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

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1. Elemental analysis and molecular weight determination of fructose show that it has the molecular formula C6H12O6.

2. Fructose on reduction with Hl and red phosphoms gives a mixture of n – hexane (major product) and 2 – iodohexane (minor product). This reaction indicates that the six carbon atoms in fructose are in a straight chain.

3. Fructose reacts with NH2OH and HCN. It shows the presence of carbonyl groups in the molecules of fructose.

4. Fructose reacts with acetic anhydride in the presence of pyridine to form penta acetate. This reaction indicates the presence of’ five hydroxyl groups in a fructose molecule.

5. Fructose is not oxidized by bromine water. This rules out the possibility of presence of an aldehyde (-CHO) group.

6. Partial reduction of fructose with sodium amalgam and water produces mixtures of sorbitol and mannitol which are epimers at second carbon. New asymmetric carbon is formed at C – 2. This confirms the presence of keto group.

7. On oxidation with nitric acid, it gives glycolic acid and tartane acids which contain smaller number of carbon atoms than in fructose. This shows that a keto group is present in C – 2. It also shows the presence of 10 alcoholic groups at C- 1 and C- 6. From the above reaction the structure of fructose is

This shows that a keto group is present in C – 2. It also shows the lpresence of 10 alcoholic groups at C – 1 and C – 6. From the above reaction the structure of fructose is

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