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Fundamentals of Organic ChemistryChemistryBiomolecules

D-Glucose reacts with anhydrous methyl alcohol in the presence of dry HCl gas to form:

Options

  1. A-Methyl D-glucopyranoside
  2. B-Methyl D-glucopyranoside
  3. C2,3,4,5,6-Penta-O-methyl D-glucose
  4. 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

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