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Topic: 2-bromo-2-methylbutane in tert-butoxide/tert-butyl alcohol  (Read 5980 times)

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Offline blueblueblue

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2-bromo-2-methylbutane in tert-butoxide/tert-butyl alcohol
« on: February 03, 2011, 02:20:55 AM »
I need to come up with the products of the solvolysis reaction of 2-bromo-2-methylbutane in tert-butoxide in tert-butyl alcohol. 

My answer is

Since this is a reaction between a bulky, tertiary alkyl halide and again a bulky, strong tertiary tert-butoxide, the major elimination product will be 2-methyl-1-butene.  The minor elimination product will be 2-methyl-2-butene.  Both are too bulky to follow zaitsev's rule.

However, I am not sure about the SN1 product.  Does an SN1 reaction even occur between tertiary alkyl halide and a tertiary strong nucleophile?  I think that it would not proceed to SN1 reaction, but it may produce even a tiny bit of SN1 product. 

Does anybody know if these produce SN1 product at all beside E2 products?

Thanks in advance for your help.

Offline bolo

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Re: 2-bromo-2-methylbutane in tert-butoxide/tert-butyl alcohol
« Reply #1 on: February 03, 2011, 05:43:20 PM »
It is impossible in my opinion. 2-Methyl-1-butene sounds pretty good to be a product of this almost only E2 reaction.

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