Multiple Choice
Which of the following forms of glucose or its derivatives is capable of undergoing mutarotation?
9. Carbohydrates
Mutarotation
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Which of the following sugars undergoes mutarotation in neutral aqueous solution?
A
I and III.
B
III and IV.
C
II, III and IV.
D
I and IV.
E
I, II and IV.
Verified step by step guidance1
Identify the sugars that can undergo mutarotation. Mutarotation occurs in sugars that have a hemiacetal or hemiketal group, which allows them to open into an aldehyde or ketone form and then close again, forming a different anomer.
Examine structure I. It is a monosaccharide with a hemiacetal group, as indicated by the presence of an -OH group attached to the anomeric carbon. This allows it to undergo mutarotation.
Examine structure II. It is also a monosaccharide with a hemiacetal group, allowing it to undergo mutarotation.
Examine structure III. This sugar has an acetal group (indicated by the -OCH3 group attached to the anomeric carbon), which prevents it from undergoing mutarotation.
Examine structure IV. It is a disaccharide with a free hemiacetal group on one of the sugar units, allowing it to undergo mutarotation. Structure V is a disaccharide with no free hemiacetal groups, so it cannot undergo mutarotation.
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