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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

J. Chem. Educ., 2002, 79 (5), p 629

DOI: 10.1021/ed079p629

Publication Date (Web): May 1, 2002

Section:

History, Education, and Documentation

Abstract

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.

Keywords (Domain):

Organic Chemistry

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