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Introduction to Ethers

Two alcohol molecules will react under the proper conditions to produce compounds with the general formula R-O-R'. These compounds are called ETHERS. The other product of the reaction is water which is taken up by a dehydration agent. 2ROH ROR + H2O

Simple ethers are prepared commercially by dehydration of the corresponding alcohols by sulfuric acid: A typical reaction is: 2CH3-CH2-OH --H2SO4 --> CH3-CH2-O-CH2-CH3 + H2O also written: 2C2H5OH --H2SO4--> C2H5OC2H5 + H2O The ethers are named by naming the radical on either side of the oxygen atom, and adding the word ether. The two side chains can be the same, of course, in which case the name is mentioned just once, but preceded by the prefix di-. Thus, in the preceding reaction, 2 moles of ethanol will react to form 1 mole of diethyl

ether.

Ethers may also be named as OXY DERIVATIVES of the hydrocarbons. In the IUPAC nomenclature system, ethers are named using the general formula "alkoxyalkane", for example CH3-CH2-O-CH3

is methoxyethane. If the ether is part of a more complex molecule, it is described as an alkoxy substituent, so -OCH3 would be considered a "methoxy-" group. The nomenclature of describing the two alkyl groups and appending "ether", e.g. "ethylmethyl ether" is a trivial usage. The ether radicals for the first four alkanes are: CH3-OCH3-CH2-OCH3-CH2-CH2OCH3-CH2-CH2CH2-OMethoxyEthoxyPropoxyButoxy-

Another name for diethyl ether is ethoxyethane. Dimethyl ether is methoxymethane, and methylheptyl ether is 1-methoxyheptane. CH3-O-CH3 CH3-O-CH2-CH2-CH2-CH2-CH2-CH2-CH3 dimethyl ether methylheptyl ether The structural formula for 1,4-dimethoxy-2-pentene is CH3-O-CH2-CH=CH-CH(CH3-O)-CH3 Many ethers are used in industry as solvents. Diethyl ether has found widespread use as an anesthetic since 1846, in which application it is referred to simply as ether. It and other ethers are valuable solvents for gums, fats, waxes, and resins. Ethers are highly flammable and have relatively high vapor pressures, so they constitute a significant fire hazard. Moreover, on standing in air many simple ethers react slowly with

atmospheric oxygen to form unstable and highly explosive organic peroxides, a significant hazard in distillations which use ethers. It would be uncommon (but correct) to name diethyl ether as ethoxyethane, but the name paraethoxybenzoic acid would be appropriate for C2H5OC6H6COOH. The two simplest aromatic ethers carry the nonsystematic names of anisole (methoxybenzene) and phenetole (ethoxybenzene). More complex ether structures are prepared in multistep synthesis.

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