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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3218

Which ethers give a phenol as one of the products when heated with one equivalent of concentrated HI?

  1. Abenzyl methyl ether
  2. Banisole
  3. Cdiphenyl ether
  4. Dethyl 4-methylphenyl ether

Answer: B, D

Aryl alkyl ethers cleave at the alkyl-oxygen bond, because iodide cannot attack the aryl carbon, and give a phenol plus an alkyl iodide. Diphenyl ether has no alkyl group to be attacked and does not cleave. Benzyl methyl ether cleaves at an alkyl carbon and gives benzyl-type or methyl products, not a phenol.
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