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Resolution of Racemic Phenylsuccinic Acid Using (-)-Proline as a Resolving Agent: An Introductory Organic Chemistry Experiment
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Abstract
The resolution of phenylsuccinic acid by salt formation with (-)-proline can be easily used as an undergraduate organic laboratory experiment. Isolation of the (+)-enantiomer can be completed in about two hours and this procedure can also be used to introduce the reflux and recrystallization techniques. This resolution offers several advantages, such as use of relatively nontoxic odorless reagents, high yields of both enantiomers, and a high specific rotation for phenylsuccinic acid.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
StereochemistryCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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Marsha R. Baar and Andrea L. Cerrone-SzakalJournal of Chemical Education2005 82 (7), 1040Enantiomeric Resolution of (±)-Mandelic Acid by (1R,2S)-(–)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism
Marsha R. Baar and Andrea L. Cerrone-SzakalJournal of Chemical Education2005 82 (7), 1040There has been an increasing need, particularly in the pharmaceutical industry, to prepare chiral substances in single-isomer form. A chiral technique that makes an excellent introductory organic chemistry experiment is enantiomeric resolution. The ...
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- Received: August 03, 2009
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