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Question
Enlist the properties of glucose that can not be explained on the basis of open chain structure of it
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Solution
Although the open chain structure of D (+) − Glucose explains most of its reactions, it fails to explain the following facts:
a) D (+)-Glucose does not undergo certain characteristic reactions of aldehydes
eg., Glucose does not form NaHSO3 addition product, aldehyde-ammonia adduct 2, 4 − DNP derivative and does not respond to Schiff’s reagent test.
b) Glucose reacts with NH2OH to form an oxime but glucose pentaacetate does not react
with NH2OH, which implies that the free aldehyde group is absent in glucose pentaacetate
c) D(+)-Glucose exists in two stereoisomeric crystalline forms, i.e. α-glucose and
β-glucose, called anomers. α-D(+)-Glucose is obtained when a concentrated aqueous or
alcoholic solution is crystallised at 303 K. It has a melting point of 419 K and has a
specific rotation of +111° in a freshly prepared aqueous solution.
However, when glucose is crystallised from water above 371 K, β-D(+)-glucose is
obtained. It has a melting point of 423 K and has a specific rotation of +19.2° in a
freshly prepared aqueous solution. This behaviour could not be explained by the open
chain structure of glucose.
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