CH3CH2CH H Organic Chemistry, 5th Edition BrC.h L.G. Wade jr Chapter 11 Reactions of alcohols Jo blackburn Richland college, dallas TX Dallas County Community College District c 2003. 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 © 2003, Prentice Hall Organic Chemistry, 5th Edition L. G. Wade, Jr
CH3 CH2CH 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
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 =>
CH3CH2CH H H Summary Table HH TABLE 11-1 Types of Reactions of Alcohols R-OH type of reaction Product dehydration esterification R—OH alkenes R—OH R-0—C-R oxidation R—OH ketones, aldehydes, acids R—OH tosylation R-OTS substitution R-OH R一X tosylate esters (good leaving group halides reduction R—OH R—H R-OH (1) form alkoxide R-0—R′ (2)RX alkanes ethers Chapter 11
CH3CH2CH2 C H H Br O H H Chapter 11 3 Summary Table =>
CH3CH2CH H H Oxidation States HH Easy for inorganic salts >CrO4- reduced to Cr2O3 >KMnO4 reduced to MnO2 Oxidation: loss of H2, gain of O, O2, or X2 Reduction: gain of H2 or H, loss ofo, o23 orⅩ2 Neither: gain or loss of H+, H2O, HX Chapter 11
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 =>
CH3CH2CH H 10,20,3° Carbons0H OXIDATION H OH R一C—H R一C一H O R—C—H O R-C-OH +Ho H H alkane primary alcohol aldehyde carboxylic acid no bonds to o one bond to o two bonds to o three bonds to o OH R—C-p,Ol →R—C-RO R—C-R′( no further +H, H alkane secondary alcohol ketone no bonds to o one bond to o two bonds to o H OH RC-R、R-C一R( sually no further oxidation) R alkane tertiary alcohol no bonds to o one bond to o REDUCTION
CH3CH2CH2 C H H Br O H H Chapter 11 5 1º, 2º, 3º Carbons =>