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Fundamentals of Organic ChemistryChemistryBiomolecules

Which of the following compounds will not show mutarotation?

Options

  1. A-D-(+)-glucopyranose
  2. B-D-(+)-glucopyranose
  3. C-D-(+)-galactopyranose
  4. DMethyl -D-glucopyranoside

Correct answer

D. Methyl -D-glucopyranoside

Step-by-step solution

Mutarotation is the change in specific rotation of a chiral compound due to the interconversion of and anomers in solution. This process requires the sugar to have a free hemiacetal or hemiketal group, which allows the cyclic form to open into an acyclic aldehyde or ketone intermediate. -D-(+)-glucopyranose, -D-(+)-glucopyranose, and -D-(+)-galactopyranose all contain a free hemiacetal group at their anomeric carbon (C1) and are reducing sugars. Thus, they will undergo mutarotation in aqueous solution. Methyl -D-gl

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