A guidebook to mechanism in organic chemistry; sixth edition (Sykes,P

A quick review of the sixth edition of this text shows the degree of improvement made in this classic text where the author is skilled at explaining c...
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been replaced by a listing of Nobel LaureChemistry; pmhahly more useful al. though perhaps less exciting, erpecially for the instructor. Aa in the previous edition, the early chapters provide structural background including the desirable description of all common functional groups before the detailed ehemistry of each is presented later. The decision toplace Reaction Mechanism before Stereochemistry may he questionable. The six chapters 8-13 (250 pp) all have titles with the word "nucleophilic" in them. I t is in these middle chapters that the author has done considerable reorganization. Three new chapter headings are introduced. Clearly Pine believes, with considerable justifieation, in the centrality of the chemistry associated with the structure and reactivitv of nuclwphiles and the diversity of the reactions made possible by attack on carbonyl and on orher susceptible functional groups with associated stereochemical consequences. He has also moved the section on terpenes into thelipid chapter, and he introduces a separate chapter on polycyclics in which he continues to eschew the dubious oractice of usine circles inserihed in heaagons The one hesr resonance structure for arrangmg double band cunlugatwn m such structures consists of minimizing quinoidal and maximizing Kekulb rings and only three deviations (naphthalene p 695 and 1044,pyrene, p 694) were noted. The unfortunate suggestion that methoxymethane is an aceeptahle name for dimethyl ether violates a fundamental nomenclature tenet of treatinn hke things alike, essentially a symmetry argument Simrlarly, where rs an organic teat that demonstrates hydrogen atom equivalency in methane due to its four Cgaxes; and what text states that there is only one CH& because of the Ca in CHsCI? Instructors who have used the previous editions will accept this new edition enthusiastically. I t is asound, accurate (the structure of aspartame excepted), very readable text. The arrow pushing is unambiguous. There is a good choice of problems, (but no answers) which are prominently displayed, and it has a comprehensive index. Milton Orchin University of Cincinnati Cincinnati. OH 45221 ates in

reactions of phosphonitrilic compounds; 21, additional inner-sphere electron transfer examples; 23 (the most extensively revised) additional organometallic structures, carhem and carbyue complexes, and a transition metal alkene elimination mechanism; 24, biainorganicchemistry of HhandMb;25 new data on the titanium family, as well as an addition of excited state Ru(hipy)?+ chemistry. By design the second edition maintains the strong emphasis on experimental ohservations and less on valence theories. Thus, reaction chemistry is systematically presented on the basis of thermodynamic or kinetic considerations, allowing more descriptive chemistry to he presented. The author has succeeded admirably in adhering to his stated intent. However, the underplay on theory tends to mask the tension hetween experiment and theory which often fuels advance in the discipline. Often, too, refinements in the theories may be neglected (to the students' detriment) in the overviewspresented. For example, the notions of molecular structure popularized hy Nyholm and Gillespie (VSEPRTheory) have been refined to account for some of the "supposed" anomalies illustrated in Sections 5.2 and 16.5. Recent advances in solid state. bioinorennic. lanthanide or actinide. and areanometallic chemistries arr omitted hy design. While the book is addressed to the rtudent. same of the field's luster is tarnished by these omissions. Nevertheless, the text overall continuesto he a very good descriptive inorganic text with numerous thermodynamic applications but with limited emphasis on structure and bonding theories. David E. Pennington Bayior University WBCO,TX 76798 ~~~~~~

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Organlc Chemistry S. Pine. McGraw-Hill: New York, NY, 1187 pp. Figs. and tables. 1987. xix 19.5 X 24.3 cm. $46.50.

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I t is hard to believe that the first edition of Cram and Hammond appeared almost 30 years ago! After a second edition, the authors were joined by Hendrickson for the third, and in the fourth edition Pine joined the triumvirate. Now in the fifth edition Pine is the sole author, hut this change in authorship is not explained. The author states that ". . . the major changes are in presentation. The writing has been modified so as to make subject materials even more interesting and understandable to students". I t is, of course, impossible to validate this latter claim and one would think that since the baok has endured all these years the earlier editions probably possessed these qualities. In fact it appears that most of the changes have more to do with organization than with presentation. An immediate difference is apparent in the inside cover and facing page which in the earlier edition showed the structure of some exotic hydrocarbons whose syntheses have challenged organic chemists. These have

Advanced Organic Chemistry: Reactions, Mechanisms, a n d Structure Jerry March Wi ey: New York. NY. 1985. xi i 1346 pp Figs. andtab es. 16.2 X 24 cm.

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Since the first edition of this advanced textbook was published in 1968, Jerry March has carried out the monumental and successful effort of major revisions twice, most recently with this impressive third edition. The 5M10 carefully selected new references replacing many deleted older ones, along with a refreshingly clear and concise writing style, make this text useful not only for specialists and teachers in the field, but also for nonspecialists needing a useful entry to the literature of organic mechanisms.

The division of the 19 chapters and two appendices into two major parts-tructure and general mechanistic tools in Part I, and reactions and reaction mechanisms in Part II-makes it possible to find rapidly just what one needs either for general background or specific information about a particular reaction. Part I topics include three chapters on bonding, and individual chapters on stereochemistry, reactive intermediates (carbocations,carhanions, free radicals, carbenes, and nitrenes), mechanistic methods, photochemistry, acids and bases, and reactivity-structure relationships. Part I1 includes five chapters on aliphatic, aromatic and free-radical substitutions, other chapt e n devoted to additions, eliminations, rearrangements, redox reactions, and two appendices, on the literature of organic chemistry and the classification of reactions by type of synthesized compound. One of the most telling observations confirming the usefulness of this text is that it is on the "regdy access" shelf of most of my nonorganie as well as organic colleagues, and is obviously well used. I t is an excellent textbook far an advanced course in organic chemistry reaction mechanisms, as well as being a first-rate reference hook for any practicing chemist. Bruce E. Norcross State University of New Yo* Binghamton, NY 13901

A Guidebook to Mechanism In Organic Chemistry, Sixth Edltlon P. Sykes. Wiiey: New York. NY. 1986. xii 416 pp. Figs. and tables. 14 X 23.3 cm. $21.95.

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A quick review of the sixth edition of Mechanism in Organic Chemistry by Peter Sykes shows the degree of improvement made in this classic text. I t is important to note that the sixth edition, as in all of the previous productions, the author has been able to explain complicated topics in a simple way. This is the main feature of this edition. The detailed index will also serve the senior undergraduate or beginning graduate student well in order to locate those topics that require further explanation and understanding. The inclusion of "old" name reaction listed as the Knoevenagelreaction under the heading of nucleophilic addition to carbonic systems is helpful for reference purposes. I find this edition to be an excellent book in the mechanism of organic chemistry and a must for anv undereraduate.. iunior. senior, or graduate chemistry rtudent. As an organic chemist, I find Peter Sykes 3Iwho. nirm in O ~ p a n i cChemistry to be a good reference in my library. Aris Merijanian University of Montevalio Montevalio. AL 35115

Volume 65

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(Continued on page A140) Number 5

May 1988

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