Organic Chemistry

9.

Reactions of Alcohols, Ethers, and Epoxides

9.1.

9.1.1.

Structure and Classification

9.1.2.

Physical Properties

9.1.3.

Acidity and Basicity

9.1.4.

Conversion to Alkyl Halides

9.1.4.1.

Reaction with Hydrogen Halides

9.1.4.2.

Reaction with Thionyl Chloride

9.1.4.3.

Reaction with Phosphorus Tribromide

9.1.5.

Dehydration Reactions

9.1.5.1.

Acid-Catalyzed Dehydration

9.1.5.2.

9.1.5.3.

Regioselectivity

9.1.5.4.

9.1.6.

Oxidation Reactions

9.1.6.1.

Primary Alcohols

9.1.6.1.1.

9.1.6.1.2.

To Carboxylic Acids

9.1.6.2.

Secondary Alcohols

9.1.6.2.1.

9.1.6.3.

Tertiary Alcohols

9.1.6.4.

Oxidizing Agents

9.1.6.4.1.

Chromium-Based Reagents

9.1.6.4.2.

9.1.6.4.3.

Swern Oxidation

9.1.6.4.4.

9.2.

9.2.1.

Structure and Properties

9.2.2.

Synthesis of Ethers

9.2.2.1.

Williamson Ether Synthesis

9.2.2.2.

Acid-Catalyzed Dehydration

9.2.3.

Reactions of Ethers

9.2.3.1.

Cleavage by Strong Acids

9.2.3.2.

9.3.

9.3.1.

Structure and Properties

9.3.2.

Synthesis of Epoxides

9.3.2.1.

9.3.2.2.

Intramolecular Cyclization

9.3.3.

Ring-Opening Reactions

9.3.3.1.

Acid-Catalyzed Ring Opening

9.3.3.2.

Base-Catalyzed Ring Opening

9.3.3.3.

Regioselectivity

9.3.3.4.

Stereochemistry

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8. Substitution and Elimination Reactions

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10. Aromatic Compounds and Their Reactions