Package Title: Solomons Test Bank

Course Title: Solomons 11e

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

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

a) Diethylmalonate
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

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

a) Malonic ester
b) 2-Butanone
c) Ethyl pentanoate
d) All of these choices.
e) Two of these choices.

1
Answer: A

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

a) Ethyl 2-oxocyclohexanecarboxylate
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

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

a) Ethyl 3-oxopentanoate
b) 2-Pentanone
c) Pentanal
d) All of these choices.
e) Two of these choices.

Answer: A

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

a) Diethyl malonate
b) 2-Pentanone
c) Pentanal
d) All of these choices.
e) Two of these choices.

Answer: A

2
Topic: Relative Acidities
Section: 18.1
Difficulty Level: Medium

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

a) Malonic ester
b) 2-Pentanone
c) Pentanal
d) All of these choices.
e) Two of these choices.

Answer: A

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

a) Ethyl 2-oxocyclohexanecarboxylate
b) 2-Pentanone
c) Pentanal
d) All of these choices.
e) Two of these choices.

Answer: A

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

3
e) V

Answer: C

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

II O
H
H I
H

H H

V
H O
H H
H H

IV
III

a) I
b) II
c) III

4
d) IV
e) V

Answer: A

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

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

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

5
 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

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

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

6
Topic: Relative Acidities
Section: 18.1
Difficulty Level: Medium

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

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

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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

7
Answer: E

Topic: Relative Acidities

Section: 18.1
Difficulty Level: Medium

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
Difficulty Level: Medium

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
Difficulty Level: Medium

8
19) Considering only the highlighted hydrogens, list the following compounds in order of
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
d) IV,V,II,I,III
e) V,IV,III,II,I

Answer: C

Topic: Acid/Base
Section: 18.1
Difficulty Level: Medium

20) Considering only the highlighted hydrogens, list the following compounds in order of
increasing acidity:
O O
O H

H H O H
O H

I II III V
IV

a) I,II,III,IV,V
b) II,V,III,I,IV
c) III,I,IV,II,V
d) IV,V,II,I,III
e) V,II,III,I,IV

Answer: E

Topic: Acid/Base
Section: 18.1

9
Difficulty Level: Medium

21) Considering only the highlighted hydrogens, list the following compounds in order of
decreasing acidity:
O O
O H

H H O H
O H

I II III V
IV

a) I,II,III,IV,V
b) II,V,III,I,IV
c) IV,I,III,II,V
d) IV,V,II,I,III
e) V,IV,III,II,I

Answer: C

Topic: Acid/Base
Section: 18.1
Difficulty Level: Medium

22) Considering only the highlighted hydrogens, list the following compounds in order of
increasing acidity:
O O O
H
H
H H C N
O H

O O

I II III V
IV

a) I,II,III,IV,V
b) II,V,III,I,IV
c) III,I,IV,II,V
d) IV,V,II,I,III
e) V,II,III,I,IV

Answer: E

10
Topic: Acid/Base
Section: 18.1
Difficulty Level: Medium

23) Considering only the highlighted hydrogens, list the following compounds in order of
decreasing acidity:
O O O
H
H
H H C N
O H

O O

I II III V
IV

a) I,II,III,IV,V
b) II,V,III,I,IV
c) IV,I,III,II,V
d) IV,V,II,I,III
e) V,IV,III,II,I

Answer: C

Topic: Acid/Base
Section: 18.1
Difficulty Level: Medium

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
e) Two of these choices.

Answer: E

Topic: Enolates
Section: 18.1
Difficulty Level: Medium

11
25) Which of the following is a keto-enol tautomeric pair?
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

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

O OH OH
O O OH

and and OH
and

II III
I

O OH O OH

and and

IV V

a) I
b) II
c) III
d) IV
e) V

Answer: B

12
Topic: Tautomerization and Keto-Enol Equilibrium
Section: 18.2
Difficulty Level: Easy

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

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

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Easy

28) Which of the following represent tautomers?

a)

b)

13
c)
d) All of these choices.
e) None of these choices.

Answer: C

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Easy

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

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Easy

30) Which of the following represent keto-enol tautomers?

