Fundamentals of Organic ChemistryChemistryBiomolecules
When methyl D-glucopyranoside is oxidised with periodic acid, how many moles of the oxidising agent are consumed per mole of the glycoside?
Options
- A3
- B4
- C5
- D2
Correct answer
D. 2
Step-by-step solution
Methyl D-glucopyranoside is an acetal of D-glucose and exists as a six-membered pyranose ring. Its structure contains a methoxy group at C1 and hydroxyl groups at C2, C3, C4, and C6. Periodic acid ( HIO₄ ) cleaves the C-C bond between adjacent carbon atoms that both possess hydroxyl groups (vicinal diols). In methyl D-glucopyranoside: C1 has a methoxy group and no free hydroxyl group, so the C1-C2 bond is not cleaved. C2 and C3 both have hydroxyl groups, so the C2-C3 bond is cleaved, consuming 1 mole of HIO₄ . C3 a