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Carbonyl α-Substitution using Enols: Reactions, Limitations, and Advantages

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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Carbonyl α-Substitution using Enols: Reactions, Limitations, and Advantages

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  1. 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

  2. I. Carbonyl a-Substitution using Enols 3. Limitations of Enols a. Equilibrium p. 696

  3. I. Carbonyl a-Substitution using Enols 3. Limitations of Enols a. Equilibrium b. Reactivity p. 696

  4. II. Carbonyl a-Substitution using Enolates 1. Advantages of Enolates a. Reactivity p. 696

  5. Electron Distribution in Enolates Resonance Hybrid Fig. 17-5, p. 703

  6. II. Carbonyl a-Substitution using Enolates 1. Advantages of Enolates a. Reactivity b. Quantitative formation p. 696

  7. II. Carbonyl a-Substitution using Enolates 2. Preparation of Enolates a. pKa’s of important a-hydrogens

  8. 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

  9. II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates a. The reactive site p. 696

  10. 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

  11. 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

  12. II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates d. Active methylene compounds i. Malonic ester synthesis p. 696

  13. II. Carbonyl a-Substitution using Enolates 3. Reactions of Enolates d. Active methylene compounds ii. DAM amino acid synthesis p. 696

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