SECTION 18 ² ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION
REACTIONS
18-1 -- Nomenclature of Aldehydes and Ketones
x Common Names of Aldehydes and Ketones
x Substituents or ´Branchesµ
x IUPAC Names of Aldehydes and Ketones
18-3 -- Strength of the Carbonyl Bond (C=O)
18-4 -- Spectroscopy of Aldehydes and Ketones
x IR, 1H NMR, and 13C NMR
18-5 -- Nucleophilic Addition Reactions of the Carbonyl Group
x 7 Reactions to be Examined in Detail
x Why are Aldehydes More Reactive than Ketones?
x Effect of Alkyl Groups (Branches)
18-6 -- The Hydration Reaction
x Mechanism of Base-Catalyzed Hydration
x Mechanism of Acid-Catalyzed Hydration
18-8 -- Formation of Acetals (2 Alkoxy Groups, -OR, on a Carbon)
x Acid-Catalyzed Mechanism
x Use of Acetals as Protecting Groups
18-11 -- Cyanohydrin Formation (-CN and -OH on a Carbon)
x Can be Acid-Catalyzed or Base-Catalyzed
x Mechanism of Cyanohydrin Formation
18-11 -- Hydride Reactions
x Use of Lithium Aluminum Hydride, LiAlH4 (or ´LAHµ)
x Use of Sodium Borohydride, NaBH4
18-12 -- Grignard Additions to the Carbonyl
x Addition of R·-MgX to the Carbonyl (R2C=O)
18-12 -- Reactions of the Carbonyl (C=O) with Amines
x Yields Different Products Depending on the Type of Amine (1° or 2°)
x Mechanisms: Formations of Imines, Carbinolamines, and Enamines
x Tautomerization is Observed
18-14 -- Imine Derivatives
x Hydrazone, Semicarbazone, and Oxime
18-15 -- Reduction of Carbonyls to Methylene Groups (-CH2-)
x Wolff-Kishner Reaction Requires Basic Conditions
x Clemmenson Reduction (Zn/Hg in aqueous HCl)
x Reduction of Thioacetals
18-16 -- The Wittig Reaction
www.OChemNotes.com
x Phosphonium Ylides (´The Wittig Reagentµ)
x Mechanism of Ylide Preparation
x Why is the Reaction not Stereospecific?
18-18 -- Oxidation of Aldehydes
x Oxidation Using Chromium Reagents (PCC, H2CrO4, Jones Reagent, etc«)
x Oxidation Using the Tollens Reagent
18-19 -- Preparation of Aldehydes
x Via Ozonolysis of Alkenes
x Via Hydroboration of Terminal Alkynes (HCƱCR)
x Via Oxidation of Alcohols Using PCC
x Via the Use of Mild Reducting Agents (´:H-´)
18-20 -- Preparation of Ketones
x Via Ozonolysis of Alkenes
x Via Friedel-Crafts Acylation (AlCl3 as Catalyst)
x Via Alkyne Hydration
x Via Oxidation of Alcohols Using PCC or H2CrO4
x Via Addition of ´:R-´ to Acid Chlorides
18-21 -- Conjugate Additions of Nucleophiles to Ĵ,ǀ-Unsaturated Carbonyls
x ´Michael Additionµ
x Resonance-Stabilized Enolate Ion
x Protonation and Tautomerization
18-22 -- Some Nucleophiles Add Directly to the Carbonyl Carbon
x Less Basic Nucleophiles vs. Strongly Basic Nucleophiles
x Kinetic vs. Thermodynamic Control
x Resonance-Stabilization of the Negative (-1) Charge
www.OChemNotes.com
SECTION 18 – ALDEHYDES and KETONES:
NUCLEOPHILIC ADDITION REACTIONS
Were the FREE Section 18 Notes Useful?
Want the FULL VERSION of the Section 18 Notes?
Download Them Instantly for Only $6.99 at:
OChemNotes.com
www.OChemNotes.com