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Ether
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Ether

For ether, in physics and philosophy, see Aether.

For the Book of Mormon Prophet Ether, see Book of Ether.


Ether is the trivial name for the compound diethyl ether, CH3CH2OCH2CH3; the systematic (IUPAC) name of the compound is ethoxyethane. Chemist Raymundus Lullus discovered the compound in 1275. It was first synthesized in 1540 by Valerius Cordus, who called it "sweet oil of vitriol" (oleum dulci vitrioli), and noted some of its medicinal properties. At about the same time, Theophrastus Bombastus von Hohenheim, better known as Paracelsus, discovered ether's analgesic properties. The name ether was given to the substance in 1730 by F. G. Frobenius.

The American doctor Crawford Williamson Long, M.D., was the first surgeon to use it as an general anesthetic, on March 30, 1842. Its first use is normally associated with the Etherdome in Boston.

In more general chemical terminology, an ether is a C-O-C functional group - for example CH3OCH3, methoxymethane (or dimethyl ether). Note that if either carbon bonded to the oxygen bridge is also double-bonded to another oxygen atom (eg CH3COOCH3) then the compound is an ester, not an ether.

Table of contents
1 Reactions
2 Physical properties
3 Nomenclature

Reactions

Synthesis

  1. 2alcohol → ether
    • This direct reaction is not suitable in most synthetic pathways. There exist several milder methods to produce ethers.
  2. alkoxide + alkyl halide → ether
    • This is called Williamson ether synthesis. It involves treatment of a parent alcohol (R-OH) with a strong base to form the alkoxide ion (R-O-) followed by addition of an appropriate aliphatic compound bearing a suitable leaving group (R-L). Suitable leaving groups (L) include Iodine, Bromine or Sulfonate esters.
  3. alkene + alcohol + acid catalyst → ether

Physical properties

Like
esters, ethers are limited in their ability to form hydrogen bonds. They tend to be more hydrophobic than other, analogous condensation products (such as esters or amides). They are resistant to hydrolysis.

Ethers which have a CH group next to the oxygen form peroxides, which are highly explosive. Due to this and the low ignition point of diethyl ether, diethyl ether is one of the risk factors in laboratories.

Despite their comparably attenuated reactivity, ethers can act as Lewis basess (see Acid-base reaction theories). For instance, diethyl ether forms a complex with boron compounds, such as boron trifluoride etherate, F3B:O(CH2CH3)2

Nomenclature

Ethers can be named in two ways according to the IUPAC naming system. The first, used for simple ethers, simply lists the two groups attached to the ether in alphabetical order followed by the word "ether". Thus CH3-CH2-O-CH3 is ethyl methyl ether. When the ether is part of a more complex molecule, it is named as an alkoxy substituent, so -OCH3 would be considered a "methoxy-" group.

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