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lgould lgould
wrote...
12 years ago
Can someone please explain this to me? Thanks!
Thank you for your response but I am still unsure of why those two particular sugars form the same osazone.
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datageekgh Author
wrote...
12 years ago
Osazones are a class of carbohydrate derivatives found in organic chemistry formed when sugars are reacted with phenylhydrazine. The famous German chemist Emil Fischer developed and used the reaction to identify sugars whose stereochemistry differed by only one chiral carbon. The reaction involves formation of a pair of phenylhydrazone functionalities, concomitant with the oxidation of the hydroxymethylene group adjacent to the formyl center. The reaction can be used to identify monosaccharides. It involves two reactions. Firstly glucose with phenylhydrazine gives us glucosephenylhydrazone by elimination of a water molecule from the functional group.The next step involves reaction of one mole of glucosephenylhydrazone with two moles of phenylhydrazine (excess).First phenylhydrazine is involved in oxidizing the alpha carbon to a carbonyl group, and the second phenylhydrazine involves in removal of one water molecule with the formyl group of that oxidized carbon and forming the similar carbon nitrogen bond .The alpha carbon is attacked here because its more reactive than the others.They are highly coloured and crystalline compounds and can be easily detected.
wrote...
12 years ago
From the structures of D-glucose, D-fructose and their derived osazones, the chirality at C2 is lost. And the C3 to C6 of D-glucose and D-fructose are identical. Thus, the osazones derived from them are identical.
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