The Chemistry of Organic Compounds

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102

JOUKNAL OF CHEMICAL EDUCATION

Many would prefer earlier and greater emphasis on atomic structure. Nowhere in the book is there a complete listing of electron configurations by principal quantum groups (2, 8, 18, 8; etc.). (Such a table would be particularly helpful in Chapter 20: Electronic Structure and Chemical Properties.) In general, at the beginning of descriptive chapters, electron configurations are listed for the elements to be discussed. A complete listing by subgroups (2; 2,6; 2,6,10; 2,6) is given in Appendix VI. A long form of the periodic table is used, and includes atomic numbers (which were not included in the periodic table of the preceding edition!). Influence of Atomic Size upon Physical Properties is discussed on page 385 (more than three-fourths of the way through the book), followed by the statement: "That the relative sizes of atoms should be important in determining chemical prope~tieshas already been hinted a t (page 211) and will be developed more fully now, (page 385)." The concept of kernel charge is never developed nor effectivelyused. Often the author tends to emphasine rules instead of reasons. (Cf.properties of ionic us. covalent oompounds, page 207, for example.) Errors of fact occur oceasionslly. (In the fission of Us35 'heutrons are shot off with an energy of 200 million electron volts each." (page 182).) However. in eeneral the book is verv carefullv and well written. It is attrabtivzly printed, contains~excellen~ diagrams, many excellent problems, and bas very few typographical errors. WILLIAM

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E. MORRELL

COLLEGE CHEMISTRY

Paul R. Prey, Pmfeasor of Chemistry, Colorado Agricultural and Mechanical College. Prentice-Hell, Inc., New Yak 1952. m v i 653 pp. Illustrated. 23 X 15 om. $5.95.

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CONSIDERABLE attention is being paid of late to the course in general chemistry. Although this course often is designed to meet the requirements of students in other fields as well as those preparing for a career in science, there is now a. strong tendency to separate chemistry students into at least two beginning courses. The book under review is designed for those whose interest in science is already well-established. An examimtion of the mechrtnical features of the book make8 this purpose clear. The 36 chapters are well set up and are packed with useful information and carefully explained principles. Scattered through the text are many, many chemical eouations. At the end of each c h a ~ t e ris a reasonable set of rxercises. Thore that call for a witten snsacr HIP not 31nyyr h carefully cxpressrd as those eallin~for a nunleriral answer. In thc c:qrly vhnprrri nunlerirnl cxeni.rrs ournunher the othcrn two to one, but this situation is reversed in the later, more descriptive chapters. The numerical exercises are separated into two categories according to difficulty. The index is good, but not as complete as it should be if students are to keep this book as a reference. For example, the word "binary" is used on page 65, but is defined later. Until the reader thinks of looking in the index under "Compounds, naming of," the definition on page 92 remains coyly hidden. At the end of each chapter there is a carefully chosen list of two or three films, and there are a number of references to articles in periodicals. The major source of these OF CHEMICAL EDUCATION.Book reierarticles is the JOURNAL enees are hcluded in an zppendix of 115 items. Most of these references are of the "magie-in-a-bottle" variety, but one looks for and finds, Mary Elvira Weeks, Bragg, Jeans, and Eddington. An unusual feature is the inclusion at the end of each chapter of a list of leeture-demonstration experiments. Although these directions are most convenient, the purpose is occasionally in doubt. This doubt is mast evident on pages 66-7 where it is hard to decide whether the directions are for the benefit of the students or of the teacher. The discussion of the mechanical features of the book will be concluded with a word or two about the illustrations. The photograph8 are well-chosen and respect-

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ably few in number. The mat seems rather coarse but such evidence of disdain may possibly be premeditated. The line diagrams are charming but indecisive. Although the form of the book clearly indicates that it is intended for science majors, the reasons given for paying attention to particular topics in the particular way are not clearly established. For example, the second sentence in the prefaoe states that future developments in ohemistry will be based upon the unchanging principles treated in the book. On page 19 we are told that our fundamental concepts concerning the nature of matter are changing rapidly, and a. few lines later that the study of chemistry is a study of the physical and chemical properties of the elements. Again, the explicit purpose for the study oi the periodicity of the elements is said to be that such study makes the remembrance of facts easier, hut having said it, the author proceeds to utilize the principles of Mendeleev, Moseley, and a host of other men in such a way as to reveal much of the power and beauty of the intellectual structure formed by these principles. Explicitly, thephilosophy of the text is confused although implicitly it is sound. Perhaps part of this soundness derives from the fact that the writing is admirably restrained throughout. There is no striving far effect. The language is appropriate. Usually, the sentences are short. a first-class aid to claritv. This restraint is most the final chapter of tbe'haok telling the story of effective nuclear energy. Not all is made clesr. Although the explanation of "mass" on page two leaves nothing to be desired, the explanation of "mass spectrograph" on page 46 is confusing. The methods of solving problems shown in the worked examples stresses the aleebraic treatment of dimensions as well as of quantities, au empiasis that is wholly admirable.. In spite of certain imperfections, this new text will probably he successful. Most of the topics ordinarily included in a beginning course are to be found in it and these topics are arrctnged in an orderly fsahion. The treatment is rigorous, hut fairly easy to follow. There is an abundance af suitable exercises, m d judicious use of the demonstrations described will make it easy for the teacher to maintain st,udent interest.

