Base-catalysed enolization

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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 ketones, acids, esters, amides, nitriles etc.

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