a) CH 3 CO 2 Et + CH 3 CH 2 CO 2 Et Interpretation: The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given. 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 give: The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Question

Provide the principle organic product for the following reactions. If more than one product is formed indicate which one you expect to be the major product.

Answer 1

Question

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

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Provide the principle organic product for the following reactions. If more than one product is formed indicate which one you expect to be the major product.

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Predict the product. Draw the structure(s) of the major organic product(s) formed in the following reactions. Please indicate stereochemistry if appropriate.

Answer 2

Question

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

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Answer 3

Question

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

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Answer 4

Question

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

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Answer 5

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

Answer 6

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Answer 7

Chapter 23.SE, Problem 58AP

Interpretation Introduction

a) CH₃CO₂Et + CH₃CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.

Answer 8

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Answer 9

Interpretation Introduction

b) C₆H₅CO₂Et + C₆H₅CH₂CO₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.

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 give:

The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.

Answer 10

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Answer 11

Interpretation Introduction

c) EtOCO₂Et + cyclohexanone

Interpretation:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.

Answer 12

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

Answer 13

Interpretation Introduction

d) C₆H₅CHO + CH₃CH₂Et

Interpretation:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.

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 give:

The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.

Answer 14

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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 the Claisen condensation reaction, which involves a reversible condensation between two molecules of an ester that has -hydrogen atoms.

Chapter 23 Solutions