Deck 23: Ester Enolates and the Claisen Condensation: Synthesis of B-Dicarbonyl Compounds; Acyl Anion Equivalents

Question 1

What missing reactant would be required to provide the product shown?

A)

B)

C)

D)

E) None of these would work.

Answer 1

Question 2

Which of the following would be the most acidic?

A)

B) CH₃CH₂CO₂CH₃
C)

D)

E)

Answer 2

Question 3

What problem is encountered in the synthesis of ethyl acetoacetate (shown below)if sodium methoxide is used rather than sodium ethoxide?

A) Sodium methoxide is too weak a base to cause this reaction to occur.
B) The condensation proceeds further to give tri-carbonyl products.
C) The reaction would produce some of both the methyl ester and the ethyl ester.
D) Sodium methoxide is too insoluble in methanol to promote the reaction.
E) Sodium methoxide is not basic enough to drive the reaction to completion.

Answer 3

The reaction would produce some of both the methyl ester and the ethyl ester.

Question 4

Which of the following reaction sequences will affect the following transformation?

A)

B)

C)

D)

E)

Question 5

What product would be expected to result from the reaction sequence shown?

A)

B)

C)

D)

E)

Question 6

What would be the expected product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 7

Predict the products of the following reaction.

A)

B)

C)

D)

E) None of these.

Question 8

Predict the major product of the following reaction?

A)

B)

C)

D)

E) No significant reaction occurs.

Question 9

What factors contribute to the stability of the following structure?

A) structure has a 6 $\pi$ electron aromatic system
B) stabilized by conjugation between C=C and C=O
C) C=C is generally more stable than C=O
D) structure has intramolecular hydrogen bonding
E) More than one of the above are true.

Question 10

What would result from the reaction shown below?

A)

B)

C)

D)

E)

Question 11

Which of the following compounds will not readily undergo decarboxylation (loss of CO₂)upon heating in an appropriate solvent?

A)

B)

C)

D)

E)

Question 12

What product would result from the following reaction sequence?

A)

B)

C)

D)

E)

Question 13

Predict the major organic product of the following reaction.

A)

B)

C)

D)

E) The reaction does not occur.

Question 14

Predict the major product of the following reaction.

A)

B)

C)

D)

E)

Question 15

The Dieckmann reaction is best described by which of the following statements?

A) Intermolecular Aldol Condensation
B) Intramolecular Aldol Condensation
C) Intermolecular Claisen Condensation
D) Intramolecular Claisen Condensation
E) Michael Addition followed by intramolecular Aldol

Question 16

To which side,if any,would the following equilibrium lie?

A) To the left
B) To the right
C) Equally to the left and right
D) Reaction cannot occur at all
E) Equilibrium favors a different product

Question 17

Why is the following reaction typically done?

A) To protect the aldehyde against oxidation
B) To render the molecule inert to organometallic reagents
C) To make the aldehyde CH more acidic
D) To render the molecule more fragrant
E) To protect the aldehyde against reduction

Question 18

What would be the organic product of the following reaction?

A) 2 HO₂CCH₂CO₂H
B) 2 CH₃C(=O)CH₃
C) 2 CH₃CO₂H
D) HO₂CCH₂C(=O)O₂CCH₂C(=O)O₂CCH₂CO₂H
E) No reaction occurs.

Question 19

Predict the major product of the following reaction.

A)

B)

C)

D)

E)

Question 20

Predict the major organic product of the following reaction.

A)

B)

C)

D)

E)

Question 21

Which of the following processes involves loss of one carbon as carbon dioxide?

A) Claisen condensation
B) Michael addition
C) Malonic ester synthesis
D) None involve loss of CO₂.
E) All involve loss of CO₂.

Question 22

Which of the indicated hydrogens would be the most acidic?

A) Hydrogens a
B) Hydrogens b
C) Hydrogens c
D) Hydrogens d
E) Hydrogens e

Question 23

What product do you expect from the following reaction?

A)

B)

C)

D)

E)

Question 24

After treatment with aqueous base + heat,followed by acidification to pH 2 followed by heating,which carbon in the molecule below would be lost as carbon dioxide?

A) Carbon a
B) Carbon b
C) Carbon c
D) Carbon d
E) Carbon e

Question 25

What product do you expect from the following reaction?

A)

B)

C)

D)

E) no reaction

Question 26

What product do you expect from the following reaction?

A)

B)

C)

D)

E)

Question 27

What product do you expect from the following reaction?

A)

B)

C)

D) Some of these would be formed.
E) None of these would be formed.

Question 28

Which would be the most acidic proton in the molecule below?

A) Protons a
B) Proton b
C) Proton c
D) Protons d
E) Protons e

Question 29

What would be the expected product of the following reaction sequence?

A)

B)

C)

D)

E)