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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap089

1-(4-Methoxyphenyl)-2-methyl-1-phenylpropane-1,2-diol, , is treated with dilute . The main product is

  1. A2-(4-methoxyphenyl)-2-methyl-1-phenylpropan-1-one
  2. B1-(4-methoxyphenyl)-2-methyl-2-phenylpropan-1-one
  3. C2-methyl-1-(4-methoxyphenyl)-1-phenylprop-1-ene
  4. D3-(4-methoxyphenyl)-3-phenylbutan-2-one

Answer: D

Loss of the hydroxyl on C-1 gives a diarylcarbenium ion that is far more stable than the tertiary alkyl cation at C-2, and the 4-methoxy group stabilises it further. The only groups on C-2 that can migrate are the two methyls, so one methyl moves to C-1. C-2 becomes and C-1 becomes , giving 3-(4-methoxyphenyl)-3-phenylbutan-2-one.
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