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Topic: SNi in alcohols  (Read 2418 times)

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Offline insertwittyname

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SNi in alcohols
« on: August 30, 2014, 03:01:03 PM »
Every book that I have referred to, gives SNi mechanism only with secondary alcohols. Frankly speaking, I just can't fathom why a primary alcohol wont work. Sure, the carbocation formed might undergo rearrangement, but how does that affect SNi mechanism?
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Offline clarkstill

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Re: SNi in alcohols
« Reply #1 on: September 01, 2014, 02:59:29 AM »
With SOCl2? It definitely works on primary too... I think they choose secondary examples since they are often trying to make a point about retention/inversion of absolute stereochemistry, and primary alcohols don't have any such stereochemistry...
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Offline insertwittyname

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Re: SNi in alcohols
« Reply #2 on: September 17, 2014, 02:16:25 PM »
That point never crossed my mind. Thanks a lot, clarkstill!
And the carbocation formed from primary alcohol, it might undergo rearrangement if that is a possibility right?
« Last Edit: September 17, 2014, 02:29:15 PM by insertwittyname »
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