Chapter 17 Questions for Boson Organic Chemistry II

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Ch17 - Chapter 17 Questions for Boson
Organic Chemistry II (The City College of New York)
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Package Title: Solomons Test Bank

Course Title: Solomons 12e
Chapter Number: 17
Question type: Multiple choice
1) Which of the following is the best name for the following compound?
O
a) Isobutyl ethanoate
b) Ethyl isopropanoate
c) 3-methylbutyl ethanoate
d) Ethoxy isobutyl ketone
e) Ethyl 3-methylbutanoate
Answer: E
Topic: Nomenclature
Section: 17.2
Difficulty Level: Medium
2) The correct structure for ethyl 3-methylbutanoate is:
O O O
O O O
I II III
O O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 17.2

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3) The correct structure for bicyclo[1.1.1]pentane-2-carboxylic acid is:
COOH
COOH
COOH
I II III
COOH
COOH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 17.2

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4) The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:
COOH
COOH
COOH
I II III
COOH COOH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 17.2

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5) The correct structure for bicyclo[1.1.0]butane-2-carboxylic acid is:
COOH
COOH
COOH
I II III
COOH COOH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 17.2

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6) The correct structure for methyl bicyclo[1.1.1]pentane-2-carboxylate is:
COOCH3
COOCH3
COOCH3
I II III
COOCH3
COOCH3
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 17.2

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7) The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is:
COOCH3
COOCH3
COOCH3
I II III
COOCH3 COOCH3
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 17.2

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8) The correct structure for methyl bicyclo[1.1.0]butane-2-carboxylate is:
COOCH3
COOCH3
COOCH3
I II III
COOCH3 COOCH3
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 17.2

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9) The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is:
COOCH3
COOCH3
COOCH3
COOCH3
I II III
COOCH3
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 17.2
O
10) A correct name for is:
a) 2-Methylbutyl 2-methylbutanoate
b) 2-Methylbutyl 3-methylbutanoate
c) 3-Methylbutyl isovalerate
d) Isopentyl isovalerate
e) Isopentyl isobutyrate
Answer: B
Topic: Nomenclature
Section: 17.2

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11) The correct structure for ethyl 3-methylbutanoate is:

O O O
O O O
I II III
O O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 17.2
Cl
Cl
12) What is the IUPAC name for O
a) -Chlorovaleryl chloride
b) 2-Chloropentanoyl chloride
c) 1-Chloropentanoyl chloride
d) 1,2-Dichloropentanal
e) 1-Chloro-1-butanecarbonyl chloride
Answer: B
Topic: Nomenclature
Section: 17.2

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13) The correct structure for ethyl 2-chloropentanoyl chloride is:

O
O O
OH Cl
Cl OH OH
Cl
I II III
O
Cl O
Cl
Cl
Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 17.2
O O
14) What is the IUPAC name for
a) -Dimethylbutyl acetate-
b) -Dimethyl-4-oxoethanal
c) -Dimethylbutyl methanoate
d) -Dimethylbutyl methylate
e) -Dimethylbutyl formylate
Answer: C
Topic: Nomenclature
Section: 17.2
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15) The correct structure for -methylbutyl methanoate is:

O O O
H O H O H O
I II III
O O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature
Section: 17.2
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16) Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?
H
N N N
O O O
I II III
N N
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 17.2
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17) Which of the following structures is 3,4-dimethylpentyl chloroformate?

H O Cl O Cl O
O O O
Cl
I II III
O Cl O
O Cl O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 17.9
Difficulty Level: Hard
18) Which compound would be the strongest acid?
a) CHCl2CH2CH2CO2H
b) ClCH2CHClCH2CO2H
c) CH3CCl2CH2CO2H
d) CH3CHClCHClCO2H
e) CH3CH2CCl2CO2H
Answer: E
Topic: Acidity
Section: 17.2
Difficulty Level: Easy
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19) Which compound would be the weakest acid?
a) CHCl2CH2CH2CO2H
b) ClCH2CHClCH2CO2H
c) CH3CCl2CH2CO2H
d) CH3CHClCHClCO2H
e) CH3CH2CCl2CO2H
Answer: A
Topic: Acidity
Section: 17.2
a) 4,4-dichlorobutanoic acid
b) 3,4-dichlorobutanoic acid
c) 3,3-dichlorobutanoic acid
d) 2,3-dichlorobutanoic acid
e) 2,2-dichlorobutanoic acid
Answer: E
Topic: Acidity
Section: 17.2
21) Which compound would be expected to have the lowest pKa?
Answer: E
Topic: Acidity
Section: 17.2
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22) Which compound would be expected to have the highest pKa?
Answer: A
Topic: Acidity
Section: 17.2
Answer: A
Topic: Acidity
Section: 17.2
a) water
b) acetic acid
c) ethane
d) acetylene
e) ethanol
Answer: B
Topic: Acidity
Section: 17.2
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a) water
b) acetic acid
c) ethane
d) acetylene
e) ethanol
Answer: C
Topic: Acidity
Section: 17.2
26) Which compound would be expected to have the highest pKa?
a) water
b) acetic acid
c) ethane
d) acetylene
e) ethanol
Answer: C
Topic: Acidity
Section: 17.2
27) Which compound would be expected to have the lowest pKa?
a) water
b) acetic acid
c) ethane
d) acetylene
e) ethanol
Answer: B
Topic: Acidity
Section: 17.2
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28) In which of the following sequences are the compounds listed in order of decreasing acidity?
a) CH3COOH > H2O > CH3CH2OH > HCCH > NH3

b) CH3CH2OH > CH3COOH > H2O > HCCH > NH3
c) CH3COOH > CH3CH2OH > H2O > NH3 > HCCH
d) H2O > CH3COOH > CH3CH2OH > HCCH > NH3
e) CH3CH2OH > H2O > CH3COOH > HCCH > NH3
Answer: A
Topic: Acidity
Section: 17.2
29) In which of the following sequences are the compounds listed in order of increasing acidity?
a) NH3 < HCCH < CH3CH2OH < H2O < CH3COOH

b) CH3CH2OH < NH3 < H2O < HCCH < CH3COOH
c) CH3COOH < CH3CH2OH < H2O < NH3 < HCCH
d) H2O < CH3COOH < CH3CH2OH < HCCH < NH3
e) NH3 < H2O < CH3COOH < HCCH < CH3CH2OH
Answer: A
Topic: Acidity
Section: 17.2
a) CH3COOH > H2O > PhOH > HCCH > NH3

b) PhOH > CH3COOH > H2O > HCCH > NH3
c) CH3COOH > PhOH > H2O > HCCH > NH3
d) H2O > CH3COOH > PhOH > HCCH > NH3
e) PhOH > H2O > CH3COOH > HCCH > NH3
Answer: C
Topic: Acidity
Section: 17.2
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a) PhCOOH > H2O > PhOH > PhCH2OH > PhH

b) PhCOOH > PhOH > H2O > PhCH2OH > PhH
c) PhH > H2O > PhOH > PhCH2OH > PhCOOH
d) PhOH > H2O > PhCOOH > PhCH2OH > PhH
e) PhCOOH > H2O > PhOH > PhH > PhCH2OH
Answer: B
Topic: Acidity
Section: 17.2
32) Which of the following would be the strongest acid?

Cl
CO2H CO2H CO2H
Cl Cl Cl
I II III
CO2H CO2H
Cl Cl Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Acidity
Section: 17.2
33) Which of the following would be the weakest acid?

