Destroyer '15 OC #10

[cacajuate]

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Why does Dichromate oxidize this molecule? Does the resonance extend to over to the unconjugated ring?

 

[FeralisExtremum]

There is a benzene ring present (other groups attached to it don't change the fact that a benzene is still there) and we're adding K2Cr2O7, so we should immediately think of this as a side chain oxidation problem. Treat every C attached to it (even if it's part of another ring) as a side chain that can be potentially oxidized. As long as the benzylic carbons have Hydrogens available, they will be transformed into COOH groups.

 

[DAT Destroyer]

Why does Dichromate oxidize this molecule? Does the resonance extend to over to the unconjugated ring?

Dichromate or Permanganate will oxidize any Carbon group if it contains at least one BENZYLIC hydrogen. This is a very important problem. The benzylic hydrogen is adjacent to the benzene ring carbon.

Hope this helps.

Dr. Romano

 

[cacajuate]

I knew permanganate would, just didn't realize Dichromate would also.