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Topic: Reduction ability  (Read 2146 times)

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Offline vhpk

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Reduction ability
« on: March 03, 2010, 09:32:20 AM »
I have one problem that needs your help:
Why does LiAlH4 reduce C=O but not C=C, it only reduces C=C in case of conjugation between C=C and C=O ?
Thank you  :)
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Offline Smrt guy

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Re: Reduction ability
« Reply #1 on: March 03, 2010, 09:12:04 PM »
After hydride attack, for carbonyls, the product is a lithium alkoxide.  If it were to attack a non-conjugated double bond, the product would be an alkyl lithium.  In the case of conjugated double bonds, the hydride attack yields a lithium enolate (this is far less basic and far more stable than an alkyl lithium).  Quite simply, LAH reduction of carbonyls and/or conjugated alkenes yields a thermodynamically favored intermediate while reduction of isolated alkenes does not.

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