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Two sugars are epimers of each other. Is it possible to convert one to the other without breaking covalent bonds? Why?

a) For chiral molecules with adjacent stereocenters, such as monosaccharides, a coordinated set of bond rotations can reverse th stereocenter.
b) For molecules with fourbr more stereocenters, the two epimers can interconvert by selected bond rotations
c) Rotation around bonds will not alter the chirality of a stereocenter )
d) A sing le rotation around each of two specific bonds of a stereocenter will alter the chirality at that stereocenter.

2 Answers

6 votes

Final answer:

Epimers are diastereomers that differ in the configuration of only one chiral carbon. Rotation around bonds cannot change this configuration; the interconversion of epimers requires a chemical reaction that breaks and reforms covalent bonds.

Step-by-step explanation:

Two sugars that are epimers of each other differ only in the configuration around one specific carbon atom. For example, D-glucose and D-mannose are epimers; they differ only at the second carbon atom. Similarly, D-glucose and D-galactose are epimers differing at the fourth carbon atom.

Epimers are a type of stereoisomer called diastereomers. In order to convert one epimer to another, a change in the configuration of a single chiral carbon is required. However, rotation around bonds, such as single-bond rotation, will not change the absolute configuration of the chiral carbon; hence, the configuration of a stereocenter cannot be altered by simple rotation. The only way to convert one epimer into the other is through a chemical reaction that breaks and reforms covalent bonds. Thus, simple physical rotation around single bonds cannot lead to the interconversion of epimers.

User Dierdre
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1 vote

Answer:

Option c) is correct

Step-by-step explanation:

No, it is not possible to convert one sugar to the other without breaking covalent bonds as rotation around bonds will not alter the chirality of a stereocenter.

(A stereocenter refers to any point in a molecule that consists of various substituents, such that as two substituents are interchanged, it results in a stereoisomer.)

Therefore,

Option c) is correct

User Wilmer
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3.3k points