Fundamentals of Organic ChemistryChemistryBiomolecules
D-Glucose and D-fructose both form the same osazone derivative because they have:
Options
- Athe same configuration at C -5
- Bthe same constitution at C -1 and C -2
- Cthe same constitution and configuration at C -3, C -4, C -5 and C -6 but different constitution and configurat
- Dthe same constitution
Correct answer
C. the same constitution and configuration at C -3, C -4, C -5 and C -6 but different constitution and configurat
Step-by-step solution
Osazone formation involves the reaction of a reducing sugar with excess phenylhydrazine, which occurs at C -1 and C -2 . D-glucose is an aldohexose with an aldehyde group at C -1 and a hydroxyl group at C -2 . D-fructose is a ketohexose with a primary alcohol at C -1 and a ketone group at C -2 . Thus, they have different constitution and configuration at C -1 and C -2 . During osazone formation, both C -1 and C -2 are converted into phenylhydrazone groups, making them identical in the product. The rest of the carbo