Oxidation Reagents

Oxidation Reagents - OH PCC or PDC O H (stops at the...

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III. Reactions of alcohols: Oxidation. Alcohols can be oxidized to carbonyl compounds by a number of high oxidation state chromium reagents (e.g., Na 2 Cr 2 O 7 , PCC, and PDC). i. Primary (1°) alcohols. Primary alcohols can be oxidized to either aldehydes or carboxylic acids. Oxidation to the carboxylic acid is easy and can be done with Na 2 Cr 2 O 7 . The tricky reaction is to oxidize primary alcohols to aldehydes and not go on to the carboxylic acids. These selective oxidations to aldehydes are done in non-aqueous solutions (free of water) and several reagents can be used to do this. The two that you need to know are pyridinium chlorochromate, PCC, and pyridinium dichromate, PDC. OH Na 2 Cr 2 O 7 O OH (bypasses the aldehyde and goes on to the carboxylic acid)
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Unformatted text preview: OH PCC or PDC O H (stops at the aldehyde) NH ClCrO 3 PCC = PDC = NH 2 Cr 2 O 7 2 ii. Secondary (2) alcohols. Secondary alcohols can be oxidized to ketones and no farther. OH PCC or PDC O R R or Na 2 Cr 2 O 7 iii. Tertiary (3) alcohols. Tertiary alcohols cannot be oxidized to anything worth a damn. iv. Oxidation and reduction is a two-way street. It is important to take note of the relationship between oxidations of alcohols and reductions of carbonyl compounds. They go in opposite directions: reductions put hydrogens on and/or take oxygens off, while oxidations put oxygens on and/or take hydrogens off. O Reduction OH H Oxidation...
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This note was uploaded on 09/25/2009 for the course CH 223 taught by Professor Brown during the Summer '08 term at N.C. State.

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