Comprehensive organic transformations: a guide to functional group

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sion series. All chapters are provided with self-tests, matching sets to review vocabulary, and questions; answers to the first two items are given at the back of the book. The volume includes coverage of dozens of "relevant", practical, up-to-date topics such as bioteehnology, radon dangers, "cold fusion", polyacetylene conductors, superconductors, acid rain, CFCs, the greenhouse effect, "fake fats", abuse of steroids in sports, "crack" and "ice", AZT, and RU 486 to a greater extent than most general chemistry texts that I have seen. Considering the length and scope of the book, the number of errors, mast involving proper names or history, is not excessive. For example, Perkin (not Perkins) diseov; ered mauve in 1856 (not 1865) (p 9); Nikolai Aleksandrovich Menshutkin (not Mendeleev, who was visiting cheesemaking cooperativesat the time) delivered the latter's paper on the periodic law before the Russian Chemical Society (pp 91 and 93); Charles Goodyear worked on rubber for five (not 10) years before making his momentous discovery, and William Broekedon (not Goodyear) named the product "vulcanized" rubber although Gwdyear reludantly used the designation after the term became popular (p 419); G. J. (not G. T.) Mulder was Dutch (not German) (p 454); and Linus Pauling won the 1962 (not 1963) Nobel Peace Prize (p 458). Misspellings include Heroult for HBroult (p 302) and Joule-Thompson for Joule-Thamson (p 309). Also, hexacyanoferrate(II1) (not cyanoferrate) is the correct IUPAC name for Fe(CN)&, and NH40H (ammonium hydroxide) does not exist (p A14) (seeDavis, J. B. J. Chem.Educ. 1953,30, 511; Laing, M. Spectrum 1988,26(41,11). I am pleased to recommend highly this society and applieations-oriented textbook, which is supplemented by two "packages". The telecourse package consists of Gilbert Castellan, Nava Ben-Zvi, and Isidore Adler's Telecourse Study Guide ($16.00), which is keyed to both the video programs and the text and provides aconsistent method for correlating the two; Laboratory Manual to Accompany World of Chemistry ($16.00), containing 20 experiments selectedfrom the fifth edition of Jones, Johnston, Netterville, Woad, and Joesten's Laboratory Manual for Chemistry and Society; and Ben-Zvi, Castellan, Adler, and Lisa Ragsdale's Faculty Telecourse Manual ($10.75), containing general guidelines, teaching tips, and resources for each study guide unit and is available free to institutions licensing the telecourse. The text package consists of Jones, Johnston, Netterville, Wood, and Joesten's Laboratory Manual to Accompany World of Chemistry: Extended Version ($29.50), containing 45 experiments, and an accompanying lnstructork Manunl; an Instructor's Manual and Test Bank ($26.75), containing teaching suggestions, test questions, and solutions; Computerized Test Banks for IBM or Macintosh computers ($66.50 each); and Overhead Transparencies of 100 color images ($425.75) from the hoak, all of which are free upon textbook adoption. For information on the videocassettes call 1-800-LEARNER and for information on the accompanying books and materials call 1-800-447-9479,Ext. 7628. George B. Kauffman California State University. Fresno Fresno. CA 93740 A86

Journal of Chemical Education

Cornprehenslve Organlc Transforrnatlons: A Gulde lo Functional Group Transformations Richard C. Larock. VCH: New Ywk, NY, 1989. uxiv 1160 pp. 18.5 X 26.2 crn. $55.00.

