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Fundamentals of Organic ChemistryChemistryBiomolecules

Which of the following sugars forms an osazone derivative identical to that of D-glucose?

Options

  1. ABoth D-mannose and D-fructose
  2. BD-Fructose
  3. CD-Galactose
  4. DD-Mannose

Correct answer

A. Both D-mannose and D-fructose

Step-by-step solution

Osazone formation involves the reaction of a reducing sugar with excess phenylhydrazine, which reacts at the C1 and C2 positions of the sugar. Since the reaction destroys the stereocenter at C2 (in aldoses) and C1 (in ketoses), sugars that have identical configurations at all other chiral centers (C3, C4, and C5 in hexoses) will yield the exact same osazone. D-glucose, D-mannose, and D-fructose have identical stereochemistry at C3, C4, and C5. D-mannose is the C2 epimer of D-glucose, while D-fructose is the corresp

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