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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap030

2-Methyl-1,1-diphenylpropane-1,2-diol, , is treated with dilute (pinacol rearrangement). The ionisation occurs at the carbon that gives the more stable cation, followed by migration of a group from the neighbouring carbon. The major product is

  1. A2-methyl-1,2-diphenylpropan-1-one
  2. B3,3-diphenylbutan-2-one
  3. C1,1-diphenylpropan-2-one
  4. D3,3-diphenylbutan-2-ol

Answer: B

Loss of the OH on the diphenyl carbon gives the diphenylmethyl-type cation, which is better stabilised than the tertiary dimethyl cation. A methyl group then migrates from the carbinol carbon, which becomes . The result is , 3,3-diphenylbutan-2-one.
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