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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Aldehydes and Ketones

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