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Homework Help: Guess the Mechanism help! (Organic Chemistry)

  1. Jan 19, 2013 #1
    "Guess the Mechanism" help! (Organic Chemistry)

    1. The problem statement, all variables and given/known data
    After identifying my reactants and products via spectral analysis, I am now tasked with figuring out the mechanism behind converting a diol into a ketone.

    2. Relevant equations


    3. The attempt at a solution
    The key to this appears to be tautomerization somewhere in the reactant (whereby the oxygen atoms donate electrons in order to create a double bond), but everything I've tried with that has failed so far. I'm really stuck.
  2. jcsd
  3. Jan 19, 2013 #2
    Re: "Guess the Mechanism" help! (Organic Chemistry)

    So I was able to figure it out myself. Apparently, this is a pinacol rearrangement (http://en.wikipedia.org/wiki/Pinacol_rearrangement), which would explain many things...namely that we never even covered it in lecture at this point. >.>
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