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Homework Help: Organic Chemistry Synthesis/Mechanism

  1. Nov 23, 2011 #1
    1. The problem statement, all variables and given/known data
    Problems: http://imgur.com/qN7Iq
    2. Relevant equations
    3. The attempt at a solution
    For the synthesis, I tried opening the epoxide with HBr and then adding OMe- in HOMe to substitute the Br with the OMe group in the product. However, I am unsure how to substitute the alcohol (from the epoxide opening) into the ethyl group (my friend also suggested Grignard's, but I'm not familiar with tha reaction). For the mechanism problem, I can't seem to figure out how a double bond can be formed on the 3-4 carbon bond, since an elimination on the Br would leave a double bond on the 2-3 bond. I might be completely off the right track, so I appreciate any help on the issue. Thanks!
  2. jcsd
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