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2004
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In the Laboratory
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The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment
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Victor Cesare, Ishwar Sadarangani, Janet Rollins, and Dennis Costello
Department of Chemistry, St. John's University, Jamaica, NY 11439
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May 2004
Vol. 81 No. 5
p. 713
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| Abstract |
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The synthesis and isolation of the succinamic acids, 4-(tert-butylamino)-4-oxo-3-phenylbutanoic acid (3) and 4-(tert-butylamino)-4-oxo-2-phenylbutanoic acid (4), obtained by reacting phenylsuccinic anhydride (1) with tert-butylamine (2), is described. This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic of carboxylic acid derivatives into the organic chemistry laboratory. In addition, the 1H NMR spectrum of either product 3 or 4 clearly demonstrates that the methylene protons in a molecule containing a chiral center are diastereotopic. 
Scheme 1. Synthesis of the two isomeric phenylsuccinamic acids.
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| Supplement |
Instructions for the students, notes for the instructor, and spectra of the compounds are available.
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 Contents |
JCE2004p0713W.doc (Microsoft Word)
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| Download |
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| More Information |
Citation |
Cesare, Victor; Sadarangani, Ishwar; Rollins, Janet; Costello, Dennis. J. Chem. Educ. 2004 81 713.
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Keywords |
Chirality / Optical Isomers; Laboratory Instruction; NMR Spectrometry; Organic Synthesis
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History |
Created:
Last Updated: |
April 1, 2004
February 18, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
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May
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713
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