Textbook of organic chemistry (Noller, Carl R.) - Journal of Chemical

Textbook of organic chemistry (Noller, Carl R.) Bernard A. Nelson. J. Chem. Educ. , 1967, 44 (3), p 181. DOI: 10.1021/ed044p181.2. Publication Date: M...
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BOOK

This book would not be appropriate as a text for our own chemistry majors. I t is, however, competitive with books currently in use by many of the secondary schools of high quality, and competitive with books used by many large sectioas of collegiate level general chemistry classes.

REVIEWS

JR. DWIGHTA. PAYNE, Tulane U n w m i l y New Orleans, Lmisiana Chemistry: A Structural View

D. R . Stranks, University of Adelaide, Australia, el al. Cambridge, st the 475 pp. University Press, 1965. x Figs. and tables. 16 X 24 cm. $9.50.

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If d l sophomore students of chemistry were fluent in all aspects of chemistry covered in "Chemistry: A Structural View," teachers of chemist~ywould be more than pleased. Coverage of the essentials of introductory chemistry is excellent except for the lack of a cohesive introduction to chemical thermodynamics and some subsequent relation of this subject to equilibrium, oxidation-reduction, etc.

to the level bf the novice of more than enough material; (2) straightforward, workable problems and exercises at the chapter endings with answers given at the back of the hook; (3) coverage of banding and structure (and the authors do, indeed, give their chemical view as explained by the book's title) in modern terms and with just enough sophistication to maintain student interest and to provide him with an accurate conceptual baekground; end (4) figures, especially those depicting molecules, electron charge density, and crystal structures, which are all very well done. I n addition, the presentation of stoichiometry is methodical and thorough. The chapters on reaction rates, equilibrium principles, and acid-base treatment (12, 13, and 14) are especially concise. I t is,

indeed, a. treat to find the care these authors have taken in the separation of rate and equilibrium principles, yet making use of them together as is appropriate. Also appreciated is theshort chapter which covers reaction mechanisms (No. 20). I t war well arritnged to follow the introduction of the neoessary basics of rate, stoichiometry, and equilibrium. The examples far this chapter were well chosen. Chspters oovering the periodic table and descriptive chemist~y (21 through 30) are perhaps skimpy. The traditional descriptive material is covered, however, e.g., the oxyacids of the representative nonmetals. Since descriptive aspects are more readily supplemented by other readings and lectures, it is no doubt better to skimp on descriptive material rather than basics. Although Chapter 5 on energy relationships is well done in view of the material it intends to convey, it is inadequate. This chapter, and a subsequent one covering relationships, should hsve been used to introduce thermodynamics. An introductory treatment of chemical thermodynamics can be rtccomplished consistent with the level of other portions of this hook. I n fact, it seems rather ineonsistent to present bonding and structure at this level and omit the fundamentals of macroscopic treatment of the chemical world. A less serious omission. nerhsns. is the

have been presented in the second chapter without any undue lengthening of the chapter.

Reviewed in this Issue I D. R. Stmnks, Chemistry: AStroctural View Cad R. Noller, Textbook of Organic Chemistry R. T. Mowism and R. N . Boyd, Organic Chemistry Irvin E. Liener, Organic m d Biological Chemistry Bianco Tchouhar,Reaction Mechanisms in Organic Chemistry F. Alhert Cotton and Geoffrey Wilkinson, Advanced Inorganic Chemistry George B. Kauffman,Alfred Werner: Founder of Coordination Chemistry A. F. Alahyshev, M . F . Lantratov, and A. G. Moracheuskii, Reference Electrodes for Fused Salts V .I . V e h e y e v , et al., Bond Energies, Ionization Potentials, and Electron Affinities James J . Brophy, Basic Electronics for Scientists Enrico Femi, Molecules, Crystals, and QuantumStatistics Walter Kauzmann, Kinetic Theory of Cases James W . Robinson, Atomic Absorption Spectroscopy Lewis La~more,Introduction to PhotographiePrineiples George L. C l a ~ keditor, , The Encyclopedia of Chemistry D m l d E. H . Frear, editor, Pesticide Handbook-Entoma, 1966 E. A. Guggenheirn,Applications of Statisticnl Mechanics

New Volumes in Continuing Series

Texlbook of Organic Chemistry

Carl R . Noller, Stanford University, Stanford, California. W. B. Saunders 760 pp. Co., Philadelphia, 1966. vii Figs. and tables. 18.5 X 25.5 em. $10.

