.
Br
NaCN
Answer:
CN
i. C2H5Li, Et2O
ii. H3O+

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

Section: 16.5
162) Suggest a synthetic strategy for the synthesis of 6-methyl-3-heptanol from 4methylpentanenitrile, (CH3)2CHCH2CH2CN.
i. DIBAL-H
CN
ii. H2O
OH
iii. C2H5MgBr, Et2O

iv. H3O+
OR
i. C2H5MgBr, Et2O
CN
ii. H3O+
OH
iii. NaBH4, H2O
Answer:

Section: 16.5
163) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene.
Answer:
HBr
ROOR
Br
NaCN
CN
i. C2H5Li, Et2O
ii. H3O+
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.
Ph
Ph
Ph
Ph
multiple steps
cis-stilbene
trans-stilbene
Answer:
Ph
m-CPBA
H
Ph
Ph
PPh3
Ph3P
Ph
Ph
Ph
Ph

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

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

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

Section: 16.7
96

168) Complete the following reaction sequence, giving structural details of all
significantintermediates and the final product.
O
KMnO4, OH-, heat
H+
HO
H+
H2 O
Answer:
O
O
H+
HO
KMnO4, OH-, heat
H
O
H
O
H+
O
HO
H2O
OH

Section: 16.7
intermediates X, Y, and final product Z.
CH3
1. KMnO4,
OH-,
heat
2. H3O+
COOH
SOCl2
COCl
1. LiAlH(O-t-Bu)3
ether, -78 oC
2. H2O
CHO
Answer:
Section: 16.4
intermediates.
97
i. Br2, h
ii. Mg, CH3CH2CN
iii. H3O+
iv. NaBH4
Answer:
O
NaBH4
Br i. Mg, CH CH CN
3
2
Br2, h
HO
ii. H3O+

Section: 16.5
intermediates.
i. O3
i. EtMgBr
?
+
ii.Zn, CH3CO2H
ii. H3O , heat
O
i. EtMgBr
ii. H3O+, heat
i. O3
ii.Zn, CH3CO2H
HO
O
O
Answer:
Section: 16.5
Br2
Mg
1. C6H5CHO
H2Cr2O4
Benzene
?
FeCl3
acetone
ether
2. H3O+
OH
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:
H+
H
H
N
H
N
H
HO
N
~H
H2O
N
H
-H2O
-H+
102
Topic: Mechanisms
Section: 16.8
187) Draw a complete mechanism, using arrow convention to indicate electron movement,for the
following transformation:
O
H3C
PPh3
CH3
H3 C
Ph3P
CH3
Answer:
O H3C
O
H
H3C
PPh3
PPh3
H3C
CH3
PPh3
PPh3
rotation 180o
as shown
CH3
H
CH3
+
H3C
H3C
H3C
Ph3P
CH3
Topic: Mechanisms
Section: 16.10
188) Draw a complete mechanism, using arrow convention to indicate electron movement, for
the following transformation:
O
H
H3 C
H3C
PPh3
CH3
Answer:
103
CH3
Ph3P
O H3C
O
H
H3C
PPh3
CH3
PPh3
H
H3C
CH3
PPh3
H3C
PPh3
rotation 180o
as shown
CH3
CH3
CH3
+
H
Ph3P
CH3
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 2methylbenzaldehyde?
Answer: Tollens 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
and
C6H5COCH3
C6H5CH2CHO
3 signals
2 signals
approximate ppm
approximate ppm
singlet (-CH3) 2.0
doublet (-CH2-) 2.5
multiplet (C6H5) 7.2
multiplet (C6H5) 7
triplet(-CHO) 9
Topic: Spectroscopy
Section: 16.14
192) 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
Answer:
CH3CH2CH2CCH3
Topic: Spectroscopy
Section: 16.14
C5H10O
IR: 1720 cm1
1
H NMR: 1.1 (triplet, 3H), 2.4 (quartet, 2H)
Answer:
Topic: Spectroscopy
Section: 16.14
105

