Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 19.SE, Problem 51MP
Interpretation Introduction

Interpretation:

A mechanism for the following reaction of an α,β- unsaturated ester is to be proposed.

Organic Chemistry, Chapter 19.SE, Problem 51MP

Concept introduction:

The steps involved in the conversion are i) Nucleophilic attack of the amine on the carbon on the α,β- unsaturated ester ii) Proton abstraction from the acid iii) A proton exchange from N to O iv) Another nucleophilic attack of N on the carbonyl carbon v)Another proton exchange from N to O vi) Loss of methanol and a proton.

To propose:

A mechanism for the reaction of an α,β- unsaturated ester with methylamine.

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Chapter 19 Solutions

Organic Chemistry

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