1.

Explain aboutthe structure of Fructose . (OR) Elucidate the structure of Fructose .

Answer»

Solution :(i) ELEMENTAL analysis and molecularweight determinationof FRUCTOSE show thatit has themolecularformula `C_(6)H_(12)O_(6)`.
(ii) Fructoseon reducing with HI and red phosphorus givesa mixture of n - hexane (majorprodcut) and 2 - iodohexane(minor product) . This reactionthatthesixcarbon atoms in fructoseare ina straight CHAIN.

(iii) Fructosereacts with`NH_(2)OH` and HCN . It Shows the presence of carbonylgroup in themolecules of fructose .
(iv)Fructosereactswithacetic anhydride inn the presence of phyridine to form penta acetate .Thisreactionindicatesthe presence of fivehydroxylgroup in a fructosemolecule.
(v) Fructose is notoxidized bybrominewater . This rules outthe possibilityof presence of analdehyde (-CHO) group.
(vi)Partial reduciton of fructosewith sodium amalganand waterproduces mixtureof sorbitol andmannitol whichareepimers at second carbon. New asymmericcarbon is formedat C - 2. Thiconfirmsthe presenceof keto group.

(vii) On oxidation withnitricaicd,it gives glycolic acid and tartaricacids whihcontainssmallernumberof carbon atoms thanin fructose .

This shows thata ketogroupis present in C- @ . Italosshownthe presenceof 10 alcoholicgroups atC - 1and C - 6 . From the above reactionthe structureof fructose is .


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