Chemical Education Today
Book & Media Reviews Modern Projects in Organic Chemistry: Miniscale and Standard Taper Microscale, 2nd Edition by Jerry R. Mohrig, Christina Noring Hammond, Paul F. Schatz, and Terence C. Morrill W. H. Freeman and Co.: New York, 2003. 504 pp. ISBN 0176797798. $73.75
Modern Projects in Organic Chemistry: Miniscale and Williamson Microscale, 2nd Edition by Jerry R. Mohrig, Terence C. Morrill, and Paul F. Schatz W. H. Freeman and Co.: New York, 2003. 504 pp. ISBN 01716739216. $73.75 reviewed by Richard Pagni
I still remember vividly, even after four decades, my first few days in the undergraduate organic chemistry laboratory. For a shy, not very secure, young man of 18 the experience was overwhelmingly negative. With no lab lecture to guide me (but with a very good book—Fieser’s 3rd edition (1)), and seemingly little help from my TA, I was lost. Fortunately, given time, I found my wings and prospered there. What I learned was classical organic methodology. Many reactions common today were unknown then. Reactions were often cookbookish and carried out individually on a large scale. Standard taper glassware was unknown (oh, those awful rubber stoppers, corks, and cork borers!). Spectroscopy was not an essential part of the experience because in 1960 it was largely unknown or unavailable. How things have changed. What do chemical educators today want students to learn in the organic laboratory? What should a lab manual contain to make this possible? In the abstract we wish today’s students to be conversant in basic, modern organic chemistry laboratory practice. They need to run old and modern reactions and learn how to isolate, purify, and identify compounds. To accomplish this, students must be exposed to the techniques, methods, procedures, and apparatus in common use in organic chemistry. Students should carry out inquiry-based experiments and projects. It is a lot more fun—and realistic—to seek an answer than to know it ahead of time. This gives a real sense of how research is carried out. Because of the pedagogical value of group learning, students should carry out several group projects. They must be exposed to some forms of chromatography and all elementary spectroscopy including FT NMR (1H and 13C), FT IR, mass, and perhaps a little Raman. This can be done in the context of identifying reaction products or unknowns, for example. Students clearly must be exposed to the fundamentals of chirality, which can be accomplished in several guises including optical resolution, polarimetry, chiral chromatography, chiral shift reagents, natural products, stereochemistry of reactions, and enzyme-catalyzed reactions to name more than a few. www.JCE.DivCHED.org
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Modern Projects and Experiments in Organic Chemistry, which comes in two closely related versions, one for miniscale and standard taper microscale and the other for miniscale and Williamson microscale, in conjunction with the authors’ techniques in organic chemistry book which I favorably reviewed in this Journal (2) nicely fulfills these criteria. The book (I will consider the two versions as a single entity), which has been significantly revised from the first edition, is filled with interesting and creative, one-week and multi-week, self-contained experiments, projects, and reactions that often make heavy demands on chromatography and spectroscopy. As was the case with the authors’ techniques book, the writing, drawings, and equations are clear and error free. To give the reader a flavor of the experiments in the book, let me briefly describe several inquiry-based experiments that I liked. The student will carry out a free radical monochlorination and dibromination of an alkane, in the first instance to compare the distribution of observed chloroalkanes with that predicted statistically and in the second to deduce the stereochemistry of the product (meso versus d,l). In both cases the halogen is prepared in situ. In another experiment the student will determine the regiochemistry of the addtion of HBr to an alkene. From the structure of the product the student will be able to deduce if the reaction occurred by a free radical or ionic mechanism. (You may recall that the regiochemistry of the addition of HBr to alkenes vexed chemists during the 1930s.) The student will also examine the effect of base [CH3O- versus (CH3)3CO-] on the regiochemistry of the E2 reaction of an alkyl halide. The student will thus examine how steric effects influence the E2 reaction. The synthesis of a Grignard reagent and its subsequent reaction with a carbonyl-containing compound is a common feature of all organic lab manuals. When I took the course, the class synthesized triphenylcarbinol from bromobenzene and methyl benzoate, for example. In this book the student will prepare a Grignard reagent in order to make one of two dyes, crystal violet or malachite green. The student is thus exposed to two important topics in the same experiment. Another experiment will expose the student to a very important concept in organic synthesis: the selective reaction of one functional group in the presence of another potentially reactive functional group. Masking one group is one approach to this problem, finding selective reagents is another. The student will examine this second approach in the reduction of metanitroacetophenone with tin/HCl and sodium borohydride. Teachers frequently lecture to their classes on kinetic versus thermodynamic control, usually in the context of 1,2 versus 1,4 addition of electrophiles to conjugated dienes. Rarely is the subject ever broached again, probably because most reactions are essentially irreversible and thus under kinetic control. I do not recall ever seeing this topic studied in the undergraduate organic lab course until now. In this book kinetic versus thermodynamic control is studied in the context of two reactions: (1) the A1C13-catalyzed Friedel–Crafts reaction of chlorobenzene with isopropyl chloride and (2) the iodine and sodium acetate-catalyzed esterification of glucose with acetic anhydride (kinetic control) and equilibration of the α and β pentaacetates with acid (thermodynamic control).
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One will also find a couple of experiments in the burgeoning field of green chemistry (although none of the reactions is microwave activated) and several computer-based projects. I was disappointed to find no index. I believe this is because the experiments and projects are modular: the publisher will create a book that only contains those experiments to be used in a course, a most desirable feature. Because of the enormous effort involved, changing lab manuals should never be undertaken lightly. If I were interested in changing, I would seriously consider using this book. I am confident the interesting, pedagogically useful experiments will work as written.
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Literature Cited 1. Fieser, L. F. Experiments in Organic Chemistry, 3rd ed., rev.; D. C. Heath: Boston, 1957. 2. Mohrig, J. R.; Hammond, C. N.; Schatz, P. F.; Morrill, T. C. Techniques in Organic Chemistry: Miniscale, Standard Taper Microscale, and Williamson Microscale; W. H. Freeman: New York, 2003. This text has been reviewed by R. M. Pagni: J. Chem. Educ. 2003, 80, 388.
Richard Pagni is in the Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600; rpagni@ utk.edu.
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