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Ch19 - Chapter 19 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: 19

Question type: Multiple Choice

1) The Claisen condensation produces which of these?

a) An -keto ester
b) A -keto ester
c) A -hydroxy ester
d) A -hydroxyaldehyde
e) A -diketone

Answer: B

Topic: General Information

Section: 19.2
Difficulty Level: Easy

2) Cyclization reactions, such as the Dieckmann condensation, are best carried out using fairly
dilute solutions of the compound to be cyclized. Why is this so?

a) It then is possible to use less base.

b) The reagents generally are expensive.
c) A smaller amount of the compound to be cyclized can be used.
d) Intermolecular condensation is minimized at low concentration.
e) The concentration factor is unimportant.

Answer: D

Topic: General Information

Section: 19.2
Difficulty Level: Easy

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3) Why is CH3ONa not used in the Claisen condensation of ethyl acetate?

a) CH3O– is a weaker base than the CH3CH2O– which is used.

b) CH3O–Na+ is more difficult to prepare than CH3CH2O–Na+.
c) CH3O– would abstract a proton from the ethyl group of the ester.
d) Use of CH3O–Na+ would result in transesterification.
e) CH3O–Na+ can be used as well as CH3CH2O–Na+.

Answer: D

Topic: General Information

Section: 19.2
Difficulty Level: Easy

4) Which of these combinations is not one which would result in the formation of essentially one
Claisen condensation product when one compound is added slowly to the mixture of the other
and the base employed?

a) HCO2Et + CH3CH2CO2Et
b) PhCO2Et + CH3CO2Et
c) (CO2Et)2 + PhCH2CO2Et
d) (CH3)3CCO2Et + CH3CO2Et
e) PhCH2CO2Et + CH3CO2Et

Answer: E

Topic: General Information

Section: 19.2
Difficulty Level: Medium

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

O i. NaOC2H5
+ ?
O
ii. H3 O

O O O
O O
O O
O O O
I II III
O
O
O
OH O OH
IV V

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

Answer: C

Topic: Reaction Products

Section: 19.2
Difficulty Level: Easy

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6) What product is formed during the following reaction?

O O i. NaOC2H5, C2H5OH
+
Ph OC2H5 OC2H5 ii. HOAc

O
O O O
OC2H5 Ph
Ph Ph OC2H5 O
O
I II III
O O OH O
Ph O Ph OC2H5

IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Easy

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7) The product(s) of the reaction of 2 mol of ethyl butanoate with sodium ethoxide is(are):

a) OH + NaOH
b)
O O
O
c)
O O
O

d)
O
O
O
e)
O O
O

Answer: C

Topic: Reaction Products

Section: 19.2
Difficulty Level: Easy

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8) The reaction of diethyl heptanedioate with sodium ethoxide would give as the product:
O O
EtO EtO
I II
O O O
O O O
OEt

III IV V

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

Answer: C

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

9) The reaction of diethyl hexanedioate with sodium ethoxide would give as the product:
O O
OH
EtO EtO
I II O

O O O
O O
O
OEt
OEt

III IV V

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

Answer: E

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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10) What is the product of the Dieckmann condensation of this diester,

O
OEt
EtO
O
O
O O O
OEt O O
OEt OEt

I II III

a) I
b) II
c) III
d) I and II
e) I, II, and III

Answer: D

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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11) What is the product of the Dieckmann condensation of this diester,

O

O O O
O
O
O
O
O

I II III

O O
O

O
O

IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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12) What is the product of the Dieckmann condensation of this diester,

O

O O O
O
O
O
O
O

I II III

O
O
O

O
O

IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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13) What is the product of the Dieckmann condensation of this diester,

O

O O O
O
O
O
O
O

I II III

O
O
O

O
O

IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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14) What is the product of the Dieckmann condensation of this diester,

O

O
O

O O O
O
O
O
O
O

I II III

O
O
O

O
O

IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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15) What is the product of the Dieckmann condensation of this diester,

O

O
O

N
O

O O O
O
O
O
O

N O
N N

I II III

O O
O

O
N O
N
IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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16) What is the product of the Dieckmann condensation of this diester,

O

O
O

O
O

O O O
O
O
O
O
O O
O O

I II III

O O
O

O
O O
O
IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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17) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. CH3I
O ?
3. H3O+, heat (-CO2)

O O O O

O
O

I II III

O
O

IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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18) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. PhCH2I
O ?
3. H3O+, heat (-CO2)

O O O O
Ph

O Ph
O

I II III
O
Ph

O
O

Ph
IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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19) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. CH3I
?
3. H3O+, heat (-CO2)
O

O O O O

O
O

I II III
O

IV V

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

Answer: D

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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20) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. PhCH2Br
?
3. H3O+, heat (-CO2)
O

O O O O
Ph

O Ph
O

I II III
Ph
O

Ph

IV V

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

Answer: D

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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21) What is the product of the reaction:

O

H NaOEt
(-H2O) ?
CN

O O O
CN
CN
CN
O

I II III
CN

CN O

IV V

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

Answer: D

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

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22) What is the product of the reaction:

O

H NaOEt iii. DIBAL-H, -78oC

(-H2O) iv. H3O+ ?
CN

O O O O
CHO
H
H
O
O

I II III
CHO

CHO O

IV V

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

Answer: D

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

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23) What is the product of the reaction sequence:

O

H NaOEt
?
(-H2O)
CN

O O
CN
CN CN

I II III
O
CN

O
O

CN
IV V

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

Answer: B

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

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24) What is the product of the reaction sequence:

O

H NaOEt iii. DIBAL-H, -78oC

?
iv. H3O+
(-H2O)
CN

O O
CHO
CHO CHO

I II III
O
CHO

O
O

CHO
IV V

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

Answer: B

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

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25) What is the product of the reaction sequence:

1. 2 equiv. NaOCH3
CO2Et 2. CH3I
?
CO2Et 3. H3O+, heat (-CO2)

O O O O

CO2Et
OEt
O

I II III
O

IV V

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

Answer: E

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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26) What is the product of the reaction sequence:

1. 2 equiv. NaOEt
CO2Et 2. CH3I
?
CN 3. H3O+, heat (-CO2)

O O O

CN CO2H

I II III
O

IV V

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

Answer: E

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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27) What is the product of the Dieckmann condensation of this diester,

O

O
O

O O O
O
O
O
O
O

I II III

O
O
O

O
O

IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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28) What is the product of the Dieckmann condensation of this diester,

O

O
O

O O O
O
O
O
O
O

I II III

O
O
O

O
O

IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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29) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. CH3I
O ?
3. H3O+, heat (-CO2)

O O O O

O
O

I II III

O
O

IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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30) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. PhCH2I
O ?
3. H3O+, heat (-CO2)

O O O O
Ph

O Ph
O

I II III
O
Ph

O
O

Ph
IV V

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

Answer: B

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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31) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. CH3I
?
3. H3O+, heat (-CO2)
O

O O O O

O
O

I II III
O

IV V

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

Answer: D

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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32) What is the product of the reaction sequence:

O

1. 2 equiv. NaOCH3
O 2. PhCH2Br
?
3. H3O+, heat (-CO2)
O

O O O O
Ph

O Ph
O

I II III
Ph
O

Ph

IV V

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

Answer: D

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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33) What product(s) is (are) likely to be obtained upon Dieckmann condensation of the following
substance?
O O
O O

O O O O O O O O
O O O O

I II III IV

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

Answer: D

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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34) What would be the product of the following sequence?

