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JEE Main levelSingle correct optionDifficulty 2 of 3o3269

The methyl ether shown is treated with one equivalent of HI at 0 degrees C. Which products are obtained?

  1. AIodomethane and 2-methylpropan-2-ol
  2. BIodomethane and 2-iodo-2-methylpropane only, with no alcohol
  3. C2-Methylpropene and methyl iodide
  4. D2-Iodo-2-methylpropane and methanol

Answer: D

The compound is tert-butyl methyl ether. Protonation of the oxygen is followed by cleavage of the bond that gives the most stable cation: the tertiary C-O bond breaks () to give the tert-butyl cation, captured by iodide. The products are 2-iodo-2-methylpropane and methanol.
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