Section 18 - Aldehydes and Ketones: Nucleophilic Addition Reactions
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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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