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

    =4/2=2

    The hydrogenation product tells the carbon structure

    CH3-CH2-CH2-CH(CH3)-CH2-CH2-CH3

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

    If ozonolysis gives us

    O=CH-CH(CH3)-CH=O

    plus ethanal

    then the structure is

    CH3-CH=CH-CH(CH3)-CH=CH-CH3

    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:

    (R)-2Z,5E-4-methylhepta-2,5-diene
    (R)-2E,5Z-4-methylhepta-2,5-diene
    (S)-2Z,5E-4-methylhepta-2,5-diene
    (S)-2E,5Z-4-methylhepta-2,5-diene

  • organic chem -

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

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