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Synthetic pathway

  1. Apr 12, 2012 #1
    I need to figure out how to synthesize 3-methyl-3-hexanol from acetylene.

    So, there is a methyl and an OH on the third carbon. I am learning all the different reactions, but I am having a hard time figuring out where the triple bond is and how to do it with the methyl group on there. Is there some kind of a shift?
  2. jcsd
  3. Apr 13, 2012 #2


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    Are you having trouble determining where the triple bond is for acetylene?
  4. Apr 14, 2012 #3
    I'll take a high road with you (assume that you are not being clear with your question, but that you have the retrosynthetic concept in hand).
    You have drawn your 7 carbon product correctly and determined the functional group (-OH). You have been given that you have access to only acetylene as a functional two carbon material that you are to derive all of the backbone for the product. You have drawn some of the disconnections with these two carbon units, and even have some ideas of the reactions that will help you create the carbon carbon bonds, but are really wondering how to get an odd carbon to make the odd methyl?!?
    Since your disconnection possibilities can envision that a tertiary alcohol could be formed by C-C bond forming at the C=O of a ketone you may be needing to consider how introduce a single carbon from inorganic reactants- i.e CO2, CN-, etc...
    Does this make it easier to see a possible approach?
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