CH3CH2CH2 Organic Chemistry,6th Edition H HH L.G.Wade,Jr. Chapter 11 Reactions of Alcohols Jo Blackburn Richland College,Dallas,TX Dallas County Community College District ©2006，Prentice Hall
CH3CH2CH2 C H H Br O H H _ + Chapter 11 Reactions of Alcohols Jo Blackburn Richland College, Dallas, TX Dallas County Community College District © 2006, Prentice Hall Organic Chemistry, 6th Edition L. G. Wade, Jr
CH:CH2CH2 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
CH3CH2CH2 C H H Br O H H _ + 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 =>
CH3CH2CH2 .8H .-0 H HH Summary Table TABLE 11-1 Types of Reactions of Alcohols R-OH type of reaction Product dehydration esterification R一OH alkenes R一OH R-0- esters oxidation R-OH ketones.aldehydes. acids tosylation R一OH R-OTs substitution R一OH R一X tosylate esters halides (good leaving group) reduction (1)form alkoxide R-OH R—H R一OH R一O-R' (2)R'X alkanes ethers Copyright 2005 Pearson Prentice Hall,Inc. Chapter 11 3 =>
CH3CH2CH2 C H H Br O H H _ + Chapter 11 3 Summary Table =>
CH:CH2CH2 8 H Br---- H H Oxidation States Easy for inorganic salts >CrO42-reduced to Cr2O3 >KMnO4 reduced to MnO2 Oxidation:loss of H2,gain of O,O2,or X2 Reduction:gain of H2 or H,loss of O,O2, or X2 Neither:gain or loss of H+,H2O,HX => Chapter 11 4
CH3CH2CH2 C H H Br O H H _ + Chapter 11 4 Oxidation States • Easy for inorganic salts ➢CrO4 2- reduced to Cr2O3 ➢KMnO4 reduced to MnO2 • Oxidation: loss of H2 , gain of O, O2 , or X2 • Reduction: gain of H2 or H- , loss of O, O2 , or X2 • Neither: gain or loss of H+ , H2O, HX =>
CH3CH2CH2 1°，2°，3°Carb0ns HH H OXIDATION H OH R-C-H.R-C-H IOL R-C-H [R-C-OH H H +H0 alkane primary alcohol aldehyde curboxylie acid no bonds to O one bond to O two bonds to O three bonds to O H OH R-C-R IOL R-C-R 101,R-C-R'(no further H +HO oxidation) alkane secondary alcohol ketone no bonds to O one hond to O two bonds to O H OH R-C-R R-C-R (usually no further oxidation) R" R” alkane tertiary alcohol no honds to O one hond to O REDUCTION 三> Copyright 2005 Pearson Prentice Hall,Inc 5
CH3CH2CH2 C H H Br O H H _ + Chapter 11 5 1º, 2º, 3º Carbons =>