The goal of this text is to build on the foundation of introductory organic chemistry to provide students and other readers а deeper understanding of structure and mechanism and the relationships between them. We have provided specific data and examples with which to illustrate the general principles that are discussed. Our purpose is to solidify the students understanding of the basic concepts, but also to illustrate the way specific structural changes inAuence mechanism and reactivity.
The first three chapters discuss fundamental bonding theory, stereochemistry, and conformation, respectively. Chapter 4 discusses the means of study and description of reaction mechanisms. Chapter 9 focuses on aromaticity and aromatic stabilization and can be used at an earlier stage of а course Ы an instructor desires to do so. The other chapters discuss specific mechanistic types, including nucleophilic substitution, polar additions and eliminations, carbon acids and enolates, carbonyl chemistry, aromatic substitution, concerted reactions, free radical reactions, and photochemistry.
Both the language of valence bond theory and of molecular orbital theory are used in discussing structural effects on reactivity and mechanism. Our intent is to illustrate both approaches to interpretation. А decade has passed since the publication of the Third Edition. That decade has seen significant developments in areas covered by the text. Perhaps most noteworthy has been the application of computational methods to а much wider range of problems of structure and mechanism. We have updated the description of computational methods and have included examples throughout the text of application of computational methods to specific reactions.
References to the primary literature are provided for specific issues of structure, reactivity, and mechanism. These have been chosen to illustrate the topic of discussion and, of course, cannot be comprehensive. The examples and references chosen do not imply any priority of concept or publication. References to general reviews which can provide а broader coverage of the various topics are usually given.
The problems at the end of each chapter represent application of concepts to new structures and circumstances, rather than review of material explicitly presented in the text. The level of difficulty is similar to that of earlier editions, and we expect that many will present а considerable challenge to students. Some new problems have been added in this edition. References to the literature material upon which the problems are based ar«gii «n at the end of the book.
The companion volume, Part В, has also been revised to re8ect the continuing development of synthetic methodology. Part В emphasizes synthetic application оГ organic reactions. We believe that the material in Part А and Part В will provide advanced undergraduate and beginning graduate students with а background which will permit them to understand, analyze, and apply the primary and review literature in organic chemistry. We hope that this new edition will continue to serve students and teachers in fostering both an understanding of the structural and mechanistic foundations of organic chemistry and а broad knowledge of the most fundamental reaction types in organic chemistry. We welcome comments and suggestions which can improve the text or correct errors.
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Part В emphasizes the most important reactions used in organic synthesis. The material is organized by reaction type. Chapters 1 and 2 discuss the alkylation, conjugate addition and carbonyl addition/condensation reactions of enolates and other carbon nucleophiles. Chapter 3 covers the use of nucleophilic substitution, both at saturated carbon and at carbonyl groups, in functional group of interconversions. Chapter 4 discusses electrophilic additions to alkenes and alkynes, including hydroboration. Chapter 5 discusses reduction reactions, emphasizing alkene and carbonyl-group reductions. Concerted reactions, especially Diels — Alder and other cycloadditions and sigmatropic rearrangements, are considered in Chapter 6. Chapters 7, 8, and 9 cover organometallic reagents and intermediates in synthesis. The main-group elements lithium and magnesium as well as zinc are covered in Chapter 7. Chapter 8 deals with the transition metals, especially copper, palladium, and nickel. Chapter 9 discusses synthetic reactions involving boranes, silanes, and stannanes. Synthetic reactions which involve highly reactive intermediatescагЬocа-tions, carbenes, and radicals — are discussed in Chapter 10. Aromatic substitution by both electrophilic and nucleophilic reagents is the topic of Chapter 11. Chapter 12 discusses the most important synthetic procedures for oxidizing organic compounds. In each of these chapters, the most widely used reactions are illttstrated by а number of specific examples of typical procedures. Chapter 13 introduces the concept of synthetic planning, including the use of protective groups and synthetic equivalents. Multistep syntheses are illustrated with several syntheses of juvabione, longifolene, Prelog — Djerassi lactone, Taxol, and epothilone. The chapter concludes with а discussion of solid phase synthesis and its application in the synthesis of polypeptides and oligonucleotides, as well as to combina-torial synthesis.
The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. In the decade since the publication of the third edition, major advances have been made in the development of efficient new methods, particularly catalytic processes, and in means for control of reaction stereochemistry. For example, the scope and efficiency of palladium- catalyzed cross coupling have been greatly improved by optimization of catalysts by ligand modification. Among the developments in stereocontrol are catalysts for enantioselective reduction ойсе1опея, improved methods for control of the stereoselectivity of Diels — Alder reactions, and improved catalysts for enantioselective hydroxylation and epoxidation of alkenes.
This volume assumes а level of familiarity with structural and mechanistic concepts comparable to that in the companion volume, Part А, Structure and Mechanisms. Together, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry а sufficient foundation to comprehend and use the research literature in organic chemistry.
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