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Brooks/Cole: Pacific Grove, CA,
1997. xxiv + 919 pp. Figs. and tables. 24.2 X 19.2 cm.
ISBN: 0534249485. $87.95.
Professor Carroll has assembled a huge amount of
material in this book, whose chapters are entitled:
1. Concepts and Models in Organic Chemistry (57
pp, 197 refs)
2. Stereochemistry (61 pp, 169 refs)
3. Conformational Analysis and Molecular
Mechanics (59 pp, 207 refs)
4. Applications of Molecular Orbital Theory and
Valence Bond Theory (68 pp, 172 refs)
5. Reactive Intermediates (69 pp, 262 refs)
6. Methods of Studying Organic Reactions (77 pp, 222 refs)
7. Acid-Base Catalyzed Reactions (58 pp, 232 refs)
8. Substitution Reactions (94 pp, 244 refs)
9. Addition Reactions (92 pp, 352 refs)
10. Elimination Reactions (68 pp, 204 refs)
11. Concerted Reactions (84 pp, 181 refs)
12. Photochemistry (81 pp, 243 refs)
The book has an attractive cover. It is nicely printed
and generously lavished with well-drawn structures, figures,
and tables of data; Chapter 3 even has a six-page reproduction
of computer output detailing a molecular mechanics
calculation of gauche butane. The inevitable typos are few in
number. The book has complete subject and author indices.
In his preface, Carroll writes that he hoped to meet
two goals: to present the concepts that are central to the
understanding and practice of physical organic chemistry, and
to emphasize the role of complementary models in the
formulation of these concepts. In my opinion, the author has
succeeded better with the second aim than with the first. Or
perhaps the problem is that the two targets are too much
interwoven, with the qualifications intruding before the concepts
have had a chance to be digested. As a result, the novice senior
or graduate student is likely to become confused, if not
discouraged. The situation is compounded by a somewhat
chatty style and occasional philosophical quotations of dubious
relevance, beginning with two on the very first page (by
Senator H. Baker and T. S. Kuhn).
But the author succeeds very well in his second aim:
to point out limitations inherent in both the concepts of
physical organic chemistry and the methods used to flesh them
out. Thus, he presents an illuminating discussion of
"electronegativity" and the several scales in use to quantify it, of "strain"
and the difficulty of providing a reference level, of "stability",
and of "aromaticity" and other such hard-to-define notions,
the loose use of which so often leads to confusion and
arguments. I was especially delighted to see "Identification of
Reaction Products" listed as the first among the numerous tools
available to study reaction mechanisms. All of the chapters
end with an extensive series of meaty, multifaceted problems
that would serve very well for classwide presentation and
discussion. There is a solutions manual (which I did not see) for
most of the problems and literature references for others, but
in addition there are some that are "open-ended" and likely
to evoke lively discussion and opinions.
To summarize:
Perspectives... would not be my choice as a text for any student's first exposure to physical
organic chemistry. However, students who have already mastered
the subject will find a wealth of material here for a second
round, for review, and for ideas for advanced seminar topics,
literature group discussions, or even research propositions. All
Ph.D.-level practitioners of the art owe it to themselves to have a
close look at this book, which is clearly the result of a labor of
love.
William J. le Noble
Department of Chemistry
State University of New York
Stony Brook, NY 11794-3400
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