b~

BENTLEY EDWARDS Cnrco

S T A FCOLLEGE ~

CHICO. C*LIFORN.*

THE CHEMISTRY OF ORGANIC COMPOUNDS

0

James Bryant Conant, President of Harvard University, and Albert Harold Blatt, Professor of Chemistry, Queens College. Fourth edition. The Macmillan Company, New York, 1952. viii 655 pp, 21 figs. Tables. 16.5 X 24 cm. $5.90.

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THE fourth edition of this prominent textbook is a revision wbioh differs from its predecessor mainly because of the addition of "certain new material dealing with the mechanisms of organic reactions and the directions which the reactions take." Perhaps the direction taken in this revision was prompted as much by current fashion as by good pedagogy. The authors have used discretion and restraint with respect to placement and volume of this new material. As to placement, "the discussion of each reaction mechanism is introduced in connection with a reaction to which it applies, rather than in a separate section on mechanisms." Became this text is an elementary treatment of the chemistry of organic compounds, it seems in order for the authors to expect that an elaborate treatment of electronic structures and reaction mechanisms be reserved for an advanced course. The R ~ P tion O of new material is such that the balance between d a ~ s i c some of the classic organic in the third edition has been deleted. The format and typography are essentially the same as in the third edition, except that chapter titles and section headings are now marginal rather than pprtgecentered. In all but three minor instances chapter beadings are the same as before. The

FEBRUARY. 1953

only rearrangement in the order of presentation places the discussion of organic acids after the chapter on aldehydes and ketones instead of before the chanter on gasoline and rubber. This appears to be a decided improvement.. The questions and problems at the end of each chapter have been revised. In many cases the exercises are the same, the only change being in the order of arrangement. The discussion of heterocyclic compounds hrts been revised completely to produce a palatable treatment. The chapter on r r , a m i ~ l l y the same, rxvcpr for n:ltur~land nyntlwtit. d ~ y iri the tulditivn ui 1rit.i rrctiona on drug an13gonisrn and phnt horn o . Tltr mwr ohvious dclcrian irom thc third rdition is thc separate treatment of the polyhalogen compounds. In the chapter on certain biochemical processes, the section an metaholism of carhohydrates has been shortened. Perhaps the mast obvious improvements in presentation are found in the chapter on alkyl halides and ethers, in discussions of addition to unsaturated systems and the interpretation of orientation rules in aromatic substitution. The suffix, -yne, is used exclusively in the nomenclature of the acetylenic hydrocarbons. Excent for this discussion of systematic nomenclature appears to he t i e same as in the third &ition. Perhaps some teachers may feel that this text continues to follow too closely the traditional and conservative approach. Other teachers will maintain that the authors are much more pedagogically honest than authors of certain current texts. All teachers should agree that this revision has a singulazly distinctive quality quite in harmony with the ability, interest, and r e quirements of most students who take 8 year's course in organic . .

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improved ways for carrying out some of the elaasical operations of carbohydrate chemistry such as increasing the carbon chsjn and the formation of ketoses with a greater number of carbon &toms. Of especial interest in this volume is E. L. Hirst's short hut appreciative discussion of the life and accomplishments of Sir Walter Norman Haworth. The sudden death in 1950 of this great man took away one of the most distinguished and influential workers in carbohydrate chemistry. IRWIN B. DOUGLABS

U ~ r v r n a r ~orr M A ~ E 0 ~ 0 ~MAINE 0 ,

ADVANCES IN PROTEIN CHEMISTRY. VOLUME VII Edited by M.L. Anaon, Lever Brothers Co., Kenneth Bailey, University of Cambridge, and John T. Edsall, Harvard Medical 411 pp. Illustrated. School. Academic Press, Inc., 1952. vii 16 X 23.5 cm. $8.50.

