Reactions at the α Carbon of Carbonyl Compounds: Enols and Enolates

Flashcards covering key terms and concepts from Chapter 18 on reactions involving enols and enolates.

α Carbon

The carbon atom that is adjacent to the carbonyl group in a carbonyl compound.

α Hydrogens

Hydrogen atoms that are attached to the α carbon and are considered weakly acidic.

Enolate Anions

Reactive species formed by the deprotonation of an enol, involving resonance stabilization.

Tautomers

Isomers that can interconvert by exchanging a hydrogen and a double bond; for example, keto and enol forms.

Tautomerization

The process of interconversion between tautomers.

Keto form

The form of a compound that contains a carbonyl group (C=O).

Enol form

The form of a compound that contains a hydroxyl group (-OH) connected to a carbon-carbon double bond.

Halogenation at α Carbon

A reaction involving the introduction of halogens to the α carbon of a carbonyl compound.

Base-Catalyzed Enolization

The formation of an enol from a carbonyl compound through basic conditions.

Lithium Enolates

Enolates that are generated using lithium bases, commonly used for selective alkylation.

Racemization

A process that generates a racemic mixture from an achiral enol or enolate.

Acetoacetic Ester Synthesis

A method for synthesizing methyl ketones using acetoacetic ester.

Malonic Ester Synthesis

A reaction used to synthesize substituted acetic acids using malonic ester.

Enamines

Compounds formed from the reaction of a carbonyl compound with a 2° amine, useful in various synthetic applications.

Michael Addition

A nucleophilic addition reaction that involves a conjugate addition to an α,β-unsaturated carbonyl compound.