Advanced Organic Chemistry: Part A: Structure and Mechanisms

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9780306434402: Advanced Organic Chemistry: Part A: Structure and Mechanisms
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The purpose of this edition, like that of the earlier ones, is to provide the basis for a deeper understanding of the structures of organic compounds and the mechanisms of organic reactions. The level is aimed at advanced undergraduates and beginning graduate students. Our goals are to solidify the student's understanding of basic concepts provided by an introduction to organic chemistry and to present more information and detail, including quantitative information, than can be presented in the first course in organic chemistry. The first three chapters consider the fundamental topi~s of bonding theory, stereochemistry, and conformation. Chapter 4 discusses the techniques that are used to study and characterize reaction mechanisms. Chapter 9 focuses on aromaticity and the structural basis of aromatic stabilization. The remaining chapters consider basic reaction types, including substituent effects and stereochemistry. As compared to the earlier editions, there has been a modest degree of reorganization. The emergence of free-radical reactions in synthesis has led to the inclusion of certain aspects of free-radical chemistry in Part B. The revised chapter, Chapter 12, empha­ sizes the distinctive mechanistic and kinetic aspects of free-radical reactions. The synthetic applications will be considered in Part B. We have also split the topics of aromaticity and the reactions of aromatic compounds into two separate chapters, Chapters 9 and 10. This may facilitate use of Chapter 9, which deals with the nature of aromaticity, at an earlier stage if an instructor so desires.

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From the Back Cover:

Since its original appearance in 1977, Advanced Organic Chemistry has maintained its place as the premier textbook in the field, offering broad coverage of the structure, reactivity and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed.

The two-part fifth edition has been substantially revised and reorganized for greater clarity. Part A begins with the fundamental concepts of structure and stereochemistry, and the thermodynamic and kinetic aspects of reactivity. Major reaction types covered include nucleophilic substitution, addition reactions, carbanion and carbonyl chemistry, aromatic substitution, pericyclic reactions, radical reactions, and photochemistry.

Among the changes:

  • Coverage of the importance of computational chemistry in modern organic chemistry, including applications to many specific reactions.
  • Expanded coverage of stereoselectivity and enantioselectivity, including discussion of several examples of enantioselective reagents and catalysts
  • Chapter 10, Concerted Pericyclic Reactions, has been reorganized and now begins with cycloaddition reactions.
  • The treatment of photochemical reactions has been extensively updated to reflect both experimental and computational studies of the transient intermediates involved in photochemical reactions.
  • A companion Web site provides digital models for study of structure, reaction and selectivity. Here students can view and manipulate computational models of reaction paths. These sites also provide exercises based on detailed study of the computational models.
  • Several chapters in Part A conclude with Topics – short excursions into specific topics such as more detailed analysis of polar substituent effects, efforts to formulate substituent effects in terms of density functional theory, or the role of carbocations in petroleum refining
  • Solutions to the chapter problems are provided to instructors online

Advanced Organic Chemistry Part A provides a close look at the structural concepts and mechanistic patterns that are fundamental to organic chemistry. It relates those mechanistic patterns, including relative reactivity and stereochemistry, to underlying structural factors. Understanding these concepts and relationships will allow students to recognize the cohesive patterns of reactivity in organic chemistry. Part A: Structure and Mechanism and Part B: Reaction and Synthesis - taken together - are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a foundation to comprehend and use the research literature in organic chemistry

About the Author:

Francis A. Carey is a native of Pennsylvania, educated in the public schools of Philadelphia, at Drexel University (B.S. in chemistry, 1959), and at Penn State (Ph.D. 1963). Following postdoctoral work at Harvard and military service, he was appointed to the chemistry faculty of the University of Virginia in 1966. Prior to retiring in 2000, 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. Along with Francis A. Carey he is the author of “Advanced Organic Chemistry. Professor Sundberg is also interested in synthetic methodology in heterocyclic chemistry and is the author of “Indoles” in the Best Synthetic Methods Series (Academic Press, 1996).

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