Ch18 - Chapter 18 Questions For Boson Ch18 - Chapter 18 Questions For Boson

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Ch18 - Chapter 18 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: 18
Question type: Multiple Choice
1) Which of the compounds listed below is more acidic than 1-butanol?
a) Ethyl acetoacetate
b) 2-Butanone
c) Ethyl pentanoate
d) All of these choices.
e) Two of these choices.
Answer: A
Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium
a) Diethylmalonate
b) 2-Butanone
c) Ethyl pentanoate
Answer: A

Section: 18.1
a) Malonic ester
b) 2-Butanone
c) Ethyl pentanoate
Answer: A
Section: 18.1

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a) Ethyl 2-oxocyclohexanecarboxylate
b) 2-Butanone
c) Ethyl pentanoate
Answer: A

Section: 18.1
5) Which of the compounds listed below is more acidic than 2-pentanol?
a) Ethyl 3-oxopentanoate
b) 2-Pentanone
c) Pentanal
Answer: A

Section: 18.1
a) Diethyl malonate
b) 2-Pentanone
c) Pentanal
Answer: A

Section: 18.1

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a) Malonic ester
b) 2-Pentanone
c) Pentanal
Answer: A

Section: 18.1
a) Ethyl 2-oxocyclohexanecarboxylate
b) 2-Pentanone
c) Pentanal
Answer: A

Section: 18.1
9) Which of the following hydrogens is the most acidic?

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

Section: 18.1

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10) Which is the most acidic hydrogen in the compound shown?

V
III
O II
v
v
v O
v v O
IV I
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.1

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

Section: 18.1
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II
O O
IV
H H H
H
H O
H H
H
H
H H III
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.1

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

Section: 18.1

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II
O
I
H H
C N
H
H H
H
H
H H III
IV
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.1

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

Section: 18.1
16) Which of the following compounds is the strongest acid?

OH O
CN
CN CN O
I II III
O CN CN
CO2Et
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 18.1

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17) Which compound contains the most acidic hydrogens?
a) CH3CH2CH3
b) CH3CHCH2
c) Cyclohexane
d) (CH3)2C=O
e) Benzene
Answer: D
Topic: Acid/Base
Section: 18.1
18) Considering only the highlighted hydrogens, list the following compounds in order of
increasing acidity:
O O O O
H H
H
H H
O
O O
I II III V
IV
a) IV, II, III, I, V
b) II, V, IV, I, III
c) III, I, IV, II, V
d) IV, V, II, I, III
e) V, IV, III, II, I
Answer: D
Topic: Acid/Base
Section: 18.1

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decreasing acidity:
O O O O
H H
H
H H
O
O O
I II III V
IV
a) I, II, III, IV, V
b) III, V, IV, I, II
c) III, I, II, V, IV
Answer: C
Topic: Acid/Base
Section: 18.1
increasing acidity:
O O
O H
H H O H
O H
I II III V
IV

b) II, V, III, I, IV
e) V, II, III, I, IV
Answer: E
Topic: Acid/Base
Section: 18.1
decreasing acidity:
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O O
O H
H H O H
O H
I II III V
IV

c) IV, I, III, II, V
Answer: C
Topic: Acid/Base
Section: 18.1
increasing acidity:
O O O
H
H
H H C N
O H
O O
I II III V
IV

e) V, II, III, I, IV
Answer: E
Topic: Acid/Base
Section: 18.1
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decreasing acidity:
O O O
H
H
H H C N
O H
O O
I II III V
IV

c) IV, I, III, II, V
Answer: C
Topic: Acid/Base
Section: 18.1
24) Which structure represents an ester enolate?

O O O O
O O O O
I II III IV
a) I
b) II
c) III
d) IV
Answer: E
Topic: Enolates
Section: 18.1
25) Which of the following is a keto-enol tautomeric pair?
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O OH O OH O OH
and and and
OH
I II III
O OH O OH
and and
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Easy

O OH OH
O O OH
and and and OH
II III
I
O OH O OH
and and
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Section: 18.2
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O OH O OH
and and
I II
O OH O OH
and
and
OH
III IV
O OH
and
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.2
28) Which of the following represent tautomers?
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a)
b)
c)
e) None of these choices.
Answer: C

Section: 18.2
29) Which of these compounds would exist in an enol form to the greatest extent?
a) CH3COC2H5
O O
b) CH3CCH2CCH3
O
c) CH3CCH3
CH3CH
d) O
CH3CCH2CH2CCH3
e) O O
Answer: B

Section: 18.2
30) Which of the following represent keto-enol tautomers?
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O OH
a) CH3CCH2CH3 and CH3C=CHCH3

OH O
b) CH2=CCH2CH3 and CH3CCH2CH3

O O
HOCH2CCH=CH2 and CH3CCH2CH3
c)
d) More than one of these choices.
Answer: D

Section: 18.2
31) Simple enols are less stable than the tautomeric keto forms because:
a) severe angle strain exists in the enol forms.

b) fewer atoms are coplanar in the keto form.
c) the enol cannot be chiral.
d) the C-C  bond is weaker than the C-O  bond.
e) Actually, simple enols are the more stable.
Answer: D

Section: 18.2
32) Which of these compounds would exist primarily in an enol form?
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a)
O
b) O
O
c) O
O
d)
O
e)
Answer: C

Section: 18.2
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a)
O
O
b)
O
c)
O
d)
O
e)
Answer: B

Section: 18.2
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a)
O
b) O
O
c)
O
d)
O
e)
Answer: C

Section: 18.2
Difficulty Level: Hard
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a)
O
O
b)
O
c)
O
d)
O
e)
Answer: C
Section: 18.2
36) Which of the following would undergo racemization in base?
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CH3 O
O
CH3CH2 C CC6H5
C6H5CC6H5
CH3CH2CH2
I II
H O CH3 O
CH3CH2 C CC6H5 CH3 C CCH2C6H5
CH3 CH3
III IV
a) I
b) II
c) III
d) IV
e) Both III and IV
Answer: C
Topic: Racemization
Section: 18.3
37) Which of the following would undergo epimerization in base?
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O O O O
Ph H
I II III IV
a) I
b) II
c) III
d) IV
e) Both III and IV
Answer: C
Topic: Racemization/Epimerization
Section: 18.3
38) Which of the following would undergo epimerization in acid?