O OH

a) CH3CCH2CH3 and CH3C=CHCH3

OH O

b) CH2=CCH2CH3 and CH3CCH2CH3

14
 O O
HOCH2CCH=CH2 and CH3CCH2CH3
c)
d) More than one of these choices.
e) None of these choices.

Answer: D

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Easy

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 π bond is weaker than the C-O π bond.
e) Actually, simple enols are the more stable.

Answer: D

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Medium

32) Which of these compounds would exist primarily in an enol form?

O

a)
O

b) O

15
 O

c) O
O

d)
O

e)

Answer: C

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Medium

33) Which of these compounds would exist primarily in an enol form?

a)

b)

c)

16
d)

e)

Answer: B

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Medium

34) Which of these compounds would exist primarily in an enol form?

O

a)
O

b) O
O

c)
O

d)

17
 O

e)

Answer: C

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Hard

35) Which of these compounds would exist primarily in an enol form?

a)

b)

c)

d)

e)

Answer: C

18
Topic: Tautomerization and Keto-Enol Equilibrium
Section: 18.2
Difficulty Level: Hard

36) Which of the following would undergo racemization in base?

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
Difficulty Level: Easy

37) Which of the following would undergo epimerization in base?

19
a) I
b) II
c) III
d) IV
e) Both III and IV

Answer: C

Topic: Racemization/Epimerization
Section: 18.3
Difficulty Level: Easy

38) Which of the following would undergo epimerization in acid?

a) I
b) II
c) III
d) IV
e) Both III and IV

Answer: C

Topic: Racemization/Epimerization
Section: 18.3
Difficulty Level: Easy

39) Which of the following would undergo racemization in base?

20
 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
Difficulty Level: Medium

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: C

Topic: Racemization
Section: 18.3
Difficulty Level: Hard

41) Which of these halides is predicted to alkylate malonic ester (as the anion) in highest yield?

a) CH3I
b) C6H5Br
c) (CH3)3CCH2Cl
d) CH3CHClCH3
e) All of these choices should be equally effective.

21
Answer: A

Topic: Reaction Products

Section: 18.7
Difficulty Level: Easy

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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

43) What would be the major product of the following reaction?

22
 O

-
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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

44) What would be the major product of the following reaction?

23
 O

-
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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

45) What would be the major product of the following reaction?

O
H3O+
C6H5CCHCH2CH3 + Br2 ?
CH3

C6H5CCBrCH2CH3

a) CH3

24
 O Br

C6H5CCHCHCH3

b) CH3
O OH

C6H5CCHCHCH3

c) CH3
C6H5CBr2CHCH2CH3

d) CH3
O

m-BrC6H4CCHCH2CH3

e) CH3

Answer: A

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

46) What would be the major product of the following reaction?

O

H3O+
+ Cl2 ?

O Cl O OH
O

Cl

I II III

O
Cl Cl

Cl

IV V

a) I
25
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

47) What would be the major product of the following reaction sequence?
O

H3 O+
+ 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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

48) What would be the major product of the following reaction sequence?

26
a) I
b) II
c) III
d) IV
e) V

Answer: A

Topic: Reaction Products

Section: 18.3
Difficulty Level: Easy

49) What would be the major product of the following reaction?

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

27
 OD

C6H5CDCHCH3

e) CH3

Answer: B

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

50) What would be the major product of the following reaction?

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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

51) Which would be formed when 2-methylpropanal is dissolved in D2O containing NaOD?

28
 O

CH3CHCD

a) CH3
O

CH3CHCH

b) CH2D
O

CH3CDCH

c) CH3
O

CH3CDCD

d) CH3
D

CH3CHCHOD

e) CH3

Answer: C

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

52) Which would be formed when 2-methylpropanal is dissolved in T2O containing NaOT?

a)
b)
c)
d)
e) None of these choices.

Answer: C

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

29
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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

54) What would be the major product of the following reaction?

OH
Br2, PBr3
?

Br Br
Br OH
OH Br Br OH

O HO Br
O O O

I II III IV V

a) I

30
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

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

d) CH3
CH3CH2CDCDO

e) CH3

Answer: A

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

56) Which compound would be formed when 2-methylbutanal is treated with a solution of NaOT
in T2O?

a)
b)
c)
d)
e)

31
Answer: A

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

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

d) CH3
CH3CH2CDCDO

e) CH3

Answer: A

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

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)

32
 O
d) D

O
e) D

Answer: E

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

59) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of
NaOT in T2O?

