18: Ethers and Epoxides; Thiols and Sulfides

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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