The chemical thermodynamics of organic compounds (Stull, Daniel R

The chemical thermodynamics of organic compounds (Stull, Daniel R.; Westrum, .... on the U.S. Southeast coast reported no serious damage after Hurrica...
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accessible numerical values of free energies and (2) inaccurate information and failure to recqgnize the limitations of thin country. These courses are taught at thermodynamics. The book is divided a variety of levels, from that represented into two parts. Section I (Chapters 1 through 5) consists of a review of chemby the more sdvanced freshman chemistry ical thermodynamics as originally formulated by Lewis and Randall. The development of the three laws of thermodynamics is given together with an ed., 1966), currently best-known,' and explanation of the usual enthalpy, enPhillips and Williams (Oxford, 2 vols. tropy, and free energy functions. A 1965-66) which provide complimentary views of inorganio chemistry, but these detailed description is given of the equiptexts are obviously too extensive for coverment and methods used to measure age in s single semester, and are probably heat capacities as a function of temtoo sophisticated and detailed for the perature, heats of vaporization and other undergraduate audience as well. Heslop phase changes, and heats .of reaction. and Robinson (Elsevier, 3rd ed., 1967) and The statistical methods used for calcuDouglas snd MoDaniel (Bleisdell, 1965) lating the heat capacities and entropies me addressed to the undergraduates, and far gasa are presented. No equations have had a good reception. The recent are derived but detailed explanations text by Sanderson (Reinhold, 1967), based are given as to how they may be used to calculate numerical values. The reviewer on his earlier "Chemioal Periodicity," is feels that it it worthwhile to have the idiosyncratic; the one by Sienko, Plane and Hester (Benjemin, 1965) is s. combination information presented in Chapters 1 4 as it will make the tables in sections I1 of the paperback "Physical Inorganic and I11 more readily useable. Chemistry" sewn together with a portion an descriptive material, but the combine Chapter VI discusses methods which tion has not enjoyed the success expected may be used to estimate entropies, heat of this authorship. capacities, heats of formation, and other The text under review is the shortest of thermodynamic properties for compounds those named, and at $8.50 among the least for which no experimental thermodynamic expensive. The page format is the largest studies have been made. Most compounds in the business, and the overall impression of interest in organic research will fall created by the book is pleasing. The outin t,his category. Since changes in approlook is eenuinelv modern with emnhasis on prist,e thermodynamic quantities deterevidence from bhvsical techniou& strucmines an equilibrium constant, it seems to the reviewer t o do no good to guess a t their absolute values. Such a procedure will almost always give erroneous shape; 6 bonds appear in the chapter on results and this is what the authors wished covalent molecules and again when to avoid. I t would be better at this RelClsz- is mentioned. Organometdic i.s-a n t i a.t.. i d-.. point to drop thermodynamic method - -. compounds of the transition metals and and go over completely to statistical The book contains descript,ionsof a1a1.ge metalloids are included, but Linnett's mechanics. The equilibrium constant number of important reactions and their double-quartet approach is ignored. The can be expressed in terms of partition mechanisms, is easy to read, dear and coutelegraphic chapter on experimental functions and appropriate terms then cise. I t contains an adequate selection of methods is, however, too short to be satiscan be cancelled. This requires only references following each chapter and a. list fying. Nuclear chemistry is not treated of books for supplemental reading. Couthst the structure of the compounds be separately. Descriptive chemistry gets known and that one understand a little pled with lectures stressing the experislightly over 50% of the pages. about the deviations from the rule of mental approach and stressing alternate Teachers seeking a brief "Introduction constant bond energies. This information interpretations, this book would conto Modern Inorganic Chemistry" written is available to most organic chemists. tribute significantly to a course in inorat a. modest level of sophistication, should ganic reaction mechanisms. Chapter VII discusses the application look at this book. of thermodynamics to industrial problems. R. KENTMURMANN This covers the petroleum industry, d. J. ZUCKERMAN University of Missouri the problem of getting chemicals from Stale University o j New York Columbia, 65801 methane, the synthesis of styrene, acryAlbany, New York 18803 lonitrile, vinyl chloride, methanol, acetic acid, and several others. I t illustrates very well the uses of reliable thermoThe chemical Thermodynamics of dynamic data. Organic Compounds Mechanisms of Inorganic Reactions The second part of the book, sections in Solution: An Introduction I1 and 111. consists of tables of thermoDaniel R. Stull, Dow Chemical Co., dynamic data. The functions tabulated Midland, Michigan, Edgar F. WeatD. Bemon, Widnes Technical College, are heat capacity, C,', entropy S o , Gibbs rum, Jr., University of Michigan, Englend. MeGraw-Hill Book Co., energy function, (GT' - H d / T , enAnn Arbor, and Gerard C. Sinke, New York, 1969. xii 218 pp. Figs. enthalpy of form* thdpy, H o - HDpm' Dow Chemical Co. John Wiley & and tables. 14 X 21.5 cm. Softbound. tion, AH,', Gibbs energy of formation Sons, Inc., New York, 1969. xvii $5.95. A G and ~ log If,. The data are furnished 865 pp. Figs. and tables. 16 for some common elements and 39 simple This paperbound hook is an accqunt of X 23.5 cm. $29.95. inorganic compounds (Chapter 8), hydrothe mechanisms of inorganic reactlons in carbons (Chapter 9), compounds of The purpose of this book is to provide homogeneous solution meant far seniors carbon, hydrogen and oxygen (Chapter a comprehensive and systematic treatment and graduate students beginning their lo), nitrogen compounds (Chapter l l ) , of organic chemical thermodynamics. study in this ares. halogen compounds (Chapter 12), and The authors feel thst there are two main I t begins with a brief chapter of sevensulfur compounds (Chapter 13). Each reasons why thermodynamic reasoning teen pages reviewing theory of reaction chapter begins with a summary statement has not been applied to the solution rates, rate laws and mechanism, stationconcerning the st,atus of the patticuler of organic problems as often as it should ary-state approxim&ion, the solvent and (Continued a page A304) be and these are: (1) the lack of easily solvation of ions, and inert and labile com-

