Chapter 10 - Chapter 10. The Chemistry of Alcohols...

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Unformatted text preview: Chapter 10. The Chemistry of Alcohols and Thiols Dehydra9on: not promoted by strong base Acid ­catalyzed dehydra9on Alcohol dehydra9on vs. E1 Product distribu9on Alkene rearrangement products ROH+HCl ROH+HBr Rearrangement Roles of the acid catalysts Sulfonate ester of alcohols Prepara9on of sulfonate esters Chemistry of sulfonate esters Triflate is a func9onal mimic of halide Useful method to prepare alkenes Ester deriva9ves of strong inorganic acids Reac9on of ROH with SOCl2 Reac9on of ROH with PBr3 Red ­ox reac9ons Oxida9on numbers Half reac9ons Oxidizing and reducing agents Oxida9on of alcohols to aldehydes/ketones Oxida9on of alcohols to carboxylic acids Oxida9on of thiols Chemical equivalence Enan9otopic Diastereotopic Diastereotopic groups are chemically nonequivalent •  Alcohol dehydra9on (condi9ons, mechanism, rearrangement) and the mechanis9c difference between acid ­ and base ­ promoted elimina9on; •  ROH reac9on with HBr, HCl; •  Prepara9on and applica9on of sulfonate esters (tosylate and triflate) in synthesis; •  Applica9on of thionyl chloride and phosphorus tribromide in synthesis; •  General concepts of red ­ox reac9ons (half ­reac9on, oxida9on, oxidizing and reducing agents); •  Alcohol oxida9on with chromic acid, KMnO4, K2Cr2O7; •  Oxida9on of thiols (reagents, products, condi9ons); •  Chemical equivalence and nonequivalence: iden9cal, enan9otopic, and diastereotopic groups; •  Performing subs9tu9on test. Key Points ...
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