User:Benjah-bmm27/degree/2/PJW

Introduction
"Difunctional Carbonyl Compounds", Dr Paul Wyatt.

Common dicarbonyls

 * Diketone
 * Malonates, e.g. dimethyl malonate, diethyl malonate
 * Other 1,3-dicarbonyls, e.g. ethyl acetoacetate

Reactions and synthesis of dicarbonyls

 * Claisen condensation makes 1,3-dicarbonyls
 * Keto-enol tautomerism in dimedone 95% enol (c.f. cyclohexanone 0.004% enol and ethyl acetoacetate 7.5% enol)
 * Acetoacetic ester synthesis
 * Knoevenagel condensation
 * Decarboxylation: NaOH then H+, heat (via cyclic 6-membered transition state)
 * Krapcho decarboxylation (LiI, wet DMSO)
 * Control groups
 * Double deprotonation of 1,3's with KNH2
 * Enones: conjugate (1,4) addition (e.g. Michael reaction) vs. direct (1,2) addition
 * Hard and soft nucleophiles and electrophiles
 * Michael reaction, nucleophilic conjugate addition, Gilman reagents
 * Dithianes (hard nucleophile at carbonyl carbon)
 * Nef reaction
 * McMurry reaction
 * Darzens reaction
 * Benzoin condensation
 * Acyloin condensation
 * Pinacol coupling reaction
 * Robinson annulation: ChemTube3D animation
 * OsO4: Upjohn dihydroxylation

Might have been mentioned

 * Dieckmann condensation