O
O O i. NaOC2H5, C2H5OH
+ ?
O ii. H3O+

O O OH O
O O O
O

I II III

O
O O
O
O O
IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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35) What is the expected product from the following reaction sequence?
O O O
+ i. NaOC2H5, C2H5OH
O O ?
ii. H3O+
O O
O O
O O
O O O
O O

I II III

O
O O O O
IV V

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

Answer: A

Topic: Reaction Products

Section: 19.2
Difficulty Level: Medium

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

O
OH-
CH3CH2CH
?
H2O

a) CH3CH2CH2OH + CH3CH2COO–
CH3CH2CHCH2CHO

b) OH
O

c) CH3CH2CH2OCCH2CH3
CH3CH2CHCHCHO

d) HO CH3
O

CH3CH2CHCCH2CH3

e) HO

Answer: D

Topic: Reaction Product

Section: 19.4
Difficulty Level: Medium

37) The aldol reaction of cyclohexanone produces which of these self-condensation products?

O
O O O O O

I II III IV V

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

Answer: B

Topic: Reaction Product

Section: 19.4
Difficulty Level: Medium

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38) The aldol reaction of cyclopentanone produces which of these self-condensation products?
O
O O O O O

IV V
I II III

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

Answer: C

Topic: Reaction Product

Section: 19.4
Difficulty Level: Medium

39) The aldol reaction of cyclobutanone produces which of these self-condensation products?
O
O O O O

I II III IV V

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

Answer: A

Topic: Reaction Product

Section: 19.4
Difficulty Level: Medium

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40) The aldol reaction of cycloheptanone produces which of these self-condensation products
O O O O O
O

I II III IV V

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

Answer: C

Topic: Reaction Product

Section: 19.4
Difficulty Level: Medium

41) What is the product of the Dieckmann-like condensation of this ketoester,

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O O
O O
O
O

I II O
III

O
O
O

O
O

IV V

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

Answer: C

Topic: Reaction Products

Section: 19.2 and 19.4
Difficulty Level: Medium

42) What is the product of the Dieckmann-like condensation of this ketoester,

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O O
O O
O
O

I II O
III

O
O
O

O
O

IV V

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

Answer: C

Topic: Reaction Products

Section: 19.2 and 19.4
Difficulty Level: Medium

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43) What is the product of the Dieckmann-like condensation of this ketoester,

O

O O O
O
O
O O

O
O

I II
III

O O
O

IV O
V

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

Answer: D

Topic: Reaction Products

Section: 19.2 and 19.4
Difficulty Level: Medium

44) Predict the product of the following reaction sequence:

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O i. NaOCH3, HOCH3
?
ii. NaBH4

OH O O
OH
O
O O

O
O

I II III

OH O
O

OH

IV OH
V

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

Answer: D

Topic: Reaction Products

Section: 19.2 and 19.4
Difficulty Level: Medium

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

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O
O
CH3CCH3
CH3 CH + OH- ?
100 oC

CH3 O O
CH3
C CH CH CH3 CH C CH3 CHCH2CCH3
CH3 CH3 OH
I II III
O OH
CH3 CH CHCCH3 CH3 CHC(CH3)2
OH
IV V

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

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

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

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O
O
H OH
+ ?
heat

2 mol 1 mol

O OH O OH

O
I II III

O O

(Z and E)

IV V

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

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

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

O
OH-
+ O ?

O OH O

O OH O
I II III
OH OH

O
O
IV V

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

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

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

H
O
O OH-
+ O ?
heat

O HO O
H
O O O

O OH O
I II III
HO H
O O

O
(Z and E)
O
IV V

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

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

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49) What would Hbe the major product of the following reaction?
S
O OH-
+ O ?
heat

O HO O
H
S S S

O OH O
I II III
HO H
S S

O
(Z and E)
O
IV V

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

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

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

H
OH-
O + O ?
N heat
O
HO H
O

N N O
N OH
O
I II III
HO H

N O N
O
(Z and E)
IV V

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

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

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51) What is the product of the Dieckmann-like condensation of this ketoester,

O

O
O

O O O
O
O
O

O
O

I II III

O O
O

IV V

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

Answer: C

Topic: Reaction Products

Section: 19.2 and 19.4
Difficulty Level: Medium

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52) Predict the product of the following reaction sequence:

O

O
O i. NaOCH3, HOCH3
?
ii. NaBH4

OH O OH
OH
O
O

O
OH

I II III

OH O
O

OH

IV V

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

Answer: C

Topic: Reaction Products

Section: 19.2 and 19.4
Difficulty Level: Medium

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

O O
OH-
C6H5CH + CH3CCH3 ?
heat

O OH

a) C6H5CCH2CHCH3
O O

b) C6H5CCH2CCH3
OH OH

c) C6H5CHCH2CHCH3
O O

d) C6H5CCH2CCH3
O

e) C6H5CH=CHCCH3

Answer: E

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

48

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

O O
?
OH-
O
OH O
O
O O

I II III
O
O O

IV V

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

Answer: E

Topic: Reaction Product

Section: 19.5
Difficulty Level: Medium

49

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55) The product of the following reaction is:

O weak
O + CN base ?
O

O CN
OH CN
O
O
O CN O
I II III
O O NH O
OMe
OMe
OH CN
IV V

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

Answer: D

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

50

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56) The product of the following reaction is:

CN weak
O + ?
CN base

HN CN
OH CN
O
O
O CN NH
I II III
O NH O
CN
OMe
OH CN
IV V

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

Answer: D

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

51

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57) What is the major product of the following reaction?

O
EtO
OEt
O LDA i. O
Q
-78oC ii. H3O+

O O O
OEt O O
OEt
O OEt
O O
I II III
O O
OEt OEt
O O O
IV V

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

Answer: B

Topic: Reaction Products

Section: 19.5
Difficulty Level: Medium

52

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58) What product is formed during the following reaction?

