Chapter 11 Reactions of Alcohols ?2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Chapter 11 * Types of Alcohol Reactions Dehydration to alkene Oxidation to aldehyde, ketone Substitution to form alkyl halide Reduction to alkane Esterification Tosylation Williamson synthesis of ether Chapter 11 Chapter 11 * Summary Table Chapter 11 Chapter 11 * Oxidation States Easy for inorganic salts: CrO42- reduced to Cr2O3. KMnO4 reduced to MnO2. Oxidation: Gain of O, O2, or X2; loss of H2. Reduction: Gain of H2 (or H-); loss of O or O2; and loss of X2. The gain or loss of H+, H2O, HX, etc. is neither an oxidation nor a reduction. Chapter 11 Chapter 11 * Oxidation States of Carbons Chapter 11 Chapter 11 *