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Which E2 rxn is faster?
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Topic: Which E2 rxn is faster? (Read 20555 times)
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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.
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RBF
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Re: Which E2 rxn is faster?
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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.
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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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Which E2 rxn is faster?