NCERT Class XII Chemistry
Chapter - Biomolecules
Questions with Solutions

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Question : 28
Total: 33
How do you explain the absence of aldehyde group in pentaacetate of glucose ?
Solution:  
The cyclic hemiacetal form of glucose contains an OH group at C-1 which gets hydrolysed in the aqueous solution to produce the open chain aldehydic form which then reacts with NH2OH to form the corresponding oxime. Therefore, glucose contains an aldehydic group. On the other hand, when glucose is reacted with acetic anhydride, the OH group at C-1, along with the four other OH groups at C-2, C-3, C-4 and C-6 form a pentaacetate. As the pentaacetate of glucose does not contain a free OH group at C-1, it cannot get hydrolysed in aqueous solution to produce the open chain aldehydic form and thus glucose pentaacetate does not react with NH2OH to form glucose oxime. Hence, glucose pentaacetate does not contain the aldehdye group.
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