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Can the compound butane-2,2,3,3-tetraol, $\ce{C4H10O4}$, be oxidized by $\ce{KMnO4}$? If so, in what conditions? As I have learnt in class, normally the hydroxy group would oxidize to form a ketone, but what about this particular case?

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You are talking about the dihydrate of biacetyl. gem-diols are generally not stable, the equilibrium is on the side of the aldehyde/ketone, except when the keto group is next to an electronegative atom. Glyoxal in aqueous solution is all hydrate and oligomers, as is chloral.

Biacetyl is more hindered than glyoxal, but in aqueous solution one would think they there is still some hydrate in the equilibrium. What you'd think would happen is that on reaction with permanganate you'd get the cyclic diol and under sufficiently forcing conditions (read: acidic medium) you'd get cleavage to acetic acid.

Biacetyl is awful. Run away!

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    $\begingroup$ Unless you like artificial butter flavoring. Then run toward. $\endgroup$ – jerepierre Oct 8 '14 at 19:39

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