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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro183

Which of the following transformations are correctly matched with the product after aqueous work-up?

  1. Aacetone with Mg(Hg) gives 2,3-dimethylbutane-2,3-diol
  2. Bethyl pentanoate with Na in ethanol gives pentan-1-ol
  3. Cdiethyl hexanedioate with Na in boiling xylene gives 2-hydroxycyclohexanone
  4. Dbenzaldehyde with Mg(Hg) gives phenylmethanol (benzyl alcohol) as the main product

Answer: A, B, C

Mg(Hg) couples ketyl radicals, so acetone gives pinacol. Bouveault-Blanc reduction gives the primary alcohol, and an intramolecular acyloin condensation of the six-carbon diester gives 2-hydroxycyclohexanone. Benzaldehyde under Mg(Hg) couples similarly to hydrobenzoin (1,2-diphenylethane-1,2-diol), not benzyl alcohol.
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