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

Answer: D

Topic: Reaction Products

Section: 19.6
Difficulty Level: Medium

53

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O O

59) When CH3CCH2CH2CH2CH2CH2CCH3 cyclizes in basic solution, which of these compounds

will be formed?

O CH3 O CH3 O CH3 O

CH3 O
C C C
CH3 CH3 O
CH2
CH3

I II III IV V

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

Answer: A

Topic: Reaction Product

Section: 19.6
Difficulty Level: Medium

54

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60) What is the missing reagent?

OH-
?
heat
O

O O

a) CH3CCH2CH2CCH3
O O

b) CH3CCH2CH2CH2CH
O O

c) CH3CCH2CH2CH2CH2CH
O O

d) CH3CCH2CH2CH2COEt
H O

e) O=CCH2CH2CH2CH2COEt

Answer: B

Topic: Predict Reactants

Section: 19.6
Difficulty Level: Medium

61) What product results from the intramolecular aldol reaction of 2,5-hexanedione?

O O O
CH3
CH3 CCH3 CH3 CCH3
CH3 CH3 O O

I II III IV V

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

Answer: A

Topic: Reaction Product

Section: 19.6
Difficulty Level: Medium

55

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

O
NaCN
?
O C2H5OH/CH3COOH

a)
CH3CH2CHCO2C2H5

CN
b) CH3CHCHCO2CN
c) CH3CHCHCN
CH3CHCH2CO2C2H5

d) CN
CN

CH3CH=CHCOC2H5

e) OH

Answer: D

Topic: Reaction Product

Section: 19.7
Difficulty Level: Medium

56

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

O
CH3CH2OH
+ CN - ?
C6H5CH=CHCCH3
CH3COOH

C6H5CH2CHCCH3

a) CN
O

C6H5CHCH2CCH3

b) CN
OH

C6H5CH2CH2CCH3

c) CN
O

d) C6H5CH2CH2CCN
OH

C6H5CHCH=CCH3

e) CN

Answer: B

Topic: Reaction Product

Section: 19.7
Difficulty Level: Medium

57

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64) Which of these is a product of the reaction of C6H5MgBr with

O

C6H5CH=CHCCH3 ?

C6H5CH=CCCH3

a) C 6H 5
OH

C6H5CH=CHCCH3

b) C 6H 5
O

c) C6H5CH=CHCCH2C6H5
O

d) p-C6H5 C6H4 CH=CHCCH3

OC6H5

e) C6H5CH=CHCHCH3

Answer: B

Topic: Predicting Reactants

Section: 19.7
Difficulty Level: Medium

65) What product(s) result from the Claisen condensation carried out with an equimolar mixture
of ethyl acetate and ethyl propanoate?
O O O O O O O O
O O O O

I II III IV

a) I
b) II
c) III
d) IV
e) All of these choices.

Answer: E

Topic: Reaction Products

Section: 19.2

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Difficulty Level: Hard

66) What is the expected product from the following reaction sequence?
O
+
i. N , H
H
?
O ii.
O
iii. H+/H2O
iv. NaOH, heat

N
OH
O O
II III
I
O

O V
IV

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

Answer: C

Topic: Reaction Products

Section: 19.2
Difficulty Level: Hard

59

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67) What final product is obtained when 2,8-nonanedione is treated with base, followed by
reaction with sodium borohydride?
OH OH

O
I II III

OH

O
IV V

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

Answer: A

Topic: Reaction Product

Section: 19.6
Difficulty Level: Hard

60

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68) What final product is obtained when 2,8-nonanedione is treated with base, followed by
reaction with lithium aluminum hydride?
OH OH

O
I II III

OH

O
IV V

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

Answer: A

Topic: Reaction Product

Section: 19.6
Difficulty Level: Hard

61

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69) Predict the major product from the following reaction:

OH
?

O O

OH
OH
OH
I II III
O
O

OH

IV OH
V

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

Answer: B

Topic: Reaction Product

Section: 19.6
Difficulty Level: Hard

62

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

O

EtO
H CN ?
EtOH
(-H2O)
OH
O
O O

O
OH
HO CN O

O
I II III
O

CN CN

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

Answer: E

Topic: Reaction Product

Section: 19.5 and 19.6
Difficulty Level: Hard

63

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

O

EtO DIBAL-H
H CN ?
EtOH -78oC
(-H2O)

O
O O

H O H
H O

I O II O
III
O

CN CN

IV V

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

Answer: C

Topic: Reaction Product

Section: 19.5 and 19.6
Difficulty Level: Hard

64

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

O
EtO
CN
H EtOH
? OH O

O O O OH

CN
HO O O

I II III

CN
CN

IV
V

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

Answer: E

Topic: Reaction Product

Section: 19.5 and 19.6
Difficulty Level: Hard

65

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

O

CN EtO DIBAL-H
H
?
EtOH -78oC
O
O O O O

H
H H O O

I II
III
O

CN
CN

IV
V

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

Answer: C

Topic: Reaction Product

Section: 19.5 and 19.6
Difficulty Level: Hard

66

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74) Predict the major product of the following reaction:

O
O O
OH
+ ?
Ph Ph
Ph Ph

O O OH
Ph Ph Ph

Ph Ph Ph

Ph Ph Ph
Ph Ph Ph
II III
I
O
OH
Ph
Ph

Ph Ph

Ph Ph
Ph
Ph
IV V
a) I
b) II
c) III
d) IV
eV

Answer: B

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

67

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75) In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-

methylbenzaldehyde how many products are possible?

a) 1
b) 2
c) 3
d) 4
e) 5

Answer: C

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

76) In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-

methylbenzaldehyde what is the relationship between the products formed?

a) enantiomers
b) conformational isomers
c) constitutional isomers
d) diastereomers
e) unrelated

Answer: D

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

68

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

O
EtO-, EtOH
C6H5CH + CH3CH2CN ?

a) C6H5CHCHCH2CN
O

C6H5CCHCN

b) CH3
C6H5CH=CCN

c) CH3
OH

d) C6H5CHCH2CH2CN
OH

C6H5CCH2CH2CN

e) OCH2CH3

Answer: C

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

69

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

O
O
EtO
+
CN ?
H EtOH
(-H2O)

O
O O NC
O
CN O

CN
H

I II
III

O
O O
CN
CN

V
IV

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

Answer: B

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

70

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79) What would be the product of the following reaction?

O
S
EtO
H
+
CN ?
EtOH
(-H2O)

O
S S NC
O
CN S

CN
H

I II
III

O
S S
CN
CN

V
IV

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

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

71

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80) What would be the product of the following reaction?

