Book Reviews

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Stereochemistry

David G. Morris, Royal Society of Chemistry, Cambridge, , viii + 170 pp., price £9.95, ISBN 0-85404-602-8 Search PubMedThis short volume is aimed at university undergraduates and forms one of the RSC ‘Tutorial Chemistry Texts’, somewhat akin to the more familiar (at least to me) ‘Oxford Primer’ series. The book brings together a range of topics under the banner of ‘stereochemistry’ that could easily form the basis of a coherent undergraduate course on the subject. The areas covered by the book range from a fairly elementary level treatment of molecular structure, including orbitals, hybridisation and conformation, to prochirality, topicity and ‘chirality without stereogenic carbon’. The book should therefore be especially useful to both first and second year students enrolled in undergraduate degree courses in chemistry.

Each of the chapters of the book includes the expected descriptive text, accompanied by clear structures and schemes, but also includes coloured text for key points and highlighted boxes for chapter aims, student tasks, problems (answers at the back of the book) and worked problems. A short collection of references and suggested further reading is also included at the end of each section.

In addition to the types of topic mentioned above, the book also includes aspects of chemical reactivity, such as orientation and stereochemistry of additions to alkenes and the stereochemical implications of reaction mechanism in substitutions at saturated carbon centres. Additional subjects that are interwoven at appropriate points include description of the anomeric effect and the use of NMR to obtain stereochemical information.

As with most new texts there are places where things could be tightened up or enhanced, and I always look first to the index to see what has been left out. In this case the omission of important terms such as ‘stereoselective’ and ‘stereospecific’ seem rather serious omissions, especially since the terms syn and anti are introduced with respect to alkene reactions such as dihydroxylation and bromination. In a few places clarity could be improved by minor changes to the wording or structure drawings. One could also take issue with the organisation of material, for example chirality due to a single stereogenic carbon centre is treated in Chapter One, whereas the conceptually identical sulfur, silicon, phosphorus, etc. centres are dealt with much later in Chapter Five.

However, I should not dwell on these minor deficiencies, since for the most part I feel that the book is an admirable effort, and certainly one that students will find very accessible and informative. The style is clear and crisp, the illustration mostly very good, and the inclusion of so many problems with answers is extremely helpful. By some coincidence the book follows almost exactly a course that I give to our second year undergraduates at Nottingham and I shall certainly be recommending it to them in the strongest possible terms.

Nigel Simpkins
University of Nottingham

Basic Organic Stereochemistry

E. L. Eliel, S. H. Wilen and M. P. Doyle, Wiley, New York, , xiv + 688 pp., price £57.50, ISBN 0-471-37499-7 Search PubMedThe preface to this book explains how it came about, by an apparent need for an abbreviated version of the comprehensive text Stereochemistry of Organic Compounds, which would be more suitable for college level teaching. Thus, the new book is about half the length of the original volume, this being due to some general trimming of material, and to the removal of the section in the original book concerning stereoselective synthesis. Nevertheless, the new book still weighs in at well over 600 pages and contains in excess of 2000 references.

The topics included in the book will be familiar to all those who have consulted the earlier text, and it is hard to see where the new book is any less comprehensive. All of the expected material concerning the nature of stereoisomerism is included, ranging from the most straightforward manifestation of chirality right through to molecular propellers. Along the way, all of the appropriate historical background is included, and there is an emphasis on the determination of stereoisomer structure, the properties of racemates, resolution and enantiomer separation. Fairly extensive treatment of conformational analysis is also included, as is a chapter concerning the chiroptical properties of chiral substances.

The approach of the book remains uncompromising and it is fairly heavy going for anything other than reference use (the excellent index makes the book ideal for this use). Some of the chapters in particular will prove rather inaccessible to undergraduate students, whilst overall the core aspects are somewhat buried in the dense text. My view is that this book remains a comprehensive and authoritative reference volume (the ‘bible’ of organic stereochemistry), most useful for those involved in stereochemical research at the graduate level or beyond, rather than a text book. This book should be in university libraries everywhere and will prove very useful to researchers in industry and academia, but I would hesitate to point undergraduates in this direction for fear that they run from stereochemistry, never to return.

Nigel Simpkins
University of Nottingham

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