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JEE Advanced levelSingle correct optionDifficulty 3 of 3co155

Propanone is reduced with magnesium amalgam in benzene followed by water to give P. P is heated with concentrated to give Q (pinacol-pinacolone rearrangement). Q is treated with / and acidified to give R. R is

  1. A3,3-dimethylbutanoic acid
  2. B2,3-dimethylbutanoic acid
  3. C2-methylpropanoic acid
  4. D2,2-dimethylpropanoic acid

Answer: D

Bimolecular reduction gives P = 2,3-dimethylbutane-2,3-diol. Acid causes methyl migration to give Q = , 3,3-dimethylbutan-2-one. The haloform reaction removes the as , so R = , 2,2-dimethylpropanoic acid.
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