It seems that long gone are the days when one picked up a Gould, a March, a House, or, more recently, a Carey & Sundberg and built an advanced organic chemistry course around such a major text. Instead, many advanced organic courses use the primary literature supported by reserve copies of the more comprehensive texts and perhaps augmented by a paperback or two focusing on a particular subset of the course. It is into this latter category that Adam Jacobs' Understanding Organic Reaction Mechanisms falls.

This no-nonsense, well-organized book divides a study of reaction mechanism into nine chapters that discuss, in order, chemical structure, ionic species, why reactions happen, reactive carbon species, the effect of heteroatoms, types of reaction, investigative techniques, analyzing for mechanistic type, and four case histories. Each chapter concludes with a summary and a handful of problems, for which answers are provided at text's end. The author uses MO theory to explain mechanistic pathways for several reactions; otherwise, the approach to explanations for the mechanisms presented is quite traditional. Part way through the first few chapters, I was uncertain at what level of understanding the text was aimed, but later it became clear that the material is much too sophisticated to complement an introductory organic course, but is fine for an advanced offering.

The topics and emphasis within the text are most appropriate for the audience that would use the text. The writing is very efficient and the cross-referencing of material is useful, and appreciated. The depth and clarity of presentation are quite uneven, however. In the discussion of resonance-aromaticity and the Hammett equation, for example-I missed supporting information, such as rules for resonance and aromaticity and a table of Hammett values to reinforce the textual material; whereas in the chapter on heteroatoms, the relentless collection of information and reactions becomes quite tedious. Since the text is hardly comprehensive, it would gain a greater personality by covering less material in more depth, sending readers to other sources of information as needed. The book, in fact, has no reference list, a serious shortcoming.

The book makes extensive use of "curly" arrows, as expected, but frequently omits bonds and unshared electron pairs, which is a bit disconcerting and could confuse students. The text is relatively free of errors, though three occur in rapid succession in Chapter 6. Within the text the presentation of structures and graphics are fine, but drab.

The concluding chapters on "suggesting mechanisms" and case histories (formation of 9-benzylfluorene, DCC-mediated ester formation, Favorskii rearrangement, and olefin ozonolysis) provide a fine conclusion to the information presented beforehand.

I know of no academic text that is so good, so appropriate, that it eliminates all its competition and is the only book anyone uses. Clearly, the needs of each of us are sufficiently different that competition is encouraged. Jacobs' book may be exactly what your course needs. It's worth considering.