Chemical Education Today
Book & Media Reviews Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry by Paul M. Dewick John Wiley & Sons, Ltd: Chichester, West Sussex, UK, 2006. 710 pp, ISBN 978-0470016664 (paper), $70. ISBN 978-0470016657 (cloth), $205 reviewed by Thomas H. Eberlein
Do you want to add life to your organic chemistry course? If so, Essentials of Organic Chemistry (1) may be for you. Author Paul Dewick has set out to produce a reduced-sized text highlighting those features of organic chemistry that would be most useful to students of pharmacy and related fields. His purpose is to “provide thorough grounding in fundamental chemical principles” and, simultaneously, to illustrate these principles with wide a array of pharmaceutical and biochemical examples. He has succeeded in doing not only this but also in producing a text that will find a home as supplemental reading, or even as a main text, in any course where biological connections to organic chemistry are stressed. Dewick uses literally hundreds of biological examples to illustrate the related chemistry of non-biological systems. Let’s look at three:
1. When discussing chemistry of enols and enolates, the author refers to loss of stereochemistry at asymmetric carbons adjacent to carbonyl groups. He cites the wellknown example of metabolic racemization of ibuprofen, among other compounds. Likewise, when amino acid residues with the unnatural d-configuration are found in peptides and proteins, enolization was the cause. Interestingly, l-configuration centers undergo enzyme-assisted epimerization after they are incorporated into the peptide chain. They are not produced through inversion of lamino acids (which would be difficult, given the ionized nature of the carboxlate) and subsequent incorporation into the growing peptide.
2. Thioesters, such as acetyl coenzyme A, are both better electrophiles and better nucleophiles than ordinary esters. Biological examples abound. We expect that amines will react with thioesters to produce amides, and this is illustrated with non-ribosomal peptide biosynthesis. And the use of acetyl CoA as a nucleophile in aldol reactions and Claisen condensations is abundantly illustrated with biological examples.
3. Near the end of the book, three chapters are devoted to biological macromolecules, thus deviating from the mechanism-oriented chapters that precede them. On
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the first page of the chapter “Carbohydrates”, the author lays out his philosophy plainly: “We want to avoid giving the impression that the reactions described here are something special to this group of compounds. Instead, we have deliberately used carbohydrates as examples of reactions in earlier chapters, and you will find suitable cross-references.”
A further noteworthy feature is the use of boxes to set off examples of biologically-relevant systems that illustrate the fundamental concepts being addressed in the main text. The boxed material can function as freestanding reading (for example, when one is tracking down a cross-reference), or it can be skipped if one does not wish to interrupt the flow of the text. But don’t skip them! They are “the good stuff ”! Quite often these examples read like stories, such as the case of fatal hemorrhages in livestock fed spoiled sweet clover. Identifying the toxic contaminant (dicoumarol) led to the development of warfarin, an anticoagulant rodenticide, which has more recently found application in stroke prevention for certain types of patients. And it provides the author with a memorable way of illustrating conjugate addition reactions. Another interesting attribute of the book concerns end-ofchapter problems. There aren’t any. Instead, the author devotes the entire final chapter strictly to problem-solving. In it, he teaches students strategies for solving conceptual, multi-part questions. In so doing, he also shows instructors how to design such problems. Answers include common mistakes taken from authentic student work. This approach “helps emphasize links and the integration of different ideas”. It also avoids difficulties inherent to the modular approach, in which “particular themes become imprisoned in self-contained packages”. His approach to learning problem-solving is in line with the philosophy of the book: “By applying principles and deductive reasoning, we can reduce to a minimal level the amount of material that needs to be committed to memory.” The book is not perfect. It contains errors, like any textbook. The explanation for strain in medium-sized rings is misleading (2); he uses the term stereospecific when he means stereoselective (3, 4); and there are a couple of trivial errors in figures or tables. Remarkably, however, the book is almost entirely free of mistakes, which is especially gratifying considering this is the first edition. Whatever the shortcomings, they are completely obscured by the book’s many excellent features, some of which have already been described. Additional positive aspects are noteworthy. The author provides clear and concise explanations with appropriate examples to illustrate the concept under consideration. He offers many helpful hints for producing or interpreting structural drawings correctly. He is a good judge of the important or interesting features of a system. He anticipates students’ potential misunderstandings and heads
Journal of Chemical Education • Vol. 85 No. 2 February 2008 • www.JCE.DivCHED.org • © Division of Chemical Education
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Book & Media Reviews these off before they cause problems. He reinforces concepts through frequent use of cross-referencing, both by reviewing previously learned material and by previewing related material yet to be covered. He writes in an engaging and often humorous fashion that will not intimidate readers. And he peppers the book with fascinating tidbits that will engage and sustain interest. To be sure, sacrifices had to be made to accommodate all the biochemistry. So what’s missing? First, there’s no substantive discussion of spectroscopy in any form. That may be a deal-breaker for some prospective adopters. Second, there is little emphasis on synthesis. Although plenty of sophisticated synthetic methodology is presented, developing facility as a synthetic organic chemist is not a targeted skill. Finally, the book features very simple and inexpensive black and white graphics. The diagrams are clear and quite useful, but they are not flashy. As advertised, the book will find a home in organic chemistry classes geared toward pharmacy students or related majors. Likewise, it could be used as an effective supplement in any course where the instructor wished to present a significant number of biochemistry-related special topics. I teach such a course,
and I look forward to using Dewick’s book in coming years to add even more “life” to the subject of organic chemistry. Literature Cited 1. Textbook Web site; http://www.wiley.com/go/dewick (accessed Sep 2007). 2. Smith, M. B.; March, J. March’s Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001; p 184. 3. Adams, D. L. J. Chem. Educ. 1992, 69, 451–452. 4. Smith, M. B.; March, J. March’s Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001; pp 166–167.
Supporting JCE Online Material
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Thomas H. Eberlein is a member of the School of Science, Engineering, and Technology at Penn State Harrisburg, Middletown, PA 17057;
[email protected].
© Division of Chemical Education • www.JCE.DivCHED.org • Vol. 85 No. 2 February 2008 • Journal of Chemical Education
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