Keto-enol tautomerism is one of the most important aspects of the reactivity of aldehydes or ketones. The movement from an aldehyde or ketone to its enol isomer involves proton exchange between an ?-carbon and the carbonyl oxygen of an aldehyde or ketone. Although continuous interchange between the carbonyl compound and its enol does exist normally in neutral conditions, keto-enol tautomerism can be catalyzed by the addition of either acid or base. The particular events differ between the cases, but the same net intramolecular process occurs with either acid or base catalyzed enol formation, the transfer of a proton from the α-carbon to the carbonyl oxygen, accompanied by the shifting of electron pairs up toward oxygen, forming the vinylic alcohol known as an enol. α halogenation, the haloform reaction, and aldol condensation, among other reactions, involve the reactivity of the enol form, which, in these processes, is approached by an electrophile at the α-carbon. In another instance, the presence of enolate anion intermediate contributes to the special reactivity of α-β unsaturated carbonyl compounds to nucleophiles at the β carbon.
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