Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
Book Icon
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.

Blurred answer
Students have asked these similar questions
Which of the esters cannot undergo Claisen self‑condensation?
Which of the following compounds is easier to decarboxylate?
Which of the following does not support a nucleophilic attack of a covalent catalysis? a. Hydroxyl b. Sulfhydryl c. Imidazole d. Amino e. Methyl

Chapter 13 Solutions

Essential Organic Chemistry, Global Edition

Knowledge Booster
Background pattern image
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning