BOOK
REVIEWS
Advanced Organic Chemistry
G. W . Wheland, University of Chicago, Chicago, Illinois. 3rd ed. John Wiley & Sons, Inc., New York, 1960. xi 871 pp. Figs. and tables. 16 X 23.5 cm. $17.50.
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With this third edition Professor Wheland maintains his reputation as the most verbal and superbly critical of the American authors of books on organic chemistry. This hook contains chapters, particularly those on Stereoisomerism, Configuration of Carbon Compounds, and The Stereochemistry of Carbon, which are the most careful and sophisticated presentations of the fundamentals of their subjects to he found in any single volume. The first edition of this book was not publicly offered so that the nominal second edition of 1949 was artudly the first available. When one compares s. beginning organic text of 1949 with a beginning text of 1960 he is struck by the almost revolutionary change in the nature of the material covered. The beginning student is now almost universally trusted with theoretical concepts and mechanisms thought too advanced for him 11 years ago and thus placed in the advanced curriculum a t thttt time. Because of the radical nature of this shift in emphasis it is not reasonable to expect that any advanced text of 1949 could retain its function as a tezt by simple revision or editing in 1960. Wheland recognizes this f a t and has chosen to alter the expected function of his book rather than alter its approach to any significant degree. Thus, in his Preface to the second edition of 1949 Whelmd described his book as "a textbook for a
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course in advanced organic chemistry." However, in his Preface to this third edition the author states that it is "largely restricted to those aspects of the science that seem. to be inadequately treated in the other texthooks and reference books that are now available." The author also gives recognition to the fact that at his own institution, "on&alf to two-thirds of the second year of organic chemistry is devoted to the material that, although omitted [from this book] can be obtained from many [other] excellent textbooks and reference books!' Thus, this book is not a tezt but rather a unique reference, a reference in depth on a number of topica taken for granted in most texts of advanced organic chemistry. Since 1949 there have been published a number of excellent advanced organic chemistry texts, all somewhat similar in reflecting a trend toward the presentation of the subject through a. mechanistic approach utilizing the early introduction of theory into the elementary courses. In his new edition Wheland has not used this approach but nevertheless shorn an admirable willingness to refer the reeder directly to specific pages in these texts when they elaborate a point to his satisfaction. The new topios introduced into this edition, such as SN', S N ~SNI' , and SN' mechsnisms, Hammett rho-sigma relations, methods of deducing reaction mechanism etc., are treated extremely briefly. However, the reader is, in each case, referred to a modern text covering the subject adequately. The order of the chapters in the first part of the new edition has been altered extensively and effectively. The cuts of structural formulas are all new and
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in this issue
G. W . Wheland, Advanced Organic Chemistry Gerald Litwack, Experimental Biochemistry Arnold Weissberger, Editor, Physical Methods of Organic Chemistry. Part 2 Stanislas Dockz, Thwrie Fondamentale du System Periodiqne des Elements Edwa~dCartmell, Chemistry for Engineers The Harvey Lectures. Series 54 The Harvey Lectures, Series 54 R. C.Vickery. The Chemistry of Yttrium and Scandium A.A. Smales and L.R. Wagner, Editors, Methods in Geochemistry M . Stacey, J . C. Tatlow, and A. G. Sharpe, Editors, Advances in Fluorine Chemistry. Volume 1 P . .4. Ongley, Tutorial Questions in Organic Chemistry Lawrence J . Heidt, Robert S. Livingston, Eugene Rabinowiteh, and Fa-ringtan Daniels, Editors, Photochemistry in the Liquid and Solid States Jerome S. Bruner, The Process of Education M . Frank Mallette, Paul M . Althouse, and Carl 0. Clagetl, Biochemistry of Plants and Animls H . K . King, The Chemistry of Lipids in Health and Disease H. Teusche~,R. Adler, and Jerome P . Seaton, The Soil and Its Fertility
considerably improved over the earlier edition. Wheland's reluctance to succumb to the now generally accepted mechanistic symbolization using the curved arrow to represent an electron shift will make his occasional reference to mechanism rather difficultfor thestudent to follow. Updating the textual material has been done in two ways. A portion of the exposition has been left essentially unchanged from the previous edition but references to more modern literature dealing with each fiubject have been added in context. In other portions of the book the material has been rewritten. Of the over 1100 references (many multiple) almost half include direction to papers or books appearing since the second edition of the book wsspuhlished. I t is unfortunate that the cost of the book (more than double that of t,he earlier edition) will preclude much individual ownership, for it is with leisurely examination that the finer points of Wheland's arguments me fully appreciated.
QUENTINR. PETEBBEN Wabash College Crawfordsuille, Indiana Experimental Biochemistry
Gerald Litwack, University of Pennsylvania, Philadelphia. John Wiley & Sons, Inc., New York, 1960. xv 313 pp. Figs. and tables. 15 X 23 cm.
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$5.50.
This is a good book for undergraduate and beginning graduate students well prepared in organic chemistry. Most of the experiments can be done with equipment usually available in a biochemistry laboratory, such as an electronic photometer. Four sections deal with carbohydrates, lipids, amino acids and proteins, and enzymes. The enzyme section is the largest. Many new experiments stress modern quantitative instruments and use of microorganisms. They introduce elementary enzyme kinetics, with use of Thunberg tubes, Barcroft-Warburg manometry, and the Conway microdiffusion technique. There is an experiment on the enzymic decarboxvlation of elutamic acid labelled with radioactive &bon. These are a few examples. This is not just another biochemistry cookbwk with the traditional isolation of eystine from hair, etc. It is full of excitina new experiments with the look of modern researih. By working in pairs or groups and having more than one experiment on stream a t a time, the students have a chance to get to know what a research team is like. And they know what is going on, thanks to the extensive theoretical discussion preceding each experiment. Use of this manual in the student laboratory should be refreshing to the instructor and stimulating to the student. Everyone concerned with the teaching of biochemistry should examine s copy for himself.
A. R. PAWN Colorado State University Fort Collins 'olume 38, Number 4, April 1961
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