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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap032

A diol of formula consumes one mole of and gives only methanal and butan-2-one. The diol is

  1. Apentane-1,2-diol
  2. B3-methylbutane-1,2-diol
  3. C2-methylbutane-2,3-diol
  4. D2-methylbutane-1,2-diol

Answer: D

Cleavage must separate a carbon (giving ) from a carbon bearing OH, and (giving butan-2-one). That is , 2-methylbutane-1,2-diol. Pentane-1,2-diol gives butanal, the 3-methyl isomer gives 2-methylpropanal, and 2-methylbutane-2,3-diol gives propanone and ethanal.
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