Base catalysed enolate formation (Enolization)

Enolates are formed by deprotonation of a carbonyl compound by a base. This is base catalysed enolization.

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The proton that is removed by the base is perpendicular to the plane of the carbonyl group so that the breaking σ-bond is lined up with the π-bond.

The same mechanism applies to aldehydes, ketones, acids, esters, amides, nitriles etc.

Back to Conjugate addition summary

D. Seebach, Angew. Chemie Int. Ed. English, 1988, 27, 1624–1654.

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