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Topic: Which E2 rxn is faster?  (Read 19455 times)

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Offline Yggdrasil

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Re: Which E2 rxn is faster?
« Reply #15 on: November 22, 2007, 11:29:05 PM »
Well, you get interactions between the bromine and hydrogens when the methyl is equatorial.  I'm not sure how the size of a methyl compares with the size of a bromine.

Offline RBF

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Re: Which E2 rxn is faster?
« Reply #16 on: November 23, 2007, 09:43:34 AM »
According to published "A values" (a measure of 1-3 diaxial interactions), the bromine atom (A = 0.38-0.49) is considerably less sterically demanding than the methyl group (A= 1.70).  A list of these values can be found at the following link:

http://www.chem.wisc.edu/areas/organic/index-chem.HTM

You will need to select "A values" from the list at the left.


Offline Yggdrasil

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Re: Which E2 rxn is faster?
« Reply #17 on: November 23, 2007, 01:43:51 PM »
Sweet.  Thanks RBF.  So, saN, you are correct.  The preferred conformer will be the one with the methyl group equatorial and the bromine axial.

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