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Section 21 - Carbonyl Alpha-Substitution Reactions

Carbonyl Alpha-Substitution Reactions - Section 21 of Organic Chemistry Notes is 17 pages in length (page 21-1 through page 21-17) and covers ALL you'll need to know on the following lecture/book topics:


SECTION 21 – Carbonyl Alpha- Substitution Reactions


21-1 -- The Enolization Reaction
  · Keto-Enol Tautomerization
  · Enols of β-Dicarbonyls
  · Percent Enolization (%) of Various Compounds at Equilibrium
21-2 -- Acid-Catalyzed Enolization Reaction
21-2 -- Base-Catalyzed Enolization Reaction

  · Resonance Stabilization
  · Alpha-Hydrogens (α-Hydrogens) are Relatively Acidic
21-4 -- Relative Acidities of the α-Hydrogen
21-5 -- Five Reactions of Enols and Enolates: pp. 21-5 through 21-14

  · D2O-Exchange
  · Halogenation Reaction
  · Haloform Reaction
  · Alkylation Reaction
  · Preparation of α-Alkylated Carbonyl Compounds
21-5 -- D2O-Exchange
  · Usually Base-Catalyzed
21-5 -- Halogenation Reaction
  · Under Acidic Conditions
  · Under Basic Conditions
21-7 -- Haloform Reaction
  · Occurs with Methyl Ketones (RCOCH3)
  · Iodoform Test for Methyl Ketones
21-8 -- Alkylation Reactions – Occur via the Enolate Ion
  · Strong Base Required to Deprotonate the Carbonyl Compound
  · Strong Non-Nucleophilic Bases: NaH, iPr2N-, Lithium Diisopropyl Amide (LDA)
  · Enolates Can Be Alkylated at Either the Carbon (C) or the Oxygen (O)
  · Formation of Different Enolates – Kinetic Control vs. Thermodynamic Control
  · Using Triethylamine, Et3N, and/or Trimethylsilyl Chloride, Me3SiCl, or “TMS-Cl”
21-12 -- Preparation of α-Alkylated Carbonyl Compounds
21-12 -- Preparation of α-Alkylated Esters and Carboxylic Acids

  · Direct Preparation vs. Malonic Ester Synthesis
  · Diethyl Malonate = “Malonic Ester”
  · Saponification Step and Decarboxylation (-CO2) Step in the Mechanism
21-13 -- Preparation of α-Alkylated Ketones
  · Direct Preparation vs. Acetoacetic Ester Synthesis
  · Ethyl Acetoacetate = “Acetoacetic Ester”
21-15 -- Retrosynthetic Analysis
  · Definition of Retrosynthetic Analysis and the Art of “Working Backwards”
21-16 -- The Selenation Reaction
  · Useful in Making α,β-Unsaturated Carbonyl Compounds
  · Phenylselenyl Bromide, PhSeBr
  · The Oxidation Step [ox] Can Occur via H2O2 or O3
  · Selenides and Selenoxides

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