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Reaction of glucose with 2,4-dinitrophenylhydrazine (DNPH)

Discussion in 'Chemistry' started by Manish Bhatt, Nov 8, 2020.

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  1. Manish Bhatt

    Manish Bhatt Guest

    In its open-chain form, glucose possesses an aldehyde group; however, glucose does not test positive with 2,4-dinitrophenylhydrazine (which typically forms a yellow/orange/red precipitate with carbonyl compounds).

    Why is this so? Is this a reflection of the cyclic hemiacetal form (where the aldehyde group is not present)?

    Both forms are in equilibrium so I'd expect it to give a positive test.


    Consider also that glucose gives a positive test in both the Tollens' and Benedict's test. While it is true that less than one in hundred exists in the aqueous solution as the cyclic form, this is not sufficient to explain why it does not give a positive test with 2,4-dinitrophenylhydrazine but yet gives a positive test in Tollens' test and also in Benedict's test.

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