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Fundamentals of Organic ChemistryChemistryBiomolecules

Which of the following pairs of sugars forms identical osazone derivatives upon reaction with excess phenylhydrazine?

Options

  1. AD-(+)-Glucose and D-(-)-fructose
  2. BD-(+)-Glucose and (+)-maltose
  3. CD-(+)-Glucose and (+)-lactose
  4. DD-(+)-Glucose and D-(-)-arabinose

Correct answer

A. D-(+)-Glucose and D-(-)-fructose

Step-by-step solution

Osazone formation involves the reaction of excess phenylhydrazine with the C1 and C2 carbon atoms of reducing sugars. During this reaction, the stereochemistry at C1 and C2 is destroyed as both carbons are converted into phenylhydrazone groups. Sugars that have identical configurations at all chiral centers below C2 (i.e., C3, C4, and C5) will yield the same osazone. D-(+)-Glucose (an aldohexose) and D-(-)-fructose (a ketohexose) have identical stereochemistry at C3, C4, and C5. Therefore, they form the exact same

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