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THIS seventh volume of an interesting and valuable series of annual essay8 on selected topics in protein chemistry maintains the same high standards set in earlier volumes. The first review in the present volume is by F. Sanger on "The Arrangement of Amino Acids in Proteins." This significant approach, one of the most spectacular in modern protein chemistry, has. been concerned with the complex problem of determinine the ~ositionof individual amino acid residues in ~ r o chemistry. teins. he review itself. as its author frankly states. . :has centered largely on the d&elopment of methods. .and'their uses DONALD C. GREGG (rather) than tn discussion of result^, which are still rather few." U N ~ V B R ~OP ~ V T E~~ S O N T BVRLINUTON. VBAMDNT The use of 1 : 2 : 4-fluarodinitrohenzene, slld other N-suhstituents for so-called "end-group"analysi~areearefullydescrihd, and the methods for the degradation' of proteins critically discussed. Briefly, the basis of the method is the reaction of inADVANCES IN CARBOHYDRATE CHEMISTRY. tact protein with an agent which combines specifically with cerVOLUME VI tain free erouos. and then to careiullv degrade the nratein in such ~dit~ byd cloude S. ~ ~~ ~ dt ~ i~ ~ ~ of t ~i~ t~ ~ d ~d ttand h~~, a m ,y th;&t the'amino acid or peptihe combined with this agent A i~ . can~ he determined, sugar~ ~ company, f ~ ~and its~position in the peptide chain ascersidney M. contor, ~~~~i~~~ tained. Application of the procedure to certain proteins such as l ~ peat, ~ univerrdty , sociate ~ d i for t the ~ ~~ f~i t i ~~ h ~~~~~l~~ egg albumin reveals no terminal residue with a free *-amino stocey, ~h~ university ,f College of North Wales and ~~~~i~~ Birmingham. Academic Press, rnc., N~~ york, 1951. xi+ group, thereby suggesting that these proteins exist as cyclic 442 pp. Illustrated. 15.5 X 23.5 cm. $8.50. peptides. Much work remains ta he done before the full possibilities of the procedures discussed by Dr. Sanger may he conTHE hieh aualitv of the earlier volumes in this irn~ortant sidered to he deauatelv ex~lored. This brilliant exoosition series is &t&ed-by the present volume. Ten more topics tells us what so fa; has-heed accomplished, and what may be closely related to the chemistry of carhohydrates are critically hoped for. The next three reviews in the volume form something of a reviewed and thus made wsjlahle to students and experienced e Fibrils," by Richard ohemists who find difficulty in keeping up with development block. They are "The S t ~ c t ~ofr Collagen S. Bear, "Muscle Contraction and Fibrous Muscle Proteins," in this rapidly expanding field. Fundamental chemistry is rather heavily emphasized in this by Hans H. Weher and H. Portzehl, and "The Proteins of the Mammalian Epidermis,'' by K. h2 Rudall. The block referred volume with chapters devoted to: The Methyl Ethers of dGalactose (D. J. Bell), The Synthesis of Oligossccharides to is based upon the fact that all three reviews are concerned (W. L. Evans), The Farmetion of Furm Compounds from with groups of proteins in particular morphologic structure, Hexoses (F. H. Newth), Cuprammonium-Glyooside Complexes rather than with individually characterized proteins, and that (Richard E. Reeves), The Chemistry of Rihase (Roger W. these groups are characterized to a greater extent physically than Jeanloz and Hewitt G. Fletcher, Jr.), The 2-(Aldo-polyhy- chemically. The review by Dr. Bear is almost entirely based on droxyalkyl) Beuzimidoeoles (Nelson K. Richtmeyer), Friedel- X-ray spectra of the collagen fibrils, and this biophysical criterion Crafts and Grignard Processes in the Carbohydrate Series is also employed in the other two reviews to characterize the (William A. Banner), and the Nitromethane and 2-Nitroethanol muscle and epidermic proteins, respectively. It is of interest to Syntheses (John C. Sowden). Of more descriptive interest is note that nearly all of Dr. Ruddl's review is based upon his own the chapter, Acoritic Acid, a By-product in the Manufacture of work with cow's nose epidermis, apparently a. good material for Sugar (Roger Ellsworth Miller and Sidney M. Cantor). The the purpose intended; one misses in this review some consider* chapter on Trends in the Development of Granular Adsorbents tion of the extensive work on human and mouse e~idermishv for Sugar Rehing (Elliott P. Barrett) describes practical mess- Cowdry and his associates at the Barnard Free ~kin'andcancer ures which are being taken to find a, satisfactory substitute for Hospital in St. Louis. hone char, the timehonored absorbent used in the sugar industry. The last two reviews in the volume also fall together, for they Some of these chapters represent tabulations of compounds of cover "Infrared Analysis of the Structure of Amino Acids, interest only to carhohydrate specialists. Others describe in- Polypeptides, and Proteins," by G. B. B. M. Sutherland, and teresting organic reactions which can he carried out using car- "Ultraviolet Absorption Spectra of Proteins and Amino Acids," Inphydratetes aa startingmaterials. Still others, such as the chapter hv G. H. Beaven and E. R. Holidav. Both reviews are mite on Nitromethane and Nitroethane Synthesis, describe new and v h a b l e and cover a wide range of spectral phenomena. b n e

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