E2 reaction with t-But

[nwu]

Hi,

This is a quick question about a E2 reaction I stumbled upon. Perhaps my understanding of the E2 mechanism is poor, but take a look at this picture below:

http://upload.wikimedia.org/wikipedia/commons/4/48/Formation_of_the_Hofmann_Product.png


I understand that in a E2 reaction for a tertiary halide involving a bulky base, we get the Hoffman product, ie double bond with less substitution. But for this reaction wouldn't there be a second Hoffman product? That Br has three carbons each of these carbons has a hydrogen for the Base to rip off. Would another reasonable product be a double bond on that methyl outgroup?

Thank you

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[mcatstuff19]

Rotate C2 of the Hofmann. It's the same molecule.

 

[PKU]

Doesn't matter which carbon you choose, both provide the same product.

In NMR, those hydrogens are equivalent.

 

[nwu]

Thanks, didn't see that.

 

[SN2ed]

Thread closed. These types of questions belong in the MCAT Study Q&A forum only.