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Comprehensive Organic Transformations is a systematic collection of literature references designed to aid the organic chemist in evaluating synthetic methods. The highly condensed visual presentation is similar in concept to that conceived by Ian Harrison and Shuyen Harrison in the firat Compendium of Organic Synthetic Methods, but there are fewer equations and more references in Larock's hook. T o include an additional 20 years' worth of literature, Laroek has used a more highly condensed format that omits sample reactions in many cases. General reactions are introduced by one prototypical equation, followed by extensive tables of abbreviated references organized by the reagent. The information density is remarkable, with about 20,000 references stuffed into the book's 1000 pages of content. The literature covered includes an amazing 160 primary journals, with coverage through 1987. Like the Compedium, Comprehensive Organic Transformations is organized into major chapters based on the target functional groups: Alkanes and arenes, alkenes and dienes, alkynes, halides, amines, ethers, alcohols and phenols, aldehydes and ketones, and acid derivatives. Other functional groups, heterocycles, and protecting groups are not covered except as they might be used in making the listed types of compounds. Users may object to some of the exclusions, hut the difficult problem of packing a huge amount of information into a usable volume forced the author to focus on the most common functionality. Each chapter is subdivided into major processes such as oxidation, reduction, and alkylation. For example, the alcohols chapter is subdivided into general references, alprocesses such as oxidation, reduction, and alkylation. For example, the Alcohols ehapter is subdivided into general references, alcohol transposition, substitution, oxidation, additions to alkenes and alkynes, organoboranes, ether, epoxide, and acetal cleavage, reduction of earbonyl compounds, alkylation of carbonyl compounds, and miseellaneous reactions. Larock has selectively included references ta methods giving yields of 50% or better, using reagents that are readily available or easily prepared. References containing full experimental procedures have been favored over communications lacking such details, and special attention is given to reviews of specific areas of the literature. Initial reports of new reactions are generally included, although some of the subsequent articles by other authors may he omitted. The Table of Contents is sufficiently detailed and well-organized to find all the topics I have wanted. In addition, en extensive Transformation Index (164 pages) organizes the material by product and reactant using generic compound names such as alkonol, 1aryl-l-alkene, etc. As with all nomenclature systems, it takes some familiarization. For example, acids are listed under alkonoie aeid but anhydrides are listed under mid

anhydrides rather than alkanoic anhydrides or alkanoic aeid anhydrides, and nothing is listed under olkyl alkanoate, where one might logically expect 18, find esters (look under nlhanwxe rilerl. I found thesirnoteend weit-oresnized Tahle of Contents t d h e faster and more useful. The computer-like organization of the Transformation Index raises the question of whether this book, and others like it, are needed in this age of computer sciences. I believe they are. The ruthless efficiency of a computer is both its greatest strength and its weakness. A computer search regurgitates all the references that match the kevboards, no more and no less. New ideas rarely arise during compurpr searches, because browarng is made difficult by the lack of visual cues and the sheer numbers of relevant and irrelevant references. A secondary reference such as Comprehensiue Organic Transformations facilitates the generation of new ideas hv ~rovidinevisual cues and bv limiting the &;her of ieferences to tho; that will be most helpful. Comprehensiue Organic Transformations will be useful to anyone whomust do organic synthesis, especially those whose focus is not strictly synthetic organic chemistry. I t provides a relatively brief and clear road map to the synthetic literature and should be kept within easy reach of the chemist's desk. Leroy G. Wade, Jr. Whitman College Wails Walla, WA 99382 ~

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A Cornputatlonal Approach t o Chemistry David M. Hirst. Blackwell Scientific Pubiications: Boston. MA. 1990. viii 444 pp. Figs. and tables. 15.6 X 23.4 crn. $78.95 HB/$39.95 PB.

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This is described as an advanced text covering the principal areas where computational studies have made a major contribution to our understanding of a chemical problem. Theoretical treatments are described in sufficient detail for the reader to understand the basis of calculations. Topics covered come from molecular structure, spectroscopy, reaction kinetics and dynamics, and the liquid state. The computational techniquer used in treating a prohlem are outlined wilhuut going into complicated detall of numerical a n a l w s . E m ~ h a s i sis placed on the use of com~utationaimethods to model chemical systems in order to generate data which are complementary to experimental data. The book is not concerned with information on particular computer packages, nor with the use of statistical methods in the analysis of experimental data. The text illustrates that, in many cases, a computational approach can yield information that is inaccessible experimentally.