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Cl
CO2H CO2H CO2H
Cl Cl Cl
I II III
CO2H CO2H
Cl Cl Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Acidity
Section: 17.2

F
CO2H CO2H CO2H
F F F
I II III
CO2H CO2H
F F F
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Acidity
Section: 17.2
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F
CO2H CO2H CO2H
Cl F F
I II III
CO2H CO2H
F Cl Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Acidity
Section: 17.2

NO2
CO2H CO2H CO2H
O2N O2N NO2

I II III
CO2H CO2H
NO2 O2N NO2

IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Acidity
Section: 17.2
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CH3
CO2H CO2H CO2H
H3C H3C CH3

I II III
CO2H CO2H
CH3 H3C CH3

IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Acidity
Section: 17.2

OCH3
CO2H CO2H CO2H
H3CO H3CO OCH3

I II III
CO2H CO2H
OCH3 H3CO OCH3

IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Acidity
Section: 17.2
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OCH3
CO2H CO2H CO2H
H3CO H3CO OCH3

I II III
CO2H CO2H
OCH3 H3CO OCH3

IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Acidity
Section: 17.2

CH3
CO2H CO2H CO2H
H3C H3C CH3

I II III
CO2H CO2H
CH3 H3C CH3

IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Acidity
Section: 17.2
41) Which of the following acids would have the smallest value for pKa?
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a) BrCH2CH2CH2COOH
b) ClCH2CH2CH2COOH
c) Cl2CHCH2CH2COOH
d) ICHBrCH2CH2COOH
e) BrCCl2CH2CH2COOH
Answer: E
Topic: Acidity
Section: 17.2
42) Which of the following acids would be expected to have the smallest value for pKa?
a) 4-bromobutanoic acid
b) 4-chlorobutanoic acid
d) 4-bromo-4-iodobutanoic acid
e) 4-bromo-4,4-dichlorobutanoic acid
Answer: E
Topic: Acidity
Section: 17.2
43) Which of the following acids would have the largest value for pKa?
a) BrCH2CH2CH2COOH
b) ClCH2CH2CH2COOH
c) Cl2CHCH2CH2COOH
d) ICHBrCH2CH2COOH
e) BrCCl2CH2CH2COOH
Answer: A
Topic: Acidity
Section: 17.2
44) Which of the following acids would be expected to have the largest value for pKa?
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a) 4-bromobutanoic acid
b) 4-chlorobutanoic acid
d) 4-bromo-4-iodobutanoic acid
e) 4-bromo-4,4-dichlorobutanoic acid
Answer: A
Topic: Acidity
Section: 17.2
45) Which of the following acids would have the smallest value for pKa1?
a) HOOCCH2CH2CH2CH2CH2COOH
b) HOOCCH2CH2CH2CH2COOH
c) HOOCCH2CH2CH2COOH
d) HOOCCH2CH2COOH
e) HOOCCH2COOH
Answer: E
Topic: Acidity
Section: 17.2
46) Which compound would be most acidic?
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a) OH
b) OH
OH
c)
O
d)
O
e) H H
Answer: A
Topic: Acidity
Section: 17.2
47) In which of the following are the compounds listed in order of decreasing acidity?
a) CH3CO2H > CH3CH2OH > C6H5OH > H2O

b) C6H5OH > CH3CO2H > H2O > CH3CH2OH
c) CH3CO2H > H2O > C6H5OH > CH3CH2OH
d) H2O > CH3CO2H > C6H5OH > CH3CH2OH
e) None of these choices.
Answer: E
Topic: Acidity
Section: 17.2
48) In which of the following are the compounds listed in order of decreasing acidity?
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a) CH3CO2H > CH3CH2OH > C6H5OH > H2O

b) C6H5OH > CH3CO2H > H2O > CH3CH2OH
c) CH3CO2H > H2O > C6H5OH > CH3CH2OH
d) H2O > CH3CO2H > C6H5OH > CH3CH2OH
e) CH3CO2H > C6H5OH > CH3CH2OH > H2O
Answer: E
Topic: Acidity
Section: 17.2
a) Benzoic acid
b) 4-Nitrobenzoic acid
c) 4-Methylbenzoic acid
d) 4-Methoxybenzoic acid
e) 4-Iodobenzoic acid
Answer: B
Topic: Acidity
Section: 17.2
a) Benzoic acid
Answer: B
Topic: Acidity
Section: 17.2
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a) Benzoic acid
Answer: D
Topic: Acidity
Section: 17.2
52) Which of the following acids would be expected to have the largest value for pKa?
a) Benzoic acid
Answer: D
Topic: Acidity
Section: 17.2
a) 2,3-Dimethylhexanoic acid
b) 3,3-Diiodopentanoic acid
c) 3-Iodo-4-bromopentanoic acid
d) 3-Chloro-4-bromohexanoic acid
e) 2-Fluoro-4-bromopentanoic acid
Answer: E
Topic: Acidity
Section: 17.2
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a) 2,3-Dimethylhexanoic acid
b) 3,3-Diiodopentanoic acid
c) 3-Iodo-4-bromopentanoic acid
d) 3-Chloro-4-bromohexanoic acid
e) 2-Fluoro-4-bromopentanoic acid
Answer: E
Topic: Acidity
Section: 17.2
55) Which compound would be most acidic?
a) Acetic acid
b) Ethanol
c) Phenol
d) Acetone
e) Water
Answer: A
Topic: Acidity
Section: 17.2
a) Acetic acid
b) Ethanol
c) Phenol
d) Acetone
e) Water
Answer: A
Topic: Acidity
Section: 17.2
57) The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm -1 and a
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sharp band at 1710 cm-1. Which of these compounds could it be?
a) 1-Butanol
b) Propyl acetate
c) Butanoic acid
d) Acetyl chloride
e) Acetic anhydride
Answer: C
Topic: Structure Identification (Spectroscopy)

Section: 17.2
58) A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption
band near 1740 cm-1; its 1H NMR spectrum consists of two singlets, at 1.4 and 2.0. The
most likely structure for this compound is:
O
O O
O
O O
I II III
O O
O O H
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 17.2
59) A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption
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band near 1740 cm-1; its 1H NMR spectrum consists of two singlets, at 1.2 and 3.6. The
most likely structure for this compound is:
O O O
O O O
I II III
O
O
O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 17.2
60) A compound has the molecular formula C8H14O4. Its IR spectrum shows a strong absorption
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band near 1740 cm-1. Its 1H NMR spectrum consists of:
triplet, 1.3
singlet,  2.6
quartet,  4.2
The most likely structure for the compound is:

O O
O O
O O
O O
O O
O O
I II III
O
HO2C O
CO2H O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 17.2
61) A compound with the molecular formula C5H10O2 gave the following 1H NMR spectrum:
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triplet,  0.90
multiplet,  1.60
singlet,  1.95
triplet,  3.95
The IR spectrum showed a strong absorption band near 1740 cm-1. The most likely structure for
the compound is:
a) O
O
b) O
O
c) O
H O
d) O
O
HO
e)
Answer: A

Section: 17.2
62) A compound with the molecular formula C18H18O4 has a 1H NMR spectrum that consists of:
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singlet,  2.7
singlet,  3.1
multiplet,  7.3
The IR spectrum shows a strong absorption band near 1750 cm -1. The most likely structure for
the compound is:
O
O C6H5
C6H5 O
a) O
O O
C6H5
b) C6H5 O O
O
O C6H5
C6H5 O
c) O
O
O C6H5
C6H5 O
d) O
O
O C6H5
C6H5 O
e) O
Answer: C

