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E2 reaction with t-But

Discussion in 'MCAT Discussions' started by nwu, Sep 23, 2014.

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  1. nwu

    nwu Just yes 2+ Year Member

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    Aug 16, 2011
    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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  3. mcatstuff19

    mcatstuff19 2+ Year Member

    5
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    May 25, 2014
    Rotate C2 of the Hofmann. It's the same molecule.
     
  4. PKU

    PKU 2+ Year Member

    129
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    Nov 28, 2013
    Doesn't matter which carbon you choose, both provide the same product.

    In NMR, those hydrogens are equivalent.
     
  5. nwu

    nwu Just yes 2+ Year Member

    43
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    Aug 16, 2011
    Thanks, didn't see that.
     
  6. SN2ed

    SN2ed Moderator Emeritus 7+ Year Member

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    Jun 27, 2007
    Thread closed. These types of questions belong in the MCAT Study Q&A forum only.
     

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