The mechanism for the given conversion has to be proposed. Concept introduction: When two molecules of an ester undergo condensation is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile. A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base. The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester. A crossed-claisen condensation is also a condensation reaction between a ketone and an ester. Primarily one product will form from crossed-claisen condensation when one of the ketone or easter do not have any alpha hydrogens.

Question

Propose a detailed reaction mechanism for the following conversion

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19, Problem 19.35P

Interpretation Introduction

Interpretation:

The mechanism for the given conversion has to be proposed.

Concept introduction: When two molecules of an ester undergo condensation is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.

A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.

The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.

A crossed-claisen condensation is also a condensation reaction between a ketone and an ester. Primarily one product will form from crossed-claisen condensation when one of the ketone or easter do not have any alpha hydrogens.

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19, Problem 19.35P

Interpretation Introduction

Interpretation:

The mechanism for the given conversion has to be proposed.

Concept introduction: When two molecules of an ester undergo condensation is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.

A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.

The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.

A crossed-claisen condensation is also a condensation reaction between a ketone and an ester. Primarily one product will form from crossed-claisen condensation when one of the ketone or easter do not have any alpha hydrogens.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19, Problem 19.35P

Interpretation Introduction

Interpretation:

The mechanism for the given conversion has to be proposed.

Concept introduction: When two molecules of an ester undergo condensation is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.

A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.

The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.

A crossed-claisen condensation is also a condensation reaction between a ketone and an ester. Primarily one product will form from crossed-claisen condensation when one of the ketone or easter do not have any alpha hydrogens.

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See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 19, Problem 19.35P

Interpretation Introduction