O

EtO
H
+
CN ?
N EtOH
(-H2O)

O
O
NC
CN N

N CN N
H

I II
III

CN
CN
N N

V
IV

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

Answer: B

Topic: Reaction Product

Section: 19.5
Difficulty Level: Hard

72

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81) Predict the product of the following reaction sequence.

i. NaOEt, EtOH
O O O
+ ii. NaOH, heat
O O O iii. H3O+ ?
iv. heat

O
OH
O
O O
O O O O
I II III
OH
HO O
O
O
O O
OH
IV V

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

Answer: B

Topic: Reaction Products

Section: 19.7
Difficulty Level: Hard

73

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82) Consider the synthesis below: What is compound X?

CO2Et
CO2Et i. NaOEt, EtOH CO2Et
+ X
ii. H3O+

a) O=C(OEt)2
b) HCO2Et
c) EtO-CO-CO-OEt
d) CH3CO2Et
e) BrCH2CO2Et

Answer: A

Topic: Synthesis Products and Reactants

Section: 19.2
Difficulty Level: Medium

74

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83) What would be the product of the following sequence?

O
O O i. NaOC2H5, C2H5OH iii. DIBAL-H, -78oC
+ ?
O ii. H3O+ iv. H3O+

O O OH O
H O O
H
I II III

O
H O
H
O O
IV V

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

Answer: A

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

75

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84) What would be the product of the following sequence?

O
O O i. NaOC2H5, C2H5OH iii. NaBH4
+ ?
O ii. H3O+

O O OH O
O O O
O
I II III

O
O O
O
O O
IV V

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

Answer: B

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

76

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85) What would be the product of the following sequence?

O
O O i. NaOC2H5, C2H5OH
+ iii. LAH ?
O ii. H3O+ iv. H3O+

OH OH O
OH O
OH
I II III

O O
OH
O OH
IV V

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

Answer: A

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

77

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86) What would be the product of the following sequence?

O
O O i. NaOC2H5, C2H5OH
+ iii. LAH
ii. H3O+ ?
O iv. H3O+, heat (-H2O)

OH O
OH O OH

I II III

O O
OH
O OH
IV V

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

Answer: C

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

78

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87) What would be the product of the following sequence?

O
O O i. NaOC2H5, C2H5OH iii. NaBH4
+ ?
O ii. H3O+ iv. heat (H2O)

O OH O
O O O
O
I II III

O
O O
O
O O
IV V

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

Answer: A

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

79

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88) What is the expected product from the following reaction sequence?
O O O
+ i. NaOC2H5, C2H5OH iii. DIBAL-H, -78oC
O O ?
ii. H3O+ iv. H3O+

O O
O O
H H
H H O
O O

I II III

H
O O O O
IV V

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

Answer: A

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

80

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89) What is the expected product from the following reaction sequence?
O O O
+ i. NaOC2H5, C2H5OH iii. LAH
O ?
O ii. H3O + iv. H3O+

OH OH
O OH
H O
OH O

I II III

H
OH O OH OH
IV V

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

Answer: A

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

81

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90) Predict the product from the following sequence:

H OH- H3O+ NaBH4
heat CH3OH
?
O (-H2O)

OH O OH (Z and E)

H OH OH

I II III

(Z and E) OH

H H

O V OH
IV

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

Answer: C

Topic: Reaction Sequence

Section: 19.4
Difficulty Level: Medium

82

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

O O OH-
C6H5CH + CH3CH heat

a) C6H5CH2CCH3
O O

b) C6H5CCH2CH
OH OH

c) C6H5CHCH2CH2
O

d) C6H5CH2CH2CH
O

e) C6H5CH=CHCH

Answer: E

Topic: Reaction Sequence:

Section: 19.5
Difficulty Level: Medium

83

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92) The product, C, of the following sequence of reactions,

CH3
OH- H3 O+ NaBH4
CH3CCHO + CH3CH2CHO A B C
(-H2O) CH3OH
CH3

would be:

CH3

CH3CCH=CHCH2CH2OH

a) CH3
CH3

CH3CCH=CCH2OH

b) CH3 CH3
CH3

CH3CCH2CH2CH2OH

c) CH3
CH3

CH3CCH2CH2CH2CH2OH

d) CH3
CH3

CH3CCH2CHCHO

e) CH3 CH3

Answer: B

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

84

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93) Predict the product from the following sequence:

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

Answer: E

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

85

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94) Predict the product from the following sequence:

OH- H3O+ NaBH4
+ H
H ?
heat
S (-H2O)
O
O

O (Z and E)

H S OH S OH
S
O O
II III
I
(Z and E)

OH OH
S S
OH
V
IV

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

Answer: E

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

86

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95) Predict the product from the following sequence:

OH- H3O+ NaBH4

+ H
H ?
heat
N
(-H2O)
O
O

O (Z and E)

N H N OH N OH
O O
II III
I
(Z and E)

OH OH
N N
OH
V
IV

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

Answer: E

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

87

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96) Predict the product from the following sequence:

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

Answer: E

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

88

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

H OH H3O+
H
+ ?
heat
O
O (-H2O)
O

OH
O O
O O O

OH OH
H

II III
I

O
O O O

H
H
V
IV

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

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

89

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

H OH H3O+
H + ?
heat
S
O (-H2O)
O

OH
O O
S S S

OH OH
H

II III
I

O
S S O

H
H
V
IV

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

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

90

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

H OH H3O+
H + ?
N heat
O (-H2O)
O

OH
O O
N N N
OH OH
H

II III
I

O
N N O

H
H
V
IV

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

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

91

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100) What would be the major product, B, of the following reaction sequence?
H

O OH- NaBH4
+ O A B
heat H2O

OH O

OH OH OH
I II (Z and E)
III

OH
OH
(Z and E) V

IV

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

Answer: C

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

92

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101) What would be the major product, B, of the following reaction sequence?
H

O OH- H2 /Ni
+ O A B
heat

OH OH

OH OH OH
I II (Z and E)
III

OH
OH
V
IV

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

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

93

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102) What is the expected product from the following reaction sequence?
O O O
+ i. NaOC2H5, C2H5OH iii. LAH
O O ?
ii. H3O+ iv. H3O+, heat
(-H2O)
OH
O OH
H O
O

I II III

OEt
O OH
IV V

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

Answer: A

Topic: Reaction Sequence

Section: 19.2
Difficulty Level: Medium

94

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103) What would be the final product of the following reaction sequence?
O O
OH-, heat LiAlH4 Final
C6H5CH + CH3CCH3 A
ether Product

a) C6H5CH2CH2CH2CH3
OH O

b) C6H5CHCH2CCH3
O

c) C6H5CH2CH2CCH3
OH

d) C6H5CH=CHCHCH3
OH OH

e) C6H5CHCH2CHCH3

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

95

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104) What would be the product, C, of the following reaction sequence?

