Part B 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 sigma
tropic rearrangements, are considered in Chapter 6. Chapters 7, 8, and 9 cover organometallic reagents and intermediate
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
intermediates carbocations, 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 illustrated by a 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, epothilone. The chapter concludes with a discussion of solid-phase synthesis and its application
in the synthesis of polypeptides and oligonucleotides, as well as to combinatorial 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 stereo control are catalysts for enantio selective
reduction of ketones, improved methods for control of the stereoselectivity of Diels
Alder reactions, and improved catalysts for enantioselective hydroxylation
and epoxidation of alkenes. This volume assumes a level of familiarity with
structural and mechanistic concepts comparable to that in the companion volume,
Part A, Structure and Mechanisms. Together, the two volumes are intended to provide the advanced undergraduate or beginning
graduate student in chemistry a sufficient foundation to comprehend and use the
research literature in organic chemistry.
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