Fundamentals of Organic ChemistryChemistryBiomolecules
D-Glucose reacts with anhydrous methyl alcohol in the presence of dry HCl gas to form:
Options
- A-Methyl D-glucopyranoside
- B-Methyl D-glucopyranoside
- C2,3,4,5,6-Penta-O-methyl D-glucose
- DBoth - and -methyl D-glucopyranosides
Correct answer
D. Both - and -methyl D-glucopyranosides
Step-by-step solution
D-Glucose exists predominantly in its cyclic hemiacetal forms, -D-glucopyranose and -D-glucopyranose. When D-glucose is treated with anhydrous methyl alcohol in the presence of dry HCl gas, a Fischer glycosidation reaction takes place. The acid catalyzes the conversion of the hemiacetal at the anomeric carbon (C-1) into an acetal. During this process, only the anomeric hydroxyl group is replaced by a methoxy ( -OCH₃ ) group. The other hydroxyl groups remain unaffected because they are ordinary alcohols, not hemiace