UC San Diego
The Complete Mechanism of an Aldol Condensation
- Author(s): Perrin, CL
- Chang, K-L
- et al.
Published Web Locationhttps://doi.org/10.1021/acs.joc.6b00959
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 benzaldehydes with acetophenones, to produce chalcones, 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 D2O than in H2O, regardless of substitution.
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