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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro087

A compound X, , is optically inactive and cannot be resolved. It consumes one mole of per mole and gives a single organic product only. X is

  1. A2-methylpropane-1,2-diol
  2. Bbutane-1,2-diol
  3. Cmeso-butane-2,3-diol
  4. D(2R,3R)-butane-2,3-diol

Answer: C

One mole of shows a vicinal diol. A single product means the two halves are identical, which rules out butane-1,2-diol (methanal plus propanal) and 2-methylpropane-1,2-diol (methanal plus propanone). Butane-2,3-diol gives only ethanal, and the inactive, non-resolvable stereoisomer is the meso form (the (2R,3R) form is optically active).
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