It has been over three decades since this book's predecessor, Stereochemistry of Carbon Compounds (1), was published. The baby boom generation of organic graduate students learned most of what they know about stereochemistry from that text. Back then, "everything you wanted to know about stereochemistry" fit into 488 pages, and the material could be covered in a single course. The new book is almost three times as large, reflecting the rapid growth in this field. It now should be considered a reference rather than a textbook. Baby boomers (and everyone else with an interest in stereochemistry) should consider buying the updated book. Those still teaching about "asymmetric centers" (rather than stereogenic elements) need to update their vocabularies. At $75, the price per page is quite reasonable.

The material has been almost completely revised. The authors attempt to give a historical perspective by citing references with authors and year, rather than simple numbers. Unfortunately, this makes it impossible to go directly from the reference to the text where it is cited. The number of references must be well over 1000. The authors put "less important" material in smaller print so it can be skipped over, but this is like telling a reader not to peek at the footnotes at the bottom of a page.

Most aspects of stereochemistry are covered, although polymer stereochemistry, transition-state stereochemistry, and the Woodward-Hoffmann rules are examples of topics omitted. Each chapter includes many examples to illustrate the topic covered and typically contains about 150 references. The figures are nicely drawn and easy to understand. Often, experimental data are included in tables.

One minor annoyance is the extensive use of acronyms. When browsing through chapters, one is confronted with CSA's (chiral solvating agents), LSR's (lanthanide shift reagents), CDA's (chiral derivatizing agents), and the like. These would be no problem reading chapters from the beginning to the end, but they present a challenge to those opening the book to the middle of a chapter.

The vocabulary of stereochemistry is full of compound words with very carefully defined meanings. It is a challenge to read the book without pondering the meanings of such terms. Fortunately, there is a glossary at the end of the book. Here, you will learn the meanings of such words as homomers (antonym of isomers), homochiral (same sense of chirality, R or S), and pseudoasymmetric atom (too complicated!). This glossary is actually crucial to understanding many topics.

Interestingly, a book with the same title (with a subtitle) was published in India in 1991 (2). Eliel wrote the foreword to the book and proofread the manuscript and made suggestions and comments. Its author has been a visiting scientist in Eliel's department. This more modest book is about the size of Eliel's 1962 book.

Eliel has had a long and distinguished career in chemistry, recently recognized by a Priestly Medal. It is difficult to say what constitutes his greatest contribution, because that depends on one's viewpoint. Certainly the 1962 book stimulated much research and discussion on stereochemistry, and it sowed the seeds for much of the material in the 1994 book. The next generation of graduate students will have the benefit of a fine reference book that generates research ideas for the next 30 years. The new book should certainly be in every college and university library, and it should be given careful consideration for the personal libraries of organic chemists interested in stereochemistry.