Ch_322b_12.05

Ch_322b_12.05 - Oxidation of Secondary Alcohols to Ketones...

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Oxidation of Secondary Alcohols to Ketones Secondary alcohols are easily oxidized to ketones by a variety of reagents with good yields. R- CH- R' OH [O] R- C -R' O = secondary alcohol ketone Chromium VI Reagents Common oxidants are chromium VI reagents such as potassium dichromate (K 2 Cr 2 O 7 /H 2 SO 4 ), sodium dichromate (Na 2 Cr 2 O 7 /H 2 SO 4 ), and chromium trioxide (CrO 3 /H 2 SO 4 ) . In sulfuric acid solution, all of these reagents yield chromic acid (H 2 CrO 4 ) that is the actual oxidant. Stoichiometry 3 RCHR' OH + 2 H 2 CrO 4 + 6 H + 3 RCR' O + 2 Cr 3+ 8 H 2 O These oxidations typically are fast and can be carried out at, or just above, room temperature. Because of the rapid oxidation, and the very distinctive color change during the redox reaction as Cr VI ( orange) changes to Cr III ( green ), the oxidant solution can be slowly titrated into the reaction mixture until one equivalent has been added.
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The Jones Oxidation
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322b_12.05 - Oxidation of Secondary Alcohols to Ketones...

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