Q.Glucose pentaacetate (in which all five groups are acetylated) does not react with hydroxylamine, , even though hydroxylamine normally reacts readily with a free aldehyde group. What does this tell you about the actual structure of glucose in solution?
If glucose genuinely existed as the simple open-chain aldehyde structure, its pentaacetate -- in which all five hydroxyl groups are acetylated -- would still retain a completely free, unreacted aldehyde group at C1, since acetylation only affects groups, not the carbonyl. A free aldehyde group reacts readily with hydroxylamine, , to form an oxime. The fact that glucose pentaacetate does not react with hydroxylamine at all shows that no free aldehyde group is actually available in the molecule to react.
This is explained by glucose existing predominantly as a cyclic hemiacetal: the group on C5 reacts intramolecularly with the aldehyde carbon at C1, converting what would have been a free aldehyde into a ring carbon bearing an group (the anomeric ) instead. Once this cyclic form is acetylated at all five hydroxyl positions (including the anomeric one), there is no free carbonyl left anywhere in the molecule for hydroxylamine to attack.
Because glucose exists mainly as a cyclic hemiacetal (not the open chain), its C1 carbon bears an group rather than a free aldehyde -- so glucose pentaacetate has no free carbonyl group for hydroxylamine to react with.
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