Ethers definition chemistry

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Note: Ether does not possess a hydroxyl group, unlike alcohols and phenols. Those alkyl groups are listed in alphabetical order. Naming for ethers adopted by IUPAC uses a more complex group as the root name, with the oxygen atom and the smaller group named as an alkoxy substituent.

Example: ethoxyethane diethyl ether , methoxy ethane methyl ethyl ether , 2-methoxymethylpropane methyl tert-butyl ether , phenoxy benzene diphenyl ether. This IUPAC nomenclature is very useful for naming compounds with additional functional groups because these functional groups can be described in the root name.

Example: Methyl becomes methoxy and ethyl becomes an ethoxy group. Rule 3: Alkoxy name is placed with a locator number in front of the base chain name. Example: 1. The most common industrial methods for preparing ethers are: Dehydration of Alcohols Alcohol undergoes dehydration in the presence of protic acids sulphuric acid, phosphoric acid to produce alkenes and ethers under different conditions.

The formation of the reaction product depends on the reaction conditions. For example, ethanol is dehydrated to ethene at K in the presence of sulphuric acid. On the other hand, ethanol yields ethoxyethane in the presence of sulphuric acid at K. The formation of ethers by dehydration of an alcohol is a nucleophilic bimolecular reaction. That is, here the alcohol acts as a nucleophile which means it involves the attack of alcohol molecule on a protonated alcohol as shown below This method is used for the preparation of ethers having primary alkyl groups.

To synthesize ethers in this way, the alkyl group should be unhindered and must be kept at a low temperature or else the reaction will give rise to alkenes. Read More: Electrophiles and Nucleophiles Williamson Synthesis This is an important method for the preparation of symmetrical and asymmetrical ethers in laboratories. In Williamson synthesis, an alkyl halide is made to react with sodium alkoxide which leads to the formation of ether.

Example: This reaction involves an SN2 attack of an alkoxide ion on an alkyl halide. We know that alkoxides are very strong bases and they react steadily with alkyl halides and thus they take part in elimination reactions. In the case of primary alkyl halides, Williamson synthesis shows higher productivity. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents.

But on the other hand, ethers undergo cleavage by reaction with acids. The prominent chemical reactions of ethers are as follows; Cleavage Of C-o Bonds In Ethers Cleavage of C-O bonds in ether takes place in excess hydrogen halide which are acidic under extreme conditions like in concentrated acids usually HBr and HI and high temperatures.

For example, the reaction of dialkyl ether produces, initially, an alkyl halide and alcohol. This alcohol further reacts with halide to form a second mole of alkyl halide and water. Thus, the initial reaction between ether and halide produces a protonated ether. The nucleophilic attack of halide ion on this protonated ether leads to cleavage of C-O bond.

Structure of the polymeric diethyl ether peroxide The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity , they are more reactive than alkanes. Specialized ethers such as epoxides , ketals , and acetals are unrepresentative classes of ethers and are discussed in separate articles.

Important reactions are listed below. Hydrogen chloride cleaves ethers only slowly. Some ethers undergo rapid cleavage with boron tribromide even aluminium chloride is used in some cases to give the alkyl bromide. Peroxide formation[ edit ] When stored in the presence of air or oxygen, ethers tend to form explosive peroxides , such as diethyl ether hydroperoxide.

The reaction is accelerated by light, metal catalysts, and aldehydes. In addition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less volatile than the original ether, will become concentrated in the last few drops of liquid.

The presence of peroxide in old samples of ethers may be detected by shaking them with freshly prepared solution of a ferrous sulfate followed by addition of KSCN. Appearance of blood red color indicates presence of peroxides. The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran THF or ethylene glycol dimethyl ether 1,2-dimethoxyethane are avoided in industrial processes.

Lewis bases[ edit ] Structure of VCl3 thf 3. For instance, diethyl ether forms a complex with boron trifluoride , i. Ethers also coordinate to the Mg center in Grignard reagents. Tetrahydrofuran is more basic than acyclic ethers. It forms complexes with many metal halides. Alpha-halogenation[ edit ] This reactivity is similar to the tendency of ethers with alpha hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers. Synthesis[ edit ] 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.