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Reaction mechanism for ketone and vinyl lithium

  1. Mar 10, 2016 #1
    1. The problem statement, all variables and given/known data
    What is the product of 1-bromo-3-propanone treated with vinyl lithium?

    2. Relevant equations


    3. The attempt at a solution
    I know that the carbonyl is attcked by the organolithium but I am having a hard time understanding how it attaches to the carbonyl since it is sp2 hybridized. Any suggestions? Thanks!
     
  2. jcsd
  3. Mar 11, 2016 #2

    TeethWhitener

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    Something must be wrong. 1-bromo-3-propanone is not a real molecule: propane only has 3 carbons, so a carbonyl on the 3-carbon would make it an aldehyde, not a ketone. Can you draw out the structure of the molecule that you intended to say?
     
  4. Mar 11, 2016 #3
    I believe my study manual meant 1-bromo-2-propanone. But, here is the reaction that I have determined so far, attached below. The answer only says that the vinyl lithium would add to the carbonyl. Thanks!
     
  5. Mar 11, 2016 #4

    TeethWhitener

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    I don't see the attachment.

    This shouldn't matter. Just treat the organolithium compound as approximately R-Li+, with R = vinyl, and just do the same type of arrow-pushing you'd do with, e.g., butyllithium.

    The one caveat is to think about not just the carbonyl, but the bromine as well.
     
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