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2002
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In the Laboratory
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A One-Pot Synthesis of m-Terphenyls: A Guided Exploration of Reaction Chemistry, Chromatography, and Spectroscopy. A Miniproject for the Advanced Organic Chemistry Laboratory
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Kishorekumar T. Anam, Michael P. Curtis, Muhammad J. Irfan, Michael P. Johnson, Andrew P. Royer, Kianor Shahmohammadi, and Thottumkara K. Vinod
Department of Chemistry, Western Illinois University, Macomb, IL 61455
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May 2002
Vol. 79 No. 5
p. 629
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| Abstract |
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This four-week project-based laboratory exercise, developed for advanced organic chemistry students, involves a one-pot synthesis of m-terphenyls. Chemistry of aryl diazonium salts and Grignard reagents and reactivity of aryne intermediates toward nucleophilic reagents form the reaction chemistry basis for the project. The project exposes students to a number of important laboratory techniques (thin-layer chromatography, gas chromatography-mass spectrometry, and column chromatography) for monitoring reaction progress and product isolation. A variety of spectroscopic techniques, including IR, 1H NMR, 13C NMR, and attached proton test are used for product characterization. Students are also introduced to a useful empirical relationship to help predict (with considerable accuracy) the 13C chemical shift values of carbon atoms of substituted benzenes.
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| Supplement |
Detailed experimental procedures, notes for the instructor, lists of chemicals (with CAS registry numbers) and equipment, the numbering system used in m-terphenyl nomenclature, a list of calculated and observed 13C chemical shifts of carbon atoms of the m-terphenyl derivatives, 1H and 13C NMR spectra of the m-terphenyl derivatives, and APT spectra of 4-H, 4-Br, 4-I, and 4-CO2H are available.
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JCE2002p629W.doc (Microsoft Word)
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| More Information |
Citation |
Anam, Kishorekumar T.; Curtis, Michael P.; Irfan, Muhammad J.; Johnson, Michael P.; Royer, Andrew P.; Shahmohammadi, Kianor; Vinod, Thottumkara K. J. Chem. Educ. 2002 79 629.
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Keywords |
Chromatography; IR Spectroscopy; Laboratory Instruction; Mass Spectrometry; NMR Spectrometry; Organic Synthesis; Reactive Intermediates
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History |
Created:
Last Updated: |
April 1, 2002
March 16, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2002
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May
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629
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