On warming the osazone with hydrochloric acid the phenylhydrazine residues are removed and an osone results, which on reduction with zinc and acetic acid gives a ketose.
CHO CH20H Osazone o Osone -> Ketose.
A ketose may also be obtained by reducing the osazone with zinc and acetic to an osamine, which with nitrous acid gives the ketose: R R R C :N NHPh.
Osazone -> Osamine -> Ketose.
It is seen that aldoses and ketoses which differ stereochemically in only the two final carbon atoms must yield the same osazone; and since d-mannose, d-glucose, and d-fructose do form the same osazone (d-glucosazone) differences either structural or stereochemical must be placed in the two final carbon atoms.3 It may here be noticed that in the sugars there are asymmetric carbon atoms, and consequently optical isomers are to be expected.
The osazone prepared from a-acrose resembled most closely the glucosazone yielded by glucose, mannose, and fructose, but it was optically inactive; also the ketose which it gave after treatment with hydrochloric acid and reduction of the osone was like ordinary fructose except that it was inactive.
Cane sugar has no reducing power and does not form an hydrazone or osazone; the other varieties, however, reduce Fehling's solution and form hydrazones and osazones, behaving as aldoses, i.e.