Organic Chemistry: Structure and Function, 3rd ed.. By K. P. C. Volhardt and N. E . Schore. W. H. Freeman: New York, 1999. xxxiv + 1210 pp plus answers to problems, credits, index, and CD-ROM. ISBN 0-7167-2721-8.

Reviewed by: David M. Schmierer, University of Otago, New Zealand, david.schmierer@sto nebow.otago.ac.nz

Over the last three decades there has been an increasing number of undergraduate-level textbooks published in the field of organic chemistry. Many aspects of the "how, what, why, and to whom" organic chemistry is taught have changed over this period and this is reflected in the way that modern textbooks are set out. Undergraduate textbooks now target much wider audiences than before, because fewer students taking organic chemistry intend to become chemists. Examples are students taking degrees in biochemistry, pharmacy, medicine, dentistry, physiotherapy, zoology, and botany; the list is actually quite long!

The presentation of material has also changed because publishers can economically produce textbooks of much higher quality than in the past. Technology has moved ahead and the black-and-white undergraduate textbooks that were produced in the first three-quarters of the twentieth century should be entirely a thing of the past. Quality, layout, illustration, and supplementary materials have improved to the point that current texts are visual works of art! This textbook lives up to these expectations and is very well illustrated. The authors use color in many ways, especially within structures to direct attention to that part of a molecule being modified during a reaction or to a functional group being discussed.

Another of the improvements in textbooks is based upon the realization that students need to feel supported when using the text. Undergraduate texts in organic chemistry are no longer repositories of fine-detailed and often-confusing information, but now have a clear and defined structure containing obvious themes. While the authors have not followed a standard compartmentalized format, they have integrated relationships and themes throughout the text, and I think that this will produce some good teaching.

It is also important that students have a good idea of the structure of a textbook and the most productive way for them to use it. To these ends the authors include a very useful and clear preface that should make it easy for students to navigate through the textbook. In each chapter, theory is supplemented by several grades of exercises: "Integration Problems" that are solved problems to integrate theory within and between chapters, "Problems," and "Team Problems." The latter problems are more complex, and students are challenged to solve these working as a team. In my experience this is an excellent way of teaching and learning. I am impressed that the text gives answers to all exercises and not just to selected questions. There are also useful summaries of important concepts for each chapter, as well as summaries of synthetic pathways where relevant.

I like the authors' coverage of stereochemistry and their use of 3D ball-and-cylinder structures to complement the usual stick structures that emphasise the three-dimensionality of organic chemistry. This style of presentation shows more clearly the stereochemical relationships within a molecule. Enantiotopicity, diastereotopicity, and prochirality are not discussed, as is unfortunately the case with most modern textbooks. I think that these are important stereochemical concepts and belong in such undergraduate textbooks.

Acid–base chemistry is covered briefly as a review of acid–base concepts in the chapter on alkanes. These concepts are continued throughout the text, but I think acid–base chemistry is so important to so many disciplines that it warrants a stand-alone chapter.

Nuclear magnetic resonance spectroscopy (NMR) is well covered as a stand-alone topic, although 2D techniques are not discussed. Infrared (IR), UV–visible spectroscopy (UV–vis), and mass spectrometry (MS) are covered as part of other chapters. IR is introduced in the chapter on alkenes and MS in the chapter on carboxylic acid derivatives. UV–vis is covered in the chapter on extended conjugated systems and, to a degree, this is more logical. The coverage of IR and UV–vis is fairly brief, and I prefer spectroscopy and spectrometry as stand alone topics, though this might take away some of the integration of theory in the text, which is one of its attractive features.

Throughout the text there is a wonderful linkage of theory to the applied aspects of the biological and health sciences and to industrial and environmental chemistry within chapter asides called "Chemical Highlights." These highlights should be stimulating reading for any student and I think that much can be done with them, in terms of teaching. In one of them, however, it is stated that the bioactivity of penicillin is due to the fact that it is a beta lactam, sterically stressed, resulting in increased reactivity (electrophilicity) of the lactam carbonyl carbon atom as compared to aliphatic amides. This is only part of the story, because it is the stereochemistry at the lactam nitrogen atom that is of critical importance for the bioactivity of penicillins and cephalosporins. The geometry of the fused two-ring system forces the nitrogen atom into a tetrahedral geometry and it no longer behaves as a normal amide because p–p orbital overlap between the nitrogen atom and carbonyl carbon atom is not possible. Penicillins are not flat, but more like half-opened books. This could be expanded to illustrate how stereochemistry can change acid–base and reactivity (and stability) properties of compounds. Salicylic acid could be another example to illustrate unexpected spectra, and acid–base, solubility, and hydrophobicity properties.

The text comes with an easily installed CD-ROM to give practice in problem solving. Its use, although intuitive to those experienced with computers (in these days, most of us), is clearly and simply described and it is a useful adjunct to the textbook. Further support is provided in the form of a well-designed Study Guide and Solutions Manual written by Neil Schore (ISBN 0-7167-3165-7).

Any undergraduate organic chemistry textbook will be open to criticism by those who teach organic chemistry from different points of view or with different aims. There will always be things that please and displease, and such textbooks cannot be all things to all teachers. In summary, this textbook explains the basic concepts of organic chemistry clearly, is visually attractive, and is interestingly written. The underlying theory is well-integrated throughout and should increase students' interest in, and enjoyment of, the subject. I have few criticisms and I think that this text is eminently suitable as an undergraduate organic chemistry textbook.