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Chapter 12 discusses compounds, other than alkyl halides, that undergo substitution and/or elimination reactions. Because alcohols and ethers have relatively poor leaving groups compared with the leaving groups of alkyl halides, alcohols and ethers must be activated before the groups will leave. Several methods commonly used to activate leaving groups are examined. Other compounds that undergo substitution and/or elimination reactions, such as sulfonate esters, epoxides, and sulfonium salts, are also discussed. We will also look at arene oxides in this chapter. It has long been known that certain arene oxides are carcinogenic. Here you see why this is so, and you learn how to predict from their structures the ones that are most apt to cause cancer. This chapter also introduces you to organometallic compounds, compounds that contain a carbon–metal bond. In Chapter 10 you saw that an alkyl halide has an electrophilic carbon atom. In contrast, an organometallic compound has a nucleophilic carbon atom. Several coupling reactions that require transition-metal catalysts will be discussed. The chapter concludes with some problems that show you how useful organometallic compounds are to synthetic chemists.
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