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18: Ethers and Epoxides; Thiols and Sulfides

Last updated

Sep 24, 2022
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- 17.S: Alcohols and Phenols (Summary)
- 18.0: Introduction

Steven Farmer & Dietmar Kennepohl
LibreTexts

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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.

18.0: Introduction
18.1: Names and Properties of Ethers
18.2: Preparing Ethers
18.3: Reactions of Ethers - Acidic Cleavage
18.4: 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.
18.5: 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.
18.6: Reactions of Epoxides - Ring-opening
18.7: 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.
18.8: Thiols and Sulfides
Thiols are organic compounds with a sulfur atom bonded to a hydrogen atom, known for their foul smell. Sulfides have a sulfur atom bonded to two organic groups and are less odorous. Both are important in organic chemistry and have applications in various industries.
18.9: Spectroscopy of Ethers
18.10: Interchapter - A Preview of Carbonyl Chemistry
18.S: Ethers and Epoxides; Thiols and Sulfides (Summary)

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.

Learning Objectives

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