Stable lithium enolate, less substituted if an unsymmetrical ketone
Other reagents: sodium hydroxide or alkoxides with also make enolates (see aldol condensations, for example). However, the acid-base equilibrium is well-balanced and thus the catalyst and both enolates are present if an unsymmetrical ketone is used and any of these may react, especially with a halide.
Other substrates: For esters, the base catalyst must be the conjugate base of the alcohol part of the ester. 1,3-dicarbonyl compounds are more acidic (in fact they existpredominantly in the enol form), so very weak bases can be used to convert them to their enolates.
McMurry 22.5, Fessenden 17.4B, Schmid 17.11
McMurry 23.12, Fessenden 17.5, Schmid 17.14
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Last update February 1999
View more information: https://tigerweb.towson.edu/ladon/orgrxs/enolate/enolsy.htm