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Book & Media Reviews
The Vocabulary and Concepts of Organic Chemistry, Second Edition by Milton Orchin, Roger S. Macomber, Allan R. Pinhas, R. Marshall Wilson Wiley-Interscience, 2005. ISBN: 0471680281. $132 [E-book also available as a digital download using Adobe Reader 6.x or 7.0: Wiley-Interscience: New York, 2005. Mac OS 10.2.8 and above, Windows, Palm OS devices (but not Pocket PC or Symbian devices); Adobe Reader required. ISBN B000ABVAVC. $125] reviewed by R. David Crouch
The second edition of The Vocabulary and Concepts of Organic Chemistry arrived 25 years after the first edition. But rather than a simple revision of an earlier edition, the authors have made significant changes so that its primary purpose is to “identify the fundamental vocabulary and concepts of organic chemistry and present concise, accurate descriptions of them”. In their revision, the authors realized that in order to fully explain the vocabulary of a subject, one must include coverage of the underlying concepts. This expanse of coverage along with the organization of the book makes this something of an annotated dictionary with examples that illustrate the definitions. As the title implies, this book serves as a reference for someone who needs to answer a question such as “What is a carbene?” or “What’s the difference between a sulfenate and a sulfinate?” To cover the breadth of possible questions, the authors have had to sacrifice depth. Sometimes the definitions and accompanying commentary are long, but more often they are very brief. So a student seeking an answer to one of these questions will find an answer, although another reference will be needed to get the complete picture. Chapters are arranged to group topics with related concepts near one another. Those familiar with the first edition will notice that two chapters were deleted. The authors felt that so many monographs covering named reactions have been published in the last 25 years that such a chapter in the new edition was unnecessary and was omitted from the revision. The chapter on natural products has also been omitted in favor of an expanded version of this chapter to be included in a planned second volume of the new edition. Some chapters from the first edition have been re-titled and expanded and new chapters such as those on NMR spectroscopy, vibrational and rotational spectroscopy, and mass spectrometry have been added. The book begins with some heavy physical organic chemistry in the first four chapters that cover topics such as atomic orbitals, molecular orbital theory, and applications to bonding, and applications of symmetry operations to organic molecules. These chapters are most likely well beyond the grasp of the typical sophomore-level organic student, but they
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Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
would be valuable as a resource for advanced undergraduates and graduate students. Indeed, these chapters might be useful to physical chemistry instructors seeking organic examples for use in a course on the role of molecular symmetry in spectroscopy. The fifth through seventh chapters include material that is more typically in the realm of the sophomore organic student: hydrocarbons, functional groups, and stereochemistry. The chapter covering hydrocarbons now includes modern materials such as buckyballs and single-walled carbon nanotubes. The chapter on functional groups is especially detailed and includes an array of groups that are not part of most introductory organic texts. This chapter also includes modern examples such as cryptands, catenances, and rotaxanes; unfortunately the illustrations of these unusual systems are not as clear as they could be. Chapter 7 covers the broad field of stereochemistry with the heaviest emphasis on the relationships between molecules or groups within a molecule. Despite their importance, only a brief discussion of stereoselective and stereospecific reactions is provided. Chapters 8 through 11 are updates of chapters from the first edition and include an odd mix of topics—synthetic polymers, organometallic compounds, methods for separating organic molecules from one another, and fossil fuels and their uses. This sequence probably reflects the interests of the authors and will be a useful resource to advanced students. Chapter 10, “Separation Techniques and Physical Properties”, could be a good resource for sophomore-level students who are preparing for lab. Similarly, sophomore-level organic students could make use of Chapters 12–14, which include a chapter on thermodynamics, acid–base chemistry, and kinetics; a chapter on reactive intermediates; and a chapter on classes of organic reactions. Each of these chapters includes sufficient depth to make them also of benefit to advanced undergraduate and graduate students. For example, in the chapter entitled “Reactive Intermediates”, cations, anions, and radicals of carbon are accompanied by less commonly encountered intermediates such as nitrenes, oxenium ions, and ion pairs. And, in the chapter covering classes of organic reactions, IUPAC symbols for reaction mechanisms are introduced in tabular form early in the chapter and are used to describe the specific reactions in the chapter. The final section of the book is new to this edition and consists of four chapters covering various aspects of organic spectroscopy. As with the rest of the book, these chapters include coverage that is sufficiently detailed to be useful to advanced students and instructors. Students who are encountering organic chemistry for the first time may find the chapters on NMR and vibrational spectroscopy and mass spectrometry to be useful, too. If I could make one change, I would organize the chapters into groupings that seem more logical. The first four chapters fit together well, but why not include the other “physical organic” material such as the chapters on acid–base
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Chemical Education Today
Book & Media Reviews chemistry, thermodynamics, and kinetics and reactive intermediates with those first four chapters? Why not move the chapter on “Types of Organic Reaction Mechanisms” earlier in the book with the chapters on hydrocarbons, functional groups, and stereochemistry, but before a chapter on polymers? I suspect that some of my disorientation stems from reading this as a book rather than a reference piece. Nonetheless, a more logical grouping of chapters would make the book easier to use. I must admit that prior to being asked to review this book I was not familiar with the first edition. Before reviewing the second edition, I thought I should look at the first edition. I checked our library and found that both editions were in our
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collection. After reading the second edition, I’m glad that our librarians chose to add this update to our holdings. It’s written in a way that allows an introductory-level organic student to find information that is pertinent to his or her level of study while remaining useful to more advanced students and instructors. As a reference book, it’s worth having in a collection as a first place to look for an answer. But other works that provide a more detailed answer will also have to be part of the holdings. R. David Crouch is a member of the Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896; crouch @dickinson.edu.
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