Fundamentals 1. Claisen enolates a) A novice organic chermistry student took ethyl propanoate and proposed that the following nucleophile could be made by reacting ethyl propanoate with NaOEt. Explain why the structure above is not a legitimate enolate ion. b) Now write the correct enolate ion, and then explain, by drawing appropriate resonance structures, why the enolate ion you wrote is a more correct nucleophile than the one drawn in part a) above.

Fundamentals 1. Claisen enolates a) A novice organic chermistry student took ethyl propanoate and proposed that the following nucleophile could be made by reacting ethyl propanoate with NaOEt. Explain why the structure above is not a legitimate enolate ion. b) Now write the correct enolate ion, and then explain, by drawing appropriate resonance structures, why the enolate ion you wrote is a more correct nucleophile than the one drawn in part a) above.

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles

Section: Chapter Questions

Problem 2Q

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