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Chapter 18

Ch.18 Summary.docx

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Barb Morra

CHM 247 CH.18 Ethers and Epoxides; Thiols and Sulfides • Ether: A compound that has 2 organic substituents bonded to the same oxygen atom, ROR’. • Thiol: A thiol compound containing the –SH functional group. • Sulfide: A compound that has 2 organic substituents bonded to the same sulfur atom, RSR’. • Common ethers are diethyl ether and tetrahydrofuran. 18.1 Names and Properties of Ethers • Simple ethers with no other functional groups are names by identifying the 2 organic substituents and adding the word ether. • If other functional groups are present, the ether part is considered an alkoxy substituent (p-Dimethoxy benz3ne). • The oxygen is sp hybridized. It gives the molecule a slight dipole moment, leading to a slightly higher boiling point. • Ethers are relatively stable and non-reactive. Some react slowly with the oxygen in air to give peroxides. 18.2 Synthesis of Ethers • Can use a sulfuric acid catalyzed reaction of alcohols. Takes place via N S 2 mechanism. Only works with primary alcohols. The Williamson Ether Synthesis • • The alkyl halide needs to be primary. Alkoxymercuration ofAlkenes • • Alkoxymercuration: A method for synthesizing ethers by mercuric-ion catalyzed addition of an alcohol to an alkene followed by demercuration on treatment with NaBH .4 18.3 Reactions of Ethers: Acidic Cleavage • Ethers can be cleaved by strong acids. • Br or I can be used. • The mechanism varies depending on the functional group. • Ethers with only primary or secondary alkyl groups react by a N 2 mechanism in which X attacks at the less hindered site. • • 18.5 Cyclic Ethers: Epoxides • Similar to non-cyclic ethers. • 3 membered rings are one of the few groups that behave differently. Epoxides are also called oxiranes. • Crown ethers have their ether groups pointing inwards, allowing another ion to bond. They have enhanced reactivity. • • 18.6 Reactions of Epoxides: Ring-Opening Acid-Catalyzed Epoxide Opening • Dilute acid is enough to cause hydrolys
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