
Keto-enol tautomerization • enolization • “normal” aldehydes and ketones • Keq = ~ 10-8
Stabilized aldehydes and ketones • -diketones • Keq = ~ 10
Acidity of carbonyl compounds • enolate ion formation • pKa = ~ 16-20
Ester Enolates • pKa = ~22
Reactions of enolates: • The Aldol Condensation
Decarboxylation of Malonic Acids and b-Ketoacids • Malonic acid Acetoacetic acid
Acetoacetic ester synthesis of ketones • ethyl acetoacetate