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NEET levelSingle correct optionDifficulty 1 of 3o3175

tert-Butyl methyl ether, $(CH X_{3}) X_{3} C - O - CH X_{3}$ , is treated with one equivalent of HI at room temperature. Because the tertiary carbocation is easily formed (SN1), the products are

A $(CH X_{3}) X_{3} C - OH$ and $CH X_{3} - I$
B $(CH X_{3}) X_{3} C - OH$ and $CH X_{3} - OH$
C $(CH X_{3}) X_{3} C - I$ and $CH X_{3} - I$
D $(CH X_{3}) X_{3} C - I$ and $CH X_{3} - OH$

Answer: D

After protonation of the oxygen, the

C - O

bond to the tertiary carbon breaks to give the stable

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

cation, which is captured by iodide. The methoxy group leaves as methanol. The products are

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

and

CH X_{3} OH

.

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