Section: 17.2
63) What would be the product of the following reaction?
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18
OH O HA ?
+ H
O
18O O 18O
O 18O 18 O
I II III
18
O O O
O O
II III
\
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Reaction Products

Section: 17.7
64) What is the product of this reaction?
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O
H2O
HN ?
OH-
O O
H H2N O
N CO2H O N
H
I II III
O O HO O
HN
O N
H
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.8
65) Predict the major organic product of the reaction sequence,
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O O O i. NH3, H2O
M
ii. dilute HCl, cold
O O O
OH NH2 NH2
HO HO H2 N
O O O
I II III
H
O N O HN O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.8
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i. NH3, H2O
O ?
ii. dilute H+, cold
O
O O O
OH NH2 NH2
OH OH NH2
O II O III O
I
O NH
NH O
IV O V O
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.8
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O O O i. NH3, H2O
M
ii. dilute HCl, cold
O O
OH NH2
O
NH2 NH2
NH2
HO
O O O
I II III
H
O N O HN O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 17.8
68) The product of the following reaction is:
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O
OH
heat ?
O +
O
(1 mol) (1 mol)
O O O O
O O OH
CO2H CO2H
I II III
O O O
O H O
O
Cl O Cl
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 17.7

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O
CH3OH ?
O
O O
O CO2H HO O
O O
I II III
O O HO O
O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.7
70) What is the reactant of the following reaction sequence?
OH
i. Mg/ether
?
ii. CO2
iii. H+ O
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2Cl
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Answer: C

Section: 17.3
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71) Predict the major organic product of the reaction sequence below:
heat H3O+
+ KMnO4 ?
H2O, OH
OH
OH CO2H CHO
I II III
OH
CHO
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.3
72) What is the expected product, A, of the following reaction sequence?

Cl i. NaCN A + NH4+
ii. 70% H2SO4, reflux
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OSO3H
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Answer: B

Section: 17.3
73) What would be the final organic product of the following reaction?
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i. Mg, Et2O i. LAH, Et2O

Br ?
ii. CO2 ii. H2O
iii. H3O+
a) (CH3)3CCO2H
b) (CH3)3CCOCH3
c) (CH3)3CCH2OH
d) (CH3)3COCH3
e) (CH3)3CCO2CH3
Answer: C

Section: 12.3 and 17.3

Cl
i. Mg/ether
ii. CO2 A
iii. H+
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OSO3H
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Answer: B

Section: 17.3
42

lOMoARcPSD|7465873
O 1. LAH
?
+
2. H3O
O HO
OH OH
I III
II
OH
O
HO OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: E

43

lOMoARcPSD|7465873
O
i. DIBAL-H, -78oC ?
ii. H3O+
O HO
OH OH
I III
II
OH
O
HO OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D

44

lOMoARcPSD|7465873
i. DIBAL-H, -78oC ?
O
ii. H3O+
O
OH HO OH
I III
II
OH
O HO OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D

45

lOMoARcPSD|7465873
i. DIBAL-H, -78oC ?
O
ii. H3O+
O
OH
OH
OH
O
OH
I III
O II OH
O O
V
O
IV
a) I
b) II
c) III
d) IV
e) V
Answer: E

46

lOMoARcPSD|7465873
DCC
OH ?
CH3NH2
O O O
NH2 NHCH3
I II III
O
OH
O
IV
V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.8
80) The product, Z, of the following sequence of reactions is which compound?
47

lOMoARcPSD|7465873
i. KMnO4, OH , heat

ii. H3O+
p-Chlorotoluene Z
iii. SOCl2
iv. CH3CH2OH, base
O O
O O
Cl Cl
I II III
O O
Cl
Cl Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

81) What would be the final product?

i. PCl5
CO2H ?
ii. NH3
iii. P4H10, heat
a) CH3CH2CH2NH2
b) CH3CH2CONH2
c) CH3CH2CONHCOCH2CH3
d) CH3CH2CN
e) CH3CH2COO-NH4+
Answer: D

48

lOMoARcPSD|7465873
82) What would be the final product of this reaction sequence?

CO2H i. PCl3
?
ii. NH3
iii. P4O10
O
CN NH2 NH2
I II III
H H
CO2 NH4 N N
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

49

lOMoARcPSD|7465873
a) CH3CH2CH2NH2
b) CH3CH2CONH2
c) CH3CH2CONHCOCH2CH3
d) CH3CH2CN
e) CH3CH2COCH3
Answer: E

Section: 16.5, 17.5, and 17.8
84) What would be the final product of this reaction sequence?
50

lOMoARcPSD|7465873
i. PCl3
CO2H ii. NH3
?
iii. P4O10
iv. CH3Li, ether
v. H3O+
O
CN NH2 NH2
I II III
H H
COCH3 N N
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 16.5, 17.5 and 17.8
85) What is the final product of this sequence of reactions?
51

lOMoARcPSD|7465873
i. Mg, Et2O i. SOCl2

Br ?
ii. CO2 ii. excess NH3
iii. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.3, 17.5 and 17.8
52

lOMoARcPSD|7465873
i. Mg, Et2O i. SOCl2 P4O10

Br ?
ii. CO2 ii. excess NH3 heat
iii. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.3, 17.5 and 17.8
87) What is the product of the reaction of 1-propanol with phenyl isocyanate, C6H5N=C=O?
53

lOMoARcPSD|7465873
H
N O
C6H5
a) O
CO2H
N
b) C6H5
CHO
N
c) C6H5 O
H
N O
C6H5
d) O
H
N
C6H5
e) O
Answer: A

Section: 17.9
88) What is the ultimate product of this sequence of reactions?

O
CH3CH2OH CH3NH2
Cl Cl ?
(1 eq.)
O O O
H H O Cl
N N Cl N
O N O O
H O
H O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 17.9
89) Identify the product(s) of the following reaction.
54

lOMoARcPSD|7465873
O
heat
CO2H ?
O O
O O + CO2
OH O
I II III
CO2H
+ CO 2 CO2H
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.10

55

lOMoARcPSD|7465873
O H3O+
CO2CH3 ?
heat
O O
O O + CO2 + CH3OH
OH O
I II III
CO2H
+ CO 2 CO2H
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.10
56

lOMoARcPSD|7465873
COOH
heat
?
OH O
COOH COOH
I II III
COOH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.10
57

lOMoARcPSD|7465873
O
O
heat
OH ?
OH O
COOH COOH
O
I II III
COOH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.10
i. LiAl(OC(CH3)3)3H,-78oC
C6H5COCl ?
+
ii. H3O
a) C6H5CO2H
b) C6H5CH3
c) C6H5COOCH3
d) C6H5CHO
e) C6H5CH2OH
Answer: D
Sections: 16.4 and 17.13
58

lOMoARcPSD|7465873
i. LiAl(OC(CH3)3)3H HO OH
C6H5COCl ?
+ +
ii. H3O H
a)
b) C6H5CH3
c) C6H5COOCH2CH2OH
d) C6H5CHO
e) C6H5CH2OH
Answer: A

Sections: 16.4, 16.7 and 17.13
i. KMnO4
HO OH
ii. SOCl2 ?
C6H5CH3 iii. LiAl(OC(CH3)3)3H +
H
iv. H3O+
a)
b) C6H5CH3
c) C6H5COOCH2CH2OH
d) C6H5CHO
e) C6H5CH2OH
Answer: A

