4: 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.
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- 4.5: Reactions of Ethers - Claisen Rearrangement
- The Claisen rearrangement is a key organic reaction that involves the thermal rearrangement of allyl vinyl ethers to form β-aryl allyl ethers. It's a valuable tool in organic synthesis, enabling the creation of complex molecular structures with high selectivity and efficiency.
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- 4.6: Cyclic Ethers - Epoxides
- Cyclic ethers, specifically epoxides, are organic compounds with a ring structure containing an oxygen atom. Epoxides are characterized by a highly strained, reactive three-membered ring. They find applications in organic synthesis, polymerization, asymmetric synthesis, and biology. Despite their utility, they require careful handling due to their reactivity and potential health hazards.
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- 4.8: Crown Ethers
- Crown ethers are a fascinating class of chemical compounds known for their unique structure and remarkable properties. These molecules consist of a ring-shaped arrangement of oxygen atoms, typically with carbon atoms forming the backbone. The name "crown" comes from their crown-like shape when viewed in three dimensions.
- 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.