Section 18 - Aldehydes and Ketones

Aldehydes and Ketones -- Section 18 of Organic Chemistry Notes is 24 pages in length (page 18-1 through page 18-24) and covers ALL you'll need to know on the following lecture/book topics:


SECTION 18 – Aldehydes and Ketones


18-1 -- Nomenclature of Aldehydes and Ketones
  · Common Names of Aldehydes and Ketones
  · Substituents or “Branches”
  · IUPAC Names of Aldehydes and Ketones
18-3 -- Strength of the Carbonyl Bond (C=O)
18-4 -- Spectroscopy of Aldehydes and Ketones
  · IR, 1H NMR, and 13C NMR
18-5 -- Nucleophilic Addition Reactions of the Carbonyl Group
  · 7 Reactions to be Examined in Detail
  · Why are Aldehydes More Reactive than Ketones?
  · Effect of Alkyl Groups (Branches)
18-6 -- The Hydration Reaction
  · Mechanism of Base-Catalyzed Hydration
  · Mechanism of Acid-Catalyzed Hydration
18-8 -- Formation of Acetals (2 Alkoxy Groups, -OR, on a Carbon)
  · Acid-Catalyzed Mechanism
  · Use of Acetals as Protecting Groups
18-11 -- Cyanohydrin Formation (-CN and -OH on a Carbon)
  · Can be Acid-Catalyzed or Base-Catalyzed
  · Mechanism of Cyanohydrin Formation
18-11 -- Hydride Reactions
  · Use of Lithium Aluminum Hydride, LiAlH4 (or “LAH”)
  · Use of Sodium Borohydride, NaBH4
18-12 -- Grignard Additions to the Carbonyl
  · Addition of R’-MgX to the Carbonyl (R2C=O)
18-12 -- Reactions of the Carbonyl (C=O) with Amines
  · Yields Different Products Depending on the Type of Amine (1° or 2°)
  · Mechanisms: Formations of Imines, Carbinolamines, and Enamines
  · Tautomerization is Observed
18-14 -- Imine Derivatives
  · Hydrazone, Semicarbazone, and Oxime
18-15 -- Reduction of Carbonyls to Methylene Groups (-CH2-)
  · Wolff-Kishner Reaction Requires Basic Conditions
  · Clemmenson Reduction (Zn/Hg in aqueous HCl)
  · Reduction of Thioacetals
18-16 -- The Wittig Reaction
  · Phosphonium Ylides (“The Wittig Reagent”)
  · Mechanism of Ylide Preparation
  · Why is the Reaction not Stereospecific?
18-18 -- Oxidation of Aldehydes
  · Oxidation Using Chromium Reagents (PCC, H2CrO4, Jones Reagent, etc…)
  · Oxidation Using the Tollens Reagent
18-19 -- Preparation of Aldehydes
  · Via Ozonolysis of Alkenes
  · Via Hydroboration of Terminal Alkynes (HCΞCR)
  · Via Oxidation of Alcohols Using PCC
  · Via the Use of Mild Reducting Agents (“:H-“)
18-20 -- Preparation of Ketones
  · Via Ozonolysis of Alkenes
  · Via Friedel-Crafts Acylation (AlCl3 as Catalyst)
  · Via Alkyne Hydration
  · Via Oxidation of Alcohols Using PCC or H2CrO4
  · Via Addition of “:R-“ to Acid Chlorides
18-21 -- Conjugate Additions of Nucleophiles to α,β-Unsaturated Carbonyls
  · “Michael Addition”
  · Resonance-Stabilized Enolate Ion
  · Protonation and Tautomerization
18-22 -- Some Nucleophiles Add Directly to the Carbonyl Carbon
  · Less Basic Nucleophiles vs. Strongly Basic Nucleophiles
  · Kinetic vs. Thermodynamic Control
  · Resonance-Stabilization of the Negative (-1) Charge

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