Enolate Attack in Ketone Alkylation

Ketone alkylation with enolate ions starts when a strong base such as lithium diisopropylamide, or LDA, removes an alpha proton. This forms an enolate ion, which is stabilized by resonance. In the resonance hybrid, negative charge is shared between the carbonyl oxygen and the alpha carbon.

An eno...

A ketone, in the presence of a strong base like LDA, loses an acidic α hydrogen to give an enolate ion, which is stabilized by resonance.

Its hybrid structure reveals negative charges on the carbonyl oxygen and the α carbon.

The ambident enolate nucleophile can attack an electrophile via two potential reactive sites: the anionic ox...