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Topic: Reaction of a carbocation  (Read 2706 times)

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Offline cseil

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Reaction of a carbocation
« 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?

Offline Hunter2

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Re: Reaction of a carbocation
« Reply #1 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.

Offline orgopete

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Re: Reaction of a carbocation
« Reply #2 on: June 04, 2015, 06:24:25 AM »
 Would add another product. Hint, pinacol....
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline cseil

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Re: Reaction of a carbocation
« Reply #3 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?

Offline Hunter2

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Re: Reaction of a carbocation
« Reply #4 on: June 04, 2015, 06:31:22 AM »
Here we go, mechanism below.

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

Offline cseil

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Re: Reaction of a carbocation
« Reply #5 on: June 04, 2015, 06:34:14 AM »
Thank you!  :)

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