ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Chapter 22, Problem 59P
Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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Chapter 22 Solutions

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