Chemical Education Today
Book & Media Reviews Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives by Henning Hopf Wiley-VCH: Weinheim, 2000. 547 pp. Paperback: ISBN 3527-29696-9; $49.95. Hardcover: ISBN 3-527-30216-6; $79.95. reviewed by Ronald M. Magid
Henning Hopf, a highly-regarded research scientist, has written this book for the nonspecialist. It is the second in a series Classics in …. The first, by Nicolaou and Sorensen, was about total synthesis; the third, by Carreira (in preparation), will focus on stereoselective synthesis. If any succeeding books are as thorough, as thoughtful, and as well written as the first two, the organic chemists of the world will be well served. Hopf notes that the two common definitions of classic(al) guided his choices of what to include in this relatively short (521 pages plus author and subject indices) and amazingly inexpensive volume. First, classical refers to antiquity and its culture, but because the ancient Greeks and Romans are not well known for their researches into hydrocarbon chemistry, Hopf trains his sights on the “classical period” of organic chemistry, the middle 50 years of the 20th century (not that he doesn’t also discuss chemistry from before and after this time). Second, because classic means “of acknowledged excellence”, Hopf brings us discussions of research that is both fundamentally important and brilliant in its execution. There are omissions, of course, some unintentional and others deliberate (industrially important hydrocarbons such as polystyrene, historical vignettes about simple molecules such as methane, reactive intermediates such as carbenes). But what is included is vastly more important than what is missing, and any fair-minded reader would have to conclude that Hopf has, indeed, chosen topics of wide interest and significance. The book’s organization, essential for an undertaking of this magnitude, is interesting. The author shows how just three “building units” (sp3-, sp2-, and sp-hybridized carbon) and just three bond types (single, double, and triple) can, from a simple precursor such as ethene, generate (on paper and in the lab) some of the most extraordinary and beautiful structures, unsullied by any heteroatoms. The emphasis throughout is on the synthesis and properties of “unnatural” products, materials not found on Earth save in the research lab. These are molecules of theoretical importance (e.g., cyclophanes, bridgehead alkenes), mechanistic relevance (e.g.,
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benzyne, bullvalene), aesthetic interest (e.g., the Platonic solids, the fullerenes), and synthetic challenge (e.g., dodecahedrane, the fenestranes). The book appears to be virtually error free. I’m sure that there must be typographical errors but I found only a few minor ones, nor did I find mistakes in the numerous drawings of structures and synthesis schemes. Indeed, the excellence of the drawings (their clarity and accuracy) should serve as a reprimand to other recently published organic chemistry monographs whose sometimes shoddy graphics are unacceptable in this age of computerized drawing programs. That this book has a single author guarantees that the writing style is uniform throughout. But lest one think this also means that topics far from the author’s specific research areas are slighted, that most certainly is not the case. Hopf says that forced to select between depth and breadth, he has chosen the latter. Some of the chapter titles will attest to that breadth: Adamantane and Other Cage Hydrocarbons; The Prismanes; Allenes and Cumulenes; The Annulenes; and so on. And, although the admitted focus is on “classics” from several decades ago, there is an ample smattering of references from 1999 (and even one that I spied from 2000). Now that the incomparable Organic Chemistry: The Name Game by Nickon and Silversmith is out of print, I know of no other advanced organic book than Hopf ’s that can be read both for its scientific content and for sheer pleasure. Furthermore, the writing, the ideas, and the chemical transformations are at such a level that they can be appreciated by an undergraduate in the second semester of the organic lecture course. This is a book that should be in every college library and, given its low price, in many private collections as well. What makes the book such a delight is that the reader can sense the joy and excitement that motivated the original researchers. This is summed up in a paragraph from Hopf (with a gratuitous comment about gender, which, if true, perhaps will not be true when a second edition appears): There is one final reason why the study of hydrocarbons attracts many chemists—their wish to play is often fulfilled extremely well on this exciting playing ground of organic chemistry. Whether (the mostly male) practitioners speak of tinker toy chemistry, molecular Lego or Meccano sets, the connection to an earlier part of their lives is obvious enough.
Ronald M. Magid is in the Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600;
[email protected].
Journal of Chemical Education • Vol. 79 No. 1 January 2002 • JChemEd.chem.wisc.edu
