Arrows may be curly, but they hit the spot

Organic Chemistry. Sixth Edition - Organic Chemistry. Fourth Edition - Organic Chemistry. Second Edition - The Organic Chemistry of Biological Pathways. First Edition - Modern Physical Organic Chemistry. First Edition
February 24, 2006

The first four of these books, all titled Organic Chemistry , are standard undergraduate texts. They are written by authors based in the US but contain the meat and bones of most first and second-year syllabuses in UK universities. There cannot be a "head of teaching" (or equivalent) who has not spent much time with sales representatives from publishers who hope that their particular book will be adopted as a course text. But no author dominates in this highly competitive area, so the different preferences of teachers become the deciding factor in selecting one text over another.

All four books, because they were written for the US market, are just a bit too limited for use as general course texts across the breadth of organic chemistry in most UK degree courses. Most material in these texts is common and is treated, in essence, in very similar ways and to similar depths. Indeed, the chapter headings could almost be interchangeable between one book and another. At the end, all offer standard coverage of the various types of biomacromolecules (proteins, nucleic acids and so on) as well as synthetic polymers.

Joseph Hornback does offer some basic coverage of terpenes and steroids, and there are some other minor differences, presumably stemming from personal preferences. Janice Smith offers, for example, discussion of enantioselective carbonyl reduction and illustrates this with the Corey-Bakshi-Shibata reagent. However, because there are no transition-state models to explain the stereoselectivity, the reader would learn no more than that hydride delivery to one face of the carbonyl group gives rise to one enantiomer and vice versa.

Hornback also offers a chapter on synthesis that includes basic coverage of protecting groups and retrosynthetic analysis. Here there is also a useful 11-page summary of functional group preparation tables, as well as one on C-C bond formation, though the most exotic entry here is a cuprate conjugate addition. William Brown et al have a similar "synthesis" chapter that includes basic coverage of the Heck and Suzuki reactions as well as alkene metathesis.

The two pairings from the same publisher (McGraw-Hill and Thomson Brooks/Cole) appear to offer very similar levels of web-based instructor and student support. Francis Carey's contribution includes a CD-Rom with SpartanModel, an electronic model kit to replace the traditional plastic ball-and-stick kit. Although this provides useful 3D-style visualisation of molecules, including some animated reaction mechanisms, I am unsure that this would be any more useful than the resources that are available in most serious university chemistry departments. Accompanying this text is a solutions manual, a CD-Rom with a test bank and solutions in PDF and Word format, as well as PowerPoint slides, however none of these resources was available for this review.

I do not wish to give the impression that these four texts are anything but carefully and lovingly written. Any one of them would be good choice for many first and second-year courses, especially those more limited courses taken by life and medical science students. My complaint is that they are all so similar to the books already on the market that it is difficult to choose between them. The process is a bit like fine-tuning an analogue radio, where you have to twiddle the knob a lot to get a clear signal just so as to listen to one station. In comparison, the still relatively new Organic Chemistry, by the UK-based authors Jonathan Clayden, Nick Greeves, Stuart Warren and Peter Wothers, which covers material from the whole breadth of almost all undergraduate four-year organic chemistry courses, is like tuning to a completely new radio station.

Much more exciting is The Organic Chemistry of Biological Pathways , which provides coverage of material at the increasingly important interface between chemistry and the life sciences, but which approaches the subject matter squarely from the organic chemist's perspective. There is no "P in a circle" to represent inorganic phosphate in this text. An opening chapter covers concisely many of the functional groups, reaction types and transformations that are described in more detail by the previous texts.

Even for the chemistry undergraduate who has already taken organic chemistry courses, this coverage provides a useful summary of the fundamental reaction types.

The focus is always on biological examples, as illustrated in the comparison between the Cannizzaro reaction and the NADH hydride transfers found in nature. Chapter two introduces key concepts in chirality and stereochemistry, as well as covering important biomolecules and their constituents. Separate coverage is provided of enzymes, co-enzymes and coupled reactions that are needed for full appreciation of the material that follows, which includes the metabolism of lipids, carbohydrates, amino acids and nucleotides, with a chapter on the biosynthesis of selected natural products. This material is presented logically by biological pathway, rather than by transformation type, so a final chapter is included with a summary of the biological transformations encountered but this time organised by type.

In all cases, we see mechanisms drawn with the organic chemist's beloved curly arrows, which should further emphasise for students' benefit the similarities between these mechanisms and their laboratory-based counterparts. As the authors state, this is not a comprehensive biochemistry book, nor is it a mainstream organic textbook or a text on enzymology, but it should find a place on the reading lists of many lecturers' courses. Each chapter ends with about 15 or more problems (with answers in an appendix), and there is a wealth of reference to the primary literature. This book, which is clearly and superbly presented with sensitive use of colour, will be a very useful text for undergraduate chemists and life scientists. I will make sure our university library gets a few copies.

Modern Physical Organic Chemistry is in every way a very different text from those considered above. It is a most impressive resource for researchers and teachers, and yet it also offers an accessible entree into the topics for advanced undergraduates and postgraduates. Physical organic chemistry is underrepresented in organic chemistry syllabuses across the UK. However, studying this subject can usefully reinforce a lot of material covered in a syllabus using a more descriptive treatment, and also makes accessible more difficult concepts in these topics.

The 17 chapters are split into three parts: "Molecular structure and thermodynamics", "Reactivity, kinetics and mechanisms" and "Electronic structure". All the topics one would expect are covered, from the simple acid-base chemistry through to molecular recognition and supramolecular chemistry, from fundamental concepts in catalysis through to organometallic reaction mechanisms. The section on electronic structure covers not only the standard thermal pericyclic reactions but a wide range of photochemical processes and includes a topical chapter on electronic materials.

Each chapter begins with a section on "Intent and purpose" that sets out concisely the material to be covered and the rationale behind the authors'

approach. This is followed by treatment of the basic concepts and terminology needed to develop the themes in the chapter. The chapter on stereochemistry, for example, begins with the simplest coverage of the "wedge and dash notation" for 2D-representation of 3D structures, yet seamlessly takes the reader through to advanced stereochemical issues in chemical biology. Each chapter ends with a "Summary and outlook", an excellent array of problems and exercises and a comprehensive bibliography that often refers to the review literature.

This type of text is often not easily accessible to the undergraduate reader, but I found this one to be well structured and very pleasant to read. Although there is appropriate mathematical treatment where needed, the feeling for the shapes and structures of organic molecules is not lost, as it is in many such texts. Modern Physical Organic Chemistry is a book I am very happy to have on my shelf.

Andrew Boa is lecturer in organic chemistry, Hull University.

Organic Chemistry. Sixth Edition

Author - Francis A. Carey
Publisher - McGraw-Hill
Pages - 1,1
Price - £42.99
ISBN - 0 07 111663 X

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