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JEE Main levelSingle correct optionDifficulty 2 of 3ro177

Acetone is treated with magnesium amalgam in dry benzene, followed by water. The product is

  1. A2,3-dimethylbut-2-ene
  2. B2,3-dimethylbutane-2,3-diol
  3. C2,3-dimethylbutane
  4. Dpropan-2-ol

Answer: B

Mg(Hg) transfers an electron to the carbonyl to give a ketyl radical anion, and two ketyl radicals couple through carbon. After hydrolysis the 1,2-diol (pinacol) is obtained. Simple reduction to propan-2-ol would need a hydride or protic dissolving metal conditions.
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