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Topic: Clemmensen Reduction  (Read 4752 times)

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Offline EtOH

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Clemmensen Reduction
« on: March 15, 2007, 12:06:23 PM »
Hey, does amalgamated zinc in HCl reduce a nitro group to an amine? In my notes it seems that it would but i can't find the evidence for it anywhere. I know hydrogen catalyzed reduction does but would clemmensen do that as well?

Also, some kid in class was trying to explain that clemmensen would only reduce a carbonyl that's attached directly to a benze ring and not one that is in the middle of a substituent, like any type of ketone. Is there any truth to that?

Thanks in advance,
Anton

Offline movies

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Re: Clemmensen Reduction
« Reply #1 on: March 15, 2007, 02:00:45 PM »
Yup.  Nitro groups on aromatics are pretty easy to reduce.  I would say a more common combination is Zn/HOAc.

There are definitely examples of aliphatic ketones reduced to alkanes by Clemmensen reduction.  I don't know if it would be possible to get selectivity for a phenyl ketone over an aliphatic one though.

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