Sections: 16.4, 16.7 and 17.13
59

lOMoARcPSD|7465873
i. LiAl(OC(CH3)3)3H CH3NH2
C6H5COCl ?
+
ii. H3O pH 4-5
a) C6H5CO2H
b) C6H5CH2CH2NCH3
c) C6H5CH2CH2CN
d) C6H5CH=NCH3
e) C6H5CH2NCH3
Answer: D

Sections: 16.4, 16.8 and 17.13
i. KMnO4
CH3NH2
C6H5CH3 ii. SOCl2 ?
iii. LiAl(OC(CH3)3)3H
pH 4-5
iv. H3O+
a) C6H5CO2H
b) C6H5CH2CH2NCH3
c) C6H5CH2CH2CN
d) C6H5CH=NCH3
e) C6H5CH2NCH3
Answer: D

Sections: 16.4, 16.8 and 17.13
98) Predict the major organic product, P, of the following sequence of reactions:
60

lOMoARcPSD|7465873
Cl i. OH (2eq.), H2O heat H2 i. SOCl2

P
CO2H +
ii. H3O cat. ii. CH3OH
Cl
O O
O
CO2H O
O
I II III
Cl
O O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

61

lOMoARcPSD|7465873
O
i. CH3COOOH
ii. DIBAL-H, -78oC ?
iii. H3O+
O
OH HO OH
I III
II
OH
O HO OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D

62

lOMoARcPSD|7465873
i. CH3COOOH
ii. DIBAL-H, -78oC ?
iii. H3O+
OH
OH
O O
I II III
OH
O
HO OH
IV
a) I
b) II
c) III
d) IV
e) V
Answer: D

63

lOMoARcPSD|7465873
i. NBS, ROOR
ii. Mg/ether
A
iii. CO2
iv. H+
a) HCO2CH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OSO3H
d) C6H5CHClCOOH
e) O=C(CH2C6H5)2
Answer: B

Section: 17.3

Cl i. NaCN A + NH4+
a) Benzyl formate
b) Phenylacetic acid
c) Benzenesulfonic acid
d) 1-Chloro-1-phenyl acetic acid
e) Dibenzylketone
Answer: B

Section: 17.3
64

lOMoARcPSD|7465873
i. NBS, ROOR
ii. NaCN
toluene A
iii. H3O+
a) Benzyl formate
e) Dibenzylketone
Answer: B

Section: 17.3

i. Br2, ROOR
ii. NaCN
toluene A
iii. H3O+
a) Benzyl formate
e) Dibenzylketone
Answer: B

Section: 17.3
65

lOMoARcPSD|7465873
i. NaCN COOH
? + NH4+
a) BrCH2C6H5
b) C6H5CH2COOH
c) C6H5CH2OH
d) C6H5CH2CH2COOH
e) O=C(CH2C6H5)2
Answer: A

Section: 17.3

i. NBS, ROOR COOH
? + NH4+
ii. NaCN
iii. 70% H2SO4, reflux
a) C6H5CH3
b) C6H5CH2COOH
c) C6H5CH2OH
d) C6H5CH2CH2COOH
e) O=C(CH2C6H5)2
Answer: A

Section: 17.3
66

lOMoARcPSD|7465873
107) What would be the final product, F, of the following sequence of reactions?
i. LAH, Et2O PBr3 i. Mg, Et2O
CO2H ii. H O F
2 ii. CO2
iii. H3O+
CO2H O
Br CO2H CO2H
Br
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 17.3
i. LAH, Et2O SOCl2 i. Mg, Et2O
CO2H F
ii. H2O ii. CO2
iii. H3O+
CO2H O
Br CO2H CO2H
Br
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 17.3
67

lOMoARcPSD|7465873
CO2H ii. H O F
2 ii. CO2
iii. H3O+
a) 1-Bromo-2-methyl propane
b) 3-Bromo-3-methylbutanoic acid
c) Butanoic acid
d) 3-Methylbutanoic acid
e) Methyl 2-methylproanoate
Answer: D

Section: 17.3
CO2H F
ii. H2O ii. CO2
iii. H3O+
a) 1-Bromo-2-methyl propane
b) 3-Bromo-3-methylbutanoic acid
c) Butanoic acid
d) 3-Methylbutanoic acid
e) Methyl 2-methylproanoate
Answer: D

Section: 17.3
68

lOMoARcPSD|7465873
2-methylpropanoic acid F
ii. H2O ii. CO2
iii. H3O+
CO2H O
Br CO2H CO2H
Br
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 17.3
2-methylpropanoic acid F
ii. H2O ii. CO2
iii. H3O+
CO2H O
Br CO2H CO2H
Br
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D
Section: 17.3
69

lOMoARcPSD|7465873
? i. LAH, Et2O PBr3 i. Mg, Et2O

CO2H
ii. H2O ii. CO2
iii. H3O+
Br CO2H CO2H
Br CO2H
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 17.3

? i. LAH, Et2O SOCl2 i. Mg, Et2O
CO2H
ii. H2O ii. CO2
iii. H3O+
Br CO2H CO2H
Br CO2H
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 17.3
70

lOMoARcPSD|7465873
i. Mg, Et2O i. LAH, Et2O

Br ?
ii. CO2 ii. H2O
iii. H3O+
a) 2,2-Dimethylpropanoic acid
b) Methyl 2,2-dimethylpropanoate
c) 2,2-Dimethyl-1-propanol
d) t-Butyl methyl ether
e) 3,3-Dimethyl-2-butanone
Answer: C

i. Br2, ROOR
ii. Mg, Et2O i. LAH, Et2O
?
iii. CO2 ii. H2O
vi. H3O+
a) 2,2-Dimethylpropanoic acid
b) Methyl 2,2-dimethylpropanoate
c) 2,2-Dimethyl-1-propanol
d) t-Butyl methyl ether
e) 3,3-Dimethyl-2-butanone
Answer: C

71

lOMoARcPSD|7465873
NaCN i. excess LAH, Et2O

C6H5 Cl ?
ii. H2O
a) C6H5CH2CH2CO2H
b) C6H5CH2CH2NH2
c) C6H5CH2CH(CH3)CN
d) C6H5CH2CH=NH
e) C6H5CH2NH2
Answer: B

i. Br2, ROOR i. excess LAH, Et2O

?
ii. NaCN ii. H2O
a) C6H5CH2CH2CO2H
b) C6H5CH2CH2NH2
c) C6H5CH2CH(CH3)CN
d) C6H5CH2CH=NH
e) C6H5CH2NH2
Answer: B

72

lOMoARcPSD|7465873
i. Br2, ROOR
ii. Mg, Et2O i. LAH, Et2O
?
iii. CO2 ii. H2O
iv. H3O+
a) (CH3)3CCO2H
b) (CH3)3CCOCH3
c) (CH3)3CCH2OH
d) (CH3)3COCH3
e) (CH3)3CCO2CH3
Answer: C


O
i. m-CPBA
?
+
ii. CH3OH, H
O O
O CO2H HO O
O O
I II III
O O HO O
O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.7
73

lOMoARcPSD|7465873
O
i. m-CPBA
?
+
ii. CH3OH, H
O O
O
COOH HO O O O
I II III
O O HO O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.7
122) What final product, Q, would be obtained via the following reaction sequence?
O
H3C H C6H5 Cl OH / H2O O
Q +
H OH pyridine heat C6H5 O
a) cis-3-Methylcyclopentanol
b) trans-3-Methylcyclopentanol
c) Equal amounts of a) and b)
d) 3-Methylcyclopentanone
Answer: B

