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NEET levelSingle correct optionDifficulty 1 of 3ap264

The ether shown is heated with excess concentrated . Which structure is the organic product that still contains the benzene ring?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The ether is anisole (methoxybenzene). Protonated oxygen is attacked by iodide at the methyl carbon, because cannot occur at an sp2 ring carbon. The products are phenol and methyl iodide; the phenol does not react further to give iodobenzene.
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