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Q. Which of the following reactions and facts of $\text{D}$ -glucose cannot be explained by its open chain structure?

(i) Despite having the aldehyde group, glucose does not give Schiff test and $\text{2,4-DNP}$ test.

(ii) Glucose does not react with sodium hydrogen sulphite to form addition product.

(iii) The pentaacetate of glucose does not react with hydroxyl amine showing the absence of free- $\text{CHO}$ group.

NTA AbhyasNTA Abhyas 2020Biomolecules

Solution:

The above behaviour could not be explained by the open chain structure. Because one of the –OH groups of glucose 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. This explains the absence of –CHO group.