Extent of Enolization.

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Presentation transcript:

Extent of Enolization

Regiochemistry of Enolization Thermodynamic base, more stable enolate Kinetic base, Less substituted enolate Thermodynamic base, more stable enolate “Middle” protons are most acidic due to additional resonance stability involving both carbonyls

Substitution-type Reactions

Aldol-type Reactions

Claisen-type Reactions

Michael-type Reactions

Tandem and Related Reactions

Reactions of Enamines

Mechanism (a)

Mechanism (b)

Mechanism (c)

Mechanism (d)

Synthesis (a) Essentially Claisen condensation followed by acetoacetate synthesis

Synthesis (b)

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