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Question

What product(s) is/are obtained when ethyl isopropylether is cleaved with hot HI in polar aprotic solvent?

A
Iodoethane
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B
2-Methyl propane
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C
Isopropyl alcohol
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D
Ethanol
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Solution

The correct option is C Isopropyl alcohol
Ethers can be reactive under ​drastic reaction conditions (high temperature, high concentration) due to the cleavage of the C-O bond.​
In first step of the reaction, protonation of ether (O) group take place.
In second step, I will undergo SN2 nucleophilic attack at less hindered site.
Thus, the reaction of ethyl isopropylether with concentrated HI in polar aprotic solvent give Iodoethane and Isopropyl alcohol. Hence option (a) and (c) are correct. The reaction is as follow:

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