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Advanced organic chemistry: Part A: Structure and mechanisms | University of St Andrews

Francis A. Carey is a native of Pennsylvania, educated in the public schools of Philadelphia, at Drexel University B. Following postdoctoral work at Harvard and military service, he was appointed to the chemistry faculty of the University of Virginia in Prior to retiring in , he regularly taught the two-semester lecture courses in general chemistry and organic chemistry. With his students, Professor Carey has published over forty research papers in synthetic and mechanistic organic chemistry.

Professor Sundberg is primarily engaged in teaching and chemical education.


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Along with Francis A. Carey , Richard J.

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Paperback: ISBN Their discussions begin at a level accessible to most upper-level undergraduate and first-year graduate students and develop the topics to a level that would be expected of a Ph. They also appear to have reasonably covered the literature through — However, they largely used the text, examples, and problems of the third edition in their efforts.

The major changes are related to the application of computational methods to many of the specific reactions discussed. The chapter organization is the same as in the third edition.

Advanced Organic Chemistry, Part A: Structure and Mechanisms

The first three chapters deal with data and theories that help us understand organic structure and develop the fundamentals of bonding, stereochemistry, and conformational analysis to provide a firm structural basis for understanding the reactions considered in later chapters. Both valence-bond and molecular-orbital approaches are presented and their specific strengths compared. A new section in Chapter 1 presents recent developments in molecular orbital theory including density functional theory, and there are 3 new problems.

Chapter 2 introduces some new methods for resolving racemic mixtures and a few new chiral catalysts, but no new problems. Although there are 5 new problems and a few new references in Chapter 3, its treatment of conformational analysis is es- sentially the same as in the previous edition.

Chapter 4 discusses physical methods for studying reaction mechanisms. Included are thermodynamics and kinetics, isotope effects, characterization of intermediates, acid—base catalysis, and solvent effects. Gone is third-edition material on the Swain—Lupton approach to linear free energy relationships and added is new material on Lewis acid catalysis along with 3 new problems. Chapters 5 through 11 deal with mechanisms of the major ionic organic reactions: nucleophilic substitution, polar addition and elimination, carbanion, carbonyl, aromatic substitution, and pericyclic reactions.

In each case evidence for and examples of the predominant mechanisms are thoroughly presented. There is considerable new material on carbocation rearrangements and nonclassical cations Chapter 5 , new data on substituent effects on carbonyl group stability Chapter 8 , and calculations of activation hardness of aromatic and heteroaromatic compounds Chapter 10 , together with 15 new problems in these 7 chapters.

Free radical reactions are considered in Chapter The discussion begins with consideration of the structure and stabilities of free radicals and then follows through with treatment of the mechanisms of the major types of free radical reactions.

Advanced organic chemistry: Part A: Structure and mechanisms

A new section on free radical halogen, sulfur, and selenium group transfer reactions, several new references, and 1 new problem are included. Chapter 13 deals with photochemistry. Orbital symmetry considerations are developed and applied to reactions of alkenes and dienes as well as carbonyl and aromatic compounds. There are several new references and 2 new problems.