Chemical Education Today
Book & Media Reviews Keynotes in Organic Chemistry by Andrew F. Parsons Blackwell Publishing: Oxford, UK, 2003. 228 pp. ISBN 0632058161. $19.95 reviewed by Joel M. Karty
Tendencies of our “fast food society” are increasingly becoming manifest in chemical education. This is particularly true for undergraduate organic chemistry, largely because of its perceived difficulty coupled with its importance in admission to medical programs. Currently, student demand is incredibly high for that one special recipe—that one special book—that is short in length and lays out organic chemistry in a manner that makes the material easy without requiring much time or effort (i.e. critical thinking and problem solving) on the part of the students. Publishers have taken advantage of such demand, offering supplementary texts that appear to make those promises, even in their titles. But truly making good on those promises is analogous to fast-food filet mignon—first, it can’t be done, and second, even if it could, you won’t remember it (or, perhaps won’t want to remember it) for very long. Keynotes in Organic Chemistry, by Andrew F. Parsons may appear to be in that genre of panacea texts, but, in fact, is not. It is a short paperback text— 228 pages, including problem solutions and index—but it does not promise to make organic chemistry easier. Rather, as a result of “the trend towards modularization of chemistry courses,” it attempts to meet “the need for smaller, highly focused and accessible organic chemistry textbooks, which complement the very detailed ‘standard texts,’ to guide students through the key principles of the subject.” The title of the book is an accurate description of its contents. Parsons has successfully distilled an entire 1200 page textbook to the essentials that a student should take away from a full year of undergraduate organic chemistry. The organization of concepts and reactions is similar to that found in most traditional text books—it begins with structure and bonding, and later moves on to reactions involving alkyl halides, alkenes/alkynes, benzenes, aldehydes/ketones, and finally carboxylic acid derivatives. However, there are two chapters that stand out and deserve favorable mention. One is “Reactivity and Mechanisms.” This chapter outlines the essentials necessary to understand mechanisms, delving into the factors that govern ion and radical stability and also discussing steric effects. Furthermore, this chapter provides an overview of reaction types, and briefly discusses kinetic and thermodynamic control of reactions. In a book of its size, one might not expect discussions in these topics. The second of those chapters is “Spectroscopy,” in which four of the most common techniques for organic analysis (MS, UV, IR, and NMR) are discussed. Doing so in a single chapter may allow students to better see the complementarities among the four techniques. The best use for Keynotes in Organic Chemistry is not clear. It may be as a review for a course final exam or for a www.JCE.DivCHED.org
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standardized exam. The reason is that in Parson’s distillation, it was done without loss of emphasis on the most important aspects of organic chemistry—fundamental concepts and mechanisms. In fact, the majority of the end-of-chapter problems either directly ask for a mechanism or ask one to use a mechanism to explain a particular phenomenon. Therefore, if a student at one time had a solid understanding of organic chemistry, this text will serve as a good refresher. If, on the other hand, a student did not leave organic chemistry with a solid understanding, this text provides an outline of what should be known and understood, including fundamental concepts and mechanisms. However, don’t expect Keynotes in Organic Chemistry to provide a better understanding than a student attained the first time through the material. It most likely will not. Instead, the text can allow the student to discern quickly which reactions/concepts they understand and which ones they don’t. With this knowledge, they might then open a traditional textbook to study those areas in which they are weak. If used in such a manner, this text may also be incorporated into a student’s organic chemistry course. Perhaps the only negative aspect of this text is that, in many instances, it goes beyond what I would consider to be a key point. For example, when discussing electrophilic aromatic substitution reactions, electron donation of Cl, Br, and I substituents via resonance is said to be weak, due to the poor overlap of the 3p orbital of the halogen atom and the 2p orbital of the C atom on the benzene ring. It seems that in the interest of simply providing the essential information, the argument could have been finessed using an electronegativity argument. In the same chapter, electrophilic substitution reactions involving naphthalene and pyridine are discussed, whereas the typical organic chemistry course and the typical standardized exam do not expect that students have seen them. The same is true for the benzoin condensation reaction discussed in a later chapter. In the spectroscopy chapter, high resolution mass sepctrometry is discussed—something that, again, I would not consider to be a key point. I simply fear that these discussions that are essentially extraneous for the average organic student will serve to confuse more than enlighten. My greatest concern with this text, however, is whether students will, in fact, use it correctly. I think that a large fraction will not. Most students struggle in organic chemistry, largely because they rely heavily on memorization without having a solid foundation of fundamental principles or a good understanding of mechanisms. The truth of the matter is that organic chemistry encompasses such a vast amount of material, rendering memorization essentially futile. What I envision is that students will view the text as a shortcut. They will see that the important material has been outlined, and they will do nothing more than attempt to use such an outline to streamline their memorization. If so, Keynotes in Organic Chemistry will serve to do nothing except provide a false sense of security. In summary, Keynotes in Organic Chemistry achieves its goal of providing an outline of important concepts, reactions, and mechanisms that is quite complete and well written. It maintains strong emphasis on fundamental organic principles and mechanisms throughout, which is somewhat unique for
Vol. 81 No. 5 May 2004
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Journal of Chemical Education
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Chemical Education Today
Book & Media Reviews a text of its size. If a student uses it correctly, it may be an asset. If not—and I envision that most students will not—it may be a detriment.
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Journal of Chemical Education
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Joel M. Karty is in the Department of Chemistry, Elon University, 2625 Campus Box, Elon, NC 27244;
[email protected] Vol. 81 No. 5 May 2004
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www.JCE.DivCHED.org
