18: Ethers and Epoxides; Thiols and Sulfides

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We shall begin in a very traditional manner, with a discussion of the nomenclature of ethers. We will then describe how ethers may be prepared in the laboratory, and discuss the relative inertness of these compounds. A discussion of the chemistry of cyclic ethers follows, with particular emphasis on the preparation and reactions of epoxides (cyclic ethers containing a three-membered ring). We will then introduce crown ethers—compounds that consist of large rings containing several oxygen atoms and the spectroscopic properties of ethers. The unit will close with a description of the chemistry of thiols and sulfides, the sulfur-containing analogues of alcohols and ethers.

Learning Objectives

fulfill all of the detailed objectives listed under each individual section.
design a multi-step synthesis using one or more of the reactions introduced in this chapter, along with any number of the reactions you have studied to date.
solve “road-map” problems that may require a knowledge of the chemistry of ethers, epoxides, thiols and sulfides, in addition to any of the material you have studied up to this point in organic chemistry.
define, and use in context, the key terms introduced in this chapter.

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