Section: 17.7
123) (R)-3-Hexanol is subjected to the following sequence of reactions: i) acetyl chloride,
74

lOMoARcPSD|7465873
pyridine; ii) NaOH(aq), heat. What is(are) the likely final product(s)?
a) (R)-3-Hexanol
b) (S)-2-Hexanol
c) Equal amounts of (R)-3-hexanol and (S)-2-hexanol
d) 2-Hexene (cis and trans)
e) 1-Hexen-2-ol
Answer: A

Section: 17.7
124) Predict the final product likely to be obtained when (S)-2-methyl-3-pentanol is subjected to
the following sequence of reactions: i) benzoyl chloride; ii) NaOH(aq), heat.
a) (S)-2-methyl-3-pentanol
b) (R)-2-methyl-3-pentanol
c) (±)-2-methyl-3-pentanol
d) 2-Methyl-2-pentene
e) (±)-2-methyl-3-pentanol and 2-methyl-2-pentene in more or less equal amounts
Answer: A

Section: 17.7
P4O10 i. CH3MgI, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+
a) C6H5CH2CO2CH3
b) C6H5CH2CH2NHCH3
c) C6H5CH2COCH3
d) C6H5CH2CH(CH3)CN
e) C6H5CH2CH=NCH3
Answer: C

Section: 17.8
75

lOMoARcPSD|7465873
P4O10 i. CH3Li, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+
a) C6H5CH2CO2CH3
b) C6H5CH2CH2NHCH3
c) C6H5CH2COCH3
d) C6H5CH2CH(CH3)CN
e) C6H5CH2CH=NCH3
Answer: C

Section: 17.8
P4O10 i. DIBAL-H, -78oC

C6H5CH2CONH2 heat ?
ii. H3O+
a) C6H5CH2CO2CH3
b) C6H5CH2CH2NHCH3
c) C6H5CH2COCH3
d) C6H5CH2CH(CH3)CN
e) C6H5CH2CHO
Answer: E

Section: 17.8
76

lOMoARcPSD|7465873
P4O10 i. PhLi, Et2O

C6H5CH2CONH2 ?
heat ii. H3O+
a) C6H5CH2CO2Ph
b) C6H5CH2CH2NHPh
c) C6H5CH2COPh
d) C6H5CH2CH(Ph)CN
e) C6H5CH2CH=NPh
Answer: C

Section: 17.8

i. Br2, light
ii. Mg, Et2O i. SOCl2
iii. CO2 ?
ii. excess NH3
iv. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.3, 17.5 and 17.8
77

lOMoARcPSD|7465873
i. Br2, light
ii. Mg, Et2O DCC
iii. CO2 ?
iv. H3O+ NH3
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.3, 17.5 and 17.8

78

lOMoARcPSD|7465873
i. Br2, light
ii. Mg, Et2O DCC
iii. CO2 ?
iv. H3O+ CH3NH2
O NHCH3
NHCH3
CN
O O
I II III
NHBr
NHCH3
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 17.3, 17.5 and 17.8

79

lOMoARcPSD|7465873
i. Br2, light
i. SOCl2 P4O10
ii. Mg, Et2O ?
iii. CO2 ii. excess NH3 heat
iv. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.3, 17.5 and 17.8
80

lOMoARcPSD|7465873
i. Br2, light
ii. Mg, Et2O i. SOCl2 (CH3CO)2O
?
iii. CO2 ii. excess NH3 heat
iv. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.3, 17.5 and 17.8
81

lOMoARcPSD|7465873
i. Br2, light
ii. Mg, Et2O DCC (CH3CO)2O
?
iii. CO2 NH3 heat
iv. H3O+
O NH2
NH2
CN
O O
I II III
NHCl
NH2
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 17.3, 17.5 and 17.8
135) N,N-Dimethylbenzamide can be made from which of the following?
C6H5 O + N
H
a) O
C6H5 Cl
+ N
b) O H
C6H5 O C6H5
+ N
O O H
c)
C6H5 NH2
+ CH3MgCl
d) O
e) More than one of these choices.
Answer: E
Topic: Synthesis
Section: 17.8
136) N,N-Dimethylbenzamide can be made from which of the following?
82

lOMoARcPSD|7465873
C6H5 O + N
H
a) O
C6H5 Cl
+ N
b) O H
N DCC
C6H5COOH + H
c)
C6H5 NH2
+ CH3MgCl
d) O
e) More than one of these choices.
Answer: E
Topic: Synthesis
Section: 17.8
137) Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?
i. Mg, Et2O
Br
ii. CO2
a) iii. H3O+
OH i. KMnO4, OH , heat
b) ii. H3O+

i. CN
Br
ii. OH , H2O, heat
c) iii. H3O+
d) All of these choices.
e) Only two of these choices.
Answer: E
Topic: Synthesis
Section: 17.3
83

lOMoARcPSD|7465873
138) Choose the reagent(s) that would bring about the following reaction:
CH3CH2CH2COCl  CH3CH2CH2CHO

a) H2/Ni
b) Li/liq. NH3
c) LiAl(OC(CH3)3)3H
d) NaBH4, CH3OH
e) LiAlH4, ether
Answer: C
Topic: Synthesis
CH3CH2CH2COCl  CH3CH2CH2CHO
a) H2/Ni
b) DIBAL-H
c) LiAl(OC(CH3)3)3H
d) NaBH4, CH3OH
e) LiAlH4, ether
Answer: C
Topic: Synthesis
140) Which of the following compounds is capable of forming a -lactone?
a) 5-Hydroxypentanoic acid
b) Pentanedioic acid
c) 4-Hydroxypentanoic acid
d) 3-Hydroxypentanoic acid
e) 2-Hydroxypentanoic acid
Answer: A
Topic: Synthesis
Section: 17.7
84

lOMoARcPSD|7465873
141) Which of the following reactions could be used to synthesize ethyl acetate?
a) CH3CH2OH + (CH3CO)2O + pyridine 

b) CH3CH2OH + (CH3CO)2O 
c) CH3CH2OH + CH3CO2H + H3O+ 
d) Two of these choices.
e) All of these choices.
Answer: E
Topic: Synthesis
Section: 17.7
CH3CH2CH2CO2CH3  CH3CH2CH2CHO

