book reviews Editor: W. F. KIEFFER College of
W-ter
Woostor, Ohio
Organic Synthesis
Robert E. Ireland, Califomis. Institute of Technology, Pasadena. Prentice-Hall, Inc., Englewood Cliffs, New Jersey, 147 pp. Figures. 15 X 1969. xi 23 cm. Softbound, $3.95; hardbound, $6.95.
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"All men can see the tactics whereby I conquer, but what, none can see is the strategy out of which victory is evolved." Sun Tsu, "The Art of War" If there is to he s, handbook on the assault and conquest of synthetic ohjeetives, then this should probably be it. The adversary is carefully measured, his vulnerability ascertained, and his downfall engineered with delicate precision. One might question the ideology implied in statements such 6 s "analogy is the cornerstone of synthesis," hut in this brief accomrt, the stratagems are laid bare, the tactical maneuvers expounded wit,h veteran authority. The tenth in t.he Prentice-Hall series "Foundations of Modern Organic Chemistry," t,his monograph is intended to round out s. program designed for a oneyear course in organic chemistry. The first three volumes of the series form a general introduct,ion to the subject and provide background for the next six which deal with specific reaction types. The Ireland hook assumes ready familiarity with the foregoing material or its equiv-
-Reviewed
is offeredin chapter 1. The presentation is in two parts, the first of which sets forth prinoiples of synthetic desien while the second develons
is stressed. The conceptual and operative elements of 8. synthetic scheme are delineated, and t,he various gambits open to the synthetic chemist are elaborated here-the focus on kev intermediates. use
in this section with well-chosen examples; the Sheehxn penicillin synthesis, for instance, nicely demonstrates the design of a synthetic scheme based on relative react i d i e s of confluent functional erouos. A
book the reader 6 enoouraged to-reduce the synthetic problem to its component bondforming reactions, and to view the synthetic enterprise as a symbiotic process involving construction of theearbonskeleton and introduction, modification and/or removal of functionsl groups. Part I1 takes several examples of synthesis including some of t.he notable achievements in the field, and applies the algorithms promulgated in part I. The first eleven syntheses range from 2,4dimethyl-2-hydro~pent~noic acid to (i)-
Peter A. Rock, University of California, Davis. Macmillen Co., New York, 504 no. Fim. and trshles. 3969. xiv 16 X 24 cm. ~ardb'&nd, $11.95; softbound, $6.95.
. ..A391 Peter A. Rock, Chemical Thermodynamics: Principles and Applications . . .A391 Robed E. Ireland, Orgenic Synthesis
G. L. Pralt, Gas Kinetics
. . .A392 . . .A396
John A. Dean, Chemicd Separation Methods
. . .A396
.ll&in ('&in, Chemical Ev~lt#iior~: >loleculnr Evolutions toward thr Origin of Living S J . % ~ ~ Iin . Sthe t k r h and EIwwh~re
J. D . W H I T E Harvard University Cambridge, Mass.
Chemical Thermodynomirr: Principles and Applicotionr
in this /sue
George C . P i m t e l and Richard D. Spralley, Understanding Chemical Thermodynamics
aearalenone, and the reader is led tenderly through an occasionally contrived reasoning process behind construction of the carbon skeleton. The portentous titles of chapters 5 and 6, Stereochemistry Rears Its Ugly Head, and Logistics and Stereochemistry Combine to Produce Nightmares, belie the real condition, for it b seen that, in the exercise of steric control, the most creative and refined aspects of the synthetic art are practised. The a-onocerin, longifolene and quinine syntheses serve as testimony, and dissection of these complex synthet,ic operations reveals somet,hing of the inexorable logic and penetrating insight which went into salut,ion of these problems. The one unsettling feature in this discussion is the format in which the synthetic schemes are presented. Reading from bottom right, (starting material) to top left (product) would seem to have little pedagogic value. The final chapter provides a set of approximately sixty synthetic problems, some of which are uncomfortably challenging. Fortunately, references are furnished in all but a few instances to assuage the pangs of self-doubt. The book starts from a point towards the end of a basic organic course and concludes at the level of a relatively sophisticated graduate course. The diligent reader will not only have assimilated the principles and prsctieal details of synthetic planning hut will also have added extensively to his repertory of synthetic reactions and will have glimpsed the complex interaction of orgenic synthesis with its peripheral areas of chemistry. In reality, of course, syntheses almost never fallow the paths originally planned for them and, perhaps in the end, the most useful of the synthetic chemist's resources is his ability to capitalize on the sdversary's diversionary tactics.
H . J . M . Bowen, Chemical Applications of Radioisotopes
. . . A308 .. .A398
Ira D. Garard, Invitation to Chemistry: An Informal History of Man and Science
. . .A400
Grrhorl Hnnlkt,, editor, Gmelinj Ilxndhu~~h der Anorgnnisrhen Chemis!. h, .\ullage, S y ~ t mNufiumr: i 17, Dlei. Teil (.', l.,eierurvg 1, Terhnologie d e i Blris. Verbindungw his Hlet und Chlw
. . .A4UU
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This is a clearly-written, conventional, standard "p-chem" level, one-semester introduction to classicsl thermodynamics, with special emphasis on applications of thermodynamics to solutions. Possibly not all instmctors will wish to devote, as does this book, 20% of a semester's effort to the activity function and activity coefficients-functions that are to thermodynamics what, in a way, normality is (or was) to andlytical chemistry (oomputationslly convenient artifices that do, however, tend to divert beginners' attention away from simple, fundamental principles). Still, to achieve
(Continued on page A392) Volume 47, Number 5, May 1970
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