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organic chem

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7. An unknown compound, C8H14, is optically active. Hydrogenation of the unknown
yields 4-methylheptane. Ozonolysis of the unknown yields ethanol and 2-
methylpropandial. Suggest a structure for the unknown consistent with the above date.

please help

  • organic chem - ,

    With all this type of problem start by calculating the number of double bond equivalents.

    see (Broken Link Removed)

    So here the DBE = {(2x8+2)-(14-0)}/2


    The hydrogenation product tells the carbon structure


    and so the unknown contains two double bonds or one triple bond

    If ozonolysis gives us


    plus ethanal

    then the structure is


    Which is two DBE.

    The structure is only chiral if one double bond is Z and the other E.

    So there are four possible structures:


  • organic chem - ,

    I think I have the absolute configurations correct, but please check using a model.

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