O O O O
Ph H
I II III IV
a) I
b) II
c) III
d) IV
e) Both III and IV
Answer: C
Topic: Racemization/Epimerization
Section: 18.3
39) Which of the following would undergo racemization in base?
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O
O O
H3C H H3C CH3 H3C CH3
I II III
O O
H H
IV V
a) I
b) II and III
c) IV and V
d) I and V
e) I, IV and V
Answer: D
Topic: Racemization
Section: 18.3
40) Which of the following would not undergo racemization in base?
a) (S)-2-phenylbutanal
b) (S)-3-phenylbutanal
c) (S)-3-phenyl-2-butanone
d) (S)-3-methyl-2-phenylbutanal
e) All of these choices will undergo racemization in base.
Answer: B
Topic: Racemization
Section: 18.3
41) Which of these halides is predicted to alkylate malonic ester (as the anion) in highest yield?
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a) CH3I
b) C6H5Br
c) (CH3)3CCH2Cl
d) CH3CHClCH3
e) All of these choices should be equally effective.
Answer: A
Topic: Reaction Products

Section: 18.7
42) What would be the major product of the following reaction?

O
OH-
CCHCH3 + Br2 ?
CH3
O O O
CCHCH3 Br CCHCH3 CCBrCH3
Br CH3 CH3 CH3

I II III
O O
CCHCH2Br CCHCH2Br
CH3 CH2Br
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
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-
OH
+ Cl2 ?
O Cl O OH
O
Cl
I II III
O
Cl Cl
Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
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-
OH
+ I2 ?
O I O OH
O
I II III
O
I I
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
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O
H3O+
C6H5CCHCH2CH3 + Br2 ?
CH3
C6H5CCBrCH2CH3
a) CH3
O Br
C6H5CCHCHCH3
b) CH3
O OH
C6H5CCHCHCH3
c) CH3
C6H5CBr2CHCH2CH3
d) CH3
O
m-BrC6H4CCHCH2CH3
e) CH3
Answer: A

Section: 18.3
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H3O+
+ Cl2 ?
O Cl O OH
O
Cl
I II III
O
Cl Cl
Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
47) What would be the major product of the following reaction sequence?
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H 3O +
+ Br2 ?
O O O
Br Br Br OH
Br
Br
Br
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.3
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H3O+
+ Br2 ?
O O O HO
Br Br
Br
Br
Br Br
Br
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.3
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O CH3 OD-
+ D2O ?
C6H5C CHCH3 room
temp.
O CD3
a) C6H5C CHCH3
O CH3
b) C6H5C CDCH3
O CH3
c) C6D5C CDCH3
O CD3
d) C6H5C CDCD3
OD
C6H5CDCHCH3
e) CH3
Answer: B

Section: 18.3
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O
D+ ?
D2O
room temperature
O CD3
a) C6H5C CHCH3
O CH3
b) C6H5C CDCH3
O CH3
c) C6D5C CDCH3
O CD3
d) C6H5C CDCD3
OD
C6H5CDCHCH3
e) CH3
Answer: B

Section: 18.3
51) Which would be formed when 2-methylpropanal is dissolved in D2O containing NaOD?
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CH3CHCD
a) CH3
O
CH3CHCH
b) CH2D
O
CH3CDCH
c) CH3
O
CH3CDCD
d) CH3
D
CH3CHCHOD
e) CH3
Answer: C

Section: 18.3
52) Which would be formed when 2-methylpropanal is dissolved in T2O containing NaOT?
CH3CH(CH3)CTO
a)
CH3CH(CTH2)CHO
b)
CH3CT(CH3)CHO
c)
CTH2CH(CH3)CHO
d)
Answer: C

Section: 18.3
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53) Which would be formed when 2-methylpropanal is dissolved in D2O containing D+?
CH3CHCD
a) CH3
O
CH3CHCH
b) CH2D
O
CH3CDCH
c) CH3
O
CH3CDCD
d) CH3
D
CH3CHCHOD
e) CH3
Answer: C

Section: 18.3
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OH
Br2, PBr3
?
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
55) Which compound would be formed when 2-methylbutanal is treated with a solution of
NaOD in D2O?
CH3CH2CDCHO
a) CH3
CH3CH2CHCDO
b) CH3
CH3CHDCHCHO
c) CH3
CH2DCH2CHCHO
CH3
d)
CH3CH2CDCDO
e) CH3
Answer: A
Section: 18.3
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56) Which compound would be formed when 2-methylbutanal is treated with a solution of NaOT
in T2O?
CH3CH2CT(CH3)CHO
a)
CH3CH2CH(CTH2)CHO
b)
CTH2CH2CH(CH3)CHO
c)
CH3CTHCH2CH(CH3)CHO
d)
CH3CH2CH(CH3)CTO
e)
Answer: A

Section: 18.3
57) Which compound would be formed when 2-methylbutanal is treated with a solution of D+ in
D2O?
CH3CH2CDCHO
a) CH3
CH3CH2CHCDO
b) CH3
CH3CHDCHCHO
c) CH3
CH2DCH2CHCHO
CH3
d)
CH3CH2CDCDO
e) CH3
Answer: A

Section: 18.3
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58) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of
NaOD in D2O?
D
O
a)
D
O
b) D
D
O
c)
O
d) D
O
e) D
Answer: E

Section: 18.3
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NaOT in T2O?
T
O
a)
T
O
b) T
T
O
c)
O
T
d)
O
T
e)
Answer: E

Section: 18.3
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D+ in D2O?
D
O
a)
D
O
b) D
D
O
c)
O
d) D
O
e) D
Answer: E

