Chapter_11 - Types of Alcohol Reactions Dehydration to...

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1 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 =>
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2 Summary Table =>
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3 1º, 2º, 3º Carbons =>
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4 Oxidation States Easy for inorganic salts CrO 4 2- reduced to Cr 2 O 3 KMnO 4 reduced to MnO 2 Oxidation: loss of H 2 , gain of O, O 2 , or X 2 Reduction: 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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7 Oxidation of 2° Alcohols 2° alcohol becomes a ketone 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 CH 3 CHCH 2 CH 3 OH Na 2 Cr 2 O 7 / H 2 SO 4 CH 3 CCH 2 CH 3 O =>
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11 Final Examination Saturday, December 13, 2008 3:30 - 6:30 pm Comprehensive
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12 Review Session Saturday - 3:00 - 5:00 pm NSC 201 Everyone who attends must bring one written question.
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13 Alcohol to Aldehyde? OH O H O OH Useful to stop reaction at aldehyde
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14 OH O H O OH Na 2 Cr 2 O 7 OH H OH Na 2 Cr 2 O 7 O OH H 2 O 4 H 2 O 4 Alcohol to Aldehyde?
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15 Alcohol to Aldehyde OH N H CrO 3 Cl O H N H CrO 3 Cl pyridinium chlorochromate can be used in organic media such as CH 2 Cl 2
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16 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. CH 3 CH 2 CH 2 CH 2 OH N H CrO 3 Cl CH 3 CH 2 CH 2 CH O =>
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18 3° Alcohols Don’t Oxidize Cannot lose 2 H’s Basis for chromic acid test =>
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19 Other Oxidation Reagents Collins reagent: Cr 2 O 3 in pyridine Jones reagent: chromic acid in acetone KMnO 4 (strong oxidizer) Nitric acid (strong oxidizer) CuO, 300°C (industrial dehydrogenation) Swern oxidation: dimethylsulfoxide, with oxalyl chloride and hindered base, oxidizes 2 ° alcohols to ketones and 1 ° alcohols to aldehydes.
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