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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap218

Which of the following ethers give an alkyl iodide and an alcohol (or phenol) on cleavage with one equivalent of as stated?

  1. A gives phenol and
  2. B gives and methanol
  3. C gives and propan-2-ol
  4. D gives iodobenzene and ethanol

Answer: A, B, C

Aryl alkyl ethers cleave at the alkyl C-O bond to give phenol and an alkyl halide, never an aryl halide, so (A) is correct and (D) is wrong. A tert-butyl ether cleaves by SN1 to the tertiary iodide, (B). A methyl isopropyl ether cleaves by SN2 at the less hindered methyl group, (C).
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