Vol. 24, No. 5
A: Structure and Mechanisms
Part B: Reactions and Synthesis
A. Carey and Richard J. Sundberg
Kluwer Academic/Plenum Publishers, 4th edition, (Part A: 823 pages),
(Part B: 965 pages) 2001.
edition, of Carey and Sundbergs 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.
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.
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are both outdated and dull, but that is not the case (if you dont
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
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
chemists 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 Sundbergs 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
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 Sundbergs
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 SynthesisA 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.
Leiv K. Sydnes,
University of Bergen, Norway.