T
O
a)
T
O
b) T
T
O
c)

O
d) T

O
e) T

Answer: E

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

60) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of
D+ in D2O?

D
O
a)

33
 D
O
b) D
D
O
c)

O
d) D

O
e) D

Answer: E

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

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
Difficulty Level: Hard

62) What would be the major product of the following reaction sequence?

34
 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

Topic: Reaction Products

Section: 7.6 and 18.3
Difficulty Level: Medium

63) What would be the major product of the following reaction sequence?

a) I
b) II
c) III

35
d) IV
e) V

Answer: B

Topic: Reaction Products

Section: 7.6 and 18.3
Difficulty Level: Medium

64) What would be the major product of the following reaction?

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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

65) What would be the major product of the following reaction sequence?

36
 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

Topic: Reaction Products

Section: 7.6 and 18.3
Difficulty Level: Medium

66) What would be the major product of the following reaction?

37
 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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

67) What would be the major product of the following reaction?

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

38
e) V

Answer: B

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

68) What would be the major product of the following reaction?

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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

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

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

39
a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

70) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

71) What would be the major product of the following reaction?

40
a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

72) What would be the major product of the following reaction?

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

Topic: Reaction Products

41
Section: 18.3
Difficulty Level: Medium

73) What would be the major product of the following reaction sequence?
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

Topic: Reaction Products

Section: 18.4
Difficulty Level: Medium

74) What would be the major product of the following reaction?

42
 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

Topic: Reaction Products

Section: 18.3
Difficulty Level: Medium

75) What would be the major product of the following reaction sequence?
O
i. LDA(-78oC)
?
ii. C2H5OTs
O O

O
I II III
O

IV V

a) I
b) II
c) III
43
d) IV
e) V

Answer: A

Topic: Reaction Products

Section: 18.4
Difficulty Level: Medium

76) What would be the major product of the following reaction sequence?
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

Topic: Reaction Products

Section: 18.4
Difficulty Level: Medium

77) What would be the major product of the following reaction sequence?

44
 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

Topic: Reaction Products

Section: 18.4
Difficulty Level: Medium

78) What would be the major product of the following reaction sequence?

45
 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

Topic: Reaction Products

Section: 18.4
Difficulty Level: Medium

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

Topic: Reaction Products

Section: 18.7
Difficulty Level: Hard

46
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

Topic: Reaction Products

Section: 18.7
Difficulty Level: Hard

81) What would be the major product of the following reaction sequence?

a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Products

Section: 18.4
47
Difficulty Level: Hard

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

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

83) What product is finally formed when the initial compound formed from cyclohexanone and
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

48
Answer: C

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

84) What product is finally formed when the initial compound formed from cyclohexanone and
piperidine is mixed with methyl iodide and that product is heated and then hydrolyzed?

a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

85) What product is finally formed when the initial compound formed from cyclohexanone and
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

49
b) II
c) III
d) IV
e) V

Answer: E

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

86) What product is finally formed when the initial compound formed from cyclohexanone and
morpholine is mixed with methyl iodide and that product is heated and then hydrolyzed?

a) I
b) II
c) III
d) IV
e) V

Answer: E

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

87) What product is finally formed when the initial compound formed from cyclopenatone and
piperidine is mixed with allyl chloride and that product is heated and then hydrolyzed?

50
 Cl
HO N O

I II III

O O

IV V

a) I
b) II
c) III
d) IV
e) V

Answer: E

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

88) What product is finally formed when the initial compound formed from cyclopenatone and
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

51
e) V

Answer: E

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

89) What product is finally formed when the initial compound formed from cyclopentanone and
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

Topic: Reaction Products

Section: 18.9
Difficulty Level: Hard

90) What would be the major product of the following reaction sequence?

52
a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Products

Section: 18.4
Difficulty Level: Hard

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, hν; ii) (CH3)3COK, (CH3)3COH, heat
e) None of these choices.

Answer: A

Topic: Synthetic Strategy

Section: 7.6 and 18.3
Difficulty Level: Hard

53
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
Difficulty Level: Medium

93) Which reagent would best serve as the basis for a simple chemical test to distinguish between
acetophenone and propiophenone?

