Advanced Organic Chemistry: Part B: Reaction and Synthesis, fifth edition


FRANCIS A. CAREY and RICHARD J. SUNDBERG, University of Virginia, Charlottesville, Virginia


There is increased emphasis throughout Part B on the representation of transition structures to clarify stereoselectivity, including representation by computational models. The current practice of organic synthesis requires a thorough knowledge of molecular architecture and an understanding of how the components of a structure can be assembled. Structures of enantioselective reagents and catalysts are provided to help students appreciate the three-dimensional aspects of the interactions that occur in reactions.

Key features

  • A new feature of this edition is a brief section of commentary on the reactions in most of the schemes, which may point out a specific methodology or application. Instructors who want to emphasize the broad aspects of reactions, as opposed to specific examples, may wish to advise students to concentrate on the main flow of the text, reserving the schemes and commentary for future reference.
  • The selection of material in the examples and schemes does not reflect priority, importance, or generality. It was beyond our capacity to systematically survey the many examples that exist for most reaction types, and the examples included are those that came to our attention through literature searches and reviews.
  • Several computational studies have been abstracted and manipulable three-dimensional images of reactants, transition structures, intermediates, and products provided. This material provides the opportunity for detailed consideration of these representations and illustrates how computational chemistry can be applied to the mechanistic and structural interpretation of reactivity. This material is available in the Digital Resource at
  • As in previous editions, the problems are drawn from the literature and references are given. In this addition, brief answers to each problem have been provided and are available at the publishers website.


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