Page 6 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

vi the important area of stereoselectivity of concerted pericyclic reactions. Instructors
may want to consider dealing with these three chapters directly after Chapter 3, and
Preface
we believe that is feasible.
Chapters 11 and 12 deal, respectively, with free radicals and with photochemistry
and, accordingly, with the chemistry of molecules with unpaired electrons. The latter
chapter has been substantially updated to reflect the new level of understanding that
has come from ultrafast spectroscopy and computational studies.
As in the previous editions, a significant amount of specific information is
provided in tables and schemes. These data and examples serve to illustrate the issues
that have been addressed in the text. Instructors who want to achieve a broad coverage,
but without the level of detail found in the tables and schemes, may choose to advise
students to focus on the main text. In most cases, the essential points are clear from
the information and examples given in the text itself.
We have made an effort to reduce the duplication between Parts A and B. In
general, the discussion of basic mechanisms in Part B has been reduced by cross-
referencing the corresponding discussion in Part A. We have expanded the discussion
of specific reactions in Part A, especially in the area of enantioselectivity and enantios-
elective catalysts.
We have made more extensive use of abbreviations than in the earlier editions.
In particular, EWG and ERG are used throughout both Parts A and B to designate
electron-withdrawing and electron-releasing substituents, respectively. The intent is
that the use of these terms will help students generalize the effect of certain substituents
such as C=O, C≡N, NO , and RSO as electron withdrawing and R (alkyl) and RO
2 2
(alkoxy) as electron releasing. Correct use of this shorthand depends on a solid under-
standing of the interplay between polar and resonance effects in overall substituent
effects. This matter is discussed in detail in Chapter 3 and many common functional
groups are classified.
Several areas have been treated as “Topics”. Some of the Topics discuss areas that
are still in a formative stage, such as the efforts to develop DFT parameters as quantitative
reactivity indices. Others, such as the role of carbocations in gasoline production, have
practical implications.
We have also abstracted information from several published computational studies
to present three-dimensional images of reactants, intermediates, transition structures,
and products. This material, including exercises, is available at the publishers web site,
and students who want to see how the output of computations can be applied may want
to study it. The visual images may help toward an appreciation of some of the subtle
effects observed in enantioselective and other stereoselective reactions. As in previous
editions, each chapter has a number of problems drawn from the literature. A new
feature is solutions to these problems, which are also provided at the publisher’s
website at springer.com/carey-sundberg
Our goal is to present a broad and fairly detailed view of the core area of organic
reactivity. We have approached this goal by extensive use of both the primary and
review literature and the sources are referenced. Our hope is that the reader who
works through these chapters, problems, topics, and computational studies either in an
organized course or by self-study will be able to critically evaluate and use the current
literature in organic chemistry in the range of fields in which is applied, including
the pharmaceutical industry, agricultural chemicals, consumer products, petroleum
chemistry, and biotechnology. The companion volume, Part B, deals extensively with
organic synthesis and provides many more examples of specific reactions.