Chemical Education Today
Book & Media Reviews Organic Chemistry Principles and Industrial Practice by Mark M. Green and Harold A. Wittcoff Wiley-VCH Verlag GmbH & Co.: Weinheim, Federal Republic of Germany, 2003. 341 pp. ISBN 3527302891 (paper). $39 reviewed by Alan M. Rosan
Why study organic chemistry? Many would respond simply: such effort is utilitarian. Few, however, would venture that such studies stem from any interest in why and how organic molecules are produced. Yet, while the worldwide economic and environmental impact of making and trading in organic chemicals is huge (in 2003 the U.S. reported $20.4 billion in exports and $32.6 billion in imports), organic industrial processes are rarely taught. This richly laden text provides a way to fill this gap. This modern, intelligent book, part of the continuing series of authoritative monographs from Wiley-VCH, provides an enthusiastic and detailed description of the history and applications of selected organic processes. In ten dense chapters of from 19 to 42 pages each, the authors succeed admirably in telling the story of progress in chemical manufacture. The chapters are ordered logically and historically, beginning with petroleum processing extending to polyalkenes, aromatic functionalization, plastics and epoxy resins, nylon, methyl methacrylate, rubbers and elastomers, transformations of ethylene and propylene, and the rise and fall of acetaldehyde. The book concludes with a timely and cogent chapter entitled “Doing Well by Doing Good” that describes efforts to circumvent the use of four useful but toxic compounds. These chapters relate to and roughly coincide with the normal progression of organic topics: carbocation formation in hydrocarbon cracking, radical and electrophilic addition to alkenes, nucleophilic alkyl substitution and epoxide opening, acyl substitution, and condensation polymerization. Herein lies the strength of this book. Chapters are subdivided into 10 to 22 relatively short sections of from 1 to 7 pages each. They are often given illustrative, whimsical headings ranging from the inquisitive (“What did Carothers do at DuPont?”) to the effusively descriptive (“Acetylene was Widely Available before Steam Cracking and (it was) Exceptionally Useful but Everyone wanted to replace this Dangerous Industrial Intermediate. Happily, Double Bonds replaced Triple Bonds”). These titles portend the conversational and energetic tone of the text which here portrays the drama of catalytic cracking and the intrigue of stereoregular polymerization. The most compelling sections begin with a question, i.e., “What do the Opposite ‘Faces’ of Propylene have to do with the formation of Isotatic Polypropylene by the Ziegler-Natta Catalyst?”, followed by a lesson; that coordinated propene is chiral. Less engaging are those that ask and answer a question www.JCE.DivCHED.org
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in the title. Each chapter is accompanied by functional drawings, includes an excellent summary augmented by a list of important terms and ideas, and concludes with excellent study problems. These questions demand high level problem solving skills, an organic text, and access to information far beyond what is taught here. Finally, a brief concluding epilogue that looks into the future and a 24-page index are provided. This text is written with unbridled admiration for the industrial utilization of organic chemistry, and it is saturated with historical gems and insights. We learn why many European forests were clear cut prior to the 18th century (this has to do with soap!), which paper W. A. Carothers probably wished he had not written (and why such publication cost millions), how horse chestnuts played a central role in the defense of Britain during WWII, and what unexpected reward His Majesty’s government was compelled to provide a young Russian emigre in 1917. Wonderful descriptions and explanations abide. To cite a few, the mechanism of addition polymerization is summarized as “passing the buck”, epoxide opening is characterized as deriving from the “spring-loaded tension” inherent in the small ring, and the unconsummated reactive functionality in epoxy resin crosslinking is said to be “left at the altar”. The authors pepper the text with bold exclamations. They champion the ICI-Celanese palladiumcatalyzed vinyl acetate process as “look(ing) like a winner” but note that at the end it “was a nightmare”; they delight in the thermodynamics of elasticity with “How Beautiful!” and revel in the remarkable properties of silicones with the delightful, “Wonderful stuff!”. Such acclamations are unexpected, captivating, and wholly refreshing. Throughout this book the far-reaching consequences of support for basic research are emphasized, as are the moral implications attendant the use of chemicals such as HCN and phosgene. The history of discovery is woven into every chapter and attention is drawn to those decisions, often inadvertently made, that promote or discourage discovery: the unintended leakage of trace oxygen into high pressure ethene polymerization reactors at ICI leading to LDPE; the use of an unsuspected nickel-contaminated reactor that lead Ziegler to HDPE; the subsequent surprising discovery of stereo regular polypropylene by Natta. The authors have taken considerable care to reiterate their theme of interrelated reactivity by continually referring back to previous sections and discussions. Most commendably, they spotlight what is yet to be learned. In regard to isomerization of methyl-2-pentenoate they comment that, “we do not clearly understand it” and, later, exhort readers to “think of good reasons” why formaldehyde is so electrophilic. I was impressed that the still unresolved mechanism of the Mitsubishi methyl methacrylate process is highlighted and left “to the reader to look (into) further”, suggesting that new chemistry lies unexplored. One drawback is the lack of any references. The text contains no footnotes, and no primary work is cited. The authors occasionally refer to a specific source among a list of 25 classic reference books offered for further study, but I found this list under utilized, incomplete, and dated. Although the discussion is modern and expertly presented, some
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Journal of Chemical Education
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Chemical Education Today edited by
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
topics are abbreviated and at times mechanisms are presented as reaction equations lacking curved arrows. Inevitably some typos creep in along with sporadic errors in structures, spelling, and usage. Occasionally explanations are convoluted as in, “high temperature increases the equilibrium constant favoring the endothermic direction”, referring to radical scission in steam cracking. On the other hand, an extremely cogent analysis of elastomer behavior, polymer processing, and the subtleties of copolymers is offered. As the emphasis here is on what good comes from chemistry, the authors can be forgiven such well-meaning but simplified statements as “whatever the molecules are really doing makes no difference to the outcome” since it is the outcome that fascinates and motives this exciting book.
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As a text for a course in industrial chemistry or as judiciously selected reading in an organic course, this book excels, providing a wealth of information, insight, and inventive teaching. History, personality, and organic chemistry on the multi-kilogram scale intersect here. Further, the book reads as if the authors were conversing directly with you—explicating, bantering, offering asides, suggesting experiments, and questioning. I intend to enjoy this text again and refer to it often. If you open these densely worded pages, you and your courses will be enriched for the effort. Alan M. Rosan is in the Department of Chemistry, Drew University, Madison, NJ 07940;
[email protected] Vol. 81 No. 8 August 2004
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