Section: 18.3
61) Which of the following would not undergo racemization in base?
a) (R)-3-methyl-4-heptanone
b) (R)-3-methyl-2-heptanone
c) (R)-4-methyl-2-heptanone
d) (R)-2,4-dimethyl-3-heptanone
e) All of these choices will undergo racemization in base.
Answer: C
Topic: Racemization
Section: 18.3
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O
-
H3O+ OH
+ Br2 ?
heat
O O O
Br Br Br OH
Br
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 7.6 and 18.3
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O
H3O+ OH
+ Br2 ?
heat
O O O Br Br
Br
Br
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

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OH
Br2, P
?
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
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O
H3O+ -
OH
+ Cl2 ?
heat
O Cl O
O
Cl
I II III
O
Cl Cl
Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

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i. Br2, NaOH
?
ii. H3O+
O
Br
HO
O O O
I II III
Br
Br
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
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i. I2, NaOH
?
ii. H3O+
O
I
HO
O O O
I II III
I
I
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
45

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OH
i. Br2, P
?
ii. H2O
O
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
46

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OH
i.Cl2, P
?
ii. H2O
O
Cl Cl
Cl OH
OH Cl Cl OH
O HO Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
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70) What would be the major

OH
product of the following reaction?
SOCl2, HCl
?
O
O N Cl
O
Cl Cl
Cl Cl
OH Cl Cl OH
O Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
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71) What would be the major

OH
product of the following reaction?
SOCl2, HBr
?
NBS
O
Cl Br Br
Br
Cl Br
OH OH Cl
O O
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.3
49

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OH
Cl2, P
?
Cl Cl
Cl OH
OH Cl Cl OH
O HO Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
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O
i. LDA ?
ii. C2H5I
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
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i. Cl2, NaOH
?
ii. H3O+
O
Cl
HO
O O O
I II III
Cl
Cl
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
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O
i. LDA(-78oC)
?
ii. C2H5OTs
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
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O
1. LDA (-78oC)
?
2. CH3CH2Br
O HO O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.4
54

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OH
PCC 1. LDA (-78oC)

?
CH2Cl2 2. CH3CH2Br
O HO O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.4
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OH
DMSO, (COCl)2 1. LDA (-78oC)

?
Et3N 2. CH3CH2Br
O HO O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.4
79) Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl
bromide, potassium tert-butoxide, isobutyl chloride, hot aqueous NaOH, HCl, and heat. What is
the final product?
a) 4-Ethyl-2-methylpentanoic acid
b) 6-Methylheptanoic acid
c) 2-Ethyl-3-methylpentanoic acid
d) 2-Ethyl-4-methylpentanoic acid
e) Ethylisobutylmalonic acid
Answer: D

Section: 18.7
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80) Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), 1-
bromopentane, potassium tert-butoxide, iodomethane, hot aqueous NaOH, HCl, and heat. What
is the final product?
a) 2-Methylheptanoic acid
b) 3-Methylhexanoic acid
c) 3-Methylpentanoic acid
d) 2-Methylpentanoic acid
e) Ethyl 2-methylheptanoate
Answer: A

Section: 18.7
1. BH3 PCC 1. LDA (-78oC)
?
2. H2O2, OH- CH2Cl2 2. CH3CH2Br
O HO O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.4
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82) What product is finally formed when the initial compound formed from cyclohexanone and
pyrrolidine is mixed with allyl chloride and that product is heated and then hydrolyzed?
HO O Cl
N
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.9
piperidine is mixed with allyl chloride and that product is heated and then hydrolyzed?
O
HO -
Cl
N
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Section: 18.9
58

lOMoARcPSD|7465873
piperidine is mixed with methyl iodide and that product is heated and then hydrolyzed?
O
HO -
Cl
N
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.9
59

lOMoARcPSD|7465873
morpholine is mixed with allyl chloride and that product is heated and then hydrolyzed?
O
HO Cl- O
N
I II III
O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 18.9
60

lOMoARcPSD|7465873
morpholine is mixed with methyl iodide and that product is heated and then hydrolyzed?
O
HO Cl- O
N
I II III
O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 18.9
61

lOMoARcPSD|7465873
87) What product is finally formed when the initial compound formed from cyclopentanone and
piperidine is mixed with allyl chloride and that product is heated and then hydrolyzed?
Cl
HO N O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 18.9
62

lOMoARcPSD|7465873
piperidine is mixed with methyl iodide and that product is heated and then hydrolyzed?
Cl
HO N O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 18.9
63

lOMoARcPSD|7465873
piperidine is mixed with benzyl chloride and that product is heated and then hydrolyzed?
Cl
HO N Ph O
Ph
Ph
I II III
O O
Ph
Ph
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.9
64

lOMoARcPSD|7465873
1. BH3 DMSO, (COCl)2 1. LDA (-78oC)
?
2. H2O2, OH- Et3N 2. CH3CH2Br
O HO O
I II III
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.4
91) What synthetic strategy would accomplish the following transformation?

?
O O
a) i) Br2, H3O+; ii) NaOC2H5, C2H5OH, heat

b) i) Cl2, FeCl3; ii) NaOC2H5, C2H5OH, heat
c) i) HCN; ii) H3O+, heat
d) i) Br2, h; ii) (CH3)3COK, (CH3)3COH, heat
Answer: A
Topic: Synthetic Strategy

65

lOMoARcPSD|7465873
92) Which reagent would best serve as the basis for a simple chemical test to distinguish between
2-pentanone and 3-pentanone?
a) NaOI (I2 in NaOH)

b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) Ag(NH3)2+
Answer: A
Topic: Chemical Tests

Section: 18.3
acetophenone and propiophenone?

b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) Ag(NH3)2+
Answer: A

Section: 18.3
acetophenone and benzophenone?

b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) Ag(NH3)2+
Answer: A

Section: 18.3
66

lOMoARcPSD|7465873
m-chloroacetophenone and m-chloropropiophenone?

b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) Ag(NH3)2+
Answer: A

Section: 18.3
96) Which of the reagents listed below would serve as the basis for a simple chemical test to
distinguish between 2-methyl-1-propanol and 2-butanol?

