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A one-pot synthesis of m-terphenyls
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.
Address (URL): http://pubs.acs.org/doi/abs/10.1021/ed079p629?prevSearch=%255Bauthor%253A%2BT.%2 BK.%2Bvinod%255D%2BNOT%2B%255Batype%253A%2Bad%255D%2BNOT%2B%255Batype%253A%2Bacs -toc%255D&searchHistoryKey=