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Strong acids protonate the oxygen to give "oxonium ions". For instance, diethyl ether forms a complex with boron trifluoride , i. Ethers also coordinate to the Mg II center in Grignard reagents.
This reactivity is similar to the tendency of ethers with alpha hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers.
Ethers can be prepared by numerous routes. In general alkyl ethers form more readily than aryl ethers, with the later species often requiring metal catalysts.
The synthesis of diethyl ether by a reaction between ethanol and sulfuric acid has been known since the 13th century. The dehydration of alcohols affords ethers: .
The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be protonated, which would give a mixture of products.
Diethyl ether is produced from ethanol by this method. Cyclic ethers are readily generated by this approach. Elimination reactions compete with dehydration of the alcohol:.
The dehydration route often requires conditions incompatible with delicate molecules. Several milder methods exist to produce ethers.
Nucleophilic displacement of alkyl halides by alkoxides. This reaction is called the Williamson ether synthesis. It involves treatment of a parent alcohol with a strong base to form the alkoxide, followed by addition of an appropriate aliphatic compound bearing a suitable leaving group R—X.
Suitable leaving groups X include iodide , bromide , or sulfonates. This method usually does not work well for aryl halides e. Likewise, this method only gives the best yields for primary halides.
Secondary and tertiary halides are prone to undergo E2 elimination on exposure to the basic alkoxide anion used in the reaction due to steric hindrance from the large alkyl groups.
In a related reaction, alkyl halides undergo nucleophilic displacement by phenoxides. The R—X cannot be used to react with the alcohol.
However phenols can be used to replace the alcohol while maintaining the alkyl halide. Since phenols are acidic, they readily react with a strong base like sodium hydroxide to form phenoxide ions.
The phenoxide ion will then substitute the —X group in the alkyl halide, forming an ether with an aryl group attached to it in a reaction with an S N 2 mechanism.
The Ullmann condensation is similar to the Williamson method except that the substrate is an aryl halide. Such reactions generally require a catalyst, such as copper.
Acid catalysis is required for this reaction. Often, mercury trifluoroacetate Hg OCOCF 3 2 is used as a catalyst for the reaction generating an ether with Markovnikov regiochemistry.
Using similar reactions, tetrahydropyranyl ethers are used as protective groups for alcohols. Epoxides are typically prepared by oxidation of alkenes.
The most important epoxide in terms of industrial scale is ethylene oxide, which is produced by oxidation of ethylene with oxygen. Other epoxides are produced by one of two routes:.
From Wikipedia, the free encyclopedia. Class of organic compounds. For the substance whose common name is ether, see Diethyl ether. For other uses of ether or aether, see Aether.
This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed.
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