Francis A. Carey. McGraw-Hill: New York, 1996; xxvi + 1151 + A-87 + I-31 pp.

The area of organic chemistry is blessed with more than its share of excellent introductory textbooks. The majority of these books follow the functional group approach that was pioneered by Morrison and Boyd, and this works well for the standard American sophomore year-long courses. F. A. Carey's excellent textbook is now available in its third incarnation, and continues to maintain the high standards set in the earlier editions. The figures and diagrams in the third edition have been completely revised and for the most part these make good use of both color and design. In some textbooks, color is used purely for its own sake, needlessly increasing the cost of the book without adding to its clarity. Although this charge can be laid against Carey's text in places (e.g., the pastel colored backgrounds for the figures and schemes add very little), the excellent presentation of molecular models and conformations cannot be faulted. Organic chemistry remains a very visual subject, and the clear presentation of three-dimensional molecular structures is pedagogically valuable. The author notes in the introduction that "functional group analysis such as the Lucas, Hinsberg and Tollen's test, which are almost never used in the modern practice of organic chemistry, are not included". While this is certainly true, these tests do illustrate some important chemical concepts and processes, and perhaps remain somewhat relevant.

The author continues to stress the use of reaction mechanisms, and this remains a strong point in the new edition. The heart and soul of modern organic chemistry revolves around these concepts, and this framework is essential for a textbook of this type.

The organization of the new edition is similar to the previous version, starting off with a chapter on chemical bonding, and proceeding with chapters on alkanes and conformational analysis. Chapter 4 ("Alcohols and Alkyl Halides") introduces the concepts of acidity and basicity, and the chemistry of alcohols including S_N1 and S_N2 reactions. Two chapters are designated to the chemistry of alkenes, and Chapter 7 covers stereochemistry (including the use of Fischer projection formulae). The stereochemical concepts are nicely tied in with previously discussed chemical reactions and the principle of stereoselectivity is introduced at this stage. The expected chapters on nucleophilic substitution, alkynes, conjugated dienes, aromaticity, and electrophilic aromatic substitution reactions follow. Chapter 13 allocates 50+ pages to spectroscopy and covers the standard materials. I believe that it is a mistake to continue to use so many outdated 60 MHz proton NMR spectra (although the author addresses this point in the introduction), but this is a minor quibble. The spectra would be clearer, however, without the chart paper backgrounds and this change might be considered for the 4th edition.

Chapter 14 covers organometallic chemistry (primarily Grignard and organolithium reactions) and subsequent chapters relate the functional group chemistry of alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, and so on. It is nice to see the inclusion of some sulfur chemistry, particularly given the biological relevance of this area. The final chapters include, inevitably, carbohydrates, lipids, and amino acids/peptides/proteins. Nucleic acids are covered in minimal detail, but this is appropriate as time does not really permit this material to be covered in sophomore-level organic chemistry courses. Molecular modeling exercises are suggested at the end of each chapter, and while a few of these are a little contrived, the principle is laudable. A number of short essays are included within the main chapters, and some of these are new including the interesting topics "enediyne antibiotics" and "chiral drugs". These are really just short snippets, but they are all the better for that and add life to the text. The author has attempted to make the writing style less formal, and has succeeded to a certain extent. A dryer style may be preferred by some instructors, but in my experience students find this to be less accessible and I am pleased to see the author take this important stylistic consideration on board.