Advanced Organic Chemistry

Part A: Structure and Mechanisms

  • Francis A. Carey
  • Richard J. Sundberg

Part of the Advanced Organic Chemistry book series (AOC)

Table of contents

  1. Front Matter
    Pages I-XXI
  2. Francis A. Carey, Richard J. Sundberg
    Pages 1-117
  3. Francis A. Carey, Richard J. Sundberg
    Pages 119-251
  4. Francis A. Carey, Richard J. Sundberg
    Pages 253-388
  5. Francis A. Carey, Richard J. Sundberg
    Pages 389-472
  6. Francis A. Carey, Richard J. Sundberg
    Pages 473-577
  7. Francis A. Carey, Richard J. Sundberg
    Pages 579-628
  8. Francis A. Carey, Richard J. Sundberg
    Pages 629-711
  9. Francis A. Carey, Richard J. Sundberg
    Pages 713-770
  10. Francis A. Carey, Richard J. Sundberg
    Pages 771-831
  11. Francis A. Carey, Richard J. Sundberg
    Pages 833-964
  12. Francis A. Carey, Richard J. Sundberg
    Pages 965-1071
  13. Francis A. Carey, Richard J. Sundberg
    Pages 1073-1153
  14. Back Matter
    Pages 1155-1203

About this book


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


Aromaticity Nucleophilic substitution Pericyclic reaction bonding carbon organic chemistry photochemistry structure synthesis

Authors and affiliations

  • Francis A. Carey
    • 1
  • Richard J. Sundberg
    • 1
  1. 1.Department of ChemistryUniversity of VirginiaCharlottesville

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