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JEE Main levelSingle correct optionDifficulty 2 of 3ap209

tert-Butyl ethyl ether is treated with one equivalent of $HI$ at low temperature. The products are

Aiodoethane and 2-methylpropan-2-ol
Biodoethane and 2-iodo-2-methylpropane
C2-iodo-2-methylpropane and ethanol
D2-methylpropene and iodoethane

Answer: C

Protonated ether ionises to the stable tertiary cation

(CH X_{3}) X_{3} C X^{+}

(SN1) and ethanol. Iodide captures the cation to give

(CH X_{3}) X_{3} C - I

, so the alkyl halide comes from the tertiary group.

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