Ch_322b_12.04

Ch_322b_12.04 - Chapter 12.4 lecture note

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Oxidation of Alcohols Primary Alcohols Primary alcohols undergo stepwise oxidation to aldehydes and then carboxylic acids: R- CH 2 OH primary alcohol [O] R- C-H O = aldehyde [O] R- C-OH O carboxylic acid Selective Oxidation Selective oxidation of a primary alcohol to an aldehyde is difficult because aldehydes tend to undergo oxidation faster than primary alcohols. However, there are methods for carrying out this transformation.
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Removal of the Aldehyde Product by Distillation Aldehydes have lower boiling points than the corresponding alcohols and may be fractionally distilled from the reaction mixture as they are formed. These oxidations are carried out with either potassium or sodium dichromate in sulfuric acid under moderate reaction conditions.
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Selective Oxidation with Pyridinium Chlorochromate, PCC The oxidation of primary alcohols to aldehydes is more easily accomplished with a reagent of chromium trioxide (CrO 3 ) complexed with pyridine and HCl in dichloromethane, CH 2 Cl 2 . The resulting reagent is called
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Ch_322b_12.04 - Chapter 12.4 lecture note

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