Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 13.8, Problem 18P
Interpretation Introduction

Interpretation:

Esters that cannot undergo Claisen Condensation have to be identified.

Concept Introduction:

Reaction of an ester having an α hydrogen with one equivalent of a base to yield a β keto ester.

Mechanism for Claisen Condensation:

Essential Organic Chemistry, Global Edition, Chapter 13.8, Problem 18P

  • A base abstracts a proton from the αcarbon forms enolate ion.
  • The enolate ion gets attached to the carbonyl carbon of another ester.
  • The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

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Essential Organic Chemistry, Global Edition

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