b) KMnO4 in H2O
c) Br2 in CCl4
d) Cold concd H2SO4
e) CrO3 in H2SO4
Answer: A

Section: 18.3
97) Which of the reagents listed below would serve as the basis for a simple chemical test to
distinguish between isopropyl alcohol and isobutyl alcohol?

b) KMnO4 in H2O
c) Br2 in CCl4
d) Cold concd H2SO4
e) CrO3 in H2SO4
Answer: A

Section: 18.3
67

lOMoARcPSD|7465873
98) A compound, C5H10O, reacts with phenylhydrazine and gives a positive iodoform test. The
compound could be which of these?
a) CH3CH2CH2CH2C=O
H
CH3CHCH2C=O
b) CH3
c) CH2=CHCH2CHOHCH3
O
CH3CHCCH3
d) CH3
O
e) CH3CH2CCH2CH3
Answer: D

Section: 18.3
O O
C C
CH3 and CH3 ?

b) Br2/CCl4
c) CrO3/H2SO4
d) NaHCO3/H2O
e) Ag(NH3)2+
Answer: B

68

lOMoARcPSD|7465873
100) Which reagent would best serve as the basis for a simple chemical test to distinguish
between CH3CHO and CH3COCH3?

b) Br2/CCl4
c) C6H5NHNH2
d) NaHCO3/H2O
e) Ag(NH3)2+
Answer: E

101) A compound, X, C9H10O, which reacts with I2/NaOH to give a pale yellow precipitate, gives
the following 1H NMR spectrum.
Singlet, 2.0
Singlet, 3.0
Multiplet, 7.7
Which is a possible structure for X?
O
O
O
I II III
O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Reagents, Intermediates, and Spectroscopy
Section: 18.3
69

lOMoARcPSD|7465873
102) A compound, X, C9H10O, which reacts with I2/NaOH to give a pale yellow precipitate, gives
the following 1H NMR spectrum.
Singlet, 2.38
Singlet, 2.54
Multiplet (centered), 7.50
Which is a possible structure for X?
O
O
I II III
O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
70

lOMoARcPSD|7465873
O O
103) The conversion of C6H5CCH3 to C6H5COH is accomplished by the use of which

oxidizing agent?
a) Ag(NH3)2+
b) O3
c) NaOI (I2 in NaOH)
O
d) RCOOH
e) Cu2+
Answer: C

Section: 18.3
O O

oxidizing agent?
a) Ag(NH3)2+
b) O3
c) NaOCl (Cl2 in NaOH)
O
d) RCOOH
e) Cu2+
Answer: C

Section: 18.3
71

lOMoARcPSD|7465873
O O

oxidizing agent?
a) Ag(NH3)2+
b) O3
c) NaOBr (Br2 in NaOH)
O
d) RCOOH
e) Cu2+
Answer: C

Section: 18.3
106) Which compound could be subjected to a haloform reaction to produce m-chlorobenzoic

acid?
O O
CH2OH CO2H CCH2CH3 CCH3 CH2Cl
Cl Cl Cl Cl
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.3
72

lOMoARcPSD|7465873

Br i. Mg, ether i. Br2, P
?
ii. CO2
iii. H3O+ ii. H2O
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Reaction Sequence

Section: 18.3
73

lOMoARcPSD|7465873
108) What would be the major product of- the following reaction?
i. KMnO4, OH , heat i. Br2, P
?
ii. H3O+
ii. H2O
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
74

lOMoARcPSD|7465873

I2 i. Br2, P
?
NaOH ii. H2O
O
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
75

lOMoARcPSD|7465873

i. KMnO4, OH-, heat i.Cl2, P
?
ii. H3O+
ii. H2O
Cl Cl
Cl OH
OH Cl Cl OH
O HO Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
76

lOMoARcPSD|7465873

I2 i.Cl2, P
?
NaOH ii. H2O
O
Cl Cl
Cl OH
OH Cl Cl OH
O HO Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.3
77

lOMoARcPSD|7465873
i. KMnO4, OH , heat Br2, P
?
ii. H3O+
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
78

lOMoARcPSD|7465873

I2 Br2, P
?
NaOH
O
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
79

lOMoARcPSD|7465873

i. KMnO4, OH-, heat Cl2, P
?
ii. H3O+
Cl Cl
Cl OH
OH Cl Cl OH
O HO Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
80

lOMoARcPSD|7465873

I2 Cl2, P
?
NaOH
O
Cl Cl
Cl OH
OH Cl Cl OH
O HO Cl
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
81

lOMoARcPSD|7465873
116) What would be theOH

major product of the following reaction?
SOCl2 I2, HI
?
SOCl2
O
I I
I OH
OH Cl I OH
O HO I
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
82

lOMoARcPSD|7465873
i. KMnO4, OH , heat Br2, PBr3
?
ii. H3O+
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
83

lOMoARcPSD|7465873

I2 Br2, PBr3
?
NaOH
O
Br Br
Br OH
OH Br Br OH
O HO Br
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
84

lOMoARcPSD|7465873
119) What would OH

be the major product of the following reaction?
Br2, PBr3 H2 O 2 NH3
?
Br NH2
Br Br NH3
Br NH2
OH NH2 O
O O
O O O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.3
85

lOMoARcPSD|7465873
120) What would OH

be the major product of the following reaction?
Br2, PBr3 H2 O K2CO3, H2O
?
100oC
O
OH
Br OH
Br
OH OH Br OH
OH
O
O O O
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.3
86

lOMoARcPSD|7465873
OH
PCC i. LDA ?
CH2Cl2 ii. C2H5I
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
87

lOMoARcPSD|7465873
OH
DMSO, (COCl)2 i. LDA ?
Et3N ii. C2H5I
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
88

lOMoARcPSD|7465873
OH
PCC i. LDA ?
CH2Cl2 ii. C2H5OTs
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
89

lOMoARcPSD|7465873
OH
DMSO, (COCl)2 i. LDA ?
Et3N ii. C2H5OTs
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
90

lOMoARcPSD|7465873
125) Predict the product of the following reaction sequence.

