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Question

If there is no rotation of plane-polarized light by a compound in a specific solvent, thought to be chiral, it may mean that


A

the compound may be a racemic mixture

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B

the compound is certainly chiral

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C

the compound is certainly meso

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D

there is no compound in the solvent

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Solution

Due to the rotation of plane polarised light caused by an optically active molecule, the substance can be a racemic combination. However, the optically active chemical loses its optical activity as a result of some external compensation (heat, light, catalyst, solvent, etc.). Due to an intramolecular rearrangement, the molecule then exists as a racemic mixture, meaning that both the d and l forms are present in the solution. Therefore, plane polarised light is not rotated, the compound has no asymmetric centre, and when it forms the symmetric centre once more, both the d and l forms are acquired in an equal amount.

Conclusion: Hence, option (B) is the correct answer.


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