[tdod]

Here's the reaction:




I can't figure out why a radical is forming... would love some help.


Thanks!

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[Archer]

Where did you source this scheme?

[tdod]

answers.yahoo.com :/

[Archer]

Ok, let's just put a pin in Yahoo Answers for a minute.

What are you trying to establish?

The mechanism of aerial oxidation of benzoin to benzil?  Or just the mechanism of any oxidation of benxoin?

Or are you trying to rationalise an incomplete mechanism posted on the internet?

[tdod]

I am trying to rationalize the incomplete mechanism posted on the internet.

[Archer]

I am not familiar with this reaction or whether it even occurs but given the information provided I would say the hydroxide acts as a nucleophile towards the benzil present.

The product of this loses a hydroxyl radical leaving one of the radical anion.

The hydroxyl radical abstracts the hydrogen from the benzoin to form water and a benzoin radical which is deprotonated to give the second radical anion (note that there ate two in this scheme).

The only reaction which comes close to this is the Cannizzaro reaction.

This may be completely wrong but I am going on the scheme provided. I am sure someone will correct me if I am off the mark.

I can't draw a mechanism for you as I am on a mobile device so I apologise to the text description. I will try to upload something tomorrow.