(a) Interpretation: The complete, detailed mechanism for the given reaction and the major product are to be drawn. Concept introduction: In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester. If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

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Answer 1

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 2

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 3

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 4

Question

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

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Answer 5

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 6

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Answer 7

Chapter 21, Problem 21.62P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base, in a Claisen condensation, is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction and the major product are to be drawn.

Concept introduction:

In a Claisen condensation reaction, an ester with at least two α protons is treated with a strong base, followed by acid workup, to produce a β- keto ester. In these reactions, the base deprotonates the α carbon of one ester to produce an ester enolate anion, which acts as a nucleophile and attacks the carbonyl carbon of the second ester.

If the base in a Claisen condensation is nucleophilic, it should be identical to the alkoxide leaving group on the ester. If the solvent can be deprotonated to become strongly nucleophilic, it should be the conjugate acid of the base that is used.

In a crossed Claisen condensation reaction, the enolate anion that acts as the nucleophile derives from an ester that is different from the ester it attacks.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 21 - Prob. 21.1P Ch. 21 - Prob. 21.2P Ch. 21 - Prob. 21.3P Ch. 21 - Prob. 21.4P Ch. 21 - Prob. 21.5P Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - Prob. 21.8P Ch. 21 - Prob. 21.9P Ch. 21 - Prob. 21.10P

Solution Summary: The author illustrates the complete, detailed mechanism for the given reaction and the major product using the reactants given on the basis of Claisen condensation reaction mechanism.

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