1. Write a mechanism for three cleavage of butyl isopropyl ether with hydrobromic acid at 100 degree Celsius to form exclusively isopropyl alcohol and 1-idobutane. Explain why butyl alcohol and isopropyl iodide are not formed in the reaction. 2. A student performed the same reaction, exposed R-1-bromo-2-propanol to sodium hydroxide and isolated an optically inactive product and collected the proton and carbon nmr. What is the structure of the compound that this student isolated?

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Chapter1: Chemical Foundations
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1. Write a mechanism for three cleavage of butyl isopropyl ether with hydrobromic acid at 100 degree Celsius to form exclusively isopropyl alcohol and 1-idobutane. Explain why butyl alcohol and isopropyl iodide are not formed in the reaction. 2. A student performed the same reaction, exposed R-1-bromo-2-propanol to sodium hydroxide and isolated an optically inactive product and collected the proton and carbon nmr. What is the structure of the compound that this student isolated?
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