a) H2/Ni
b) Li/liq NH3
c) Al(CH2CH(CH3)2)H
d) NaBH4, CH3OH
e) LiAlH4, ether
Answer: C
Topic: Synthesis
143) Which of the following reactions would constitute a reasonable synthesis of propyl acetate?
OH HA
OH +
a) O
Cl pyridine
OH +
b) O
O
OH +
c) O O
Answer: D
Topic: Synthesis
144) Which of the following would serve as a reasonable synthesis of ethyl benzoate?
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lOMoARcPSD|7465873
C6H5 OH HA
+ OH
O reflux
a) excess
C6H5 Cl
+ OH base
b) O
C6H5 O C6H5
+ OH
c) O O
Answer: D
Topic: Synthesis
Section: 17.7
145) Which of the following combinations of reagents would not produce an ester?
H3C ONa
+ Br
a) O
H3C ONa
+ OH
b) O
H3C OH
+ OH HA
c) O
H3C O CH3 OH
+
d) O O
H3C Cl
+ OH
e) O
Answer: B
Topic: Synthesis
Section: 17.7
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CH3CH2CH2COOH  CH3CH2CH2CH2OH
a) H2/Ni
b) Li/liq NH3
c) LiAlH[OC(CH3)3]3
d) NaBH4, CH3OH
e) LiAlH4, ether
Answer: E
Topic: Synthesis
CH3C≡CCH2CO2CH2CH3  CH3C≡CCH2CH2OH
a) H2/Ni
b) Li/liq NH3
c) LiAlH[OC(CH3)3]3
d) NaBH4, CH3OH
e) LiAlH4, ether
Answer: E
Topic: Synthesis
148) Which of the reactions listed below would serve as a synthesis of acetophenone,
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lOMoARcPSD|7465873
C6H5COCH3 ?
AlCl3
a) (CH3CO)2O + C 6H 6
O AlCl3
+ C6H6
b) H3C Cl
O
+ CH3MgI
c) C6H5 OCH3
Answer: D
Topic: Synthesis
Sections: 15.7, 15.9, and 17.13
149) Which of the following would serve as syntheses of (CH3)3CCO2H?
O i. Cl2/OH (excess)
a) ii. H3O+

i. CN
Br
b) ii. H3O+ (heat)
i. Mg, Et2O
Br
ii. CO2
c) iii. H3O+
O i. Cl2/OH (excess) i. CN
Br
d) ii. H3O+ and ii. H3O+ (heat)
i. Mg, Et2O
Br
O i. Cl2/OH (excess) ii. CO2
+
e) ii. H3O and iii. H3O+
Answer: E
Topic: Synthesis
Section: 17.3
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150) Which carboxylic acid would decarboxylate when heated to 100–150 C?
CO2H O
HO2C HO2C CO2H
CO2H
I II III
a) I
b) II
c) III
d) More than one of these choices
Answer: D
Topic: Synthesis
Section: 17.10
151) Which reactant is unlikely to produce the indicated product upon strong heating?
a) 2,2-Dimethylpropanedioic acid  2-methylpropanoic acid

b) 2-Ethylpropanedioic acid  Butanoic acid
c) 2-Methyl-3-oxo-pentanoic acid  3-Pentanone
d) 2-Methyl-4-oxo-pentanoic acid  2-Methyl-3-butanone
e) 4-Methyl-3-oxo-heptanoic acid  3-Methyl-2-hexanone
Answer: D
Topic: Synthesis
Section: 17.10
152) Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?
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lOMoARcPSD|7465873
i. Br2, ROOR
isobutane ii. Mg, Et2O
iii. CO2
a) iv. H3O+
OH i. KMnO4, OH , heat
b) ii. H3O+
i. Br2, ROOR
ii. CN
isobutane
iii. OH , H2O, heat
c) iv. H3O+
e) Only two of these choices.
Answer: E
Topic: Synthesis
Section: 17.3

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i. Cl2/OH (excess)
3,3-dimethylbutan-2-one
a) ii. H3O+
i. Br2, ROOR
ii. CN
isobutane
b) iv. H3O+
i. Br2, ROOR
iii. CO2
c) iv. H3O+
i. Br2, ROOR
ii. CN
isobutane
i. Cl2/OH (excess) iii. OH , H2O, heat
d) ii. H3O+ and iv. H3O+
i. Br2, ROOR
i. Cl2/OH (excess) iii. CO2
e) ii. H3O+ and iv. H3O+
Answer: E
Topic: Synthesis
Section: 17.3

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O
ii. H3O+
a)
i. Br2, ROOR
ii. CN
b) iv. H3O+
i. Br2, ROOR
ii. Mg, Et2O
iii. CO2
c) iv. H3O+
i. Br2, ROOR
O ii. CN
ii. H3O+
d) and iv. H3O+
i. Br2, ROOR
O ii. Mg, Et2O
iii. CO2
ii. H3O+
e) and iv. H3O+
Answer: E
Topic: Synthesis
Section: 17.3
155) Which of the following would yield (S)-2-butanol?
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i. CH3CO2 Na+
(R)-2-Bromobutane
a) ii. OH , H2O, heat
OH , H2O, heat
b) (R)-2-Bromobutane

(S)-sec-Butyl acetate OH , H2O, heat
c)
Answer: D
Topic: Synthesis
Section: 17.7
156) Which of the reactions listed below would serve as a synthesis of benzyl acetate,
CH3CO2CH2C6H5?
a) Benzyl alcohol + acetic anhydride 

b) Benzyl alcohol + acetic acid + H3O+ 
c) Benzyl alcohol + acetyl chloride 
Answer: E
Topic: Synthesis
Section: 17.7
157) An acid chloride is prepared from the related carboxylic acid by reaction with which of
these?
a) HCl
b) Cl2
c) SOCl2
d) HOCl
e) AlCl3
Answer: C
Topic: Methods and Miscellaneous

Section: 17.5
158) An acid chloride is prepared from the related carboxylic acid by reaction with which of
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lOMoARcPSD|7465873
these?
a) PCl3
b) PCl5
c) SOCl2
Answer: E

Section: 17.5
159) A nitrile is prepared from the corresponding primary amide by reaction with which of
these?
a) HCl
b) Cl2
c) P4O10
d) HOCl
e) AlCl3
Answer: C

Section: 17.8
160) Which of these combinations will not produce benzoic acid?
a) C6H5CH2OH + KMnO4/OH–/H2O, heat; then H3O+

b) C6H5CH3 + KMnO4/OH–/H2O, heat; then H3O+
c) C6H6 + CO2, high pressure
d) C6H5COCH3 + Cl2/OH–/H2O; then H3O+
e) C6H5COCl + OH/H2O; then H3O+
Answer: C

Section: 17.3
161) Intramolecular dehydration to form a cyclic monoester is most likely to occur when which
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lOMoARcPSD|7465873
of the following is heated with acid?
a) CH3CH2CH2CHOHCO2H
b) CH3CH2CHOHCH2CO2H
c) CH3CH2CH2CH2CO2H
d) CH3CHOHCH2CH2CO2H
e) HO2CCH2CH2CO2H
Answer: D

Section: 17.7
162) - and -hydroxy acids can be esterified intramolecularly to form compounds known as
which of these?
a) Anhydrides
b) Cycloalkenes
c) Lactones
d) Lactams
e) Cyclic ketones
Answer: C

Section: 17.7
163) Which of these combinations will not produce benzoic acid?
a) C6H5CH2OH + KMnO4/OH–/H2O, heat; then H3O+

b) C6H5CH3 + KMnO4/OH–/H2O, heat; then H3O+
c) C6H6 + CO2, high pressure
d) C6H5COCH3 + I2/OH–/H2O; then H3O+
e) C6H5COCl + OH–/H2O; then H3O+
Answer: C

Section: 17.3
164) Which of the following is not a method for preparing butanoic acid?
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lOMoARcPSD|7465873
a) CH3CH2CH2Br + NaCN; then H3O+, reflux

b) CH3CH2CH2MgBr + CO2; then H3O+
c) CH3CH2CH2OH + CO
d) CH3CH2CH2CO2Et + OH–/H2O; then H3O+
e) CH3CH2CH2CH2OH + KMnO4/OH–/H2O/heat; then H3O+
Answer: C

165) Which of the following statements concerning nitriles is incorrect?
a) Nitriles can be hydrolyzed to carboxylic acids.

b) Nitriles can be formed from (many) alkyl halides by nucleophilic substitution by cyanide ion.
c) Nitriles can be reduced with excess lithium aluminum hydride to primary amines, RNH2.
d) Nitriles react with Grignard reagents to form tertiary alcohols.
e) Nitriles can be made by the dehydration of amides.
Answer: D

166) Reasoning by analogy, one would predict that the reaction of carbon disulfide with sec-
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lOMoARcPSD|7465873
butylmagnesium bromide should yield which of the following (after acidification)?

