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Question

What oxidation reactions can be used to identify the configuration of sugars?


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Solution

Oxidation reactions:

  • The reactions in which oxygen is added or hydrogen is removed are called oxidation reactions.
  • Oxidations reactions can be very useful in the identification of the configuration of sugars.

Oxidations reactions of sugars:

1. Reaction with Bromine water:

  • The reaction of an aldose with Bromine water forms aldonic acid.
Bromine water test - Preparation of bromine water solution and application  of bromine water solutions.

2. Reaction with nitric acid:

  • The reaction of an aldose or aldonic acid with nitric acid produces a dicarboxylic acid in both cases.

Prediction of the configuration of sugars:

  • The above oxidation reactions help in identifying the symmetry in the molecules.
  • On oxidation, sugars like ribose, aldose, xylose, and galactose result in the formation of achiral aldaric acids that are optically inactive.
  • The oxidation of aldose sugars (diastereomeric) results in the formation of identical chiral aldaric acids, i.e, having similar configurations. For example, Both arabinose and lyxose give identical aldaric acid.

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