Chapp-11A - Chapter 11 Reactions of Alcohols Chapter 112...

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Unformatted text preview: Chapter 11 Reactions of Alcohols Chapter 112 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 113 Summary Table Chapter 114 11-1 Oxidation States For inorganic salts CrO 4 2- reduced to Cr 2 O 3 (gain of elctrons) KMnO 4 reduced to MnO 2 In organic terms: 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 Chapter 115 Oxidation-Reduction Chart Chapter 116 11-2 Oxidation of Alcohols 11-2A Oxidation of 2 Alcohols 2 alcohol becomes a ketone Reagent is Na 2 Cr 2 O 7 /H 2 SO 4 or CrO 3 /H 2 SO 4 Active reagent probably chromic acid (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 Chapter 117 Chromic acid is prepared by dissolving chromium(VI) oxide or potassium dichromate in aqueous sulfuric acid Potassium dichromate Chromic acid K 2 Cr 2 O 7 H 2 SO 4 H 2 Cr 2 O 7 H 2 O 2H 2 CrO 4 + Chromic acid Chromium(VI) oxide CrO 3 H 2 O H 2 CrO 4 H 2 SO 4 Chapter 118 11-2B Oxidation of 1 Alcohols 1 alcohol to aldehyde to carboxylic acid Difficult to stop at aldehyde Octanal (not isolated) Octanoic acid 1-Octanol O O CH 3 (CH 2 ) 6 CH 2 OH CrO 3 H 2 SO 4 , H 2 O CH 3 ( CH 2 ) 6 CH CH 3 ( CH 2 ) 6 COH Chapter 119 Pyridinium chlorochromate Pyridinium chlorochromate (PCC) (PCC): a form of Cr(VI) prepared by dissolving CrO 3 in aqueous HCl and adding pyridine to precipitate PCC N H + CrO 3 Cl- PCC is selective for the oxidation of 1 alcohols to aldehydes; it does not oxidize aldehydes further to carboxylic acids Chapter 1110 PCC oxidation of a 1 alcohol to an aldehyde CH 2 OH CH O PCC GeraniolGeranial Chapter 1111 11-2C Resistance of 3 Alcohols to Oxidation Cannot lose 2 Hs Basis for chromic acid test (orange to green/blue) Chapter 1112 11-3 Other Oxidation Reagents Collins reagent: CrO 3 in pyridine Jones reagent: chromic acid in acetone KMnO 4 (strong oxidizer) Nitric acid (strong oxidizer)...
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Chapp-11A - Chapter 11 Reactions of Alcohols Chapter 112...

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