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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc164

Cumene is manufactured from benzene and propene, and then converted into phenol by the cumene process. Select the correct statement(s).

  1. An-Propylbenzene is the main product of the alkylation step.
  2. BThe alkylating electrophile in the first step is the isopropyl (propan-2-yl) carbocation.
  3. CPropanone is obtained as a co-product when the hydroperoxide is treated with dilute acid.
  4. DCumene is oxidised by air to cumene hydroperoxide, which is an intermediate.

Answer: B, C, D

Protonation of propene gives the secondary isopropyl cation, so cumene (not n-propylbenzene) is formed. Air oxidation at the tertiary benzylic C-H gives cumene hydroperoxide, and acid-catalysed rearrangement (phenyl shift to oxygen) gives phenol and propanone.
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