O O
OH- H3O+ H2
(CH3)3CCH + CH3CH2CH
A B C
heat Ni

a) (CH3)3CCH2CH2CH2OH
OH O

b) (CH3)3CCHCH2CH2CH
(CH3)3CCH2CHCH2OH

c) CH3
(CH3)3CCH=CCH2OH

d) CH3
O

(CH3)3CCH=CCH

e) CH3

Answer: C

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

96

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105) What would be the product, C, of the following reaction sequence?

O O
OH- H3O+ CH2 P(C6H5)3
(CH3)3CCH + CH3CH2CH A B C
heat

a) (CH3)3CCH2CH2CH2OH
OH

b) (CH3)3CCHCH2CH=CH2
(CH3)3CCH2C=CH2

c) CH3
(CH3)3CCH=CCH=CH2

d) CH3
OH

(CH3)3CCHCHCH=CH2

e) CH3

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Medium

97

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

O
O
EtO DIBAL-H
+
CN
?
H EtOH -78oC
(-H2O)

O
OH
O O
H O
CN O

CN
H

I II
III

O
O O

H
CN

V
IV

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

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

98

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

O
S
EtO DIBAL-H
+
CN ?
H EtOH -78oC
(-H2O)

O
OH
S S
H O
CN S

CN
H

I II
III

O
S S

H
CN

V
IV

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

Answer: D

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

99

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108) What would be the product, B, of the following reaction sequence?

O
EtO-, EtOH H3O+
C6H5CH + CH3CN A (C9H7N) B
heat

a) C6H5CHCHCO2H
O

b) C6H5CCH2CO2H
c) C6H5CH2CH2CO2H
OH

d) C6H5CHCH2CO2H
OH

e) C6H5CHCH2CN

Answer: A

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

100

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109) What would be the product, C, of the following reaction sequence?

O O H3O+, heat NaBH4
OH-
C6H5CH + CH3CH2CH
A B C
25 oC (-H2O) CH3OH

C6H5CCHCH2OH

a) CH3
C6H5CHCHCH2OH

b) HO CH3
O

C6H5CH2CHCH

c) CH3
O

C6H5CH=CCH

d) CH3
C6H5CH=CCH2OH

e) CH3 hi

Answer: E

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

101

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110) What would be the product, C, of the following reaction sequence?

O O H3O+, heat
OH- H2, Ni
C6H5CH + CH3CH2CH
A B C
25 oC (-H2O) high
pressure

C6H5CCHCH2OH

a) CH3
C6H5CH2CHCH2OH

b) CH3
O

C6H5CH2CHCH

c) CH3
O

C6H5CH=CCH

d) CH3
C6H5CH=CCH2OH

e) CH3

Answer: B

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

111) Which of the following statements is true about the anion formed from the reaction of
diethyl malonate with sodium ethoxide?

a) It can react with an ,-unsaturated ester by conjugate addition.

b) It can condense with aldehydes and ketones.
c) It can be alkylated with an alkyl halide.
d) It is resonance stabilized.
e) All of these statements are true.

Answer: E

Topic: Synthesis
Section: 18.1, 18.7, 19.2, 19.4 and 19.7
Difficulty Level: Easy

102

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112) Which compound could be prepared via Dieckmann condensation?

O O O HO
OC2H5 O O

I II III
O O O O
O

IV V

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

Answer: D

Topic: Synthesis
Section: 19.2
Difficulty Level: Medium

103

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113) Which of the following would afford the best synthesis of diethyl phenylmalonate,
O O
C2H5O OC2H5
Ph

a)
O O
Ph Br + C2H5O .. OC2H5
+
Na
b)
O NaOC2H5 O H3O+
Ph +
OC2H5 C2H5O OC2H5 C2H5OH
O O NaOC2H5 H3O+
Ph + OC2H5 C H OH
OC2H5 C2H5O 2 5
c) O
O O NaOC2H5 H3O+
D. Ph +
OC2H5 OC2H5 C2H5OH
e)
O NaOC2H5 H3O+
Ph CHO + 2
H OC2H5 C2H5OH

Answer: B

Topic: Synthesis
Section: 19.2
Difficulty Level: Medium

114) Which reagents would you use to prepare the following substance from ethyl acetoacetate?
O O
Ph

a) i) NaH/DMSO; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat

b) i) NaOEt/EtOH; ii) PhCOCH2Br; iii) OH–/H2O, heat; iv) H3O+; v) heat
c) i) heat; ii) NaOEt/EtOH; iii) PhCOCH2Br
d) i) NaOEt/EtOH; ii) PhCl
e) i) NaOEt/EtOH; ii) PhCOCl; iii) OH–/H2O, heat; iv) H3O+; v) heat

Answer: A

Topic: Synthesis
Section: 19.2
Difficulty Level: Medium

104

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115) 2-Methylcyclohexane-1,3-dione can be synthesized from:

O
CH3MgBr H3O+
I
O
O

II KMnO4, OH

O O
i. NaOEt
III OEt
ii. H3O+

O O
i. NaOEt
IV OEt +
ii. H3O

O O
i. NaOEt
V OEt
ii. H3O+

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

Answer: C

Topic: Synthesis
Section: 19.2 and 19.4
Difficulty Level: Medium

105

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116) 2-Phenylcyclohexane-1,3-dione can be synthesized from:

O
PhMgBr H3O+
I
O
O
Ph
KMnO4, OH
II

O O
Ph i. NaOEt
III OEt ii. H3O+

O Ph O
i. NaOEt
IV OEt ii. H3O+

O O
i. NaOEt
V OEt ii. H3O+
Ph

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

Answer: C

Topic: Synthesis
Section: 19.2 and 19.4
Difficulty Level: Medium

106

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117) Which of the following might be used to synthesize the following substance?
OH
Ph OH

a)
CH3CH2CO2Et H3O+ LiAlH4 H2O
PhCO2Et
NaOEt, EtOH Et2O
b)
Mg H3O+ LiAlH4 H2O
PhCHO + CH3CHBrCH2CO2Et
Et2O Et2O
c)
Mg PhCHO H2O
CH3CHBrCH2CO2Et
Et2O
d) Two of these choices.
e) All of these choices.

Answer: A

Topic: Synthesis
Section: 19.2
Difficulty Level: Hard

118) Which compound could be prepared using a Michael reaction?

O O O HO
OC2H5 O O
I II III
O O O O
OC2H5

IV V

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

Answer: C

Topic: Synthesis
Section: 19.7
Difficulty Level: Hard

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119) Which compound may be prepared using a Mannich reaction?

CO2Et O
CO2H O
CO2Et N

I II III
O O
N
O

IV V

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

Answer: C

Topic: Synthesis
Section: 19.8
Difficulty Level: Hard

120) Which compound may be prepared using a Mannich reaction?

