Chemical Education Today edited by
Book & Media Reviews
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
Instant Notes in Organic Chemistry, Second Edition by Graham L. Patrick Garland Science/BIOS Scientific Publishers: Abingdon, Oxfordshire, UK, 2004. 357 pp. ISBN 1859962645 (paperback). $33.95 reviewed by Thomas H. Eberlein
What would you pay for a book capturing the essentials of a comprehensive subject like organic chemistry in less than 400 pages? A book that is a quick read and is structured so you only spend time on topics you need to review, while skipping those areas where you are confident of your understanding? If you said at least $32, then Instant Notes may be for you. Instant Notes: Organic Chemistry is part of an extensive series (1), each member of which distills a complex subject down to fundamental topics and presents these in an accessible and user-friendly format. Of particular importance, each topic is introduced with a “Key Notes” section, usually less than one page, which alerts the reader to the absolute essentials characterizing the subsequent material. In this way, the reader can tell at a glance if it is necessary to spend additional time reviewing an incompletely understood topic, or if his or her understanding is adequate. The second edition of Instant Notes is divided into sixteen major sections that include most concepts covered in an introductory organic chemistry course. Beyond being completely revised and updated from the first edition, the new edition includes greatly expanded coverage of reaction mechanisms, acid–base reactions, and nucleophile–electrophile interactions. Other welcome additions are new sections on spectroscopy and spectral interpretation. There is much to recommend Instant Notes: Organic Chemistry, and these favorable features are hallmarks of the series. For the most part the author offers pithy, clear explanations of complex concepts. He shows precise and accurate reaction mechanisms, embellishing them with just the right amount of verbal detail. Importantly, when topics come up that might otherwise seem obscure or irrelevant (e.g., cyclic hemiacetals), the author immediately mentions the most important context for the topic (sugar chemistry). It seems the author subscribes, appropriately, to the “80/20 Rule”: You can get 80% of the benefit with 20% of the work (2), assuming you choose the right 20%. Regrettably, explanations are occasionally oversimplified. For example: p 10, “Ethene is a rigid…molecule” (alkenes are much more supple and flexible than “rigid” implies); p 50, “A [chiral] molecule…has optical activity if only one of the mirror images is present” (present in excess, more precisely); p 211, “Nucleophilic substitution reactions are not
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possible with aldehydes and ketones” (But what about the Cannizzaro and iodoform reactions?); p 255, “All types of alkyl halides can undergo the E2 elimination…” (What about neopentyl or benzyl halides?). Most of these oversimplifications can be forgiven, because the target audience is unlikely to be harmed by the expediency. More troubling is that other explanations are just plain wrong: p 74, the Aldol reaction was named after the scientist who developed it; p 161, Friedel–Crafts acylations can be performed on ArNO2; pp 213–215, chlorine is more electronegative than oxygen (??!) so acid chlorides are more reactive than esters. Yikes! There are also myriad trivial errors, few of which would be significant enough by themselves to deserve mention, but cumulatively they had a wearing effect on this reader: p 83, HF is a strong acid (it’s weak, pKa ~3); p 86, the pKa of ethanol is 12.4 (it’s ~16); p 222, diazomethane is CH3N2 (it’s CH2N2); p 284, RSR⬘ is a disulfide (it’s a sulfide); microwaves and radio waves have ~ 1013 s-1 (more like 3 ⫻ 1010 s-1 and 107 s-1, respectively); p 339, 32P is a magnetically active nucleus (it’s not; 31P is); and so on. Despite the errors, I found Instant Notes quite informative, and I still believe it can help students review the fundamentals of organic chemistry in an efficient way. But I’m also suspicious that I, or any instructor, might not be the best person to review this book. Why? Because I “fill in the blanks”: as I read, I unconsciously add things that aren’t really there to complete the picture. It’s much like vision: If you don’t already have a good idea of what you are looking at, you literally cannot see it (3). If I didn’t already know what I was reading, I might have had no idea what the author was talking about. But isn’t that the key assumption of the whole series? Won’t students who have some familiarity with the material focus on sections where they’re weak and skip over the familiar parts, based on a cursory inspection of the Key Notes? Fortunately, I had two students who were excellent candidates for testing this hypothesis. One was preparing to take the MCAT for a third time. This student, despite very good scores on the other two sections of the test, had been unable to achieve an “8” on the biological science portion of the test, a score he needed for early admission to the school he wanted to attend. The other student was a gifted high school junior and one of the twenty finalists for the 2005 United States National Chemistry Olympiad. He and his fellow finalists had been tasked with learning—in two weeks—the first eight chapters of a standard sophomore organic chemistry textbook in advance of the study camp. I let each student borrow my copy of Instant Notes. Each had the same praise for the book: “It’s a great way to study for a standardized exam, and the format of the notes makes it easy to skip over what you don’t need to read.” (Note: The premed got into the school he wanted, and the high school junior was
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Book & Media Reviews chosen as one of the alternates for the US team that competed in the 2005 International Chemistry Olympiad.) So how can this book best be used? At the risk of showing a complete lack of originality, let me quote David Ausubel (4): “The most important single factor influencing learning is what the learner already knows. Ascertain this and teach accordingly.” Who better to ascertain his knowledge level and teach accordingly than a student who has purchased this book for his own review? That’s exactly how the students I described used the book. Instant Notes makes self-assessment easy. Literature Cited 1. Instant Notes in Inorganic Chemistry was recently reviewed in this Journal: see Smith, P. M. J. Chem. Educ. 2005, 82, 213.
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2. Reh, F. J. Pareto’s Principle—The 80/20 Rule. http:// management.about.com/cs/generalmanagement/a/Pareto 081202.htm (accessed Sep 2005). 3. Heilbroner, R. Don’t Let Stereotypes Warp Your Judgment. (This essay is included in many anthologies, for example: Lunsford, R.; Bridges, B. The Longwood Guide to Writing, Concise Edition, 2nd ed.; Longman: New York, 2003; Chapter 10.) 4. Ausubel, D. P.; Novak, J. D.; Hanesian, H. Educational Psychology: A Cognitive View, 2nd ed.; Holt, Rinehart, Winston: New York, 1978 (as cited by Bodner, G. J. Chem. Educ. 1986, 63, 873–878).
Thomas H. Eberlein is in the Division of Science, Penn State Schuylkill, Schuylkill Haven, PA 17972;
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