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
Difficulty Level: Medium

94) Which reagent would best serve as the basis for a simple chemical test to distinguish between
acetophenone and benzophenone?

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
Difficulty Level: Medium

54
95) Which reagent would best serve as the basis for a simple chemical test to distinguish between
m-chloroacetophenone and m-chloropropiophenone?

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
Difficulty Level: Medium

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?

a) NaOI (I2 in NaOH)

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

Answer: A

Topic: Chemical Tests

Section: 18.3
Difficulty Level: Medium

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?

a) NaOI (I2 in NaOH)

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

Answer: A

Topic: Chemical Tests

55
Section: 18.3
Difficulty Level: Medium

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

Topic: Chemical Tests

Section: 18.3
Difficulty Level: Medium

99) A negative iodoform test will be observed in the case of which of these?

a) Acetone
b) Ethanal
c) Ethanol
d) 2-Butanol
e) All of these choices will give a positive test.

Answer: E

Topic: Chemical Tests

Section: 18.3
Difficulty Level: Medium

56
100) Which reagent would best serve as the basis for a simple chemical test to distinguish
between

O O
C C
CH3 and CH3 ?

a) NaOI (I2 in NaOH)

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

Answer: B

Topic: Chemical Tests

Section: 8.12 and 18.3
Difficulty Level: Hard

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

a) NaOI (I2 in NaOH)

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

Answer: E

Topic: Chemical Tests

Section: 16.12 and 18.3
Difficulty Level: Hard

102) A compound, X, C9H10O, which reacts with I2/NaOH to give a pale yellow precipitate,
gives the following 1H NMR spectrum.

Singlet, δ 2.0
Singlet, δ 3.0
Multiplet, δ 7.7

Which is a possible structure for X?

57
 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
Difficulty Level: Medium

103) A compound, X, C9H10O, which reacts with I2/NaOH to give a pale yellow precipitate,
gives the following 1H NMR spectrum.

Singlet, δ 2.38
Singlet, δ 2.54
Multiplet,(centered) δ 7.50

Which is a possible structure for X?

O
O

I II III

O
O

IV V

58
a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3
Difficulty Level: Medium

O O

104) 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) Cu++

Answer: C

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3
Difficulty Level: Medium

O O

105) The conversion of C6H5CCH3 to C6H5COH is accomplished by the use of which

oxidizing agent?

a) Ag(NH3)2+
b) O3
c) NaOCl (Cl2 in NaOH)
O

d) RCOOH
e) Cu++

Answer: C

59
Topic: Reagents, Intermediates, and Spectroscopy
Section: 18.3
Difficulty Level: Medium

O O

106) The conversion of C6H5CCH3 to C6H5COH is accomplished by the use of which

oxidizing agent?

a) Ag(NH3)2+
b) O3
c) NaOBr (Br2 in NaOH)
O

d) RCOOH
e) Cu++

Answer: C

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3
Difficulty Level: Medium

107) 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

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3
Difficulty Level: Medium

60
108) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

109) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

61
Topic: Reaction Sequence
Section: 18.3
Difficulty Level: Medium

110) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

111) What would be the major product of the following reaction?

a) I
b) II

62
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

112) What would be the major product of the following reaction?

Br i. Mg, ether i.Cl2, P
ii. CO2 ?
iii. 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

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

113) What would be the major product of the following reaction?

63
a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

114) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

64
Section: 18.3
Difficulty Level: Medium

115) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

116) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV

65
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

117) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

118) What would be the major product of the following reaction?

66
a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

119) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

120) What would be the major product of the following reaction?

67
a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

121) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

68
Section: 18.3
Difficulty Level: Medium

122) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

123) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV

69
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

124) What would be the major product of the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: D

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

125) What would be the major product of the following reaction?

70
a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Sequence

Section: 18.3
Difficulty Level: Medium

126) What would be the major product of the following reaction sequence?
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

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Medium

127) What would be the major product of the following reaction sequence?

71
 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

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Medium

128) What would be the major product of the following reaction sequence?

72
 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

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Medium

129) What would be the major product of the following reaction sequence?

73
 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

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Medium

130) Predict the product of the following reaction sequence.

