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NCERT Class XII Chemistry
Chapter - Biomolecules
Questions with Solutions

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Question : 28 of 33
Marks: +1, -0
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 NH2OHNH_2OH 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 NH2OHNH_2OH to form glucose oxime. Hence, glucose pentaacetate does not contain the aldehdye group.
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