CH3CH2CH2 Organic Chemistry,7th Edition HH L.G.Wade,Jr. Chapter 11 Reactions of Alcohols Copyright 2010 Pearson Education,Inc
Chapter 11 Reactions of Alcohols Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7th Edition L. G. Wade, Jr. CH3CH2CH2 C H H Br O H H
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 2
Chapter 11 2 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
Summary Table TABLE 11-1 Types of Reactions of Alcohols R-OH type of reaction Product dehydration R一OH alkenes R-OH esterification R-OCR esters oxidation R-OH ketones,aldehydes, acids tosylation R-OH R-OTs substitution R-OH R-X tosylate esters halides (good leaving group) reduction (1)form alkoxide R-OH R-H R-OH R-O-R' alkanes (2)RX ethers Copyright 2010 Pearson Prentice Hall,Inc. Chapter 11 3
Chapter 11 3 Summary Table
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 4
Chapter 11 4 Oxidation States • Easy for inorganic salts: ▪ CrO4 2- 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
Oxidation States of Carbons OXIDATION H OH 0 R-C-H IO,R-C-H,R-C-H,R-C-OH +H0 aldehyde no bonds to H 0 R-C-R'10L,R-C-R'1O R-C-R'(0o furtber oxidntion) H +H,O alkane secondary alcohol ketone no bonds to O one bond toO two honds toO H OH R一C-R'IoLR一C一R'ualyno fher oxidation) R“ R" alkane tertiary alcohol no bonds to O one bond to O REDUCTION Copyright 2010 Pearson Prentice Hall.Inc Chapter 11 5
Chapter 11 5 Oxidation States of Carbons