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Q.

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

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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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