O
CO2Et
CO2H O N
CO2Et

I II III
O O O

IV V

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

Answer: E
Topic: Synthesis
Section: 19.8
Difficulty Level: Hard

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121) Which reagents would be used in a Mannich reaction to synthesize

O
N

O
O
I + + (CH3)2NH
H

O
O
II + + (CH3)3N
H

III + (CH3)3N + base

O
H O
IV + + (CH3)2NH
H

V + (CH3)2NH

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

Answer: D

Topic: Synthesis
Section: 19.8
Difficulty Level: Hard

109

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122) Which reagents would be used in a Mannich reaction to synthesize

O

O O
I + + NH
H

O
O
II + + NH
H

O
III H O
+ + NH
H

O
H O
IV + + NH
H

O
V + NH

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

Answer: D

Topic: Synthesis
Section: 19.8
Difficulty Level: Hard

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123) Which is the only one of these compounds which cannot self-condense in the presence of
dilute aqueous alkali?

a) Phenylethanal
b) Propanal
c) 2-Methylpropanal
d) 3-Methylpentanal
e) 2,2-Dimethylpropanal

Answer: E

Topic: Aldol Reaction

Section: 19.4
Difficulty Level: Medium

124) Which of these compounds cannot self-condense in the presence of dilute aqueous alkali?

a) 3-(4-Nitrophenyl)propanal
b) 2-Methyl-3-pentanone
c) 2-(4-Nitrophenyl)propanal
d) 3-(4-Nitrophenyl)-2-butanone
e) All of these compounds can self-condense.

Answer: E

Topic: Aldol Reaction

Section: 19.4
Difficulty Level: Medium

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125) Which of these is not among the reaction products when a crossed aldol addition occurs
between ethanal and butanal?

OH H

a) CH3CHCH2C=O
OH H

CH3CH2CH2CHCHCH2C=O

b) CH2CH3
OH H

CH3CHCHC=O

c) CH2CH3
OH H

d) CH3CH2CH2CHCH2C=O
OH H

CH3CH2CH2CHCHC=O

e) CH2CH3

Answer: B

Topic: Aldol Reaction

Section: 19.5
Difficulty Level: Medium

126) The aldol condensation product formed from 3-pentanone in the presence of base has the
IUPAC name:

a) 5-Ethyl-4-methyl-4-hepten-3-one
b) 5-Ethyl-4-methyl-5-hepten-3-one
c) 4-Methyl-4-nonen-3,7-dione
d) 3-Ethyl-4-methyl-3-hepten-5-one
e) 3-Ethyl-4-methyl-2-hepten-5-one

Answer: A

Topic: Aldol Reaction

Section: 19.4
Difficulty Level: Hard

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127) What compound results from the aldol cyclization of

O O

CH3CCH2CH2CHCH2CCH3 ?
CH3

CH3 CH3 O
CH3
CH3 O
O O CH3
CH3 CH3

CH3 CH3 CH3

I II III IV

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

Answer: E

Topic: Aldol Reaction

Section: 19.6
Difficulty Level: Medium
O H

128) The aldol cyclization of CH3CCH2CH2CH2C=O produces which of these?

O H H CH3
O O
C CH3 CH3 C=O C=O O O

I II III IV V

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

Answer: D

Topic: Aldol Reaction

Section: 19.6
Difficulty Level: Medium

113

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O O

129) The reaction of CH3CCH2CH2CH2CCH3 with base affords which of these products?

H H O O O O
CH3 C=O CH3 C=O
CH3 CH3

I II III IV V

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

Answer: D

Topic: Aldol Reaction

Section: 19.6
Difficulty Level: Medium

114

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130) If butanal is added slowly to an aqueous solution of sodium hydroxide and 2,2-
dimethylpropanal at 25 C, the principal product is which of these?

OH H

(CH3)3CCHCHC=O

a) CH2CH3
OH H

CH3CH2CH2CHCHC=O

b) CH2CH3
OH

(CH3)3CCHCC(CH3)3

c) O
OH

d) CH3CH2CH2CHC(CH3)3
OH H

CH3CH2CH2CHCHC=O

e) C(CH3)3

Answer: A

Topic: Aldol Reaction

Section: 19.5
Difficulty Level: Hard

131) Which of these is not a reversible process?

a) Base-promoted ester hydrolysis

b) Acid-catalyzed ester hydrolysis
c) Aldol addition
d) Claisen condensation
e) Acetal formation

Answer: A

Topic: General Reactions of Carbonyl Compounds

Sections: 19.2 and 19.4
Difficulty Level: Medium

115

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132) Which reagents would you use to synthesize this compound by an aldol condensation?
O

C6H5CH=CHCC6H5

O O

a) C6H5CH and C6H5CH2CH

O O

b) C6H5CH2CH and C6H5CCH3

O

c) C6H5CH=CHCH and C6H5OH

O O

d) C6H5CCH3 and C6H5CH

O

e) (C6H5)2CuLi and CH2=CHCC6H5

Answer: D

Topic: Predicting Reactants

Section: 19.5
Difficulty Level: Medium

116

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133) Which reagents would you use to synthesize this compound by an aldol condensation?
O

C6H5CH=CCH

C6H5

O O

a) C6H5CH and C6H5CH2CH

O O

b) C6H5CH2CH and C6H5CCH3

O

c) C6H5CH=CHCH and C6H5OH

O O

d) C6H5CCH3 and C6H5CH

O

C6H5CH2Cl and C6H5CHCH

e) ONa

Answer: A

Topic: Predicting Reactants

Section: 19.5
Difficulty Level: Medium

117

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134) What starting compound(s) would you use in an aldol reaction to prepare

OH O O O

O O III
I II

O
O
O

H +
H H
H

O
IV V

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

Answer: D

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

118

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135) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

OH O O O

O O III
I II

O
O
O

+
H H
H

O
IV V

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

Answer: D

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

119

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136) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

H
O O
O

OH O O
I II III

O
O
O O

+
H
H H

IV V

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

Answer: D

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

120

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137) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

O O
O

OH O O
I II III

O
O
O O

+
H

IV V

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

Answer: D

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

121

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138) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

OH O O O

H
H

O O III
I II

O
O
O

H +
H H
H

O
IV V

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

Answer: B

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

122

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139) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

O O O

H
H

OH O O
I II III

O
O
O O

+
H

IV V

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

Answer: B

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

123

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140) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

OH O O O

O O III
I II

O
O
O

+
H H

O
IV V

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

Answer: B

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

124

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141) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:
O

O O O

OH O O
I II III

O
O
O O

IV V

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

Answer: B

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

125

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142) What starting compound(s) would you use in an aldol reaction to prepare as the major
product:

O
O O
H

OH O O
I II III

O
O
O O

IV V

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

Answer: D

Topic: Predicting Reactants

Section: 19.6
Difficulty Level: Medium

126

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143) The Robinson annulation reaction which produces

CH3

uses which of the following as starting materials?

