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This article explores the carbonyl α-substitution reactions using enols, including their reactions, limitations, and advantages. It also discusses the preparation of enolates and their reactions, including the reactions of ketones, nitriles, esters, and active methylene compounds.
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I. Carbonyl a-Substitution using Enols 2. Reactions of Enols c. a-Halogenation of aldehydes and ketones d. The Hell-Volhard-Zolinskii reaction p. 696
I. Carbonyl a-Substitution using Enols 3. Limitations of Enols a. Equilibrium p. 696
I. Carbonyl a-Substitution using Enols 3. Limitations of Enols a. Equilibrium b. Reactivity p. 696
II. Carbonyl a-Substitution using Enolates 1. Advantages of Enolates a. Reactivity p. 696
Electron Distribution in Enolates Resonance Hybrid Fig. 17-5, p. 703
II. Carbonyl a-Substitution using Enolates 1. Advantages of Enolates a. Reactivity b. Quantitative formation p. 696
II. Carbonyl a-Substitution using Enolates 2. Preparation of Enolates a. pKa’s of important a-hydrogens
II. Carbonyl a-Substitution using Enolates 2. Preparation of Enolates a. pKa’s of important a-hydrogens b. The Bases Used [6] Li+-CH2CH2CH2CH3 CH3CH2CH2CH3 44 100% p. 696
II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates a. The reactive site p. 696
II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates a. The reactive site b. Reactions of ketones i. thermodynamic and kinetic enolates. p. 696
II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates a. The reactive site b. Reactions of ketones i. thermodynamic and kinetic enolates. c. Reactions of nitriles and esters p. 696
II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates d. Active methylene compounds i. Malonic ester synthesis p. 696
II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates d. Active methylene compounds ii. DAM amino acid synthesis p. 696