formation & reaction of amide enolates

Amides are weakly acidic at the alpha-carbon with a pKa of around 30. LDA is an adequate base for the formation of amide enolates through deprotonation. Note that only tertiary amides in which the amide nitrogen has two R-groups can be deprotonated to make an enolate. The resulting enolate is nucleophilic and can attack carbonyl compounds, like aldehydes. The resulting beta-hydroxy amide and be further reacted with base to generate an alpha,beta-unsaturated amide. Amide enolates can also undergo reaction with alkyl halides through an SN2 reaction to give an alkylated amide.