i. NaOC2H5
O ii. CH3CH2CH2Br
?
O O iii. NaOH
iv. H3O+, heat
OH O O
O
OH O
O
O O
I II III
O
OH
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.6
91

lOMoARcPSD|7465873
126) What would be the product, P, of the following reaction sequence?
O O
i. NaOEt i. NaOH heat
P
O ii.PhCH2Br ii.H3O+ (-CO2)
O O O
Ph Ph
O Ph
I II III
O O
Ph
Ph O OH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.6
92

lOMoARcPSD|7465873
127) 2-Heptanone can be synthesized by which reaction sequence?
a)

NaOEt CH3(CH2)3Br i. dil.OH heat
Ethyl acetoacetate
EtOH ii. H3O +
b)
Ethyl acetoacetate heat NaOEt CH3(CH2)3Br
EtOH
c)

i. dil.OH heat NaOEt CH3(CH2)3Br
Ethyl acetoacetate
+ EtOH
ii. H3O
d)

i. dil.OH heat
Ethyl acetoacetate CH3(CH2)3Br
+
ii. H3O
e)
i. NaOEt, EtOH i. dil.OH heat
Ethyl hexanoate
ii. CH3COCl ii. H3O +
Answer: A

Section: 18.6
93

lOMoARcPSD|7465873
128) What is the product, W, of the following reaction sequence?

O O Br
Br i. NaOH heat
+ W
(2 eq) O .. O (1 eq) ii.H3O (-CO2)
Na+
HO2C CO2H HO2C EtO2C CO2Et

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

Section: 18.7
94

lOMoARcPSD|7465873

O O i. NaOEt iii. NaOtButyl iv. NaOH heat
W
O O Br v.H3O+ (-CO2)
1 equiv. ii.Br
1 equiv.
HO2C CO2H HO2C EtO2C CO2Et

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

Section: 18.7
95

lOMoARcPSD|7465873

O O + W
v.H3O (-CO2)
1 equiv. ii. Br Br
1 equiv.
COOH
CO2H HO2C
HO2C CO2H
I II III
O
CO2H
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.7
96

lOMoARcPSD|7465873

O O + W
Br v.H3O (-CO2)
1 equiv. ii. Br
1 equiv.
COOH
CO2H HO2C
HO2C CO2H
I II III
O
CO2H
OH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.7
97

lOMoARcPSD|7465873

O O + W
v.H3O (-CO2)
1 equiv. ii. Br Br
1 equiv.
COOH
CO2H HO2C
CO2H
II III
I O
CO2H
OH
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.7
98

lOMoARcPSD|7465873
133) What is the product, L, of the following reaction sequence?

i. EtBr
ii. (CH3)3COK iv. NaOH, heat
EtO2C CO2Et + NaOEt ?
iii. MeI +
v. H3O , heat
(-CO2)
O
O O Me O Et Me
EtO2C CO2Et Et O
MeO OEt O O
EtO2C CO2Et O O O
I II III
O O O O
OH
HO O O OH
Me Et
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.7
99

lOMoARcPSD|7465873
134) What is the product, L, of the following reaction sequence?

i. EtONa ?
EtO2C CO2Et ii. 0.5 equiv. CH2Br2
iii. H3O+, heat (-CO2)
O O O
Me O Et Me
EtO OEt EtO2C CO2Et Et
EtO2C CO2Et O O O
Br
I II III
O O O O
HOOC COOH HO O O OH
Me Et
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 18.7
100

lOMoARcPSD|7465873
135) What is the product, Z, of the following reaction sequence?

O H
N H3O+ PhCOCl H3O+
+ Z
(-H2O)
O O O O
N
Ph Ph Ph
I II III
Ph O
N O
O Ph
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 18.9
101

lOMoARcPSD|7465873

O
O H +
N H3O Cl H3O+
+ (-H2O) Z
O O O
O
N
I II III
O
N O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.9
102

lOMoARcPSD|7465873

O
O
H3O+ Cl H3O+
+ N (-H2O) Z
H
O O O O
N
I II III
O
N O
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.9
103

lOMoARcPSD|7465873

O
O O
H3O+ Cl H3O+
+ N (-H2O) Z
H
O O O O
N
O
I II III
O
N O
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 18.9
104

lOMoARcPSD|7465873

O O
O +
H3O Cl H3O+
+ Z
N (-H2O)
H
O O O
O
N
O
I II III
O O
N
O O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 18.9
105

lOMoARcPSD|7465873
140) Which product can be obtained via the following generalized reaction?
O
R-I + CN
NaOEt ?
EtO EtOH
O
O O
CN
EtO R CN
EtO R
R
I II III
O
O
R
EtO N CN
RO
I
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.7
106

lOMoARcPSD|7465873
i. Hg(OAc)2, H2O PCC i. LDA ?
ii. NaBH4 CH2Cl2 ii. C2H5I
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
107

lOMoARcPSD|7465873
i. Hg(OAc)2, H2O DMSO, (COCl)2 i. LDA
?
ii. NaBH4 Et3N ii. C2H5I
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
108

lOMoARcPSD|7465873
i. Hg(OAc)2, H2O PCC i. LDA ?
ii. NaBH4 CH2Cl2 ii. C2H5OTs
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
109

lOMoARcPSD|7465873
i. Hg(OAc)2, H2O DMSO, (COCl)2 i. LDA
?
ii. NaBH4 Et3N ii. C2H5OTs
O O
O
I II III
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 18.4
145) Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?
a) Sodium methoxide
b) Sodium ethoxide
c) Sodium hydride
d) Potassium tert-butoxide
e) Lithium diisopropylamide
Answer: E
Topic: General Information

Section: 18.4
110

lOMoARcPSD|7465873
146) Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?
a) Sodium methoxide
b) Sodium ethoxide
c) Sodium hydride
e) Sodium amide
Answer: E

Section: 18.4
147) Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?
a) Sodium methoxide
b) Sodium ethoxide
c) Sodium hydride
e) Lithium diisopropylamide
Answer: E

Section: 18.4
148) Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?
a) Sodium methoxide
b) Sodium ethoxide
c) Sodium hydride
e) Sodium amide
Answer: E

Section: 18.4
111

lOMoARcPSD|7465873
149) Consider the synthesis below. What is compound Z?
CO2Et CO2H
CO2Et 1) KOt-Bu "Z" 1) NaOH/H2O, heat
2) "Y" 2) H3O+
3) heat ( CO2)
CO2Et EtO2C CO2Et EtO2C CO2Et
I II III
EtO2C CO2Et O CO2Et
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Synthesis
Section: 18.7
150) What combination of reagents can be used to make the following substance via an
enamine?
112

lOMoARcPSD|7465873
I + + NH
O
O
II + + NH
O
III + Cl NH
+
O
O
NH2
IV + +
O
a) I
b) II
c) III
d) IV
e) Both reactions II and III
Answer: C
Topic: Synthesis
Section: 18.9
enamine?
113

lOMoARcPSD|7465873
O O
I + +
O N
H
O O
II + +
O N
H
O O
III + Cl
+
O N
H
O
IV + +
O NH2
a) I
b) II
c) III
d) IV
e) None of these reagents can be used.
Answer: C
Topic: Synthesis
Section: 18.9
enamine?
114

lOMoARcPSD|7465873
O
O
I + +
O N
H
O
O
II + +
O N
H
O
O
III + Cl +
O N
H
O
IV + +
O NH2
a) I
b) II
c) III
d) IV
e) None of these reagents can be used.
Answer: C
Topic: Synthesis
Section: 18.9
153) Which of the following would provide the best synthesis of 3,5-dimethyl-2-hexanone?
115

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a) Ethyl acetoacetate + NaOC2H5 + CH3I; then KO-t-Bu + (CH3)3CCH2Br; then NaOH; then
H3O+; then heat
b) Ethyl acetoacetate + NaOC2H5 + (CH3)3CBr; then KO-t-Bu + CH3I; then NaOH; then
H3O+; then heat
c) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2Br; then KO-t-Bu + CH3I; then NaOH;
then H3O+; then heat
d) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2CHBrCH3; then NaOH; then H3O+; then heat
e) Ethyl acetoacetate + NaOC2H5 + CH3I; then KO-t-Bu + (CH3)2CHBr; then NaOH; then
H3O+; then heat
Answer: C
Topic: Synthesis
Section: 18.6
154) Which of the following would provide the best synthesis of 3-ethyl-6-methyl-2-heptanone?
a) Ethyl acetoacetate + NaOC2H5 + CH3CH2I; then KO-t-Bu + (CH3)3CCH2CH2Br; then

NaOH; then H3O+; then heat
b) Ethyl acetoacetate + NaOC2H5 + (CH3)3CCH2Br; then KO-t-Bu + CH3CH2I; then NaOH;
c) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2CH2Br; then KO-t-Bu + CH3CH2I; then
NaOH; then H3O+; then heat
d) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2CH2CHBrCH2CH3; then NaOH; then H3O+;
then heat
e) Ethyl acetoacetate + NaOC2H5 + CH3CH2I; then KO-t-Bu + (CH3)2CHCH2Br; then NaOH;
Answer: C
Topic: Synthesis
Section: 18.6
155) Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl
malonate?
116

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a) Bromoethane, 1-bromopropane, sodium ethoxide, and potassium tert-butoxide

b) 3-Bromohexane and sodium ethoxide
c) 3-Bromopentane and sodium ethoxide
d) Bromoethane, 2-bromopropane, sodium ethoxide, and potassium tert-butoxide
e) 2-Bromopentane and sodium ethoxide
Answer: A
Topic: Synthesis
Section: 18.7
156) Which organic reagents would you need to make 2-ethylheptanoic acid from diethyl
malonate?
a) Bromoethane, 1-bromopentane, sodium ethoxide, and potassium tert-butoxide

b) 3-Bromooctane and sodium ethoxide
c) 3-Bromoheptane and sodium ethoxide
d) 1-Bromopropane, 2-bromopentane, sodium ethoxide, and potassium tert-butoxide
e) 2-Bromoheptane and potassium tert-butoxide
Answer: A
Topic: Synthesis
Section: 18.7
157) Which of the following could be used to synthesize the following substance in good yield?
117

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CO2H
O
a) Cyclohexanone, ClCH2COOH, AlCl3, heat

b) Cyclohexanone, (CH3CH2)2NH, HA, (-H2O); then BrCH2COOC2H5; then OH–, H2O, heat; then
H3O+
c) Cyclohexylacetic acid, KMnO4, OH–, heat; then H3O+
d) Two of these choices.
e) All of these choices.
Answer: B
Topic: Synthesis
Section: 18.9
CO2H
O

b) Cyclohexanone, (CH3)2NH, HA, (-H2O); then BrCH2COOC2H5; then OH–, H2O, heat; then
H3O+
c) Cyclohexylacetic acid, KMnO4, OH, heat; then H3O+
Answer: B
Topic: Synthesis
Section: 18.9
118

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CO2H
O

b) Cyclohexanone, pyrrolidine, HA, (-H2O); then BrCH2COOC2H5; then OH–, H2O, heat; then
H3O+
c) Cyclohexylacetic acid, KMnO4, OH–, heat; then H3O+
Answer: B
Topic: Synthesis
Section: 18.9
O OH
a) Cyclopentanone, ClCH2CH2COOH, AlCl3, heat

b) Cyclopentanone, (CH3CH2)2NH, HA, (-H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat;
then H3O+
c) 3-(2-Hydroxycyclopentyl)propanal, KMnO4, OH–, heat; then H3O+
d) Cyclopentanone, ClCH2CH2COOH, AlCl3, heat and cyclopentanone, (CH3CH2)2NH, HA, (-
H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat; then H3O+
e) Cyclopentanone, (CH3CH2)2NH, HA, (-H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat;
then H3O+ and 3-(2-hydroxycyclopentyl)propanal, KMnO4, OH–, heat; then H3O+
Answer: E
Topic: Synthesis
Section: 18.9
119

