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Can recrystallation from an achiral solvent seperate a racemic mixture of (+ -)-phenylsuccinic acid? Explain. Can...

Can recrystallation from an achiral solvent seperate a racemic mixture of (+ -)-phenylsuccinic acid? Explain.

Can recrystallization from an achiral solvent seperate a 90:10 mixture of (+ -)-phenylsuccinic acid? Explain.

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Answer #1

Chiral resolution of enantiomers from racemic mixture directly by recrystallization is not possible as they have same physical and chemical properties except the direction of rotation of plane polarized light. Thus the entiomers are first converted into a diastereomer which now has different physical and chemical properties and then it is separated by recrystallization by preferential crystallization of one diastereomer over the other.

The phenylsuccinic acid needs to be first converted into an chiral ester which is now a diastereomer. The diastereomeric ester can now be separated easily by recrystallization. After separation the diastereomers are reconverted into free acid from a 90:10 mixture of (+/-phenylsuccinic acid..

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