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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3274

The aryl dialkyl ether shown is heated with excess concentrated HI. Select all correct statements.

  1. AThe tert-butyl group is lost as a tertiary cation (captured as the iodide)
  2. BThe methyl group is lost through a methyl cation in an step
  3. CThe aromatic C-O bonds remain intact, giving a dihydroxybenzene
  4. DAn iodoarene is formed by cleavage of the aryl C-O bond

Answer: A, C

The compound is 1-tert-butoxy-4-methoxybenzene. The tert-butyl-oxygen bond breaks by (stable tertiary cation), and the methyl-oxygen bond breaks by (iodide attacks the unhindered methyl), not by , since a methyl cation is not accessible. The aryl C-O bonds are never cleaved, so the ring product is hydroquinone, not an iodoarene. Correct: first and third.
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