UH ORGANIC CHEMISTRY
Chapter 22: enol & enolates Reactions I
Brief Summary
- Carbonyl Labeling
- alpha, beta, gamma, delta
- Carbonyl Acidity
- Ketone, Esters, di-ester, beta-keto ester
- Tautomerization of Enol-Keto (Ch. 9)
- Alpha Reactions
- Halogens: Br2/ethanoic Acid
- Ketone Reactant
- Special: Haloform Reaction
- HVZ: PBr3/Br2 ; H2O
- Carboxylic Acid Reactant
- Halogens: Br2/ethanoic Acid
- Alpha Alkylation Reactions (Ketone, Esters, Nitriles)
- General: LDA (Bulky); R-X
- With Aldehyde: Use Enamine (Stork Synthesis)
- Dicarbonyl Compounds
- Malonic & Acetoacetic Ester Synthesis
- NaOEt/EtOH ; R-X; Decarboxylate
- Malonic & Acetoacetic Ester Synthesis
- Condensation Reactions
- Aldol (Aldehydes &/OR Ketones)
- Cross & Intramolecular Aldol
- H3O+/heat --> Enone (E1CB Mech.)
- Cross & Intramolecular Aldol
- Claisen (Ketone &/OR Ester)
- Cross & Intramolecular Claisen
- Can Decarboxylate (H3O+/180C)
- Cross & Intramolecular Claisen
- Aldol (Aldehydes &/OR Ketones)