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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

  1. A3
  2. B4
  3. C5
  4. 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

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