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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cseil on June 04, 2015, 05:31:09 AM

Title: Reaction of a carbocation
Post by: cseil on June 04, 2015, 05:31:09 AM

Hello everyone,
I was asked to explain what's the main product of this reaction.

I can't understand if the formation of the epoxide happens or not. What would be the main product between these two?

Title: Re: Reaction of a carbocation
Post by: Hunter2 on June 04, 2015, 06:19:30 AM

If its aquaeous solution the Diol will be the product. The carbocation will attack a water molecule and a H⁺ will be expelled.

The same reaction take place intramolecular, but I think the angle in a epoxide is very strong so the reaction is minor.

Title: Re: Reaction of a carbocation
Post by: orgopete on June 04, 2015, 06:24:25 AM

 Would add another product. Hint, pinacol....

Title: Re: Reaction of a carbocation
Post by: cseil on June 04, 2015, 06:28:56 AM

I didn't know about the pinacol rearrangement. Now I do  ;D

You mean this product, right?

Title: Re: Reaction of a carbocation
Post by: Hunter2 on June 04, 2015, 06:31:22 AM

Here we go, mechanism below.

http://en.wikipedia.org/wiki/Pinacol

Title: Re: Reaction of a carbocation
Post by: cseil on June 04, 2015, 06:34:14 AM

Thank you!  :)