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BIO NMDCAT Carbohydrates
nmdcat.online June 27, 2026

The Keto-enol tautomerization of a monosaccharide in a basic solution is the chemical basis for the phenomenon where

A. A single reducing sugar can be isomerized to a mixture, including its epimer
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B. Sucrose becomes a reducing sugar
C. Polysaccharides spontaneously depolymerize into monomers
D. Glucose is exclusively converted to its acyclic form

📝 Explanation

In alkaline conditions, monosaccharides undergo keto-enol tautomerism (Lobry de Bruyn–Alberta van Ekenstein transformation). For example, glucose can form an enediol intermediate that can then convert to either glucose, fructose, or mannose. This results in the epimerization of glucose to mannose at C-2.

📖 Additional Information

  • A single reducing sugar can be isomerized to a mixture, including its epimer
  • Sucrose becomes a reducing sugar
  • Polysaccharides spontaneously depolymerize into monomers
  • Glucose is exclusively converted to its acyclic form

In alkaline conditions, monosaccharides undergo keto-enol tautomerism (Lobry de Bruyn–Alberta van Ekenstein transformation). For example, glucose can form an enediol intermediate that can then convert to either glucose, fructose, or mannose. This results in the epimerization of glucose to mannose at C-2.

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