BOOK
REVIEWS anisms in Organic Chemistry," edited bv E. D. Huohes. American Elsevier ~"ublishineCO".. Inc.. New York. 1963. 515 Figs. and tables. viii 14.5 X 22 om. $8.
Nucleophilic Substitution af a Safurated Carbon Atom
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C. A. Bunta, University College, London. Volume 1of "Reaction Mechaniems in Organic Chemistry," edited by E. D. Hughes. American Elsevier Publishing Co., Inc., New York, 1963. ix 172 pp. Figs. and tables. 14.5 X 22 rm. S7.
These two volumes are the first of a series of monographs on Reaction Mechanisms in Organic Chemistry. The series was orxanized bv the late Professor E. D. HUK~&. for over thirtv veam eo-leader witrh S ; Christopher Ingold of the influential school of physical organic chemistry a t University College London. To the dopics of these two volumes,
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Elimination Reactions
D. V . Banthmpe, University College, London. Volume 2 of "Reaction Meeh-Reviewed
pp.
in This Issue
C . A. B m t a , Nncleophilie Substitution at a Saturated Carbon Atom D. V . Bantho~pe,Elimination Reactions John E . L e f i r and Ernest Grunwald, Rates and Equilibria. of Organic Reactions F. E. Critchfield, Organic Functional Group Analysis Erich K d , Handbook of Laboratory Distillation W . J . Potts, Jr., Chemical Infrared Spectroscopy. Volume 1, Techniques H ~ T TC. Y Allen, Jr., and Paul C. Cross, Molecular Vih-Rotors: The Theory and Interpretation of High Resolution Infrared Spectra B. Jheyer and H. H. Bauer, Alternating Current Polarography and Tensammetry H. J . J . Braddiek, The Physics of Experimental Method R. B. Heslop and P . L. Robinson, Inorxanic Chemistry: A Guide to Advanced Study Glen Tilbury, Problem Salving in Chemistry Anthony Standa, executive editor, Encyclopedia of Chemical techno log.^. Volume 2, Aluminum Compounds to Azo Dyes J . T . Davies and E. K. Rideal, Interfacial Phenomena John Turkevich, Soviet Men of Science H m r d 0.Triebold and Leonad W . Aurand, Food Composition and Analysis Willis T . Bradleu, Carrol B. Gustefson, and Mitchell J . Stoklosa, Pharmaceutical Calculations Herman A. Saymanski, editor, Infrared Band Handbook J . H. B e m n and A . E. Wzlliarns. Msss and Abundance Tables for Use in Mass ~pectr&netr~ Paul D. Boyev, Henw Lardy and Karl Myrback, editors, The Enzymes. Volume 7 David A . Hall, editor, International Review of Connective T i u e Research. Volume 1 E d i e Segrk, Gerha~tFriedlandel and H. Pierre Noyes, editors, Annual Review of Nuclear Science. Volume 13 IUPAC with Swedish Chemical Society. Coordination Chemistry M . Rocha E. Silua and U.S. Voh E u h , editors, Part 1 and Domingo 31.Aviado, editor, Part 2. Bijrje Uvnss, general editor, Proceedings of the First International Pharmsook,eiral Meetine. -, Volume 9 Francis A . Gunther, editor, Residue Reviews. Volume 3 V. Gold, editor, Advances in Physical Organic Chemistry. Volume 2 Marcel Fbrkin and Elmer H. Stotz, editors, Comprehensive Biochemistry. 7'01ume 8, Proteins (Part 2) and Nucleic Acids A. R. Katritzky, A. J . L3oulta, and J . M . Logowski, editors, Advances in Heterocyclic Chemistry. Volume 2 Elwyn T . Reese, editor. Advances in Enavmic Hvdrolvsis . . of Cellulose and Related Materials R. T . Holman and W . 0 . Lundbe~g,editors, Progress in the Chemistry of Fats and Other Lioids. Volume 6 ~
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istry, Volume 1 Hans B. Jonassa, and Arnold Weissberger, editors, Technique of Inorganic Chemistry. Volume 3 Aljmd J. Moses, International Series of Monographs on Analytical Chemistry. Volume 9, Analytical Chemistry of the Actinide Elements
406
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Journol of Chemical Education
Hughes and Ingold devoted a large share of effort for many years. For that reason, or becsuse of the importace of these reaction types, nueleophilic suhstitution a t mturated carbon sod elimination reactions have also received much attention from other workers. The present authors were both students of Hughes and Ingold and, a t the time the books were written, both were staff members a t University College. (Bunton has since taken a post a t the University of California a t Santa Barhsra.) Though neither is a major investigator in the field of his book, both have made important contributions. Both of these hooka are authoritative. They are both comprehensive in the sense that they probe into mmt it not all of the important facets of the respective rertctian types. However, no effort has made to make either book an exhaustive review. Bath authors have carefully selected their material, and all presentations are made eriticslly. In consequence, the amount of intellectual fare in each is much greater than the small page size and page counts might suggest. Though both authors tend ta stand with Hughes and Ingold on controversial questions, their allegianoe is neither absolute nor dogmatic. Also, hath authors have gone well beyond the aspects of these topics with which Hughes and Ingald were mainly concerned. This praise is not meant to imply endorsement of the way all topics are handled, or of all the judgments made. Indeed, I am less than fully satisfied with the way my o m modest contributions to each topic have been treated. Other chemists may share this feeling. Nucleophilic substitution a t saturated carbon has probably consumed more manyears of research time than any other category of organic reaction mechanisms. To do it justice in 149 pages of text waa a challenge, successfully met only by an unusually concise presentation. The economy of words is refreshing, hut in places the discussion is so terse as to dismay the reader not already familiar with the subject. For this reason, I hesitate to recommend Bunton's book for regular use by undergraduate students. Researchers active in the field will heed and respect Bunton's views, hut since the mrtterial covered is mostly familiar to them, they probably will not often return to his book. It is to the reader a t an intermediate level, such as the gmdnate student seeking to master the subject, that the volume will be most valuable. Elimination reactions have a less abundant literature. Therefore, and because his book is 25y0 longer, Banthorpe was able to use a more relaxed style of writing and to probe more deeply into single topics. The former quality makes his volume sttraotive ta beginners, and the latter makes it valuable to experts. He has dug out of the literature many relevant but seldom-mentioned facts, and has made good use of the opportunity to comment and criticize. Banthorpe's hook is a major contribution. Attractive features of both hooks are their moderate prices and good quality of printing and illustration. These hook. are essentisl to all college chemistry
