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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: insertwittyname on August 30, 2014, 03:01:03 PM

Title: SNi in alcohols
Post by: insertwittyname on August 30, 2014, 03:01:03 PM

Every book that I have referred to, gives SN_i 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 SN_i mechanism?

Title: Re: SNi in alcohols
Post by: clarkstill 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...

Title: Re: SNi in alcohols
Post by: insertwittyname 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?