74
 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

Topic: Reaction Sequence

Section: 18.6
Difficulty Level: Medium

131) 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

75
c) III
d) IV
e) V

Answer: C

Topic: Reaction Sequence

Section: 18.6
Difficulty Level: Medium

132) 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

Topic: Reaction Sequence

Section: 18.6
Difficulty Level: Medium

133) What is the product, W, of the following reaction sequence?

76
 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

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

134) What is the product, W, of the following reaction sequence?

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

77
Answer: E

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

135) What is the product, W, of the following reaction sequence?

a) I
b) II
c) III
d) IV
e) V

Answer: C

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

136) What is the product, W, of the following reaction sequence?

78
a) I
b) II
c) III
d) IV
e) V

Answer: D

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

137) What is the product, W, of the following reaction sequence?

a) I
b) II
c) III
d) IV
e) V
79
Answer: A

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

138) 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

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

139) What is the product, L, of the following reaction sequence?

80
 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

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Medium

140) 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

81
d) IV
e) V

Answer: B

Topic: Reaction Sequence

Section: 18.9
Difficulty Level: Medium

141) What is the product, Z, of the following reaction sequence?

O
O H +
N H3 O 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

Topic: Reaction Sequence

Section: 18.9
Difficulty Level: Medium

142) What is the product, Z, of the following reaction sequence?

82
 O
O
+
H3 O Cl H3 O+
+ 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

Topic: Reaction Sequence

Section: 18.9
Difficulty Level: Medium

143) What is the product, Z, of the following reaction sequence?

O
O O +
H3 O 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

83
Answer: C

Topic: Reaction Sequence

Section: 18.9
Difficulty Level: Medium

144) What is the product, Z, of the following reaction sequence?

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

Topic: Reaction Sequence

Section: 18.9
Difficulty Level: Medium

145) Which product can be obtained via the following generalized reaction?

84
 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

Topic: Reaction Sequence

Section: 18.7
Difficulty Level: Hard

146) What would be the major product of the following reaction sequence?
i. Hg(OAc)2, H2O PCC i. LDA
?
ii. NaBH4 CH 2Cl2 ii. C2H5I

O O

O
I II III
O

IV V

a) I
b) II
c) III

85
d) IV
e) V

Answer: A

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Hard

147) What would be the major product of the following reaction sequence?
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

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Hard

148) What would be the major product of the following reaction sequence?

86
 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

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Hard

149) What would be the major product of the following reaction sequence?
i. Hg(OAc)2, H2O DMSO, (COCl) 2 i. LDA
?
ii. NaBH4 Et3N ii. C2H5OTs

O O

O
I II III
O

IV V

87
a) I
b) II
c) III
d) IV
e) V

Answer: A

Topic: Reaction Sequence

Section: 18.4
Difficulty Level: Hard

150) 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
Difficulty Level: Medium

151) 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) Sodium amide

Answer: E

Topic: General Information

Section: 18.4
Difficulty Level: Medium

152) Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

a) Sodium methoxide

88
b) Sodium ethoxide
c) Sodium hydride
d) Potassium tert-butoxide
e) Lithium diisopropylamide

Answer: E

Topic: General Information

Section: 18.4
Difficulty Level: Medium

153) Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

a) Sodium methoxide
b) Sodium ethoxide
c) Sodium hydride
d) Potassium tert-butoxide
e) Sodium amide

Answer: E

Topic: General Information

Section: 18.4
Difficulty Level: Medium

154) Consider the synthesis below. What is compound Y?

CO2Et CO2H
CO2Et 1) KOt-Bu 1) NaOH/H2O, heat
2) "Y" 2) H3O+
3) heat (− CO2)

a) BrCH2CO2Et
b) EtO-CO-CO-OEt
c) CH3CH2Br
d) C6H5CH2Br
e) C6H5Br

Answer: D

Topic: Synthesis
Section: 18.7
Difficulty Level: Medium

89
155) 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
Difficulty Level: Medium

156) What combination of reagents can be used to make the following substance via an
enamine?

90
 O

I + + NH
O

O
II + + NH
O

III + Cl NH
+
O

O
IV NH2
+ +
O

a) I
b) II
c) III
d) IV
e) Both reactions II and III

Answer: C

Topic: Synthesis
Section: 18.9
Difficulty Level: Medium

157) What combination of reagents can be used to make the following substance via an
enamine?

