Although aldol condensation is one of the most important organic reactions, capable of forming new C-C bonds, its mechanism has never been fully established. It is now concluded that the rate-limiting step in the base-catalyzed aldol condensation of a substituted benzaldehyde with a substituted acetophenone, to produce a chalcone, is the final loss of hydroxide and formation of the C-C double bond. This conclusion is based on a study of the partitioning ratios of the intermediate ketols and on the solvent kinetic isotope effects, whereby the condensations are faster in D<sub>2</sub>O than in H<sub>2</sub>O.

Complete mechanism of aldol condensation

251st National Meeting (2016)

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