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Reaction-Map of Organic Chemistry Steven Murov Science, Mathematics and Engineering Division, Modesto Junior College, 435 College Ave., Modesto, CA 95350;
[email protected] A significant portion of the typical yearlong organic chemistry course includes the learning of a large number of organic reactions. While most textbooks use a mechanistic approach that facilitates the learning and understanding of the reactions, considerable memorization still is required before the students are able to apply the reactions to interesting synthetic challenges. Flash cards provide a useful method for studying the reactions but flash cards do not provide a view of the overall connections between functional groups. Some texts have attempted to simplify this learning exercise by compiling the reactions by functional group preparations or reactions. This compilation is often at the end of each chapter (1) and at least three texts have included a reaction summary in an appendix (2). Other authors have prepared partial roadmaps of the reactions to help students visualize the connecting reactions between different functional groups (3). The Reaction-Map of Organic Chemistry available in the online version of this article provides a visual overview on one page of most of the commonly studied reactions in organic chemistry as well as three keys organized by mechanism, functional-group preparations, and functional-group reactions. The chart has been partially arranged according to the periodic table on the horizontal axis and increasing carbon oxidation level for the color portions of the chart on the vertical axis. In addition, the carboxyl derivatives are grouped vertically according to decreasing reactivity, and carbon–carbon bond forming reactions are emphasized with bold arrows. The chart provides a study aid for students and should be especially useful when students are preparing for final examinations. Students should be able to classify each reaction according to mechanism, list reagents, conditions, regioselectivity, stereoselectivity, and restrictions that correlate with each reaction (with the online keys providing a check for correct answers) and give mechanisms for a selected number of reactions. The chart could also help students develop synthetic routes from one functional group to another.
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Journal of Chemical Education
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Though the layout of The Reaction-Map is related to the periodic table and oxidation level increase in the colored portion, it is not intended as an explanation for the reactions. Periodic tables for organic chemistry have been discussed but are not yet available in student-friendly form (4). The Reaction-Map has been developed to provide students with another learning aide that hopefully will make organic chemistry a little easier to master. W
Supplemental Material
The JCE Online article contains a color copy of the Reaction-Map, the complete mechanistic key, and two additional keys that classify the reactions by preparation and reactions of functional groups. Literature Cited 1. (a) Smith, J. G. Organic Chemistry; McGraw-Hill: New York, 2006. (b) Wade, L. G., Jr. Organic Chemistry, 6th ed.; Upper Saddle River, NJ, 2006. (c) Vollhardt, K. P. C.; Schore, N. E. Organic Chemistry: Structure and Function, 4th ed.; Freeman: New York, 2003. 2. Brucie, P. Y. Organic Chemistry, 4th ed.; Prentice Hall: Upper Saddle River, NJ, 2004; pp A13–A16. (b) Streitwieser, A., Jr. Introduction to Organic Chemistry; Macmillan: New York, 1976; pp 1199–1220. (c) Loudon, G. M. Organic Chemistry, 4th ed.; Oxford: New York, 2002; pp A8–A13. 3. (a) Parrill, A. L. EMOC—Organic Reaction Roadmap. http://www.cem.msu.edu/~parrill/roadmap/index.html (accessed Mar 2007). (b) Solomons, T. W.; Fryhle, C. B. Organic Chemistry, 8th ed.; Wiley: Hoboken, NJ, 2004. 4. (a) Hall, H. K., Jr. J. Chem. Educ. 1980, 57, 49–51. (b) Chen, L.; Gasteiger, J. Angew. Chem. Int. Ed. Engl. 1996, 35, 763– 765.
Vol. 84 No. 7 July 2007
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www.JCE.DivCHED.org
