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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap165

A compound CHO consumes one mole of per mole and gives a single organic product, which gives a silver mirror with Tollens reagent and a yellow precipitate with . The compound is

  1. Abutane-2,3-diol
  2. Bbutane-1,4-diol
  3. C2-methylpropane-1,2-diol
  4. Dbutane-1,2-diol

Answer: A

Cleavage by requires a vicinal diol, which excludes butane-1,4-diol. Butane-1,2-diol gives and propanal, and 2-methylpropane-1,2-diol gives and propanone, i.e. two different products. Only symmetrical butane-2,3-diol gives a single product, 2 , which is Tollens and iodoform positive.
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