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Chemical Education Today

edited by

Book & Media Reviews

Jeffrey Kovac
University of Tennessee
Knoxville, TN 37996-1600

Modern Physical Organic Chemistry

by Eric V. Anslyn and Dennis A. Dougherty
University Science Books: Sausalito, CA, 2006. 1104 pp.
ISBN 1891389319 (cloth). $132.50
reviewed by Richard Pagni

I have spent most of my career doing research in what

organic chemists call physical organic chemistry, the study of
organic chemical phenomena using the principles of physics
and physical chemistry. I have also taught various aspects of
this subject dozens of times at the senior and graduate level. I
am thus always delighted to see a new textbook on the subject,
such as Modern Physical Organic Chemistry (MPOC) by Eric
Anslyn of The University of Texas and Dennis Dougherty of
Cal Tech.
I have two dozen or more volumes dealing with physical organic chemistry in my office. All have merit but are
deficient in some respect. One is well written but has been
out of date for many years. Another is beautifully written
but is full of errors, not only in the first edition but in the
second as well. A third is rigorously mathematical, thus not
suitable for beginning graduate students. Others are research
tomes or encyclopedias rather than textbooks. Still others are
nicely written but their coverage is not sophisticated enough
for first-year graduate students. The book under review has
none of these faults.
MPOC is genuinely a textbook although it may be used
in other ways. The book, which has been designed for a oneyear course, was written with young graduate students in
mind. The writing is very clear, at times conversational. Having one author check the writing of the other, I suspect, aided
in making the exposition clear. A very large number of topics is covered in the book, each developed deliberately and
carefully. I can think of no significant topic that was omitted. I found the coverage to be sophisticated but not overly
mathematical, which is a turnoff for many students. An appealing feature is the coverage of topics of current chemical
interesttransition metal-catalyzed reactions, chemical biology, materials, supramolecular chemistry, and computational chemistry. Even when old, venerated subjects are
presented, they are illustrated with modern examples. Modern molecular orbital theory is used extensively throughout
the book, which may be off-putting to students at first because they are usually exposed to the hybridization model at
the undergraduate level. Learning molecular orbital theory
the correct way will, however, lead to a more sophisticated
and hopefully more realistic way of understanding chemical
phenomena. Each of the 17 chapters concludes with a large
number of interesting and often challenging problems on
which students may hone their skills. There is a solutions
manual, by Michael Sponsler of Syracuse University, to accompany the textbook (1).

I was pleasantly surprised to find so few errors in a book

of this immense size: just a handful in more than one thousand pages. The structures, tables, and figures are clear
throughout, although the lack of any significant color in the
book may bother some readers. (If this had been an introductory organic chemistry textbook, lack of color would guarantee the books quick demise.) Suitable, usually up-to-date,
references are found throughout each chapter and suggestions
for further reading are at the end of each chapter.
In a book of this size there will be an occasional statement with which one disagrees or something one wishes had
not been omitted. I found several such examples, a few of
which I will mention. The authors contend that the measurement of optical activity is a crude method for determining enantiomeric excess when compared to chiral HPLC.
Having dealt with both, I dont think this is necessarily the
case. The authors contend that the ultimate source of enantiomeric excess in modern chemistry is always a living system.
This is certainly not true. The crystallization of conglomerates does not require the use of any optically active molecule,
particle, or force. Reactions initiated with circularly polarized particles often yield optically active products. The authors
state that Saul Winstein was the first person to propose the
non-classical structure of the 2-norbornyl cation. The credit,
I believe, belongs to Nevell, de Salas, and Wilson who proposed a non-classical structure for a substituted 2-norbonyl
cation in 1939 (2). Although the authors correctly explain
why the reaction of ketenes with olefins in a 2 2 cycloaddition reaction is allowed, they dont explain why the reaction
in fact occurs. Just because a reaction is allowed does not mean
that it will occur; other factors must be involved. Because symmetry is an important consideration in understanding pericyclic reactions, molecular orbital theory, spectroscopy, and
other topics, I wish the authors had included a section on
group theory. On another note, I was pleasantly surprised to
see the authors cite my Ph.D. work of almost four decades
ago. Some (photo)chemistry apparently never goes out of
My quibbling over an occasional omission, error, or misjudgment should not be seen as a lack of endorsement on my
part. Quite the contrary. MPOC is the most well-rounded textbook on physical organic chemistry that I have seen. The authors are to be commended for their six-year labor of love.
Literature Cited
1. Sponsler, Michael B.; Eric V. Anslyn, Eric V.; Dougherty, Dennis A. Student Solutions Manual To Accompany Modern Physical Organic Chemistry; University Science Books: Sausalito,
CA, 2006.
2. Nevell, T. P.; de Salas, E.; Wilson, C. L. J. Chem. Soc. 1939,

Richard Pagni is in the Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600;

Vol. 83 No. 3 March 2006

Journal of Chemical Education