8/10/2019 Review of Modern Physical Organic Chemistry Textbook

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Chemical Education Today

www.JCE.DivCHED.org Vol. 83 No. 3 March 2006 Journal of Chemical Education 387

edited by

Jeffrey KovacUniversity of Tennessee

Knoxville, TN 37996-1600

Book & Media Reviews

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 whatorganic chemists call physical organic chemistry, the study oforganic chemical phenomena using the principles of physicsand physical chemistry. I have also taught various aspects ofthis subject dozens of times at the senior and graduate level. Iam thus always delighted to see a new textbook on the subject,such asModern Physical Organic Chemistry (MPOC) by Eric

Anslyn of The University of Texas and Dennis Dougherty ofCal Tech.

I have two dozen or more volumes dealing with physi-cal organic chemistry in my office. All have merit but aredeficient in some respect. One is well written but has beenout of date for many years. Another is beautifully writtenbut is full of errors, not only in the first edition but in thesecond as well. A third is rigorously mathematical, thus notsuitable for beginning graduate students. Others are researchtomes or encyclopedias rather than textbooks. Still others arenicely written but their coverage is not sophisticated enoughfor first-year graduate students. The book under review hasnone of these faults.

MPOCis genuinely a textbook although it may be usedin other ways. The book, which has been designed for a one-year course, was written with young graduate students inmind. The writing is very clear, at times conversational. Hav-ing one author check the writing of the other, I suspect, aidedin making the exposition clear. A very large number of top-ics is covered in the book, each developed deliberately andcarefully. I can think of no significant topic that was omit-ted. I found the coverage to be sophisticated but not overlymathematical, which is a turnoff for many students. An ap-pealing feature is the coverage of topics of current chemicalinteresttransition metal-catalyzed reactions, chemical bi-ology, materials, supramolecular chemistry, and computa-tional chemistry. Even when old, venerated subjects arepresented, they are illustrated with modern examples. Mod-ern molecular orbital theory is used extensively throughoutthe book, which may be off-putting to students at first be-cause they are usually exposed to the hybridization model atthe undergraduate level. Learning molecular orbital theorythe correct way will, however, lead to a more sophisticatedand hopefully more realistic way of understanding chemicalphenomena. Each of the 17 chapters concludes with a largenumber of interesting and often challenging problems onwhich students may hone their skills. There is a solutionsmanual, by Michael Sponsler of Syracuse University, to ac-company the textbook (1).

I was pleasantly surprised to find so few errors in a bookof this immense size: just a handful in more than one thou-sand pages. The structures, tables, and figures are clear

throughout, although the lack of any significant color in thebook may bother some readers. (If this had been an intro-ductory organic chemistry textbook, lack of color would guar-antee the books quick demise.) Suitable, usually up-to-date,references are found throughout each chapter and suggestionsfor further reading are at the end of each chapter.

In a book of this size there will be an occasional state-ment with which one disagrees or something one wishes hadnot been omitted. I found several such examples, a few ofwhich I will mention. The authors contend that the mea-surement of optical activity is a crude method for determin-ing 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 enan-tiomeric excess in modern chemistry is always a living system.This is certainly not true. The crystallization of conglomer-ates does not require the use of any optically active molecule,particle, or force. Reactions initiated with circularly polar-ized particles often yield optically active products. The authorsstate that Saul Winstein was the first person to propose thenon-classical structure of the 2-norbornyl cation. The credit,I believe, belongs to Nevell, de Salas, and Wilson who pro-posed a non-classical structure for a substituted 2-norbonylcation in 1939 (2).Although the authors correctly explainwhy the reaction of ketenes with olefins in a 2 2 cycload-dition reaction is allowed, they dont explain why the reaction

in fact occurs. Just because a reaction is allowed does not meanthat it will occur; other factors must be involved. Because sym-metry is an important consideration in understanding peri-cyclic reactions, molecular orbital theory, spectroscopy, andother topics, I wish the authors had included a section ongroup theory. On another note, I was pleasantly surprised tosee the authors cite my Ph.D. work of almost four decadesago. Some (photo)chemistry apparently never goes out offashion.

My quibbling over an occasional omission, error, or mis-judgment should not be seen as a lack of endorsement on mypart. Quite the contrary.MPOCis the most well-rounded text-book on physical organic chemistry that I have seen. The au-thors are to be commended for their six-year labor of love.

Literature Cited

1. Sponsler, Michael B.; Eric V. Anslyn, Eric V.; Dougherty, Den-nis A. Student Solutions Manual To Accompany Modern Physi-cal Organic Chemistry; University Science Books: Sausalito,CA, 2006.

2. Nevell, T. P.; de Salas, E.; Wilson, C. L.J. Chem. Soc.1939,1188.

Richard Pagni is in the Department of Chemistry, Univer-sity of Tennessee, Knoxville, TN 37996-1600; rpagni@utk.edu.

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