Help an idiot at organic chemistry.

It's been too long since I last tried to work out a mechanism, any help would be appreciated. It looks like it should be an easy one but I have had a mind blank (for the last twenty odd years it seams).

The reaction is:
[img]http://i66.photobucket.com/albums/h241/sonofjammers/benzil.jpg[/img]

It is benzoin being oxidised to benzil. First the nitric acid is added and heated for ten mins, which gives of nitrous oxides, and then water is added.

Any idea of the mechanism, It looks like it should be easy. On first looking at the position of the C=O and C-OH and with the addition of acid it screamed E1cB elimination, but I don't see how that could help make the product.

Does the H+ reduce the alcohol group making the C-OH bond more polar so the H20 can come in?

I can't work it out.[/img]

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It's a redox reaction - no "proper" mechanism is known, so you can (almost) take electrons from anywhere (as long as you are reducing and oxidising the right things) at any stage (using logic).

This link gives a kinda detailed answer, with lovely ascii reaction schemes!
Good luck!

http://forum.chemie.de/HyperNews/get/forums/chemstarter-2005/7085.html?inline=-1

green-goblin? :wink:

http://www.chemicalforums.com/index.php?board=3;action=display;threadid=7703

[quote="UCB Mitch"]green-goblin? :wink: [/quote]

Thats me :D

[quote="allan_chemist"]It's a redox reaction - no "proper" mechanism is known, so you can (almost) take electrons from anywhere (as long as you are reducing and oxidising the right things) at any stage (using logic).[/quote]

Thanks,I should be able to make up something knowning that, not sure how logic it will be though :?

Could anyone assist me in identify what qualitative tests could be used to distinguish between the following pairs of compounds!

1) NaI and NaBr
2) K2CO3 and K2SO4
3) CH3CH3 and CH2=CH2
4) CH3CH2OH and CH3CH2OCH2CH3
5) OH and CH3CH2OH

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