Alcohol

Chapter 20 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Carboxylic Acids Chapter 20 * Introduction The functional group of carboxylic acids consists of a C?O with ?OH bonded to the same carbon. Carboxyl group is usually written ?COOH. Aliphatic acids have an alkyl group bonded to ?COOH. Aromatic acids have an aryl group. Fatty acids are long-chain aliphatic acids. Chapter 20 Chapter 20 * Common Names Many aliphatic acids have historical names. Positions of substituents on the chain are labeled with Greek letters starting at the carbon attached to the carboxylic carbon. Chapter 20 Chapter 20 * IUPAC Names Remove the final -e from alkane name, add the ending -oic acid. The carbon of the carboxyl group is #1. Chapter 20 Chapter 20 * Unsaturated Acids

Chapter 11 * Reaction with HBr ?OH of alcohol is protonated. ?OH2+ is good leaving group. 3? and 2? alcohols react with Br- via SN1. 1? alcohols react via SN2. H 3 O + B r - R O H R O H H R B r Chapter 11 Chapter 11 * Reaction with HCl Chloride is a weaker nucleophile than bromide. Add ZnCl2, which bonds strongly with ?OH, to promote the reaction. The chloride product is insoluble. Lucas test: ZnCl2 in concentrated HCl: 1? alcohols react slowly or not at all. 2? alcohols react in 1-5 minutes. 3? alcohols react in less than 1 minute. Chapter 11 Chapter 11 * SN2 Reaction with the Lucas Reagent Primary alcohols react with the Lucas reagent (HCl and ZnCl2) by the SN2 mechanism. Reaction is very slow. The reaction can take from several minutes to several days. Chapter 11 *

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 *

Chapter 10 ?2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Structure and Synthesis of Alcohols Chapter 10 * Structure of Water and Methanol Oxygen is sp3 hybridized and tetrahedral. The H?O?H angle in water is 104.5?. The C?O?H angle in methyl alcohol is 108.9?. Chapter 10 Chapter 10 * Classification of Alcohols Primary: carbon with ?OH is bonded to one other carbon. Secondary: carbon with ?OH is bonded to two other carbons. Tertiary: carbon with ?OH is bonded to three other carbons. Aromatic (phenol): ?OH is bonded to a benzene ring. Chapter 10 Chapter 10 * Examples of Classifications C H 3 C C H 3 C H 3 O H * C H 3 C H O H C H 2 C H 3 * C H 3 C H C H 3 C H 2 O H * Primary alcohol Secondary alcohol Tertiary alcohol Chapter 10 Chapter 10 *