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O OH

b) Cyclopentanone, (CH3)2NH, HA, (-H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat;
then H3O+
d) Cyclopentanone, ClCH2CH2COOH, AlCl3, heat and cyclopentanone, (CH3)2NH, HA, (-H2O);
then BrCH2CH2COOC2H5; then OH–, H2O, heat; then H3O+
e) Cyclopentanone, (CH3)2NH, HA, (-H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat;
Answer: E
Topic: Synthesis
Section: 18.9
O OH

b) Cyclopentanone, piperidine, HA, (-H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat;
then H3O+
d) Cyclopentanone, ClCH2CH2COOH, AlCl3, heat and cyclopentanone, piperidine, HA, (-H2O);
then BrCH2CH2COOC2H5; then OH–, H2O, heat; then H3O+
e) Cyclopentanone, piperidine, HA, (-H2O); then BrCH2CH2COOC2H5; then OH–, H2O, heat;
Answer: E
Topic: Synthesis
Section: 18.9
163) Which of these amines is/are used with aldehydes and ketones to form enamines?
120

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H
N N
NH N
I II III IV
a) I
b) II
c) III
d) IV
e) Both I and II
Answer: E
Topic: Enamine Chemistry

Section: 18.9
H O
N
NH N N
H
I II III IV
a) I
b) II
c) III
d) IV
e) I, II, and II
Answer: E

Section: 18.9
121

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H O
N N
NH N H
H
I II III IV
a) I
b) II
c) III
d) IV
Answer: E

Section: 18.9
166) Which of the following statements is true of the enamine,
N:
a) The enamine can be made from cyclohexanone + pyrrolidine.

+
N
b) It has another resonance structure :
c) It can be acylated at the -carbon of the original carbonyl compound.
d) It can be alkylated.
e) All of these choices are true.
Answer: E

Section: 18.9
167) Which of the following statements is true of the following enamine?
122

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N:
a) The enamine can be made from cyclopentanone + pyrrolidine.

+
N
b) It has another resonance structure:
c) It can be acylated at the -carbon of the original carbonyl compound.
d) It can be alkylated.
e) All of these choices are true.
Answer: E

Section: 18.9
Question type: fill-in-the-blank
168) The -hydrogens on carbonyl carbons are unusually acidic (pKa 19-20) because: ___.
Answer: the corresponding anion is resonance-stabilized through the carbonyl
Topic: General, Active Hydrogens

Section: 18.1
169) The pKa for protons on the carbon between two carbonyls is about 9-11. This greater acidity
(as compared to single carbonyl systems) can be accounted for by ___.
Answer: resonance delocalization of the negative charge over two carbonyls rather than just one
Topic: Active Hydrogen Compounds

Section: 18.1
170) Compounds with two electron-withdrawing groups attached to the same carbon atom are
known as ___ or ___.
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Answer: active hydrogen compounds; active methylene compounds

Section: 18.1
171) Compounds having two carbonyl groups separated by a carbon atom are called ___.
Answer: -dicarbonyl compounds

Section: 18.2
Question type: Essay
172) Explain why acylation of active methylene compounds must be carried out in aprotic
solvents, typically using NaH to generate the enolate anion: why can sodium ethoxide/ethanol
not be used in these reactions?
Answer: Acylating agents such as acyl halides and acid anhydrides would react rapidly with
ethanol to form esters; also, during this process, the ethoxide ion would be neutralized.
NaH/aprotic solvent bypasses these issues and affords the expected products in good yields.

Section: 18.4
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173) The keto and enol forms of carbonyl compounds are a special type of ___ isomer called
___.
Answer: constitutional; tautomers
Topic: Keto-Enol Tautomerism

Section: 18.2
174) The interconversion of the keto and enol forms of a carbonyl compound is called ___.
Answer: tautomerization
Topic: Keto-Enol Tautomerism

Section: 18.2
175) Explain why the following tautomer equilibrium lies far to the right.
O O O OH
Answer: Conjugated system with a hydrogen bonding to form a stable 6-membered ring.
O O

Section: 18.2
176) Explain why the following tautomer equilibrium lies far to the right.
125

lOMoARcPSD|7465873
O OH
Answer: Enol tautomer is the aromatic compound phenol, with aromatic stability.

Section: 18.2
177) Diastereomers that differ in configuration at only one stereogenic center are sometimes
called ___, and their interconversion is called ___.
Answer: epimers; epimerization
Topic: Epimers
Section: 18.3
178) Dissolving a halogen in aqueous sodium hydroxide provides a solution of ___.
Answer: sodium hypohalite, NaOX
Topic: General
Section: 18.3
179) The haloform reaction is an efficient method for converting methyl ketones to ___.
Answer: carboxylic acids
Topic: Haloform Reaction

Section: 18.3
126

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180) When optically active 2-methyl-1-phenyl-1-butanone undergoes reaction with Br2/H3O+, the
product is observed to exhibit no optical activity. Explain clearly.
Answer: An achiral enol is formed in presence of H3O+, which can then undergo reaction with
Br2 from both faces, to produce a racemic mixture of the brominated product; hence, no observed
optical activity. The reaction with (R)-2-methyl-1-phenyl-1-butanone is shown below; the same
enol and products can be formed from the (S) enantiomer.
O + OH OH
H3O+
H CH3 H CH3 CH3
achiral enol
Br2
O O
+
Br CH3 Br CH3
(S) (R)
Topic: Reaction Products: Stereochemical Outcomes

Section: 18.3
181) An unsymmetrical ketone can form two possible enolates. The enolate with the more highly
substituted double bond is called the ___.
Answer: thermodynamic enolate
Topic: Kinetic/Thermodynamic Enolates

