D-(+) -Glucose ⟶5CH3CO2OD-(+) -glucose pentaacetate. Which statement is true about glucose pentaacetate?

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It will react with Tollen's reagent but not with reagent.

It will react with Tollen's reagent but not with phenylhydrazine

It will react with both of the above mentioned reagents.

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.

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