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    Acid and base: Structures, Reactions, and NMR Spectrums

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    1. If 3-bromo-1-propanol is treated with NaOH, a compound of molecular formula C3H6O is formed. Suggest a structure for this product.

    2. What product(s) would you expect to form when tetrahydrofuran is treated with excess hydroiodic acid (HI)?

    3. Write a suitable mechanism for the cleavage of butyl isopropyl ether with HI at 100 degrees C to form exclusively isopropyl alcohol and 1-iodobutane. Explain why butyl alcohol and isopropyl iodide are not formed
    in the reaction.

    4. There are only four lines in the aromatic region of the fully 1 H decoupled13C NMR spectrum of propyl p-tolyl aromatic carbon atoms. Explain.

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    Solution Summary

    A structure for C3H6O (3-bromo-1-propanol treated with NaOH) is identified. The product of tetrahydrofuran, when treated with HI is found. The reaction of butyl isoproyl ether and HI is show, along with an explanation on why other reactions do not occur. Finally, propyl p-tolyl aromatic carbon atoms are explained.