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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Carbonyl Alpha-Substitution Reactions

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