Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified. Concept introduction: The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule. To identify: The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

Question

What product is obtained when the following compound undergoes two successive elimination reactions?

Answer 1

Question

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

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Answer 2

Question

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

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Answer 3

Question

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

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Answer 4

Question

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

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Answer 5

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

Answer 6

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

Answer 7

Chapter 23.SE, Problem 24VC

Interpretation Introduction

Interpretation:

Given that the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule. The reactant, the leaving group and the product are to be identified.

Concept introduction:

The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.

To identify:

The reactant, the leaving group and the product involved in preparing the compound represented by the model is an intermediate formed by addition of an ester enolate ion to a second ester molecule.

Answer 8

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Answer 19

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

Solution Summary: The author explains that the Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has -hydrogen atoms.

Chapter 23 Solutions