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Question

Identify the product(s) obtained when hot hydrogen iodide react with benzyl ethyl ether at high temperature?

A
Ethanol
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B
Benzyl iodide
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C
Ethyl iodide
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D
Phenol
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Solution

The correct option is B Benzyl iodide
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, due to stability of benzyl carbocation it undergoes SN1 reaction.
Thus, the reaction of Benzyl ethyl ether with hot concentrated HI give Ethanol and Benzyl iodide. Hence, option (a) and (b) are correct. The reaction is as shown below:

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