Guidebook to organic synthesis (Mackie, R.K.;Smith, D.M.) - Journal of

Nov 1, 1983 - Keywords (Domain):. Organic Chemistry. Keywords (Feature):. Book and Media Reviews. Keywords (Pedagogy):. Textbooks / Reference Books ...
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The authors elearlv intend an "understanding" removwl from, but muchdoser u,, the minimum limit than the innximum. Still e is enurthe b, d\ o i k n ~ l < . d a"covrrrd" mous. I t begins with basics-units, atomic structure, molecular structure and bonding, chemical reactionsarriving (in less than "one semester or two quarters") at the ability to understand digestion, metabolism, vitamins, hormones, and the "chemistry of heredity." The pace is generally brisk (enzymes are treated in 13 pages) resulting in inevitable oversimplifications;e.g., "Bases consist of two classes of compounds, metallic hydroxides and smines" (p. 176), or (p. 421), "The structural formula [of acetyl coenzyme A] 1s CHd-S-CoA." ~

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More serious distortions result from attempts to present basic concepts in greatly abbreviated fashion in terms of "relevant" examples. A case in paint is the discussion of the effect of temperature on rates of chemical reactions (pp. 168, 169). By discussing this concept in terms of multistep processes occurring in living systems, and ignoring the comolexities arisine from different temner~ aturc dependenrlei of sepamt* rompontnt reactiuns ot the uwrall prorewc* and ot hcr complicarlons arivny from trmperaturr IIPpendent conformational changes occurring in biological macromolecules very misleading conclusions are presented. I conclude finally that the book fails hecause the eoal is too ambitious for the soace

of life. The hook has many fine features. Many discussion segments, particularly in early chapters, are excellent and the figures are eenerallv relevant and clear (althoueh errors

G. Doyle Daves, Jr. Lehigh University Bethleham. PA 18015

Chemistry Experiment and Theory, S e c o n d Edltion Thomas L. Allen and Raymond M. Keefer, Harper and Row, New York, NY, 1982. vii 809 pp. Figs. and tables. 19 X 24 cm.

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Chemistry: Experiment and Theory, Seeond Edition, by Allen and Keefer is a text that covers the principles of chemistry in the first part of the book followed by a number of chapters on descriptive chemistry. This text follows the generally accepted order of material presentation. Contemporary authors do, however, vary the order and relationship of chapters in a few areas. Allen and Keefer introduce the first law and thermochemistry early, chapter 5, followed later in chapter 15 by the topic of thermodynamics and chemical equilihra. The chapters on gases, liquids, and the solid state are separated, chapter 3,

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Journal of Chemical Education

chapter 10, and chapter 17, respectively. The chapter on chemical kinetics occurs after the one on thermodynamics and both of these chapters follow the chapters on gas phase equilihra, aqueous solution equilibra, and redox. The level of presentation in this teat is well above that in an average introductory chemistry text. The authors are thorough in both material selection and coverage. Separate chapters on kinetic molecular theory of gases and particles and waves are included in the text. The Schrodinger equation is discussed verbally along with a complete discussion of the physical significance of wave functions including mention and a diagram of contours. The d i d state chapter includes coverage of the free-electron theory of metals and electron band theory. Crystal and ligand field theories, absarotion snectra of inoreanic complcres, collic~mtheory, particle in I Ir.lx, heat engines. and transitim itnte theory are among the spcrial topics i n h d ~ in d various chapters in the text. The descriptive chemistry chapters are one chapter in the middle and seven chapters a t the end of the text. The middle chapter, The Chemical Elements and Their Compounds, makes a quick sweep through metals, nonmetals, hydrogen, and the groups in thirty one pages. The remaining descriptive chapters include further discussion of the groups and chapters on organic, biochemistry, and nuclear chemistry. Authors tend either to integrate the presentation of descriptive chemistrv into relevant aoolications such as the arnwsph~rv.water qunlity, and the en\ ~ r ~ m n ror n tprewu the drirriptive nutrr:al In 3 ~ l a s s ~ c amanner l w t h chemira. and physical properties presented in reaction and table form. This text is of the latter type. Although the preface states that the number of problems at the end of the chapters has been increased bv 60% from the previous edition, some miay still find the numher toosmall for some rhapters. ('hnpter tug, w h ~ inclmlrs h in its rurrragethe mde, simplest formula, limiting reagent, and molaity ends with twenty-seven problems. The chapters do include numerous worked examples, interesting figures, and excellent tables. In summary, this camprrhensrw trv contams allot the materlal generally thought needed in an introductory chemistry course. In addition tu this core material the text contains a number of topics which should motivate and challenge the stronger students. This text which is oriented toward ahvsical chemistry provides a very good package for those who desire this organization and approach J. L. Kirsch Butler University Indianapolis. IN 46208

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Guidebook t o Organlc Synthesis R. K. Mackie and D. M. Smith, Longman, 338 pp. Inc., New Ywk. NY, 1982. xi Figs. and tables. 15.5 X 23 cm. PB $19.95.

