Chapter 11 handouts

Chapter 11 handouts - CH3CH2CH2 Br C O H H H H Chapter 11...

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CH 3 2 2 C H H Br O H H Chapter 11 Reactions of Alcohols
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Chapter 11 2 CH 3 2 2 C H H Br O H H Types of Alcohol Reactions C-O Bond Broken: • Dehydration to _________ • Oxidation to _________________ • Substitution to form alkyl ________ • Reduction to _________ C-O Bond retained: • Esterification • Tosylation • Williamson synthesis of ether
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Chapter 11 3 CH 3 2 2 C H H Br O H H Summary Table =>
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Chapter 11 4 CH 3 2 2 C H H Br O H H Oxidation States • Easy for inorganic salts ¾ CrO 4 2- reduced to Cr 2 O 3 ¾ KMnO 4 reduced to MnO 2 • ________: loss of H 2 , gain of O, O 2 , or X 2 • ________: gain of H 2 or H - , loss of O, O 2 , or X 2 • Neither: gain or loss of H + , H 2 O, HX =>
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Chapter 11 5 CH 3 2 2 C H H Br O H H 1º, 2º, 3º Carbons =>
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Chapter 11 6 CH 3 2 2 C H H Br O H H Oxidation of 2° Alcohols • 2° alcohol becomes a ketone • Common reagent is Na 2 Cr 2 O 7 /H 2 SO 4 • Active reagent probably H 2 CrO 4 • Color change: orange to greenish-blue
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Chapter 11 7 CH 3 2 2 C H H Br O H H Oxidation of 1° Alcohols • 1° alcohol to aldehyde to carboxylic acid • Difficult to stop at aldehyde • Use pyridinium chlorochromate (PCC) to limit the oxidation. • PCC can also be used to oxidize 2° alcohols to ketones.
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Chapter 11 8 CH 3 2 2 C H H Br O H H 3° Alcohols Don’t Oxidize • Cannot lose 2 H’s • Basis for chromic acid test =>
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Chapter 11 9 CH 3 2 2 C H H Br O H H Other Oxidation Reagents • _____________: CrO 3 in pyridine • ____________: chromic acid in acetone • KMnO 4 (strong oxidizer) • Nitric acid (strong oxidizer) • CuO, 300°C (industrial dehydrogenation) • _____________: dimethylsulfoxide, with oxalyl chloride and hindered base, oxidizes 2 ° alcohols to ketones and 1 ° alcohols to aldehydes.
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Chapter 11 10 CH 3 2 2 C H H Br O H H Example of Swern Oxidation
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Chapter 11 11 CH 3 2 2 C H H Br O H H Biological Oxidation • Catalyzed by ADH, alcohol dehydrogenase.
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This note was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Pearson during the Fall '07 term at Case Western.

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Chapter 11 handouts - CH3CH2CH2 Br C O H H H H Chapter 11...

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