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    Identifying unknown substances

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    Compound A (C7H14O) burned with a yellow, nonsooty flame and did not decolorize a bromine-methylene chloride solution. It did give a positive 2,4-dinitrophenylhydrazine test, but a negative Tollens test. Treatment of the compound with lithium aluminum hydride followed by neutralization with acid, produced a Compound B, which gave a positive Lucas test in about 5 minutes. Compound B also gave a positive ceric nitrate test. The H NMR spectrum for Compound A gave the following data:

    1.02 ppm 9H, singlet
    2.11 ppm 3H, singlet
    2.31 ppm 2H, singlet

    Give suitable structures for compound A and B.

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    Solution Summary

    This solution is provided in two attached .jpg files containing scanned workings of structures of the compounds, including drawings of the steps needed to make the compound.