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Fundamentals of Organic ChemistryChemistryBiomolecules

Consider the following sequence of reactions: The major product C is expected to be:

Options

  1. AMannose
  2. BFructose
  3. CArabinose
  4. DSorbitol

Correct answer

B. Fructose

Step-by-step solution

Reaction of glucose with excess phenylhydrazine ( PhNHNH ₂ ) yields glucosazone (A). Hydrolysis of glucosazone with H ₃ O ^+ and heat removes the phenylhydrazone groups, forming an osone called glucosone (B), which contains an aldehyde group at C-1 and a ketone group at C-2. Reduction of glucosone with Zn/AcOH selectively reduces the more reactive aldehyde group at C-1 to a primary alcohol ( CH ₂ OH ), while the ketone group at C-2 remains intact. This results in the formation of fructose (C). This entire sequence

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