Separation Of Enantiomers

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Enantiomers are chiral molecules that are nonsuperimposable, mirror images of each other and have same physical properties. However, enantiomers rotate different plane polarized light. The separation of enantiomers from a racemic ibuprofen—(S)-(+)-ibuprofen and (R)-(-)-ibuprofen—occurred from the transformation of enantiomers to diastereomers. Diastereomers formed because they are chiral molecules that are not mirror images and have different physical properties. When a racemic-(±)-ibuprofen reacted with (S)-(-)-α-phenethylamine, a base—sodium hydroxide—deprotonated the carboxylic acid in both enantiomers of ibuprofen and protonated the amine in (S)-(-)-α-phenethylamine, forming two diastereomeric salts. The (S, S) salt that is insoluble in