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

Section: 17.3
167) Which of the following will not undergo hydrolysis, whether acid or base is present?
a) CH3COCl
b) CH3CONH2
c) (CH3CO)2O
d) CH3CO2CH2CH3
e) CH3COCH2CH2CH3
Answer: E
Topic: Chemical Tests, Relative Reactivities, and Physical Properties

Section: 17.4
168) Which of these compounds could not be formed by nucleophilic attack by an appropriate
97

lOMoARcPSD|7465873
reagent on acetyl chloride?
a) CH3CONH2
b) CH3CO2CH2CH3
c) ClCH2COCl
d) CH3CO2H
e) (CH3CO)2O
Answer: C

Section: 17.4
169) Which compound would be most reactive toward nucleophilic acyl addition-elimination?
a) CH3CO2Na
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Answer: B

Section: 17.4
a) CH3COCH3
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Answer: B

Section: 17.4
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lOMoARcPSD|7465873
a) CH3CHO
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Answer: B

Section: 17.4
172) Which compound would be least reactive toward nucleophilic acyl addition-elimination?
a) CH3COCH3
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Answer: A

Section: 17.4
a) CH3CHO
b) CH3COCl
c) (CH3CO)2O
d) CH3CONH2
e) CH3CO2CH3
Answer: A

Section: 17.4
99

lOMoARcPSD|7465873
a) Acetone
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Answer: B

Section: 17.4
a) Acetaldehyde
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Answer: B

Section: 17.4
a) Acetone
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Answer: A

Section: 17.4
100

lOMoARcPSD|7465873
a) Acetaldehyde
b) Acetyl chloride
c) Acetic anhydride
d) Acetamide
e) Methyl acetate
Answer: A

Section: 17.4
178) Which reagent would serve as the basis for a simple chemical test to distinguish between
benzoic acid and benzamide?
a) Cold dilute NaOH

b) Cold dilute NaHCO3
c) Cold concd H2SO4
d) More than one of these choices.
Answer: D

179) Which reagent would best serve as a basis for a simple chemical test to distinguish between
CH3CH2COOH and CH3COOCH3?
a) Concd H2SO4
b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) KMnO4/H2O
Answer: D

180) Which reagent would best serve as the basis for a simple chemical test to distinguish
101

lOMoARcPSD|7465873
between C6H5CH=CHCOOH and C6H5CH=CHCH3?
a) Concd. H2SO4
b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) KMnO4/H2O
Answer: D

181) The relative reactivity of acyl compounds toward nucleophilic acyl addition-elimination is:
a) Amide > ester > acid anhydride > acyl chloride

b) Acyl chloride > ester > acid anhydride > amide
c) Ester > acyl chloride > acid anhydride > amide
d) Acyl chloride > acid anhydride > ester > amide
e) Acid anhydride > acyl chloride > ester > amide
Answer: D

Section: 17.4
182) Alkaline hydrolysis of an ester involves initial attack by hydroxide ion on the carbonyl
carbon. The presence of substituents on the aromatic ring of ethyl benzoate may be expected to
increase/decrease the rate of hydrolysis of this ester. In what order should the five substituents
below be arranged to represent the decreasing order of the rates of hydrolysis when these
substituents are present in the para position of the aromatic ring in ethyl benzoate?
a) -NO2 > -H > -Cl > -CH3 > -OCH3

b) -NO2 > -Cl > -H > -CH3 > -OCH3
c) -OCH3 > -CH3 > -Cl > -H > -NO2
d) -Cl > -NO2 > -H > -OCH3 > -CH3
e) -H > -Cl > -CH3 > -OCH3 > -NO2
Answer: B

Section: 17.4
183) In which of these species are all the carbon-oxygen bonds of equal length?
102

lOMoARcPSD|7465873
a) Diethyl carbonate
b) Methyl butanoate
c) Lithium acetate
d) Propionic anhydride
e) Pentanoic acid
Answer: C

Section: 17.2
Question type: fill-in-the-blank
184) While the IUPAC name for HCO2H is methanoic acid, it is commonly known as ___.
Answer: formic acid
Topic: Nomenclature
Section: 17.2
185) Ethanoic acid (CH3CO2H) is usually called ___, from the Latin for “vinegar.”
Answer: acetic acid
Topic: Nomenclature
Section: 17.2
Question type: Molecular Drawing
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lOMoARcPSD|7465873
186) Draw the structure for 3-methylbutanoic anhydride.
O O
Answer: O
Topic: Nomenclature
Section: 17.2
187) Draw the structure for 3-ethyl-4,4-dimethylhexanenitrile.
CN
Answer:
Topic: Nomenclature
Section: 17.2
188) Draw the structure for 5-bromo-3-oxohexanoic acid.
OH
Answer: Br O O
Topic: Nomenclature
Section: 17.2
189) Draw the structure for 4-methylpentyl 3-ethylpentanoate.
O
Answer:
Topic: Nomenclature
Section: 17.2
190) Suggest a structure consistent with the following spectroscopic data:
104

lOMoARcPSD|7465873
C5H10O2
IR: 1745 cm−1
1
H NMR:
triplet 3H,  0.90
multiplet 2H,  1.60
singlet 3H,  1.95
triplet 2H,  3.95
13
C NMR
Broadband decoupled: 10.41, 20.91, 22.14, 66.10, 171.09 
DEPT 90: no peaks
DEPT 135: 10.41, 20.91  (positive); 22.14, 66.10  (negative)
O
Answer: O

Section: 17.2
13
191) A compound has the formula C7H14O2. The C and 1H NMR spectral data for this
compound are:
13
C NMR
Broadband decoupled 13C NMR: 22.2, 27.7, 32.2, 33.8, 51.4, 174.4 δ
DEPT-90: 27.7 δ
DEPT-135: positive peaks at 22.2, 27.7, 51.4 δ; negative peaks at 32.2, 33.8 δ
1
H NMR
0.90 δ, doublet (6H)
1.55 δ, multiplet (3H)
2.30 δ, triplet (2H)
3.67 δ, singlet (3H)
Suggest a structure consistent with this data.

