Section 21 - Carbonyl Alpha-Substitution Reactions
Purchase Section 21 Notes
To purchase and instantly download ALL 17 pages of "Section 21 - Carbonyl Alpha-Substitution Reactions," simply follow the link below.
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
The first 7 pages of "Section 21 Notes" are FREE. To view the notes, simply click the button below:
Purchase Section 21 Notes
To purchase and instantly download ALL 17 pages of "Section 21 - Carbonyl Alpha-Substitution Reactions," simply follow the link below.