Alpha Carbon Chemistry

McMurry Ch 22, 23; Klein Ch 21

Alpha-Halogenation of Aldehydes/ Ketones under acidic conditions

Alpha-Halogenation of Aldehydes/ Ketones under basic conditions

Haloform Reactions

Acid-Catalyzed tautomerization

Base-Catalyzed Tautomerization

HVZ Reaction (Alpha-Halogenation of Carboxylic Acids)

Acetoacetic Ester Synthesis

*forming substituted derivates of acetone

Malonic Ester Synthesis

*forming substituted derivatives of carboxylic acids

Direct alkylation (of ketones, esters, and nitriles)

*uses LDA over R-X as a reagent

Aldol Addition

Aldol Ketone Addition- Reverse Reaction

Aldol Condensation

Performing aldol condensations with ketones at high temperatures gives…. at low temperatures….

a high yield of aldol condensation products; low yield of aldol addition products

Intramolecular Aldol Condensation

Claisen Condensation

Crossed Claisen Condensations between two esters

Crossed Claisen Condensation between an ester and a ketone

LDA can be used in a Claisen Condensation to form 1 major product when….

both carbonyls have alpha hydrogens

Diekmann Cyclization (intramolecular Claisen Condensation)

Micheal Reaction

Robinson Annulation Reaction

Stork Reaction