D-(+) -Glucose ⟶5CH3CO2OD-(+) -glucose pentaacetate. Which statement is true about glucose pentaacetate?
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a
It will react with Tollen's reagent but not with reagent.
b
It will react with Tollen's reagent but not with phenylhydrazine
c
It will react with both of the above mentioned reagents.
d
It will react neither with phenylhydrazine nor with Tollen's reagent.
answer is D.
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Detailed Solution
During acetylation of (+)-glucose, it is the C1–OH of the hemiacetal that is acetylated and not the C5–OH that forms the ring (cyclic structure). Since equilibrium with the open-chain aldehyde is prevented, the pentaacetate does not respond the aldehydic reactions.