text: Deprotonation of enolizable ketones, aromatic alcohols, aldehydes, and esters gives enolates.  With strong bases, the deprotonation is quantitative.  Typically enolates are generated from using lithium diisopropylamide (LDA).
  Often, as in conventional Claisen condensations, Mannich reactions, and aldol condensations, enolates are generated in low concentrations with alkoxide bases.  Under such conditions, they exist in low concentrations, but they still undergo reactions with electrophiles. Many factors affect the behavior of enolates, especially the solvent, additives (e.g. diamines), and the countercation (Li vs Na, etc.).  For unsymmetrical ketones, methods exist to control the regiochemistry of the deprotonation.
  The deprotonation of carbon acids can proceed with either kinetic or thermodynamic reaction control. For example, in the case of phenylacetone, deprotonation can produce two different enolates. LDA has been shown to deprotonate the methyl group, which is the kinetic course of the deprotonation.  To ensure the production of the kinetic product, a slight excess (1.1 equiv) of lithium diisopropylamide is used, and the ketone is added to the base at −78 °C.  Because the ketone is quickly and quantitatively converted to the enolate and base is present in excess at all times, the ketone is unable to act as a proton shuttle to catalyze the gradual formation of the thermodynamic product. A weaker base such as an alkoxide, which reversibly deprotonates the substrate, affords the more thermodynamically stable benzylic enolate.
  Enolates can be trapped by acylation and silylation, which occur at oxygen. Silyl enol ethers are common reagents in organic synthesis as illustrated by the Mukaiyama aldol reaction: