The Michael reaction is a conjugate addition reaction where a nucleophile adds to an α,β-unsaturated carbonyl compound.
Example:
Consider the reaction between diethyl malonate (a nucleophile) and methyl acrylate (an α,β-unsaturated carbonyl compound) in the presence of a base like sodium ethoxide.
Step 1: The base deprotonates diethyl malonate to form a carbanion.
CH2(COOEt)2+NaOEt→[CH(COOEt)2]−Na++EtOH
Step 2: The carbanion attacks the β-carbon of methyl acrylate (conjugate addition).
[CH(COOEt)2]−+CH2=CHCOOMe→(EtOOC)2CH−CH2−CH−−COOMe
Step 3: The resulting enolate is protonated.
(EtOOC)2CH−CH2−CH−−COOMe+EtOH→(EtOOC)2CH−CH2−CH2−COOMe+EtO−
This reaction forms a new carbon-carbon bond, extending the carbon chain.