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Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic Laboratory

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Kevin W. Kittredge , Susan S. Marine and Richard T. Taylor

Department of Chemistry and Biochemistry, Miami University–Middletown, Middletown, OH 45042

J. Chem. Educ., 2004, 81 (10), p 1494

DOI: 10.1021/ed081p1494

Publication Date (Web): October 1, 2004

Section:

History, Education, and Documentation

Abstract

A combinatorial organic chemistry experiment that utilizes an inexpensive commercially available parallel reactor, Argonaut's FirstMate, is described. Students perform a metal catalyzed partial hydrogenation reaction on a multi-functionalized substrate and analyze product ratios by GC–MS. Students evaluate a simple organic reaction that yields four different products. The reactions are performed in the presence and absence of a reaction modifier, methanesulfonic acid. Differing product ratios are obtained with the different types of metal catalysts and with the presence or the absence of the reaction modifier. Students discover which set of reaction conditions can be used to produce the highest yield of any desired product. They learn that optimizing reactions is both time and labor intensive and conducting parallel reactions is an efficient way to improve productivity. This experiment is an introduction to methods used in industrial and pharmaceutical chemistry.