C9H10O
IR: 1680 cm1
1
H NMR: 1.25 (triplet, 3H), 3.0 (quartet, 2H), 7-8 (complexmultiplet, 5H)
O
Answer:
Topic: Spectroscopy
Section: 16.14
C7H6O
IR: 1703 cm1
1
H NMR: 7-8 (complexmultiplet, 5H), 10.0 (singlet, 1H)

O
Answer:
Topic: Spectroscopy
Section: 16.14
C3H6O
IR: 1730 cm1
106
H NMR: 1.1 (triplet, 3H), 2.5 (doubletofquartets, 2H), 9.8 (doublet, 1H)
H
Answer:
Topic: Spectroscopy
Section: 16.14
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
Answer:
Topic: Spectroscopy
Section: 16.14
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
Answer: CH3CH2CH2CCH3
107
Topic: Spectroscopy
Section: 16.14
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
Answer:
Topic: Spectroscopy
Section: 16.14
C6H12O
IR: 1708 cm1
DEPT Experiments show: signals at 24.61, 26.42 as CH3
Answer:
Topic: Spectroscopy
Section: 16.14
108

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
Answer:
Topic: Spectroscopy
Section: 16.14
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
Answer:
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 (doublet, 3H)
3.4 (singlet, 6H)
109
4.6 (quartet, 1H)

Propose a structure consistent with this information.
Answer:
O
Topic: Spectroscopy
Section: 16.14
110

Chapter 16 - Test Bank Chem 200

Hochgeladen von

Dokumentinformationen

Originalbeschreibung:

Copyright

Verfügbare Formate

Dieses Dokument teilen

Dokument teilen oder einbetten

Freigabeoptionen

Stufen Sie dieses Dokument als nützlich ein?

Sind diese Inhalte unangemessen?

Copyright:

Verfügbare Formate

Chapter 16 - Test Bank Chem 200

Hochgeladen von

Copyright:

Verfügbare Formate

Package Title: Solomons Test Bank

Course Title: Solomons 11e

11) A correct name for C6H5CH2CH2CH is?

26) What is the IUPAC name for

c) The phenylhydrazone of 4-methylcyclohexanone

a) Zn(Hg), HCl, reflux

Difficulty Level: Medium

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

d) C6H5CHOCH3 and C6H5COCH3

70) The product, K, of the following sequence of reactions

Topic: Reaction Products

Topic: Reaction Products

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

i) H2, Lindlar catalyst

Topic: Reaction Products

i) H2, Lindlar catalyst

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

1. KMnO4, NaOH, heat

d) Two of these choices.

a) 2CH3MgBr, then NH4+

Difficulty Level: Medium

e) All of these choices will give benzophenone.

e) All of these choices will give benzophenone.

e) All of these choices will give benzophenone.

1. KMnO4, NaOH, heat

e) All of these choices are syntheses of 3-heptanone.

e) All of these choices are syntheses of 3-heptanone.

a) I > III > IV> II > V

a) I < III < V < II < IV

145) Which is the general formula for a thioacetal?

Topic: Synthetic Strategy

Topic: Synthetic Strategy

Topic: Synthetic Strategy

iii. C2H5MgBr, Et2O

iii. NaBH4, H2O

Topic: Synthetic Strategy

Topic: Synthetic Strategy

Topic: Synthetic Strategy

Topic: Reaction Sequence

Topic: Reaction Sequence

Topic: Reaction Sequence

Difficulty Level: Hard

KMnO4, OH-, heat

KMnO4, OH-, heat

Topic: Reaction Sequence

Topic: Reaction Sequence

Difficulty Level: Hard

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

Difficulty Level: Medium

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

201) Propose a structure that fits the following spectroscopic data:

4.6 (quartet, 1H)

Das könnte Ihnen auch gefallen