Preface
This Fifth Edition marks the beginning of the fourth decade that Advanced Organic
Chemistry has been available. As with the previous editions, the goal of this text is to
allow students to build on the foundation of introductory organic chemistry and attain
a level of knowledge and understanding that will permit them to comprehend much
of the material that appears in the contemporary chemical literature. There have been
major developments in organic chemistry in recent years, and these have had a major
influence in shaping this new edition to make it more useful to students, instructors,
and other readers.
The expanding application of computational chemistry is reflected by amplified
discussion of this area, especially density function theory (DFT) calculations in
Chapter 1. Examples of computational studies are included in subsequent chapters
that deal with specific structures, reactions and properties. Chapter 2 discusses the
principles of both configuration and conformation, which were previously treated in
two separate chapters. The current emphasis on enantioselectivity, including devel-
opment of many enantioselective catalysts, prompted the expansion of the section on
stereoselective reactions to include examples of enantioselective reactions. Chapter 3,
which covers the application of thermodynamics and kinetics to organic chemistry,
has been reorganized to place emphasis on structural effects on stability and reactivity.
This chapter lays the groundwork for later chapters by considering stability effects on
carbocations, carbanions, radicals, and carbonyl compounds.
Chapters 4 to 7 review the basic substitution, addition, and elimination mecha-
nisms, as well as the fundamental chemistry of carbonyl compounds, including enols
and enolates. A section on of the control of regiochemistry and stereo- chemistry of
aldol reactions has been added to introduce the basic concepts of this important area. A
more complete treatment, with emphasis on synthetic applications, is given in Chapter
2 of Part B.
Chapter 8 deals with aromaticity and Chapter 9 with aromatic substitution, empha-
sizing electrophilic aromatic substitution. Chapter 10 deals with concerted pericyclic
reactions, with the aromaticity of transition structures as a major theme. This part of
the text should help students solidify their appreciation of aromatic stabilization as a
fundamental concept in the chemistry of conjugated systems. Chapter 10 also considers
v