Answer:
OCH3

Section: 17.2
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lOMoARcPSD|7465873
192) A compound has the formula C6H11BrO2. The 13C and 1H NMR spectral data for this
compound are:
13
C NMR
Broadband decoupled 13C NMR: 14.2, 27.8, 32.5, 32.6, 60.5, 172.4 δ
DEPT-90: no peaks
DEPT-135: positive peaks at 14.2 δ; negative peaks at 27.8, 32.5, 32.6, 60.5 δ
1
H NMR
2.18 δ, multiplet (2H)
4.15 δ, quartet (2H)
Suggest a structure consistent with this data.
Answer: O
Br
O

Section: 17.2
193) The presence of electron-withdrawing substituents close to the carboxylic acid functional
group will ___ the acidity of the molecule by ___.
Answer: increase; induction
Topic: Miscellaneous
Section: 17.2
194) The only carboxylic acid derivative with two carbonyl groups is the ___.
Answer: anhydride
Section: 17.2
195) Cyclic esters are called ___, while cyclic amides are called ___.
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lOMoARcPSD|7465873
Answer: lactones; lactams
Section: 17.7
196) The functional group in a lactam is ___.
Answer: amide
Section: 17.8
197) An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol) is

called a ___.
Answer: Fischer esterification

Section: 17.7
198) Base-promoted hydrolysis of esters is sometimes called ___.
Answer: saponification

Section: 17.7
199) Litmus paper turns ___ when an aqueous solution of a carboxylic acid is dropped on it.
Answer: red

Section: 17.11
200) The linkages that join amino acids together to form proteins are primarily ___ bonds.
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lOMoARcPSD|7465873
Answer: amide

Section: 17.2
Question type: Essay
201) Carbonation of a Grignard reagent or the SN2 displacement of an organic halide with
cyanide ion followed hydrolysis are both good methods for the conversion of organic halides to
carboxylic acids of one more carbon atom. For the following reaction, which of these two
procedures would be the process of choice and why?
Br
OH
Answer: Carbonation of the Grignard is the only method that would work since an SN2
displacement at an sp2-hybidized carbon on the aromatic ring will not occur.
Topic: Reaction Sequence and Mechanistic Pathways

Section: 17.3
OH
Br
O
HO
HO
Answer: SN2 displacement of the benzylic halide halide is the only method that would work since
the molecule also contains an acidic hydrogen (phenol) preventing successful formation of the
corresponding Grignard.

Section: 17.3
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lOMoARcPSD|7465873
Cl
OH
Answer: Carbonation of the Grignard is the only method that would work since elimination,
rather than an SN2 displacement, will occur with a 3 alkyl halide.

Section: 17.3
OH
Cl
Answer: Carbonation of the Grignard is the only method that would work since an SN2
displacement at an sp2-hybidized carbon will not occur.

Section: 17.3
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lOMoARcPSD|7465873
OH
Br
Answer: Both methods would work equally well. The benzylic halide is a good substrate for SN2
displacement by cyanide ion, and also serves as a successful substrate for Grignard reagent
preparation.

Section: 17.3
206) Acyl compounds tend to react by acyl substitution mechanisms because they all have a
good or reasonably good ___ attached to the carbonyl carbon.
Answer: leaving group
Topic: Reaction Mechanisms

Section: 17.4
207) When a gamma-hydroxy acid is treated with dilute acid, cyclization occurs, producing a
___.
Answer: lactone (cyclic ester)
Topic: Reactions
Section: 17.7
Question type: Molecular Drawing
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lOMoARcPSD|7465873
208) Complete the following reaction sequence, giving details of all significant intermediates.
O
i.) 2 equiv CH3Li
ii.) CH3I ?
O
O OLi OCH3
2 equiv CH3Li CH3I
O
Answer:
Topic: Reaction Sequence

209) Suggest a suitable synthetic strategy for the transformation of 3-methyl-1-pentanol into
propyl 3-methylpentanoate
OH i. KMnO4, OH-, H2O O
ii. H3O+ OH
SOCl2
O OH O
O
Answer: Cl

O i.) SOCl2
?
OH ii.) CH3CH2CH2NHCH3
O O O
SOCl2 CH3CH2CH2NHCH3
OH Cl N
Answer:

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lOMoARcPSD|7465873
OH i. COCl2 (1 equivalent) ?
ii. CH3CH2CH2CH2NHCH3
OH O Cl
COCl2 (1 equivalent)
O
H
N
O N
O
Answer:

Section: 17.9
i. KMnO4, OH-, H2O
ii. H3O+
?
iii. NaBH4, H2O
iv. H3O+
i. KMnO4, OH-, H2O O

ii. H3O+ O
OH
NaBH4, H2O
H3O+ OH
O
O
Answer: O OH

Section: 12.3, 17.3 and 17.7
213) Given a mixture of benzyl alcohol, phenol, and benzoic acid dissolved in ether, outline in a
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lOMoARcPSD|7465873
flow diagram an extraction method to separate each.
Answer:
Topic: Physical Properties, Isolation

214) The pKa of benzoic acid is 4.20. A benzoic acid substituted in the para-position with some
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lOMoARcPSD|7465873
group G (shown below) is reported to have a pKa of 3.92.

COOH
Based on this information is group G an electron withdrawing or electron donating group?
Answer: since the pKa of the G-substituted benzoic acid is lower than benzoic acid, making the
substituted benzoic acid a stronger acid than benzoic acid, the group G must be an electron
withdrawing group.
Topic Acidity
Section 17.2
215) Nylon 12 is a polyamide that has found significant commercial value in the manufacture of
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lOMoARcPSD|7465873
automobile fuel lines. Nylon 12 is prepared industrially through the polymerization of the 13-
member ring lactam monomer shown:
O
NH
13
This lactam is readily prepared by the reaction of the cyclododecanone oxime with aqueous acid.
OH
O
N
NH
conc. H2SO4
12 13
Propose a mechanism for this transformation.
Answer:
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lOMoARcPSD|7465873
N N
OH OH2
H+
12 12 -H2O
H2O OH2
N N
-H+
13 13
OH O
N NH
13 13
tautomerization
Topic: Mechanisms
Section: 17.8
116

Chapter 17 Questions for Boson Organic Chemistry II

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Chapter 17 Questions for Boson Organic Chemistry II

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Ch17 - Chapter 17 Questions for Boson

Organic Chemistry II (The City College of New York)

StuDocu is not sponsored or endorsed by any college or university

Package Title: Solomons Test Bank

Question type: Multiple choice

2) The correct structure for ethyl 3-methylbutanoate is:

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3) The correct structure for bicyclo[1.1.1]pentane-2-carboxylic acid is:

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

4) The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

5) The correct structure for bicyclo[1.1.0]butane-2-carboxylic acid is:

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

6) The correct structure for methyl bicyclo[1.1.1]pentane-2-carboxylate is:

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

7) The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is:

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

8) The correct structure for methyl bicyclo[1.1.0]butane-2-carboxylate is:

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

9) The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is:

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11) The correct structure for ethyl 3-methylbutanoate is:

12) What is the IUPAC name for O

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13) The correct structure for ethyl 2-chloropentanoyl chloride is:

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15) The correct structure for -methylbutyl methanoate is:

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16) Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?

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17) Which of the following structures is 3,4-dimethylpentyl chloroformate?

18) Which compound would be the strongest acid?

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19) Which compound would be the weakest acid?

20) Which compound would be the strongest acid?

21) Which compound would be expected to have the lowest pKa?

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22) Which compound would be expected to have the highest pKa?

23) Which compound would be the weakest acid?

24) Which compound would be the strongest acid?

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25) Which compound would be the weakest acid?

26) Which compound would be expected to have the highest pKa?

27) Which compound would be expected to have the lowest pKa?

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a) CH3COOH > H2O > CH3CH2OH > HCCH > NH3

a) NH3 < HCCH < CH3CH2OH < H2O < CH3COOH

a) CH3COOH > H2O > PhOH > HCCH > NH3

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a) PhCOOH > H2O > PhOH > PhCH2OH > PhH

32) Which of the following would be the strongest acid?

33) Which of the following would be the weakest acid?

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34) Which of the following would be the strongest acid?

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36) Which of the following would be the strongest acid?

O2N O2N NO2

NO2 O2N NO2

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H3C H3C CH3

CH3 H3C CH3