Question
Write the reactions of D-glucose which can’t be explained by its open-chain structure. How can cyclic structure of glucose explain these reactions?

Answer

Following reactions and facts could not be explained by open chain structure of glucose.
  • Despite having the aldehyde group, glucose does not give $2,4-DNP$ test, Schiff’s test and it does not form the hydrogensulphite addition product with $NaHSO_3.$
  • The pentaacetate of glucose does not react with hydroxylamine indicating the absence of free $—CHO$ group.
It was proposed that one of the $—OH$ groups may add to the $—CHO$ group and form a cyclic hemiacetal structure. It was found that glucose forms a six-membered ring in which $—OH$ at $C-5$ is involved in ring formation.

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