Advanced Organic Chemistry Part A: Structure and Mechanisms Part B: Reactions and Synthesis

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Advanced Organic Chemistry Part A: Structure and Mechanisms Part B: Reactions and Synthesis

Part A: Structure and Mechanisms

Part B: Reactions and Synthesis

Francis A. Carey and Richard J. Sundberg

Kluwer Academic/Plenum Publishers, 4th edition, (Part A: 823 pages), (Part B: 965 pages) 2001.

A fourth edition, of Carey and Sundberg’s two-volume treatise of organic chemistry is now available. Much has happened in chemistry as well as in the field of scientific textbook publishing since the third edition appeared some 12 years ago, so publication of a revised version of this almost classical text is not surprising.

The book covers are both colorful and modern, hinting that a profound revision of the books has been carried out, but this appears not to be the case. On the contrary, the completely black-and-white text looks very similar to its first edition: many of the figures are in fact identical to those used 25 years ago, the style of presentation is almost unchanged, and the division of topics between the two volumes has barely changed. Thus, part A still covers fundamental topics related to the structure of organic molecules (bonding theory, stereochemistry, and conformation) as well as reaction mechanisms in organic chemistry, whereas part B still has the subtitle "Reactions and Synthesis" and gives an overview of the main reactions used in organic synthesis. Furthermore, the material in part A is presented in chapters and subchapters, which in essence have been kept unchanged since the very first edition.

The previous paragraph may leave the impression that the new editions of the books are both outdated and dull, but that is not the case (if you don’t insist on colorful illustrations to keep the concentration). Although a significant fraction of the material has not been revised at all, the texts appear clear and lucid and serve the material very well. A few figures still give a poor impression, particularly in Part A (for instance on pages 3, 34, 41, and 149), but also in Part B (e.g., pages 200 and 201), and some are still unnecessarily large (for instance on pages 39, 44, and 45 in Part A). It is also noteworthy that there are very few outright mistakes (two rare exceptions are found on p. 100 in Part A and in the table on p. 217 in Part B). And last, but not least, the problems at the end of each chapter have been increased in number and extended in scope and are excellent exercises for those wishing to test their understanding and apply the material presented in each chapter.

Reading of Part A discloses over and over again that most chapters have been updated in a balanced manner with respect to both material and key references. (An exception is chapter 13, which gives a rather shallow presentation of bits and pieces of photochemistry.) One characteristic feature of the book is clearly visible: Advances made in computational chemistry during the last couple of decades have been applied and used pedagogically to analyze structural and mechanistic problems, particularly in discussions of strained molecules and more or less unstable intermediates. But the theoretical treatment is kept at a reasonable level from an organic chemist’s point of view; the theoretical discussions therefore serve the purpose and add clarity to the text. As a result, the perspective and style in Carey and Sundberg’s presentation of structural and mechanistic organic chemistry appear different from those found in other comparable textbooks (e.g., J. March, Advanced Organic Chemistry, and T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry). This is particularly beneficial for the clarity of some of the topics dealt with, and Part A is therefore highly recommended as a thorough graduate-level introduction to structural and mechanistic aspects of organic chemistry.

Part B gives an extensive presentation of a broad selection of organic reactions of synthetic importance, organized by reaction type. Structurally, the book is similar to W. Carruthers’ book Some Modern Methods of Organic Chemistry, but one significant difference is Carey and Sundberg’s much more comprehensive coverage of organometallic reagents and intermediates. Similarities and differences between a variety of reagents are discussed systematically and related to metal properties, particularly the metals’ ability to form complexes with substrates and ligands. As a result, the discussion becomes rather mechanistic, and this gives a profound understanding at the molecular level of stereocontrol, which is so important in modern synthetic organic chemistry. Only one chapter, which amounts to 10 percent of the book, is devoted to synthetic planning and retrosynthetic analysis, which is the modern vehicle used to present organic synthesis (for instance in S. Warren, Designing Organic Synthesis–A Programmed Introduction to the Synthon Approach, and E. J. Corey and X.-M. Cheng, The Logic of Chemical Synthesis). However, intelligent retrosynthesis requires solid reagent knowledge, and to acquire such knowledge, reading of "Advanced Organic Chemistry, Part B: Reactions and Synthesis" is highly recommended.

Reviewed by Leiv K. Sydnes, University of Bergen, Norway.

www.wkap.nl/prod/b/0-306-46243-5

www.wkap.nl/prod/b/0-306-46245-1

IUPAC News

Advanced Organic Chemistry Part A: Structure and Mechanisms Part B: Reactions and Synthesis

Conceived a couple of years ago, the Web edition of the IUPAC Compendium of Analytical Nomenclature–the "Orange Book"–has now been completed. Its purpose is to ease access to and extend the influence of the extensive information contained in its recommendations. The work involved extensive proofreading of the electronic files and editing them to correspond in detail to the printed version, or to the earlier Pure and Applied Chemistry publications when there were conflicts. This work involved all members of the Analytical Chemistry Division Committee and others.

The Officers of the Analytical Chemistry Division during 2000-2002 (F. Ingman, D. S. Moore, K. Powell, and R. Lobinski) are extremely grateful for the help provided by the ACD Committee members and the staff of the Secretariat, and to C. Townsend for hyperlinking the index.

The home page for the web edition is in frames, with the left hand frame serving as a shorthand table of contents. Clicking on a chapter loads its table of contents into the main frame. The sections of each chapter are linked to Adobe PDF files of that particular section. These can then be searched and/or printed, as desired. The margins were chosen so that they would print on either US Letter or A4 paper. The Index is presented as alphabetical sections, and each term is hyperlinked to the pdf file of the appropriate section of the book. Some book sections are quite long, so that a simple search on the term after downloading the pdf should quickly yield the appropriate location.

www.iupac.org/publications/analytical_compendium