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Fundamentals of Organic ChemistryChemistryBiomolecules

In the cyclic structure of D-fructofuranose, which carbon atom is the anomeric carbon?

Options

  1. AC-5
  2. BC-2
  3. CC-6
  4. DC-1

Correct answer

B. C-2

Step-by-step solution

D-fructose is a ketohexose with the ketone group located at the C-2 position in its open-chain structure. During the formation of the cyclic D-fructofuranose structure, the hydroxyl group at C-5 undergoes an intramolecular nucleophilic addition to the carbonyl carbon at C-2, forming a hemiketal ring. The carbonyl carbon (C-2) becomes a new chiral center in this cyclic structure. This newly formed chiral center is known as the anomeric carbon. Therefore, the anomeric carbon in D-fructofuranose is C-2. Answer: C-2

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