Wiley: New York, 2000. 265 pp. ISBN 0-471-28251-0. $31.95.

Students often find the elementary organic chemistry course difficult and forbidding. Perhaps they have never taken a challenging course before and don't know how to respond to the prodigious amount of material to which they are exposed. As a result some students don't study. Others spend too much time, in spite of warnings to the contrary, memorizing facts and too little time learning the relatively few guiding principles that pervade the entire field. It is apparently easier to memorize facts than to comprehend principles, even though the former is fruitless in the end. Teachers have developed many methods to help students master the material. Problem-solving is one of them. Putting the principles into practice by working out reaction mechanisms is an important method to make the principles one's own. This is true not only for students taking the first course in organic chemistry but also for those in senior-level and first-year graduate courses.

Groutas's goal in his book Organic Reaction Mechanisms: Selected Problems and Solutions is to help students master the fundamental principles of organic chemistry--and develop critical reasoning skills--by using critical reasoning skills to solve a large number of mechanistic problems, all of which were taken from the organic literature of the last three decades. Not only are answers provided for the problems but citations are also given for them so that the student, if curious, can see the context in which the reactions were run.

The first half of the book, which consists of a series of minireviews devoted to the fundamental principles followed by sets of relevant questions and answers, is designed for students in the first course. The second half, consisting of questions and answers only, is designed for more advanced senior-level and first-year graduate students. Each half of the book contains approximately 100 questions, all of which have been tested for their appropriateness. The minireviews cover Lewis structures, acids and bases, resonance, carbocation chemistry, anions and nucleophiles, S_N2 and E2 reactions, reactivity and strain, nucleophilic addition to aldehydes and ketones, and nucleophilic acyl substitution chemistry. The minireviews contain numerous worked-out problems so that students can see how to put together a mechanism correctly.

I was very impressed by the high quality of the problems, and by their breadth of coverage, range of difficulty, and appropriateness. The questions in the first half of the book match well with the material in the minireviews that precede them. As one would expect, the problems in the second half of the book are on average more difficult than those in the first half.

A problem book without good answers is bad pedagogy. A student who is stumped by a problem or comes up with an incorrect response learns nothing unless reference can be made to a correct answer. Beginning students don't often know if an answer is correct, again making the availability of good answers imperative. I found the answers in the book to be thorough, complete, and accurate.

There are remarkably few grammatical, typographical, and other types of errors. A few compounds are named incorrectly. The author uses H⁺, I assume for simplicity's sake, to represent a protonating agent; there are, of course, no free protons in solution. He states that acids are fully ionized in solution. I doubt if HCl in cyclohexane or methylene chloride, for example, is ionized at all. Considering that there are thousands of structures in the book, very few are poorly drawn. Those that are generally have peculiar bond angles or are excessively cluttered. I found only one structure having a carbon with five bonds. In the one problem involving nitrosation of an amine, the nitrosating agent is not nitrous acid but N₂O₃. Is base strength related to rate constants, as stated in the book, or to equilibrium constants? Two intramolecular Friedel-Crafts acylation reactions involving carboxylic acids are shown to occur by different but plausible pathways. The author should be consistent.

Groutas is to be congratulated for putting this book together. In spite of a few rough spots, it serves its stated purpose well. Students will benefit from its use and professors will have an additional source of good practice and test questions. I wonder, though, if students taking the first course in organic chemistry will spend money on a book in which only half of the material is directed at them.