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BIO NMDCAT Carbohydrates
nmdcat.online June 27, 2026

In the context of epimerism, D-glucose and D-mannose are C-2 epimers. This interconversion is catalyzed by specific enzymes, but in a simple alkaline solution, this isomerization occurs through a common

A. Free radical intermediate
B. Enediol intermediate
✓
C. Carbocation intermediate
D. Carbanion intermediate

📝 Explanation

The Lobry de Bruyn–Alberta van Ekenstein transformation proceeds through the removal of a proton from C-2, forming an enediol (or enolate) intermediate. This intermediate can reprotonate to give either the original aldose (glucose), its C-2 epimer (mannose), or the ketose (fructose).

📖 Additional Information

  • Free radical intermediate
  • Enediol intermediate
  • Carbocation intermediate
  • Carbanion intermediate

The Lobry de Bruyn–Alberta van Ekenstein transformation proceeds through the removal of a proton from C-2, forming an enediol (or enolate) intermediate. This intermediate can reprotonate to give either the original aldose (glucose), its C-2 epimer (mannose), or the ketose (fructose).

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