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The first, quick examination of the third edition of this text gave a distinct favorable impression, contrasted with previous editions, regerding its format, quality of paper, and ease of reading. The author has retained the fundamental outline of its predecessors with its emphasis on functional group chemistry and the separation of the aliphatic and a m matic series. However, much of the text has been rewritten to accommodate the impact of physical chemical concepts upon organic chemistry. Thermodynamic p r o p erties, thennochemical data, ionization potentials, electronegstivities, and solvent participation are interwoven into the text to give meaning and understanding where most desirable. Three new chapters have been introduced. Chapter 2 deals with chemical bonding, atomic and molecular orhitals, bond energies end distances, and intermolecular forces. Chanter 3 discusses vhemiv~lnwt:vity, cquil~brium,rcnctnon kinetivs, ewrgv changes nnd briefly rcnclion iuechnnisrom Thwe two chnptrri nre primarily for review or introduction to these concepts, which me recalled and amplified as the student progresses. Chapter 31 emphasiaes the characterieatian of organic structures through the molication of modern instrumentation:

frared absorption spectra. is taken up separstely and introduced early for use throughout the text. The extensive reorganization has given better integration and emphasis among related topics. Geometric isomerism is now included with the rtlkenes. The organametdie compounds have been brought together i n s section in the chapter on alkyl halides. The metalloid elements are considered in a section by themselves. The alicyclic compounds have their own chapter with greater depth. Mechanistic discussions, formerly in small print, are now part of the main text. Some descrip tive material, such as sources and commercial preparations, are set aside in finer print. The reorganiaation har also included the deletion of duplicating chemical equations with wide use of cross references; B replitcement of the term "Geneva System" by "International System" for nomenelaVolume 44, Number 3, March 1967

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ture; employment of curved arrows to trsce electron movement. and of Newman and three-dimensional formulas for spatiality of molecules. The more recent topics of benzynes, carbenes, enamines, and hydroboration bave been introduced. Likewise, new problems have been added, but at the expense of omitting the review questions and decreasing the number of problems having similarity. The answers for the problems are given in the appendix. I t would be an added featureif suggested readings or references to pertinent topics could be included. Many students desire to go beyond the text and this would provide an avenue into the use of the journals or other references. The author should be commended for his blending of the modern with the treditiond and far his successful attempt "to present a well-rounded text by giving equal weight to the theoretical, experimental, and practical aspects of the subject." It is a text worthy of consideration either for classroom use or for reference.

Wheaton College Wheaton, Illinois

Organic Chemistry

Robert T . Morrisa and Robert N e i k a Boyd, both of the New York University. 2nd ed. Allyn and Bacon, Inc., Boston, 1966. ix 1204 pp. Figs. and tables. 16.5 X 24.5 cm. $13.95

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This excellent and well-known text for the beginning student of organic chemistry has been revised in many important aspects. Recalling that the first edition pioneered in bringing theory of organic chemistry to these students, stereochemistry isintroduced quiteearly sndspeetroscopy becomes an integral part of the new text. Optical aotivity and enitntiomers are presented in Chapter 3 rand diastereoisomers in Chapter 7. Conformationd isomers are discussed with the alkanes in Chapter 4. These concepts are then used

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Str;eture, comes one thud way through the book; major emphasis is on NhIR and secondarily on IR. Over 100 spectra of both types are reproduced in text and problems for interpretation; about six dozen additional problems involve spectroscopic data. This text will be most generally compared with that by Roberts and Caserio. Botb place heavy emphasis on spectros copy, but Roberts and Caserio begin this study in their second chapter. Morrison and Boyd reason that the relationship between structure and spectra is better understood "after the student has begun to find his way about this strange new landscape." (Page v.) The valued features of numbered sections within esrh chaprer and rhe cutlines of prepnmrionz and renrrions of iunctionnl Knupi are rw~incd; nuw wferenrra ro sections for discussion of each are given. There is little deleted from the f i s t edi-

