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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro198

Open-chain fructose, , is oxidised completely by excess . Count every cleavage, including the cleavage of the alpha-hydroxy acid formed from the ketone carbon. The number of moles of consumed and of formed per mole of fructose are respectively

  1. A5 and 0
  2. B4 and 1
  3. C6 and 1
  4. D5 and 1

Answer: D

The chain has five C-C bonds, each between carbons carrying oxygen functions, and each is cleaved once, so 5 mol HIO4 are used. Cleavage of C1-C2 (alpha-hydroxy ketone) gives HCHO and turns C2 into a carboxyl group, and this alpha-hydroxy acid is then cleaved at C2-C3, releasing C2 as . C1 and C6 give HCHO and C3, C4, C5 give HCOOH, so 1 mol of is formed.
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