Stereochemistry (Morris, David G.)

Royal Society of Chemistry: Cambridge, UK, 2001. vii + 170pp. ISBN 0-85404-602-X. £ 9.95.

Since the earliest recognition that three-dimensional structure could affect the behavior of compounds, stereochemistry has played an increasingly important role in our understanding of chemical interactions. Once considered to be the realm of organic chemists, stereochemistry is now actively studied by chemists in all areas. But, students' introduction to the field continues to occur in organic chemistry courses; the average organic textbook contains an early chapter on stereochemistry with later references in the text back to that chapter. By necessity, most organic texts include the basics and little more, omitting detail and a number of interesting topics that some instructors may wish to include in their course. This book attempts to fill that gap by providing a more detailed coverage of stereochemistry than is available in standard organic texts but that is written at a level appropriate for use by the typical undergraduate chemistry student.

Since the book is designed to be used as supplementary material, the author assumes no prior knowledge of stereochemistry on the part of the students and the content of the stereochemistry chapters in standard textbooks is repeated. One might view this repetition as good because students can often pick up more material when it is presented from different approaches. But the material common to other textbooks is mixed with topics unique to this monograph beginning in Chapter 2, with the introduction of terms such as scalemic and homochiral. With the basics covered, later chapters introduce increasingly more advanced topics. Chapter 3, for example, includes bicyclic compounds in a discussion of diastereomers and Chapter 4 adds the stereochemistry of imines to a consideration of alkenes. The author has included ample coverage of the stereochemical outcomes of reactions that are typically a part of an introductory organic course: additions to alkenes and nucleophilic substitution reactions.

The most advanced topics are included in Chapters 5 and 8. Chapter 5 examines chiral compounds lacking a stereogenic center and includes allenes and biphenyls and compounds in which the center of chirality is a heteroatom, topics rarely touched in undergraduate organic texts. Chapter 8 provides an in-depth look at prochirality including enantiotopic and diastereotopic groups and faces and the importance of NMR techniques. Although these topics are briefly mentioned in some textbooks, the discussion here is more detailed while still being written at a level that a typical undergraduate can manage.

Chapters are easy to read and well illustrated and include questions with solutions. Key words are printed in bright colors and defined in the margin. At the end of each chapter, the author provides a review list of concepts and a set of practice problems, the solutions to which are given at the back of the book.

This book is designed for undergraduates and is probably not written at a level that is sufficiently challenging for seniors or graduate students. The author, in fact, points out in the preface that many important topics were left out for the sake of brevity. The most appropriate use is probably as a supplement for a sophomore-level organic chemistry course, perhaps in a program that distinguishes chemistry majors from other science majors. Instructors of courses at this level and their students will certainly find the array of topics in this book and the presentation to be of interest.