book review

Organic Synthesis Books
Reviewed By

Vogel's Textbook of Practical Organic Chemistry, 5th ed.
Furniss, Hannaford, Smith, and Tatchell, Pearson-Prentice-Hall, 1989, 1514 pages

T he wealth of real-world detail in this remarkable textbook makes it especially useful for chemists who have limited access to a chemistry research library, and for those from other fields who have been volunteered into service as organic chemists. Unlike most other organic chemistry textbooks, this book describes procedures in exact detail, including the amounts of reagents, reaction times, and handling of products. In contrast, most organic chemistry texts only mention that the reaction exists and (if you're lucky) give a literature citation. However, the discussion is not as detailed as that in Organic Syntheses.

There are chapters on experimental techniques (228 pages), spectroscopic analyses (141 pages), common solvents and reagents, including their safe handling (75 pages), and characterization and derivatization of functional groups (102 pages), as well as a collection of useful tables (153 pages). However, the most important section is the collection of organic syntheses (726 pages). The reactions are mostly single-step reactions of general applicability. Typical examples are: the preparation and use of dipyridine chromium (VI) oxide, synthesis of benzyl methyl ketone from phenylacetic acid using thorium carbonate catalyst, and Claisen-Schmidt synthesis of 4-phenylbut-3-en-2-one. These are not particularly difficult reactions, but the practical details of the reactions are not intuitively obvious and are easily forgotten, even by experienced chemists. Hundreds of other reactions are also described.

The few problems include an occasional Britishism, such as calling ketene by its old name, "keten" (p. 694) and calling dry ice "Cardice". In matters straying from organic chemistry, the book does have some errors:

Of course, most people would probably not do electrical wiring based on information in a chemistry book. Another problem is that the drawbacks and limitations of the reactions are not discussed. Even with 1514 pages, not every reaction can be discussed, and the latest modifications to the reactions are not always present. For example, the section on Simmons-Smith cyclopropanation uses the obsolete method of zinc dust and sonication instead of diethylzinc. But for most reactions, the wealth of detail makes this book indispensable in the laboratory.

Disclaimer: I have not read any of these books in their entirety.

Strategic Applications of Named Reactions in Organic Synthesis
Kürti and Czakó, Elsevier, 2005, 758 pages

A t first glance, this paperback compilation of 250 "named" reactions (that is, reactions named after the originators) might appear to be aimed at the Internet generation. The molecules are printed in all different colors, the text is in sans-serif font with almost no page margins, and the products are drawn in shadow boxes. In fact, despite the unusual appearance, the approach is conventional. Each reaction gets two 8½ × 11 inch pages and one page of references. A single, often gigantic paragraph, titled "Importance", summarizes the salient features of the reaction, its current status, the most recent variations and improvements, and the scope and limitations of the reaction. Next is "Mechanism", followed by "Synthetic Applications", which consists of examples from the literature of how the reaction has been used. No detailed procedures are given.

This approach is completely different from Vogel's Textbook. Although Kürti and Czakó have written a very informative reference work, it would not be useful in the laboratory unless you have access to a library. Although many of the examples are multi-step reactions, to save space the authors often use a single arrow with the word "steps" printed over it. For students, this is often taken to mean "and then a miracle occurs."

The book also has an excellent index. For some reason, the entries in the index are also printed in random colors.

Practical Synthetic Organic Chemistry
Stéphane Caron, ed, Wiley, 2011, 856 pages

T his long-awaited book has the same format as a standard organic chemistry book, with about the same level of detail as Morrison & Boyd or Carey. The objective, stated in the Preface, was to offer a compendium of reaction conditions that are generally useful and reliably scalable. In their descriptions of the reactions, the authors succeed magnificently. In general, though, you'll have to look up the original papers to get the complete reaction details. This is made possible by comprehensive citations to the literature, and it's clear that a lot of effort was made in selecting the most useful reactions for each transformation. That makes this book especially useful to younger synthetic chemists, who can be overwhelmed by the sheer vastness of the chemistry literature.

Even so, it would be unfair to compare this book to a true compendium like Vogel's Textbook. For example, I couldn't find either the dipyridine chromium oxide reaction or the diethylzinc reactions that are described in such excruciating detail in Vogel's. Hydroperoxide synthesis gets two pages, and silane chemistry gets a total of four—but there is another section on silanes later that's neither mentioned in the index nor in the table of contents. I found it only by accident. So it's possible that chromium and Et2Zn are mentioned ... but darned if I know where.

The first 660 pages are the most generally useful; after this, the authors, forgetting their original mission, fly off into topics like the synthesis routes to conivaptan, tipranavir, and the infamous torcetrapib (which should give you a hint where this guy works), followed by chapters on green chemistry, IUPAC rules, and solvent tables. The biggest problem is with the index. "Transesterification" and "hydroperoxides" are not listed, even though there are sections on both in the text. "Transetherification" directs you to the section on the preparation of thioethers, a different topic altogether. This book could be an excellent adjunct to a general organic text, if you don't mind searching through the text to find things. I plan to use it a great deal in the lab, but I'm hoping the second edition will be better organized and better indexed.