Fundamentals of Organic ChemistryChemistryBiomolecules
Which of the following compounds will not show mutarotation?
Options
- A-D-(+)-glucopyranose
- B-D-(+)-glucopyranose
- C-D-(+)-galactopyranose
- 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