Virtual Textbook of Organic Chemistry

http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm#info



contents

Functional Group Reactions
Alkanes

Combustion
Substitution (of H by halogen)
Practice Problems

Alkenes

Electrophilic Additions
Strong Brønsted Acids
Lewis Acids (non-Proton Electrophiles)
Electrophilic Halogen Reagents
Other Electrophilic Reagents
Reduction
Oxidation
Radical Additions
Allylic Substitution
Practice Problems
Dienes
Addition Reactions
Diels-Alder Cycloaddition
Practice Problems

Alkynes

Addition Reactions
Hydrogenation
Electrophiles
Hydration & Tautomerism
Hydroboration
Nucleophilile Addition & Reduction
Acidity of Terminal Alkynes (Substitution of H)
Practice Problems

Alkyl Halides

General Reactivity
Substitution(of X)
SN2 Mechanism
SN1 Mechanism
Elimination (of HX)
Summary of Substiution vs. Elimination
Substitution by Metals
Elimination Reactions of Dihalides
Practice Problems

Alcohols

Nomenclature
Reactions of Alcohols
Substitution of the Hydroxyl H
Substitution of the Hydroxyl Group
Elimination of Water
Oxidation of Alcohols
Reactions of Phenols
Acidity of Phenols
Ring Substitution of Phenols
Oxidation to Quinones
Practice Problems

Ethers

Nomenclature
Preparation of Ethers
Reactions of Ethers
Acid Cleavage
Peroxide Formation
Epoxide Reactions
Practice Problems

Thiols & Sulfides

Sulfur Analogs of Alcohols & Ethers

Benzene & Derivatives

Electrophilic Substitution
A Substitution Mechanism
Reactions of Substituted Benzenes
Reaction Characteristics
Reactions of Disubstituted Rings
Reactions of Substituent Groups
Nucleophilic Substitution, Elimination & Addition Reactions
Practice Problems

Amines

Nomenclature & Structure
Properties of Amines
Boiling Point & Solubility
Basicity of Nitrogen Compounds
Acidity of Nitrogen Compounds
Important Reagent Bases
Reactions of Amines
Electrophilic Substitution at Nitrogen
Preparation of 1º-Amines
Preparation of 2º & 3º-Amines
Practice Problems
Reactions with Nitrous Acid
Reactions of Aryl Diazonium Intermediates
Elimination Reactions of Amines
Oxidation States of Nitrogen
Practice Problems

Phosphines

Phosphorus Analogs of Amines

Aldehydes & Ketones

Nomenclature of Aldehydes & Ketones
Occurrence of Aldehydes & Ketones
Natural Products
Synthetic Preparation
Properties of Aldehydes & Ketones
Reversible Addition Reactions
Hydration & Hemiacetal Formation
Acetal Formation
Imine Formation
Enamine Formation
Cyanohydrin Formation
Irreversible Addition Reactions
Complex Metal Hydrides
Organometallic Reagents
Carbonyl Group Modification
Wolff-Kishner Reduction
Clemmensen Reduction
Hydrogenolysis of Thioacetals
Oxidations
Reactions at the α-Carbon
Mechanism of Electrophilic α-Substitution
The Aldol Reaction
Ambident Enolate Anions
Alkylation of Enolate Anions
Practice Problems

Carboxylic Acids

Nomenclature of Carboxylic Acids
Natural Products
Related Derivatives
Physical Properties
Acidity
Preparation of Carboxylic Acids
Reactions of Carboxylic Acids
Salt Formation
Substitution of Hydroxyl Hydrogen
Substitution of the Hydroxyl Group
Reduction & Oxidation
Practice Problems

Carboxylic Derivatives

Physical Properties
Nomenclature
Reactions of Carboxylic Acid Derivatives
Acyl Group Substitution
Mechanism
Reduction
Catalytic Reduction
Metal Hydride Reduction
Diborane Reduction
Reaction with Organometallic Reagents
Practice Problems
Reactions at the α Carbon
Acidity of α C–H
The Claisen Condensation
Synthesis Applications
Practice Problems