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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: g_orbital on November 19, 2006, 08:54:35 AM

Title: Oxidation of primary alcohol into acid
Post by: g_orbital on November 19, 2006, 08:54:35 AM

What is the mechanism of oxidation of primary alcohol into carboxylic acid, by ortho periodic acid (H₅IO₆) and catalytic chrome trioxide (CrO₃)? Below attached the discussed reaction.

I would appreciate your assistance.

Title: Re: Oxidation of primary alcohol into acid
Post by: Dan on November 19, 2006, 11:58:20 AM

I think this is a standard chromium trioxide oxidation mechanism. The H₅IO₆ then oxidises the chromium by-products back up to chromium trioxide, making the chromium trioxide catalytic (which is good because it's a nasty reagent so you don't want to be playing with alot of it)

ie.

Cr(VI) + alcohol --> Cr(IV) [by-products] + acid

Cr(IV) + I(VII) --> Cr(VI) + I(V)