Fundamentals of Organic Chemistry, (McMurry, John)

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reviews Fundamentals of Organic Chemistry, Third Edition John McMurry. Brooks/Cole: Pacific Grove. CA. 1994, xx + 552 pp. Figs. and tables. 19.4 x 24.2 cm. $63.00. The third edition of this textbook is designed far use in a brief course in organic chemistry. This edition shares much in common with its predecessors. I t is comparatively short, is organized by functlanal ~ ~ u u possesses p, fin; stylmg and rarcfully prrscnrrd nnwork, n r d is written in an currrdmgly itudcnt-friendly manner Thr tnhle nfrontrnts ofthir terms ofchapter heudings, is identical to the second edition with the sole-exception beine the inclusion of a n additional chaoter (Chanter 17) entitled " ~ h e ~ ~ r e sChemistrv nie of Metabolic ~ k b w a v s " . . ~ h new i s chanw r is wrll written and providcs clo.un: h r the hmk w t h an array o f t a n ~ ~ b l e e x s m p lielsl u i t r a t m g t h ~ theorganic t reactwnsofsimple urgmwms, w h h bemg ntoreconiplrx than those rypcnlly pcrformed in rhc lnhorntory. we gwerned, noneth&ir, by the iame prmclpla.; that are taught in the earlwr chapters. Whllc the first 16rhaptcrs possess idcnricnl hcndtngs wirh thosr from the second edition, some important changes ha& been made in terms of cantent. The greatest improvement comes in Chapter 1 where the authors have added review treatments on acid-base chemistly, electranegativity, and bonding. Further changes include a modest expansion in the number of end-chapter problems, the inclusion of mare in-chapter drill problems, and the addition of full color to several chapters. McMurry, like all his competition, treats spectroscopy (IR, W, 13c, and 'H NMR) as aself-contained unit in a l a t e chapter (Chapter 13). The earlier chapters that deal with the common functional groups possess no spectroscopic component a t all. This simplifies instruction if sneetraseonv is de-emohasized bv the instructor. If the instructor 'prefers the incluiwn uf 3truct;re detc~mination throughout t h r lunctionnl group treatment, then rhr approach taken here wll rrvrrrl,y lrmlt the u t h t y afthls b ~ r The k rumpletc omission of mass spectrometry is a clear short-fall in this text. On the absolute scale, this book has an array of strengths. The manner of writing and clarity of presentation is first-rate. An innovative vertical format to exolain reaction mechanisms is utilized. The mechanlsma are pnnted venrcally, whdr crplmatmns of rhr stcp-hg-atcp changes ore prlntcd nrvr to the rmerwn x r o w Thls appnmch works very well. A n effective means for emphnqrring key terminulugy is employed i r 11131 ~ key terms arc srgrrgnrcd from the text, being placed in the margin next to where they first appear in the text. Selected chapters conclude with well-prepared summaries of key terms and key reactions. This reviewer can find no pedagogic or chemical weaknesses inherent to this bwk, but there is same unrealized potential. For instance, the author's mechanistic approach is excellent, however, it would have been better had he extended this approach to a broader array of reactions. The author also has included several "interludes" that show interesting applications of organic chemistry to industrial and biological systems. These end-of-chapter treatments are, indeed, engaging to the student, but once mare are too few in number. And finally, while the chemistry of reactive intermediates is addressed adequately throughout the book (as ~









applied to specific reactions), the initial treatment in Chapter 2 is far too brief and should be expanded to include the structure and reactivity of anions and free radicals in addition to cations.

Robert W. Holman Western Kentucky University Bowling Green, KY 421 01

Organic Chemistry, Fifth Edition Ralph J. Fessenden and Joan S. Fessenden. BrooksICole: Pacific Grove. CA, 1994. xxii + 1122 pp. Figs. and tables. 18.7 x 26.2 cm. $77.75. I t is ohvious from the fact that this is the fifth edition of this text that it has been well received in the past. The latest edition is a quality text that presents a traditional view of organic chemistry. This edition is similar to previous editions in that it covers the fundamental principles of organic chemistry in a clear and logical manner. Two new features make this a more interesting book. The first is the inclusion of historical aspects of the development ofthe science as a part of each chapter. The second is a problem a t the end of each chaoter. referred to as a n Essav Problem. which eives a real world example uf the matrrrul drscussed IT, the chapter and then qui7,es the rcadcr on how lcnrnrd prlnciplrs apply to that ipec~firexample These pnhlem.;, hwever, may lw of more interest to the instructar than to the student. The organization of the text material is much the same as in previous editions. Introductory material is found in Chapters 1-4. The bulk of the material is presented in a section called Organic Reactions and Mechanisms (Chapters 5-18). This section is hasically the functional group approach to presentation of information. P r e s e n t a t i o n of t h e m a t e r i a l on i n f r a r e d a n d NMR spectroscopy in Chapter 9 is especially well done. Topics of Specialized Interest (Chapters 19-22) contain information in some specialized areas (perieyclie reactions, natural products, etc.) which could be used a t the discretion of the instructor. The book ends with t h e traditional chapters on Bio-organic chemistry (Chapters 23-26). As is true with most organic texts, more material is offered than can be covered in a ane-year sequence of lectures. Those who are familiar with some ofthe other widely used texts in organic chemistry will find that the a r t work, diagrams, and structures offered are not of the same oualitv that they are used to seeine. The use of color is ineffective 'due tb the verv-lieht hues used. The u w i f mercy d w v n m r i s not preientrd in as rlyorous a manner as 1.i luund in 0tht.r texts. Xu distioctmn is made lwtwteo potcnt~alcncrgy and free energy dingrams While this may not be detrimental to an understanding of organic chemistry, physical organic chemists will find it less than satisfactory Multistep reaction mechanisms are written out as consecutive reactions and not as separate halanced equations. Because the concept of a mechanism is difficult for the student a t best, this presentation adds more confusion than is necessary. Instructors who like to use the band-line format far structures will not find it used in this text


Reviewed in this Issue John McMurv, Fundamentals of Organic Chemistry, Third Edition Ralph J. Fessenden and Joan S. Fessenden, Organic Chemistry, Fifth Edition Richard 0. C. Norman and James M. Coxon, Principles of Organic Synthesis, Third Edition Titles of Interest

Reviewer Robert W. Holman Joe C. Greever Shelton Bank

Volume 72 Number 7 July 1995