Reaction of Monosaccharides: Osazone formation

Osazone formation is a general reaction of a-hydroxyl aldehydes and a-hydroxy ketones

Q. Aldehydes are more easily reduced than ketones. On this basis what product would you expect from the
reduction of glucosone by zinc and acetic acid? Outline a sequence of reactions by which an aldose can be
turned into a 2-ketose.

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 Reaction of Monosaccharides: Osazone formation

Amadori Rearrangement

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Osazone formation of glucose and fructose involve only C1 and C2 Amadori rearrangement
does not occur beyond C2 .
This is due to the fact that the osazone so formed is stabilized through intra molecular hydrogen bonding and forms stable 6-
membered cyclic ring. Two hydrogen bonded structures are possible which are shown below.

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Reaction of Monosaccharides: Osazone formation; Mechanism

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 Oxidation of Terminal Carbons

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 Periodic Acid Oxidation of Sugars

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 How many HI molecules required and what are the products?

A B
Write the structure of the product when excess HIO4
Treatment followed by aq HCl Treatment

Q. Treatment of (+)-glucose with HIO4 gives results that confirm its aldohexose structure. What
products should be formed, and how much HIO4 should be consumed?

Q. Identify each of the following glucose derivatives

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 Solve the Problem given below

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