A mechanism for the conjugate addition of a nucleophile to acrylonitrile and to nitroethylene has to be proposed with the help of resonance forms. Concept introduction: Standard nucleophilic addition to a carbonyl group is 1 , 2 -addition. In the first step, nucleophile adds to carbonyl group to give alkoxide. Then, protonation of alkoxide takes place. 1 , 4 -addition is Michael addition. The nucleophile adds to beta carbon of α , β -unsaturated system to give enolate ion followed by protonation at oxygen to give an enol or on carbon to give a keto form.

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Chapter 22.18, Problem 22.55P

Interpretation Introduction

Interpretation:

A mechanism for the conjugate addition of a nucleophile to acrylonitrile and to nitroethylene has to be proposed with the help of resonance forms.

Concept introduction:

Standard nucleophilic addition to a carbonyl group is 1,2-addition. In the first step, nucleophile adds to carbonyl group to give alkoxide. Then, protonation of alkoxide takes place. 1,4-addition is Michael addition. The nucleophile adds to beta carbon of α,β-unsaturated system to give enolate ion followed by protonation at oxygen to give an enol or on carbon to give a keto form.

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