CH3 O CH3
H CH3
HCHO + CH=CH2
+ +
CH2=CHC=O CH2 CH2=CHCCH3 O CH2

I II III

O O O
+ +
CH3CH=CHCCH3 O CH3CH=CHCCH3 O

IV V

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

Answer: B

Topic: Predicting Reactants

Section: 19.7
Difficulty Level: Hard

144) Which of these compounds can react with 4-methylhexanal to afford good yields of the
crossed aldol product?

a) 3-(4-Nitrophenyl)propanal
b) 2-Methyl-3-pentanone
c) 2-(4-Nitrophenyl)propanal
d) 3-(4-Nitrophenyl)-2-butanone
e) None of the above compounds will give good yields of the crossed aldol product with 4-
methylhexanal.

Answer: E

Topic: Crossed Aldol Reaction

Section: 19.5
Difficulty Level: Medium

127

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145) Which of these compounds can react with 4-methylpentanal to afford good yields of the
crossed aldol product?

a) 3-(4-Nitrophenyl)propanal
b) 2-Ethyl-2-methylheptanal
c) 2-(4-Nitrophenyl)propanal
d) 3-(4-Nitrophenyl)-2-butanone
e) None of the above compounds will give good yields of the crossed aldol product with 4-
methylhexanal.

Answer: B

Topic: Crossed Aldol Reaction

Section: 19.5
Difficulty Level: Medium

O
O A O
H2/Ni
B (C8H8O2)
H OH, warm
OH
(-H2O)

146) Consider the synthesis above in answering this question. What is compound A?

a) Butanone
b) Butanal
c) Propanal
d) 1-Butanol
e) 2-Methylpropanal

Answer: C

Topic: Reagents, Intermediates, and Spectroscopy

Section: 19.5
Difficulty Level: Medium

128

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O
O A O
H2/Ni
B (C8H8O2)
H OH, warm
OH
(-H2O)

147) What is the intermediate B in the synthesis shown above?

OH H
O O O

OH OH O

I II III

O
O O

OH OH

IV V

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

Answer: C

Topic: Reagents, Intermediates, and Spectroscopy

Section: 19.5
Difficulty Level: Medium

Question type: fill-in-the-blank

148) When planning a reaction with an ester and an alkoxide ion, it is important to use an
alkoxide that has the same alkyl group as the ester in order to avoid ___.

Answer: transesterification

Topic: General Information

Section: 19.2
Difficulty Level: Easy

129

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149) An aldol reaction that starts with two different carbonyl compounds is called a ___.

Answer: crossed aldol reaction

Topic: General
Section: 19.5
Difficulty Level: Easy

Question type: Essay

150) When ,-unsaturated aldehydes and ketones react with nucleophiles, they do so in one of
two ways. What are the two ways?

Answer: simple or 1,2-addition; conjugate or 1,4-addition

Topic: General
Section: 19.7
Difficulty Level: Easy

Question type: fill-in-the-blank

151) When ,-unsaturated aldehydes and ketones react with nucleophiles, simple addition is
favored when ___ nucleophiles are used, while conjugate addition is preferred by ___
nucleophiles.

Answer: strong; weaker

Topic: General
Section: 19.7
Difficulty Level: Easy

152) The sequence of a Michael addition followed by an intramolecular aldol condensation is

known as a ___.

Answer: Robinson annulation

Topic: General
Section: 19.7
Difficulty Level: Medium

130

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153) Esters frequently react in the presence of alkoxides by a reaction called the ___
condensation.

Answer: Claisen

Topic: Claisen condensation

Section: 19.2
Difficulty Level: Easy

Question type: Essay

154) Explain why ethyl 2-methylpropanoate does not undergo the usual Claisen condensation.
Answer: In order for Claisen condensation to occur efficiently, there must be at least two
hydrogen atoms alpha to the ester group. Although only one hydrogen appears to be substituted
during the reaction, a second alpha hydrogen must originally be present, otherwise the overall
reaction has an unfavorable equilibrium.

Topic: Claisen Condensation

Section: 19.2
Difficulty Level: Medium

131

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155) Suggest a reasonable synthetic strategy to carry out the following transformation.

OH
O
O
Br OH
Br Br

Answer:
O O
O EtO-, EtOH
O O
Br Br Br

i. LAH
ii. H2O

OH

OH
Br Br

Topic: Synthetic Strategy

Section: 19.2
Difficulty Level: Medium

132

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156) Suggest a reasonable synthetic strategy to carry out the following transformation.
O
O O
Br Br Br

O O
O EtO-, EtOH
O O
Br Br Br

H3O+, heat

O OH

O O
Br Br Br Br

Answer:

Topic: Synthetic Strategy

Section: 19.2
Difficulty Level: Medium

157) An intramolecular Claisen condensation is known as a ___.

Answer: Dieckmann condensation

Topic: Dieckmann Condensation

Section: 19.2
Difficulty Level: Easy

158) Explain why diethyl pentanedioate does not undergo a Dieckmann condensation.

Answer: Dieckmann condensation of diethyl pentanedioate would afford a four-membered ring.

This ring is expected to have a considerable degree of ring strain and can account for the
observed lack of reactivity.
O
O O O
O O
O

Topic: Dieckmann Condensation

Section: 19.2
Difficulty Level: Medium

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159) Predict what is likely to happen when ethyl 6-oxooctanoate is treated with NaOEt, followed
by acid work-up.

Answer: A cyclization similar to Dieckmann condensation is likely to occur, giving 2-

propanoylcyclopentanone as the major product:
O O

O
O
O

Topic: Dieckmann Condensation

Section: 19.2
Difficulty Level: Hard

160) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
O
O i. EtO-, EtOH ?
O +
O ii. H3O
iii. NaBH4, H2O

O
O i. EtO-, EtOH NaBH4
O
O ii. H3O+ O H2O HO
Answer: O O O O

Topic: Multistep Reaction Sequence

Section: 19.2
Difficulty Level: Medium

161) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
O
O i. EtO-, EtOH ?
O
O
ii. H3O+
iii. DIBAL-H (-78oC)

O
O i. EtO-, EtOH DIBAL-H
O
O
ii. H3O+ O (-78oC) O
O O H
Answer: O

Topic: Multistep Reaction Sequence

Section: 19.2
Difficulty Level: Hard

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

O i. EtO-, EtOH
?
O +
ii. H3O
iii NaOH, H2O, heat

O
O i. EtO-, EtOH

O ii. H3O+ O

O
O
iii NaOH, H2O, heat
(-CO2)

