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Write a suitable mechanism for the cleavage of butyl isopropyl ether with HI.

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

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Solution Summary

In the attached document, this solution illustrates (1) the attack of the one molar equivalent of 1-propanol, (2) base takes off proton, carbonyl is reformed, kicking out the unprotonated carboxy acid group, (3) reforming the carboxy acid group, and (4) the final product.

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