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tion, but most chapters have some sections rewritten and some sections added. Special attention has been given to revisions of discussions of mechanisms. Certain chapters are largely rearranged, especially the three on benzene, electrophilic aromatic substitution and arenes. Aromaticity particularly receives added consideration. Instead of following alkyl halides (Chapter 14), aryl halides and nucleopbilic aromatic substitution are postponed to Chapter 26. Chapters on phenols and sulfanic acids are also postponed to allow aldehydes and ketones to be discussed somewhat earlier. This important subject is split into Chapter 19 (preparations and nucleophilie additions) snd Chapter 27 (carbanion reactions). Material on aldehydes and ketones is lengthened from 39 to 89 pages. However, it is perhaps better to have the two chapters adjacent and preceding carboxylic acids and their derivatives. Epoxides are included in Chapter 28 with glycols instead of with ethers. Subsequent chapters consider palyfunctiond compounds. Although a few are indexed, a chapter on organometallic compounds was not added to the new edition. This is unfortunate considering the growing importance of this field which bridges the traditional gap between organic and inorganic chemistry. Since mechanisms are so vital a part of the hook, some oxidation mechanisms, e.g., permanganate and chromate ions might bave been included. The ttuthors have s refreshing style and are a t times humorous. I n places they may seem verbose, for instances, chlorination of methane takes 24 pages. But topics included in this first mechanism are description of the free radical mecechs, nism, bond energy, he& f reaction, active tion energy, reaction rates, structure of the methyl radical and transitions states. Errors are very few and minor. Diagrams on energy and of atomic models are enlarged. The book is primarily for students and above all it is readable. Morrison and Boyd have the ability to make difficult topics understandable. Chemists, both industrial and academic, can use this hook for an enjoyable experience in renewing their knowledge of modern organic chemistry. MORDECAI TREBLOW Bloomsburg State College Bloomsburg, Pennsylvania

Organic and Dialogical Chemistry

Zrvin E. Liener, University of Minnesota, Minne&polis. Ronald Press Co., New 466 pp. Figs. and York, 1966. ix tables. 16 X 23.5 cm. 58.

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This hook is intended ss a text for the beginning biochemistry student who has had no previous background in organic chemistry. About one quarter of the pages are devoted to the nomenclature, preparation, and reactions of the major classes of organic compounds. The remainder of the book follows the rather standard organization of a beginning biochemistry text: Composition of living

matter, intermedimy metabolism, metabolic control, itnd a few specialized topics. The text iu clear itnd easy to read, and the various figures and metabolic reactions particularly easy to follow. The selection of topics to be covered, which is a problem in any condensed book, hits for the most part been good. However, I would not agree that the metabolic pathways for the degrrtdat,ion of the individual amino acids, which are discussed, are of more importance to the beginning student than a discussion of the hexose monophospbate shunt, which is noted as being beyond the scope of the book. Over-simplification also becomes a problem in an elementary text. The student is informed that "the pyrophosphate bond yields about 60006000 cal/male when hydrolyzed" without B discussion of e l c mentary thermodynamics or the concept of the relationship of free energy changes to equilibrium constants. The suggested readings at the end of each chapter are very well chosen and would be an excellent euide to the serious

as areference text.

If it is desirable to attempt to teach biochemistry without tLn organic prerequisite, which I doubt, this book should be given consideration as a text. Theorganic section. althoueh .. it ,.rives the student no ihsight into orglnnc nlerhani.;rn., adl at .~IUW lellit wqwiinr h w w t h I I O I I I F ~ ~ C ~und atrnwturnl form~tlis. Cu.a~dtreda * a I k chemistry text alone, it compares favorably with, but does not appear to be a real improvement on a number already available for use in an undergraduate course. J. W. SUTTIE Universitu of Wisconsin Madison

Reaclion Mechanisms in Organic Chemistry

Bianco Tchoubar. 2nd ed. American Elsevier Publishing Co., New York, 1966. 197 pp. Figs. and tables. 14.5 X 22 cm. $8.75. In recent years the subject of reaction mechanisms has become an integral part of the sophomore course in introductory organic chemistry. Such textbooks ss Bordwell, Bonner and Castro, Roberts and Caserio, and Smith and Cristol provide a lucid treatment of physical organic chemistry on a level designed to convey the "orderliness" of this science to the student. The stated intent of Tchoubar's hook is "to provide a comprehensive introduction to a branch of organic chemistry.. .which is of the utmost importance to every organic chemist." The author's goal has unfortunately not been realiaed. The book is neither as cornplrherr.:ve M monographs by G N ~ J . Iline, or Wihrrg, nor u;i y ~ n dn irrtmhcFI~IIV. tcw rrxt as Br+