BOOK
REVIEWS
Organic Chemistry
D m l d J. Cram, University of California and George S . Hamwumd, a t h An& Cdiornia Institute of Technology, Pasadena. 2nd ed. McGraw-Hill Rook Co., Ine., Kew York, 1963. Figs. and tables. 17.5 X 28 em. $10.75.
"If we can gets. handle attached to this carbon, s. bimaleculsr substitution ought to give us the alcohol we want without much rearrangement." Anyone who has spent any time in organic research lab has heard comments very similar to that. More and more often, practicing chemists think in t e r m of substitution, elimination, and addition reactions, ete., and, in fact, many recent very elegant syntheses simply could not have been planned without a. detailed understanding of reaction mechmisms. "We will now discuss the alcohols, considering first methods hy which they may be prepared, and then we shall discuss the various reactions which they may be induced to undergo." Anyone who has spent any time in an organic classroom has d l too often heard the instructor carry on as if nothing hsd happened in the past 40 years. Fortunately, in their new edition of "Organic Chemistr,y," Cram and Hammond continue their practice of encouraging first-rate organic chemists to talk to their students as they talk to each other. While this text has been extensively revised and rewritten, all of the essential
features of the original have been retainel (reviewed in J. CEEM.Ennc., 37, 325-6, [1960]). The most important of these features is the classification of organic reactions according to mechanism, rather than according to functional group. h before, the text begins with several chapters on vocabulary, i.e., nomenclature of organic compounds, and some of their more typical reactions. This section now encompasses seven chapters instead of the four previously used, but this has been accomplished not so much by the addition of new material, but rather by a less compressed discussion with more illustrative examples and, primarily, by converting four long chapters into seven shorter, more easily digestible ones. The reactions described have been very carefully selected for their simplicity and use in synthesis and structure proof. Generally this section is excellent but there does seem to be a little confusion as to what happens in a KuhnRoth determination (see pp. 42 and 46). The next four chapters on structure and physical properties have beenvery considerably revised, expanded, and vastly improved. For example the chapter on the Character of Chemical Bonding has been expanded from 25 to 33 pages and almost completely reorganjzed. The molecular orbital formulation is presented first, followed by the valence bond method. The chapter is quite remarkable for its clarity and readability, whereas it must be ad-
Reviewed in this Issue
I
Donald J . Cram and George S. Hammmzd, Organic Chemistry Donald C . Gregg, Principles of Chemistry C. H. Sorum, Fundamentale of General Chemistry Robert 0 . Bolt and James G . Carroll, editors, Radiation Effects on Organic Materials V . Gold, editor, Advinces in Physical Organic Chemistry. Volume 1 Sidney SigSia, Quantitative Organic Analysis via Functional Groups M. F . Gmndon and H . B . Henbest, The Structures and Reactions of Organir Compounds Charles KiUel, Elementary Solid State Physics K. B. Lebedeu. The Chemistrv of Rhenium Frank H . Maser and Arthur L. Thomas, Phthalocyanine Compounds Hans Kramcr and Otto Matschoss, Farben in Kultur und Leben Harold C. Grey, Some Cosmoehemical Problema Andreas Awzuos, editor, Modern Chemical Engineering. Volume 1, Physiral Operations Twuor Robinson, The Organic Constituents of Higher Plants Paul Lewgans, editor, Lectures in Materials Science Mawel Flmkin and Elmer H . Stotz, editors, Comprehensive Biochemistry. l'lume 7, Proteins, Part 1 Mavcel Florkin and Howard S . Mason, editors, Comparative Biochemistry: A Comprehensive Treatise. Volume 5, Constitutents of Life, Part C F. F . Nord, editor, Advances in Enzymology. Volume 25 I. M. Kolthoff, and Philip J . Elliing editors, assisted by Ernest B. Sandell, Treatise on Analyt,ical Chemistry. Part 2, Analyticd Chemiatq of the Elements, Volume 8 R . M . Elliott, editor, Advances in Maes Spectrometry. Volume 2
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Journal of Chemical Education
mitted that the student using the first edition needed considerable assistance. The remaining chapters on Stereochemistry, Physical Properties, and Correlation of S t ~ C t u r and e Reactivity are lem drastically revised. Chapter 12, which has been almost completely rewritten and much improved, prepares the way for a. consideration of the various chemical reactions class by class. The reactions themselves, classified according to mechanism, are discussed in Chapters 13 through 23. Here the mast important changes involve the order of presenting the reactions, although new reactions such as hydroboration have been included where appropriate. The chapter on elimination reactions has wisely been moved closer to the front, and a discussion of electraphilie substitution a t saturated carbon deferred to Chapter 20. Unfortunately electrophilic substitution a t unsaturated carbon still comes pretty late in the game (Chapter 19). The section on radical rreaotians (chapter 22) is probably the moat revised and enlarged (from 12 to 24 pages) one in this section, reflecting the tremendous increase in interest in photochemical reactions. Following the discussion of the various reactions, a completely new chapter entitled Organic Synthesis appears. This chapter does not present any new material, hut does show how an expert artist can design and build the sort of molecule he needs. I t is hoped that a t least some students will read this chapter for quite a few will appreciate and enjoy it. All teachers will find these pages sheer pleasure. The remaining nine chapters on special topics are not too much changed from the first edition with the exception of Chapter 31, on spectra. I n this chapter the section on dyes has been eliminated and the pages devoted to ultraviolet, infrared, and NMR much expanded. A completely new section on emission spectra has been added. The problem a t the end of each chapter are excellent and more numerous than in the first edition. Also provided are several Reading References but these are usually to standard texts (Ingold, Hine, Gould, Wbeland, Fieser and Fieser, Organic Reactions, etc.) and it is regrettable that only i n one or two instrtnces is the original literature cited. The sdmirable practice of citing yields in moat reactions is continued. The type used in this new edition will be particularly clear. The technique of using color in equations to focus the readers attention upon the centers of reactivity is & g o d idea but it will take some getting used to. The text should certainly be more "teachable" than the first edition which this writer has used successfully not only with classes of chemistry majors a t the junior level but also, with careful choice of chapters, with arts students at the sophomore level. However, one must trust the authors. The natural tendency is to try to expand the "vocabulary" section into a lull course and if so one might as well throw away the book. But if taken as directed this text is powerful medicine as well as being lots of fun for both teacher and student. E. S. GRAHAM Canadian Serviees College Royal Roads Virtwia, B.C., Canada