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This book is designed as a text for an advanced undergraduate course in organic

synthesis. It might also be used as acme text for a beginning graduate course, with additional material provided by the instructor. The authors' decision to foreeo writine an encyclopedic reference work'has allowed them the freedom to develoo the subiect with ,~~ emphasis on iynthetic srrateg), rather than un the many different ways rhat one might acnnnplish any given synthmc transfurmation. The book is conceptually divided into five parts. The first part (21 pp.) reviews the synthetic chemistry that should have been learned in a previous one-year organic chemistry course. This chapter should bring the students to a common level of preparation. The second part (146 pp.) concerns the formation of carbon-carbon (and some carbon-heteroatom) bonds. The strategy of nucleophilic and electrophilic bond formation is discussed first, and the "synthon-disconnection" terminology is introduced at this point. Organometallics follow, with most of the emphasis going to Grignard and organolithium reaeents. Alkvlation and eondensa-

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halogens, oxygen, sulfur, and nitrogen. The final hond-forming chapter covers the formation of rings, using both classical techniques and pericyclic reactions (explained also usine frontier orbitalsi. This chaoter ~, mcl;desa very hnef t r ~ a t m mof t thv vlnsxal syntheses of oxygen, sulfur, and nltn~gen heterocycles. The next major section (78 pp.) deals with oxidation-reduction reactions and protecting groups. The chapter on reduction includes the maior classes of reductions. althoueh the ~

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student choose among the many techniques. The chapter on protective groups is minimal, covering only the classical protecting groups such as ethers. esters. ketals. carbonates. and urethanes. he hrevitv of these three funcof organic synthesis rather than the individual reactions. Some instructors may wish to include additional material, however. The fourth section (27 pp.) includes one ehaoter each on boron. ohosahorus. and sil. I c i chemitr\. .\lrhouglt these cha;,rtmare qtnre terse, they cover the most synthut~rally twrlul reagents and reartlons. Some of the newest and most remarkable reactions are omitted; however, their generality has yet to be established, so it may be appropriate to omit them from this textbook. The final section is a chaater with six seItvtcd synthe;es. Each cvnthesis 1s r~rcfull) ;ri,.dyzed,with an explnnar~moftheatrhreg) inwlved in the lhterature pwparatlm, ;m well as a comparison with related compounds and other possible ways of effecting each synthesis. The concept behind this chapter is an excellent one, that of demonstrating how one would choose among several routes far the synthesis of any particular compound. The number of examples, however, is too small. Fortunately, it is not difficult for an instructor to include additional examples of multistep syntheses from the literature. The last third of this "Selected Syntheses" chapter is devoted to a discussion of peptide synthesis,

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almost as an afterthought. Literature references are included at the ends of many of the chapters, and further readings for each chapter are listed in an appendix. Most of these references are secondary sources, such as "Organic Reactions." Although this use of secondary, rather than primary, sources is less likely to develop the students' ability to use the chemical literature. N gives them s more complete perspw tire of nnv topic the) !,light nerd I., look up. The muir ;rveredrj\rback to u w x this hot k as a text is its inadequate problem sets. There are only about a dozen problems in the book, with complete solutions for about nine. Any ~nstructorwho uses this as a textbook should be . prepared to add many additional prohlems. In summary, this "Guidebook to Organic Svnthesis" is a concise textbook for a first course in the strate:\. nnd reacrknr iiurganw y n t h e ~ iI~t merit* . serwur cun.~rleratwn1)). any in.,truvu,r tea, hiug an advnncrd undtrgraduate or beginning graduate course in organic synthesis. L. G. Wade, Jr. Cobrado State University Fort Collins, C0 80523 ~

Introduction to Organic Chemistry, Third Edition Douglas Applequisi. Charles Depuy, and Kenneth L. Rinehart. John Wiley & Sons, 384 pp. Inc., Somerset, NJ, 1982. vi Figs. and tables. 16.5 X 24 cm. $21.95.

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This is theThird Edition of a text intended as a short introduction to organic chemistry, with ahout 25-3096 of the discussion on Biochemistry. The previous edition was reviewed in this Journal (A45,1977) and much of what was said about the second edition applies to the third. The number ofchapten has remained constant, hut the text has expanded by 61 pages. The expansion includes an enhanced discussion of atomic structure, integration of IR, NMR, UV-Vis spectroscopic~into various chapters on functional group chemistry, and the inclusion of a reaction index. As in the earlier eaition, the streneth of the book derives from the inteerati& of nroblems found in industrv. ,. - .mediclne, and the envmnmmt intu ihr cherniml aiscuswn,. P r e w m t ~n