91
 O

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
Difficulty Level: Medium

158) What combination of reagents can be used to make the following substance via an
enamine?

92
 O

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
Difficulty Level: Medium

159) Consider the synthesis below. What is compound Z?

93
 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
Difficulty Level: Medium

160) Which of the following would provide the best synthesis of 3,5-dimethyl-2-hexanone?

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
94
Section: 18.6
Difficulty Level: Hard

161) 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;
then H3O+; then heat
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; then H3O+; then heat

Answer: C

Topic: Synthesis
Section: 18.6
Difficulty Level: Hard

162) Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl
malonate?

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
Difficulty Level: Hard

163) 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

95
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
Difficulty Level: Hard

164) Which of the following could be used to synthesize the following substance in good yield?

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
Difficulty Level: Hard

165) Which of the following could be used to synthesize the following substance in good yield?

CO2H
O

a) Cyclohexanone, ClCH2COOH, AlCl3, heat

b) Cyclohexanone, (CH3)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

96
Topic: Synthesis
Section: 18.9
Difficulty Level: Hard

166) Which of the following could be used to synthesize the following substance in good yield?

CO2H
O

a) Cyclohexanone, ClCH2COOH, AlCl3, heat

b) Cyclohexanone, pyrrolidine, 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
Difficulty Level: Hard

167) Which of the following could be used to synthesize the following substance in good yield?
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
Difficulty Level: Hard

97
168) Which of the following could be used to synthesize the following substance in good yield?
O OH

a) Cyclopentanone, ClCH2CH2COOH, AlCl3, heat

b) Cyclopentanone, (CH3)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, (CH3)2NH, HA, (-H2O);
then BrCH2CH2COOC2H5; then OH-, H2O, heat; then H3O+
e) Cyclopentanone, (CH3)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
Difficulty Level: Hard

169) Which of the following could be used to synthesize the following substance in good yield?
O OH

a) Cyclopentanone, ClCH2CH2COOH, AlCl3, heat

b) Cyclopentanone, piperidine, 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, piperidine, HA, (-H2O);
then BrCH2CH2COOC2H5; then OH-, H2O, heat; then H3O+
e) Cyclopentanone, piperidine, 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
Difficulty Level: Hard

170) Which of these amines is/are used with aldehydes and ketones to form enamines?

98
 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
Difficulty Level: Easy

171) Which of these amines is/are used with aldehydes and ketones to form enamines?
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

Topic: Enamine Chemistry

Section: 18.9
Difficulty Level: Easy

172) Which of these amines is/are used with aldehydes and ketones to form enamines?
H O
N N
NH N H
H
I II III IV

a) I
b) II
c) III

99
d) IV
e) All of these choices.

Answer: E

Topic: Enamine Chemistry

Section: 18.9
Difficulty Level: Easy

173) 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

Topic: Enamine Chemistry

Section: 18.9
Difficulty Level: Medium

174) Which of the following statements is true of the following enamine?

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

Topic: Enamine Chemistry

Section: 18.9
Difficulty Level: Medium

100
Question type: fill-in-the-blank

175) The α-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
Difficulty Level: Easy

176) 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
Difficulty Level: Easy

177) Compounds with two electron-withdrawing groups attached to the same carbon atom are
known as ___ or ___.

Answer: active hydrogen compounds; active methylene compounds

Topic: Active Hydrogen Compounds

Section: 18.1
Difficulty Level: Easy

178) Compounds having two carbonyl groups separated by a carbon atom are called ___.

Answer: β-dicarbonyl compounds

Topic: Active Hydrogen Compounds

Section: 18.2
Difficulty Level: Easy

Question type: Essay

101
179) 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.

Topic: Active Hydrogen Compounds

Section: 18.4
Difficulty Level: Medium

Question type: fill-in-the-blank

180) 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
Difficulty Level: Easy

181) The interconversion of the keto and enol forms of a carbonyl compound is called ___.

Answer: tautomerization

Topic: Keto-Enol Tautomerism

Section: 18.2
Difficulty Level: Easy

Question type: Essay

182) 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.

