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Standard orgo

  1. Jan 8, 2008 #1
    I'm trying to solve some organic chem reactions out of a new text book with an answer key that's confusing me. All three rxns involve anti-markovnikov addition of HBr to an alkene using a peroxide. A peroxide radical generates a bromine radical, the electrophile which then adds to the least subsituted carbon. I would think that these rxns would be non-sterospecific, thus generating a maximum of four different products. Here are the reactions and what I think the answers should be.

    I don't care about exact answers I'm just want to confirm stereochemistry:

    1) 2-methylpropene +HBr + peroxide--->a racemic mix of two products, right?

    2) 1-methylcyclopropene+HBr+peroxide---> 2 different racemic mixtures, four total different products

    3) 1-phenylpropene + HBr +peroxide---->again, a racemic mixture of two product


    My book is ambiguous in it's description of stereochem for the products, perhaps because it's an advanced text which just assumes this stuff is obvious.
     
  2. jcsd
  3. Jan 17, 2008 #2

    chemisttree

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    edit: OOPS! My bad...
    I don't get 4 products for 2). Do you postulate that the double bond migrates?
     
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