Section: 18.4
127

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182) The kinetic enolate (the less highly substituted double bond) is favored when ___ is used as
a base.
Answer: LDA or lithium diisopropylamide
Topic: Kinetic/Thermodynamic Enolates

Section: 18.4
183) Alkylation of an enolate anion must be done using either a primary, primary allylic or
primary benzylic species because the substitution follows an ___ mechanistic pathway.
Answer: SN2
Topic: Alkylation Reactions: Mechanisms

Section: 18.4
184) The ethyl acetoacetate anion is the synthetic equivalent of the ___.
Answer: acetone enolate
Topic: Acetoacetic Ester Synthesis

Section: 18.6
128

lOMoARcPSD|7465873
185) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
i. NaH, DMF
O
?
ii. CH3CH2COCl
O O
iii. NaOH, H2O
iv. H3O+, heat
i. NaH, DMF i. NaOH, H2O

O O O O
ii. CH3CH2COCl O + O
O
ii. H3O , heat
O OO OH
O O
Answer:
Topic: Acetoacetic Ester Synthesis

Section: 18.6
186) When ethyl acetoacetate is treated with one equivalent of ethoxide ion followed by one
equivalent of 1,2-dibromoethane compound, X is produced. Treatment of X with a second
equivalent of ethoxide, produces Y. Further treatment of this product to conditions of
saponification, acidification and heating produced a product, Z, that gives the following spectral
data:
1 13
H NMR: 0.88  multiplet C NMR: Broad Band Decoupled: 10.40, 21.17, 29.84,
208.30 
1.00  multiplet DEPT 90: 21.17 
1.96  multiplet DEPT 135: positive signals at 21.17, 29.84 
2.24  singlet negative signals at 10.40 
What is a reasonable structure for Z?
Answer:
Topic: Reaction Products and Spectroscopy

Section: 18.6
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187) A reaction of a particular -dicarbonyl compound that gives substituted or disubstituted

acetic acids is called the ___.
Answer: malonic ester synthesis
Topic: Malonic Ester synthesis

Section: 18.7
CO2Et i. NaH
?
CO2Et ii. Br Br
iii. NaOEt
iv. NaOH, heat
v. H3O+, heat
Br
CO2Et CO2Et Br CO2Et
NaH + Br
Na :
CO2Et CO2Et CO2Et
NaOEt
CO2Et
CO2H i. NaOH, heat CO2Et
Answer: ii. H3O+, heat
Topic: Malonic Ester synthesis

Section: 18.7
130

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CO2Et NaH CO2Et Br Ph Ph CO2Et

Na+  :
CO2Et CO2Et CO2Et
i. NaOH, H2O heat

ii. H3O+, heat (-CO2)
CO2H
i. SOCl2
ii. AlCl3
Answer: O
Topic: Malonic Ester Synthesis

Section: 18.7
131

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Br
CO2Et NaH CO2Et CO2Et

Na+  :
CO2Et CO2Et CO2Et
i. NaOH, H2O heat

ii. H3O+, heat (-CO2)
i. SOCl2 CO2H
ii. AlCl3
Answer: O

Section: 18.7
132

lOMoARcPSD|7465873
CO2Et NaH CO2Et Br Ph Ph CO2Et

Na+  :
CO2Et CO2Et CO2Et
i. KOC(CH3)3
ii. CH3I
i. SOCl2 CO2H Ph CO2Et

i. NaOH, H2O heat
ii. AlCl3 ii. H3O+, heat (-CO2) CO2Et
Answer: O

Section: 18.7
133

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i. NH , p-TsOH
O
?
O
ii. Br O
iii. H2O
NH O
:
O N N
Br
O
+ Br
p-TsOH
O O
H2O
O
O
Answer: O
Topic: Stork Enamine Reaction

Section: 18.9
134

Ch18 - Chapter 18 Questions For Boson Ch18 - Chapter 18 Questions For Boson

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Ch18 - Chapter 18 questions for Boson

Organic Chemistry II (The City College of New York)

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Package Title: Solomons Test Bank

Question type: Multiple Choice

1) Which of the compounds listed below is more acidic than 1-butanol?

Topic: Relative Acidities

2) Which of the compounds listed below is more acidic than 1-butanol?

Topic: Relative Acidities

3) Which of the compounds listed below is more acidic than 1-butanol?

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

4) Which of the compounds listed below is more acidic than 1-butanol?

Topic: Relative Acidities

5) Which of the compounds listed below is more acidic than 2-pentanol?

Topic: Relative Acidities

6) Which of the compounds listed below is more acidic than 2-pentanol?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

7) Which of the compounds listed below is more acidic than 2-pentanol?

Topic: Relative Acidities

8) Which of the compounds listed below is more acidic than 2-pentanol?

Topic: Relative Acidities

9) Which of the following hydrogens is the most acidic?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

10) Which is the most acidic hydrogen in the compound shown?

Topic: Relative Acidities

11) Which is the most acidic hydrogen in the compound shown?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

12) Which is the most acidic hydrogen in the compound shown?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

13) Which is the most acidic hydrogen in the compound shown?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

14) Which is the most acidic hydrogen in the compound shown?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

15) Which is the most acidic hydrogen in the compound shown?

Topic: Relative Acidities

16) Which of the following compounds is the strongest acid?

Topic: Relative Acidities

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

17) Which compound contains the most acidic hydrogens?

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

a) I, II, III, IV, V

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

a) I, II, III, IV, V

a) I, II, III, IV, V

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

a) I, II, III, IV, V

24) Which structure represents an ester enolate?

25) Which of the following is a keto-enol tautomeric pair?

Downloaded by Kathy Yella (kathysparkle35@gmail.com)

Topic: Tautomerization and Keto-Enol Equilibrium

26) Which of the following is a keto-enol tautomeric pair?

and and and OH

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27) Which of the following is a keto-enol tautomeric pair?

Topic: Tautomerization and Keto-Enol Equilibrium

28) Which of the following represent tautomers?