Advanced Organic Chemistry

1. Front Matter

   Pages I-XXX

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2. Alkylation of Enolates and Other Carbon Nucleophiles

   • Francis A. Carey, Richard J. Sundberg

   Pages 1-62

3. Reactions of Carbon Nucleophiles with Carbonyl Compounds

   • Francis A. Carey, Richard J. Sundberg

   Pages 63-214

4. Functional Group Interconversion by Substitution, Including Protection and Deprotection

   • Francis A. Carey, Richard J. Sundberg

   Pages 215-288

5. Electrophilic Additions to Carbon-Carbon Multiple Bonds

   • Francis A. Carey, Richard J. Sundberg

   Pages 289-365

6. Reduction of Carbon-Carbon Multiple Bonds, Carbonyl Groups, and Other Functional Groups

   • Francis A. Carey, Richard J. Sundberg

   Pages 367-471

7. Concerted Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations

   • Francis A. Carey, Richard J. Sundberg

   Pages 473-617

8. Organometallic Compounds of Group I and II Metals

   • Francis A. Carey, Richard J. Sundberg

   Pages 619-673

9. Reactions Involving Transition Metals

   • Francis A. Carey, Richard J. Sundberg

   Pages 675-782

10. Carbon-Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tin

    • Francis A. Carey, Richard J. Sundberg

    Pages 783-860

11. Reactions Involving Carbocations, Carbenes, and Radicals as Reactive Intermediates

    • Francis A. Carey, Richard J. Sundberg

    Pages 861-1002

12. Aromatic Substitution Reactions

    • Francis A. Carey, Richard J. Sundberg

    Pages 1003-1062

13. Oxidations

    • Francis A. Carey, Richard J. Sundberg

    Pages 1063-1162

14. Multistep Syntheses

    • Francis A. Carey, Richard J. Sundberg

    Pages 1163-1270

15. Back Matter

    Pages 1271-1321

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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. Among the changes: Updated material reflecting advances in the field since 2001’s Fourth Edition, especially in computational chemistry; A companion Web site provides digital models for study of structure, reaction and selectivity; Solutions to the exercises provided to instructors online.

The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. Part B describes the most general and useful synthetic reactions, organized on the basis of reaction type. Together with Part A: Structure and Mechanisms, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.

• Cycloaddition
• Electrophilic addition
• Rearrangement
• metals
• organic chemistry

From the reviews of the fifth edition:

"Advanced Organic Chemistry … the well-known textbook for graduate students – has now appeared in a 5th edition. … Carey & Sundberg will be interesting to all students who seek a detailed understanding of organic chemistry, and who wish to refresh and embellish their existing knowledge. On the strength of the scope and quality of the explanations, this pair of texts is recommended for use as the resource of first resort for specific research questions in one’s later career." (www.organische-chemie.ch, January, 2008)

• Department of Chemistry, University of Virginia, Charlottesville

  Francis A. Carey, Richard J. Sundberg

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.