102
 H

O O

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Medium

183) Explain why the following tautomer equilibrium lies far to the right.
O OH

Answer: Enol tautomer is the aromatic compound phenol, with aromatic stability.

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2
Difficulty Level: Medium

Question type: fill-in-the-blank

184) 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
Difficulty Level: Medium

185) Dissolving a halogen in aqueous sodium hydroxide provides a solution of ___.

Answer: sodium hypohalite, NaOX

Topic: General
Section: 18.3
Difficulty Level: Easy

103
186) The haloform reaction is an efficient method for converting methyl ketones to ___.

Answer: carboxylic acids

Topic: Haloform Reaction

Section: 18.3
Difficulty Level: Easy

Question type: Essay

187) 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
Difficulty Level: Hard

Question type: fill-in-the-blank

188) An unsymmetrical ketone can form two possible enolates. The enolate with the more highly
substituted double bond is called the ___.

Answer: thermodynamic enolate

104
Topic: Kinetic/Thermodynamic Enolates
Section: 18.4
Difficulty Level: Medium

189) 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
Difficulty Level: Medium

190) 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
Difficulty Level: Easy

Question type: Essay

191) What is the expected final product when phenylacetonitrile is subjected to the following
reaction sequence?
CN
i. EtO-, EtOH
?
ii. CH3CH2I

CN
i. EtO-, EtOH CN

Answer: ii. CH3CH2I

Topic: Direct Alkylation Reactions

Section: 18.4
Difficulty Level: Medium

192) What is the expected final product when phenylacetonitrile is subjected to the following
reaction sequence?

105
 CN
i. EtO-, EtOH
?
ii. PhCH2I

Ph

CN
i. EtO-, EtOH CN
ii. PhCH2I
Answer:

Topic: Direct Alkylation Reactions

Section: 18.4
Difficulty Level: Medium

193) What is the expected final product when phenylacetonitrile is subjected to the following
reaction sequence?
CN
i. EtO-, EtOH
?
ii. Br

iii. DIBAL-H (-78oC)

i. EtO-, EtOH iii. DIBAL-H

CN CN CHO
Br (-78oC)
ii.
Answer:

Topic: Direct Alkylation Reactions, Reaction Sequence

Section: 18.4
Difficulty Level: Hard

Question type: fill-in-the-blank

194) The ethyl acetoacetate anion is the synthetic equivalent of the ___.

Answer: acetone enolate

Topic: Acetoacetic Ester Synthesis

Section: 18.6
Difficulty Level: Easy

Question type: Essay

106
195) 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
O
ii. CH3CH2COCl O ii. H3O+, heat O
O OO OH
O O

Answer:

Topic: Acetoacetic Ester Synthesis

Section: 18.6
Difficulty Level: Medium

196) When ethylacetoacetate 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
H NMR: 0.88δ multiplet 13
CNMR: Broad Band Decoupled: 10.40, 21.17, 29.84,
208.30δ
1.00δ multiplet DEPT 90: 21.17δ
1.96δ multiplet DEPT 135: positive signals at 21.17, 29.84δ
2.24δ singlet negative signals at 10.40δ

What is a reasonable structure for Z?

Answer:

Topic: Reaction Products and Spectroscopy

Section: 18.6
Difficulty Level: Medium

107
Question type: fill-in-the-blank

197) A reaction of a particular β-dicarbonyl compound that gives substituted or disubstituted

acetic acids is called the ___.

Answer: malonic ester synthesis

Topic: Malonic Ester synthesis

Section: 18.7
Difficulty Level: Easy

Question type: Essay

198) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
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
Difficulty Level: Medium

199) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.

108
 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
Difficulty Level: Hard

200) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.

109
 Br

CO2Et NaH CO2Et CO2Et

Na+ −:
CO2Et CO2Et CO2Et

i. NaOH, H2O heat

ii. H3O+, heat (-CO2)

i. SOCl2 CO2H

ii. AlCl3
Answer: O

Topic: Malonic Ester Synthesis

Section: 18.7
Difficulty Level: Hard

201) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.

CO2Et NaH CO2Et Br Ph CO2Et

Na+ −:
Ph
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

Topic: Malonic Ester Synthesis

Section: 18.7
Difficulty Level: Hard

110
202) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
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
Difficulty Level: Hard

111