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JEE Main levelSingle correct optionDifficulty 2 of 3bm019

D-Arabinose, an aldopentose, undergoes Kiliani-Fischer chain extension (HCN, hydrolysis, reduction). The aldohexoses obtained are

  1. AD-glucose and D-galactose
  2. BD-mannose and D-galactose
  3. CD-glucose and D-mannose
  4. DD-glucose and D-fructose

Answer: C

HCN adds to C-1 to give two cyanohydrins that differ only at the new C-2. The old C-2 to C-4 become C-3 to C-5, which match glucose and mannose, so the products are the C-2 epimers D-glucose and D-mannose.
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