book reviews

plexes. Undue emphasis is placed on the stationary-state approximation and the treatment of the other topics is almost limited to a definition of terms nsed later. The other chapters are entitled Substitution Reactions of Metal Complexes, covering octahedral, planar t~nd tetrahedral molecules, Oxidation-Reduction Reactions of Metal Ions, Reactions of Oxoanions, Free Radical Reactions and Protolytic Reactions. For the most part a conventional selection of reactions has been presented. In a sense this is a good choice since a deeper knowledge of these reactions is available. However, onemay be left with the impression that inorganic reactions are primarily those of Werner type complexes and simple aqua and 0x0 metalions. A criticism of the presentation, as related to its use as a teaching tool, is the attitude which this reviewer felt would be created in the reader that many of the rate laws and mechanisms described are now essentially correct as stated and need little further investigation. This appears to result from an attempt to simplify and organize and from the less-than-critical approach of the author. Little emphasis has been placed on alternative explanations on the reliability and precisian of the experimental results or on the experimentalprohlems encountered in theinvestigations. I t is a fair question to ask if a need exists far a new book and further if t,his book fulfills those needs. I think there is little doubt that many would find a fresh approach to inorganic mechanisms useful and of help as a teaching tool. Unfort,unately the overlap between this hook and the earlier "Kinetics of Inorganic Reactions" hy A. G. Sykes is considemhle. Thus I donbt if t,he need for a di8el-ent viewpoillt

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A300

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Journal of Chemical Education

book reviews field. Each table is well documented with references and is very carefully done. A tremendous amount of work has been done t o produce these tables and they represent the meat of the book. The authors have done an excellent job in resenting this material. The book will be a valudde part of any library where thermodynamics is taught or used in research.

Elementary Organic Chemistry: A Brief Course

Harris 0. Van Orden and Garth L. Lee, Ut,ah State University, Logan. W. B. Saunders Co., Philadelphia, 1969. ix 329 pp. Figs. and tables. 17.5 X 25.5 cm. $8.95.

We found no significant errors in this book. At least a t one point the authors might have been rs little more up-to-date.' The introduction to chapter five leaves the impression that benzene is derived today only from coal. Of course, since World War I1 the entire aromatics picture has changed radically, and now the large volume aromatics are derived primrtrtly from petroleum. I n spite of these defects, if such they are, the authors have written a good book. The language is direct and clear; the chapters are well-outlined and illust~ated. Especially attractive me the many fine exercises a t the end of each chapter, arranged in approximate order of difficulty. This text compares favorably with the other recent one-semester books in organic chemistry. ENNOWOLTHUIS Calvin College Gmnd Rapids, Michigan 49506