Answer: O

Topic: Multistep Reaction Sequence

Section: 19.2
Difficulty Level: Hard

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

CO2Et i. NaOEt, EtOH

?
CO2Et ii. H3O+
iii NaOEt, EtOH
iv. CH3Br
v. NaOH, H2O, heat

EtO EtO
O O

CO2Et i. NaOEt, EtOH

iii NaOEt, EtOH
O iv. CH3Br O
CO2Et ii. H3O+

v. NaOH, H2O, heat

-CO2 O

Answer:

Topic: Multistep Reaction Sequence

Section: 19.2
Difficulty Level: Hard

164) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
O
O i. EtO-, EtOH ?
O
O
ii. H3O+
iii. EtO-, EtOH
iv. CH3I
v. NaOH/H2O, heat
vi. H3O+, heat

O
O i. EtO-, EtOH iii. EtO-, EtOH v. NaOH/H2O, heat
O vi. H3O+, heat (-CO2)
O
ii. H3O+ O iv. CH3I O O
O O O
Answer: O

Topic: Multistep Reaction Sequence

Section: 18.6 and 19.2
Difficulty Level: Hard

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165) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
i. O3
ii. Zn/H+
?
-
iii. OH
iv. heat, -H2O

Answer:
CHO
i. O3 iii. OH-
ii. Zn/H+ iv. heat, -H2O
CHO

CHO

Topic: Multistep Reaction Sequence

Section: 8.17 and 19.6
Difficulty Level: Hard

166) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
i. O3
ii. Zn/H+
?
iii. OH-
iv. heat, -H2O

Answer:
CHO
i. O3 iii. OH-
ii. Zn/H+ iv. heat, -H2O
CHO

CHO

Topic: Multistep Reaction Sequence

Section: 8.17 and 19.6
Difficulty Level: Hard

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

O
i. OH- ?
O
ii.
heat

O
OH-
O heat
Answer: O O

Topic: Multistep Reaction Sequence

Section: 13.11 and 19.6
Difficulty Level: Hard

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

O
i. OH- ?
O ii. O

heat

O
O -
OH
O
O heat
Answer: O O

Topic: Multistep Reaction Sequence

Section: 13.11 and 19.6
Difficulty Level: Hard

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

O
i. OH-
O
?
ii.

heat

O
OH-
O heat
Answer: O O

Topic: Multistep Reaction Sequence

Section: 13.11 and 19.6
Difficulty Level: Hard

170) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
i. NH , p-TsOH
O
?
O
ii. O , EtOH, reflux

iii. H2O

NH O
:

O N N Br
O
+
p-TsOH EtOH, reflux
O
O
H2O

O
O

Answer: O

Topic: Multistep Reaction Sequence

Section: 19.7
Difficulty Level: Hard

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171) Suggest a reasonable synthetic strategy to carry out the following transformation.
O
OH
Br
OCH3
O Br2, FeBr3 O i. O
-
EtO , EtOH O OCH3
Br ii. H3O+, heat Br

i. LAH
ii. H2O

OH
Answer: Br

Topic: Reaction Sequence and Predicting Reagents

Section: 19.5
Difficulty Level: Medium

172) When acetaldehyde is reacted with 3 equivalents of formaldehyde under alkaline

conditions, followed by treatment with sodium borohydride, the product formed shows the
following spectra data:

IR: broad peak at 3326 cm−1

1
H NMR: singlet at 3.45 
singlet at 4.78  (found to be exchangeable)

Predict a reasonable structure for this product.

HO OH

Answer: HO OH

Topic: Reaction Products and Spectroscopy

Section: 19.5
Difficulty Level: Hard

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173) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
O
i. , EtO-, EtOH
CN ?
+
ii.H3O , heat

O
CN
H3O+
Answer: EtO-, EtOH CN heat CO2H

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

174) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
O
i. EtO-, EtOH ?
O
ii. CH3CH2NH2

H
O
EtO-, EtOH CH3CH2NH2 N
O

Answer: O O

Topic: Reaction Sequence

Section: 19.6 and 19.7
Difficulty Level: Hard

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175) What is the final product of the following reaction sequence? Give structural details of all
significant intermediates.
O
+
i. N , H
H ?
O ii.
O
+
iii. H /H2O
iv. NaOH, heat

Answer:
O
+
i. N , H ii.
H O
+
iii. H /H2O
O N O
O
O
iv. NaOH, heat

-H2O

Topic: Multistep Reaction Sequence

Section: 19.2, 19.4, 19.6 and 19.7
Difficulty Level: Hard

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176) In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles of 4-

methylbenzaldehyde draw the possible products that form.

Answer:

Topic: Reaction Sequence

Section: 19.5
Difficulty Level: Hard

177) What is the product of the following reaction?

O
OH-
O ?

O
OH-
O
Answer: O

Topic: Reaction Products

Section: 19.6
Difficulty Level: Medium

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178) There are several possible cyclization products that might be formed when 5-methyl-6-
oxoheptanal undergoes intramolecular aldol condensation in presence of ethoxide. Draw the
structures of all these possible products. Comment on which of these is likely to be the major
product, clearly explaining your rationale.

Answer: There are 3 possible products (I-III) that might be formed from the 3 theoretically
possible enolates. The rationale for predicting the major product is the following: i) aldehydes
are typically more reactive toward nucleophilic addition than ketones, so I and III are more likely
than II; ii) since 5-membered rings are formed much more readily than 7-membered rings, I is
more likely than III.

O O O
O -
O EtO , EtOH HO HO HO

I II III
major product

Topic: Reaction Products

Section: 19.6
Difficulty Level: Hard

179) Predict the major product from the following reaction:

O

OH
?

Answer:
O

OH

Topic: Reaction Product

Section: 19.6
Difficulty Level: Hard

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180) In the aldol cyclization reaction of the following compound, predict the major product
formed and explain your choice.

OH
H
?
heat

O
Answer:

Of the two possible products formed, shown below as 1 and 2, 2 is the major product expected
since condensation occurs with the more reactive aldehyde carbon acting as the electrophile.

O O

H
1 2

Topic: Reaction Product

Section: 19.6
Difficulty Level: Hard

181) What is the product of the following reaction?

O
i. LDA, THF
ii. ?
O

O O OH
i. LDA, THF
ii. O
Answer:

Topic: Reaction Products

Section: 19.7
Difficulty Level: Hard

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182) Suggest a reasonable mechanism for the following reaction.

O O O
O
O i.EtONa, O
O + O O
O EtOH, 25oC O
O ii. H3O+

Answer:

Topic: Reaction Mechanisms

Section: 19.7
Difficulty Level: Hard

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