Clicker Questions

Chapter 18
Reactions at the
-Carbon
of Carbonyl
Compounds
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
2014 Pearson Education, Inc.

Which is the correct order of decreasing

acidity (increasing pKa)?

A. 4 > 3 > 2 > 1 > 5

B. 3 > 2 > 1 > 4 > 5
C. 5 > 4 > 2 > 1 > 3

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D. 1 > 2 > 3 > 4 > 5

E. 3 > 1 > 2 > 4 > 5

Which is the correct order of decreasing

acidity (increasing pKa)?

pKa = 17

20

26

45

A. 4 > 3 > 2 > 1 > 5

D. 1 > 2 > 3 > 4 > 5
B. 3 > 2 > 1 > 4 > 5
E. 3 > 1 > 2 > 4 > 5
C. 5 > 4 > 2 > 1 > 3
Loss of the most acidic hydrogen forms the most highly
stabilized conjugate bases.

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Alpha halogenation of a ketone can be

accomplished using _________.
A. Br2, acid catalyst
B. Br2, base catalyst
C. 1. LDA 2. Br2
D. NaBr, H2O, heat
E. all but D

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Alpha halogenation of a ketone can be

accomplished using _________.
A. Br2, acid catalyst
B. Br2, base catalyst
C. 1. LDA 2. Br2
D. NaBr, H2O, heat
E. all but D

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Enols and enolates,

form under basic or
acidic conditions and
can be halogenated.

Which compound is the likely starting material

for the following reaction?
A.

B.

C.

D.

E.

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Which compound is the likely starting material

for the following reaction?
A.

B.

C.

D.

E.

Addition of Br2 to E under acidic conditions

gives an alpha-bromoketone, which
undergoes nucleophilic substitution by
CH3CO2 to give the observed product.

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Which method can not be used to form an

enolate ion from a ketone?
A. KOH, ethanol
B. NaOCH2CH3 / ethanol
C. LDA
D. Na / NH3
E. NaNH2

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Which method can not be used to form an

enolate ion from a ketone?
A. KOH, ethanol
B. NaOCH2CH3 / ethanol
C. LDA
D. Na / NH3
E. NaNH2

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Sodium in ammonia does

not provide the strong base
required for enolate ion
formation.

What is the major product of the following

reaction?

C.

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A.

B.

D.

E.

What is the major product of the following

reaction?

C.

A.

B.

D.

E.

This is an aldol condensation. Rapid dehydration is caused

by conjugation with the benzene rings.

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A Michael reaction __________________.

A.
B.
C.
D.

forms a 1,5-dicarbonyl compound

forms a beta-hydroxyaldehyde or ketone
forms a cyclic beta-keto ester
forms a methyl ketone with three more carbons than the
alkyl halide
E. forms a carboxylic acid with two more carbons than the
alkyl halide

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A Michael reaction __________________.

A.
B.
C.
D.

forms a 1,5-dicarbonyl compound

forms a beta-hydroxyaldehyde or ketone aldol addition
forms a cyclic beta-keto ester Dieckmann condensation
forms a methyl ketone with three more carbons than the
alkyl halide acetoacetic ester synthesis
E. forms a carboxylic acid with two more carbons than the
alkyl halide malonic ester synthesis

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What is the major product of the following

reaction?
O

HO

A.

B.

OH

heat
O

O
O

O
OH

C.

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D.

E.

What is the major product of the following

reaction?
O

HO

A.

B.

OH

heat
O

O
O

O
OH

C.

D.

E.

Compounds C and D are also formed but the final product is E.

This is a Robinson annulation reaction.

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What type of reaction was most likely used to

prepare the following compound?

?
A.
B.
C.
D.
E.

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Aldol condensation
Acetoacetic ester synthesis
Claisen condensation
Malonic ester synthesis
Robinson annulation

What type of reaction was most likely used to

prepare the following compound?
O

Br

Alkylation followed by
hydrolysis and
decarboxylation gives
the product.

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1. base
2. H3O+, heat
Br

A.
B.
C.
D.
E.

Aldol condensation
Acetoacetic ester synthesis
Claisen condensation
Malonic ester synthesis
Robinson annulation

What type of reaction was most likely used to

prepare the following compound?

?
A.
B.
C.
D.
E.

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Aldol condensation
Acetoacetic ester synthesis
Mixed Claisen condensation
Malonic ester synthesis
Robinson annulation

What type of reaction was most likely used to

prepare the following compound?
OCH 2CH3
O
O
H

+
OCH2CH3

Mixed Claisen
condensations work best
when only one partner
has acidic hydrogens.

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1. CH3CH2O2. H3O+

CHO
OCH2CH 3
O

A.
B.
C.
D.
E.

Aldol condensation
Acetoacetic ester synthesis
Mixed Claisen condensation
Malonic ester synthesis
Robinson annulation

What is the major product of the following

reaction?

A.

C.

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B.

D.

E.

What is the major product of the following

reaction?

A.

C.

B.

D.

E.

This is a Dieckmann condensation followed by alkylation,

and decarboxylation of a beta-keto acid.

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