Question:
Enumerate the reactions of D-glucose which cannot be explained by its open chain structure.
Answer:
(1) Aldehydes give 2, 4-DNP test, Schiff s test, and react with NaHSO4to form the hydrogen sulphite addition product. However, glucose does not undergo these reactions.
(2) The pentaacetate of glucose does not react with hydroxylamine. This indicates that a free -CHO group is absent from glucose.
(3) Glucose exists in two crystalline forms - ∝ and β. The ∝-form (m.p. = 419 K) crystallises from a concentrated solution of glucose at 303 K and the β-form (m.p = 423 K) crystallises from a hot and saturated aqueous solution at 371 K. This behaviour cannot be explained by the open chain structure of glucose.
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