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This is a one-semester text on the fundamentals of organic chemist,ry, intended for the general college student,, especially the major in biology or related areas. This is a new hook, not a revision of a n earlier text. The first two chapters are devoted l o the physical principles which are used t,hroughaut to explain selected reactions. These chapters deal with "bonding and structure" and "stability and reactivity," especially as they apply to the chemistry of carbon. The latter chapter treats such subjects as theory of reaction rates, Brgnsted and Lewis acids and bases as applied to displacement reactions, for example, and free radical reactions. After these introductory chapters, organic compounds are discussed in more or less traditional order. Aliphatic and aromat,ic compounds are followed by oxygenated compounds, and then the comof nitrogen, phosphorus, and sulfur. After this a fifteen-page chapter treats stereoisomerism, and about fifty pages are devoted to biochemicals and biochemistry. An Appendix reviews atomic structure and bonding. Any review of a short organic chemistry text is hazardous. The reviewer never seems to find in i t the topics he considers important, or the emphasis where it ought to be. I n the present case, since this book is intended primarily for the general student, one could wish i t contained more on the practical significance and applications of the compounds mentioned. The subject comes "alive" to many when, for example, the student realizes that many names in the text are also those found on the bread wrapper, the catsup bottle, etc. I n our opinion, the authors should have included a t least a page or two on the analytical techniques which have contributed so much to the recent advances in the subject. For example, a brief description of infrared spectroscopy could have been fit,ted into the first chapter on bonding snd structure. Likewise, the contributions of chromatography to our understanding of protein composition, for example, .would have been appropriate.

A304 / Journol of ~ h e k i c o Education l

Rodd's Chemistry of Carbon Compounds. Volume II, Aliryclic Compounds; Part C, Polycyclic Compound%,Excluding Steroids

Edited by S. Cofey (2nd ed.), American Elsevier Publishing Co., Inc., New York, 521 pp. 65 Tables. 16 1969. xvii X 23 cm. $32.

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Volume 11, Part C of the second edition of Rodd's Chemistry of Carbon Compounds consists of six chapters (9 through 14) covering the chemistry of non-steroid polycyclic alicyclic compounds. The specific topics and authorship of these chapters m e as fallows: Chap. 9 (31 p.), Polycabocyclic Compounds with Separate Ring Systems, and Spiro Compounds, by N. A. J. Rogers (The University, Lancaster); Chap. 10 (45 p.), Polycarbocyelic Compounds. Fused or Condensed Cyclic Systems, by N. A. J. Rogers; Chap. 11 (59 p.), Polycyclic Bridged Ring Compounds, by J. D. Littlehales (Petrachemical and Polymer Laboratory, I . C. I., Ltd., Runcorn, Cheshire); Chap. 12 (120 p.), Bicyclic Monoterpenoids and Related Compounds, by A. Pelter (The University, Menchester) and S. H. Harper (University College of Rhodesia); Chap. 13 (113 p.), The Sesquiterpenoids, by R. ,Bryant (Mead Johnson Research Center, Evansville, Indiana); and Chap. 14 (113p.), The Diterpenoids, Sesterterpenoids and Triterpenoids, by R. MoCridle (The University, Glasgow) and K. H. Overton (TheUniversity, Glasgow). A guide and double column Index (40 p.) complete the book. The present volume is a direct and smooth continuation of the earlier revised Volumes IIA and IIB, which considered srstematically the chemistry of monocarhocyclio compounds of increasing ring size. The organization of the topics covered follows the effective and logical pattern of previous chapters in Volume 11, and the litersture coverage appears to be equally thorough and up-to-date. There is considerable emphasis on stereochemistry and mechanism in the oresent chanters. and

noids (Chao. . . 14). are effeetivelv and inter-

e.t>nplg unifird i r f term. of rlw Bio~rnttic Isoprene Ilule. Thr 451 te~runlpage5 t,f the present vulume rrprrsrrt R 1.7-fold it,-

crease over the number of pages covering similar topics in the first edition of Volume 11,a reflection perhaps of the increased research interest and importanceof the polycyclic alioyclic series of compounds. This volume (along withits predecessors of both editions) will clearly serve as a continuing definitive referenoe book on the subjects i t encompasses, and libraries as well as research chemists concerned with these fields will find it indispensable.

A Laboratory Manual of Experiments in Physical Chemistry

D. Brennan and C. F . H. Tipper, University of Liverpool, England. McGraw-Hill Publishine Co.. New York. 1967. x 254 pp.- ~ i and~ tables: i 15 X 23 cm. Softbound. $4.50.

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This manual was designed for use by students in universities and colleges of technology. I t gives instructions for carrying out 67 experiments which are well distributed over the field of physicd chemistrv. Each emeriment is described in te'tms u i tlwoc)', ippnmru. nnd miltcrialx, yrmcrdurr, a1.d rrralrnrlit oi rewlt.. .\t tlrr end oi eq