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Ether: Navigation Search Aether
Ether: Navigation Search Aether
From Wikipedia, the free encyclopedia Jump to: navigation, search This article is about a general class of organic compounds. For other uses, see Aether.
The general structure of an ether Ethers ( /ir/) are a class of organic compounds that contain an ether group an oxygen atom connected to two alkyl or aryl groups of general formula ROR'.[1] A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether" (CH3-CH2-OCH2-CH3). Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages in carbohydrates and lignin.
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[edit] Nomenclature
The names for simple ethers (i.e. those with none or few other functional groups) are a composite of the two substituents followed by "ether." Ethyl methyl ether (CH3OC2H5), diphenylether (C6H5OC6H5). IUPAC rules are often not followed for simple ethers. As for other organic compounds, very common ethers acquired names before rules for nomenclature were formalized. Diethyl ether is simply called "ether," but was once called sweet oil of vitriol. Methyl phenyl ether is anisole, because it was originally found in aniseed. The aromatic ethers include furans. Acetals (-alkoxy ethers R-CH(-OR)-O-R) are another class of ethers with characteristic properties. 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 simpler alkyl radical is written in front, so CH3-O-CH2CH3 would be given as methoxy(CH3O)ethane(CH2CH3). The nomenclature of describing the two alkyl groups and appending "ether", e.g. "ethyl methyl ether" in the example above, is a trivial usage.
[edit] Polyethers
Polyethers are compounds with more than one ether group. The crown ethers are examples of low-molecular weight polyethers. Some toxins produced by dinoflagellates such as brevetoxin and ciguatoxin are in a class known as cyclic or ladder polyethers. Polyether generally refers to polymers which contain the ether functional group in their main chain. The term glycol is reserved for low to medium range molar mass polymer when the nature of the end-group, which is usually a hydroxyl group, still matters. The term "oxide" or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties. Aliphatic polyethers Name of the Name of the polymers with low to polymers with high medium molar mass molar mass Polyoxymethylene Paraformaldehyde (POM) or polyacetal or polyformaldehyde Polyethylene oxide Polyethylene glycol (PEO) or (PEG) polyoxyethylene (POE) Polypropylene oxide Polypropylene glycol (PPO) ou (PPG) polyoxypropylene) Examples of trade names Delrin from DuPont Carbowax from Dow
Preparation
Repeating unit
Step-growth polymerisation of -CH2Oformaldehyde Ring-opening polymerization of -CH2CH2Oethylene oxide Anionic ringopening -CH2CH(CH3)Opolymerization of
(POP) Polytetramethylene glycol (PTMG) or Polytetramethylene ether glycol (PTMEG) Aromatic polyethers Polytetrahydrofuran (PTHF)
propylene oxide Terathane Acid-catalyzed from Invista ring-opening and polymerization of CH2CH2CH2CH2OPolyTHF tetrahydrofuran from BASF
The phenyl ether polymers are a class of polyethers containing aromatic cycles in their main chain: Polyphenyl ether (PPE) and Poly(p-phenylene oxide) (PPO).
[edit] Reactions
Structure of the polymeric diethyl ether peroxide Ethers in general are of low chemical reactivity, but they are more reactive than alkanes (epoxides, ketals, and acetals are unrepresentative classes of ethers and are discussed in separate articles). Important reactions are listed below.[2]
[edit] Alpha-halogenation
This reactivity is akin to the tendency of ethers with alpha hydrogen atoms to form peroxides. Chlorine gives alpha-chloroethers.
[edit] Synthesis
Ethers can be prepared in the laboratory in several different ways.
By the oxidation of alkenes with a peroxyacid such as m-CPBA. By the base intramolecular nucleophilic substitution of a halohydrin.
Dimethyl ether
Dioxane
Tetrahydrofuran (THF)
A cyclic ether, one of the most polar simple ethers that is used as a solvent.
Anisole (methoxybenzene)
An aryl ether and a major constituent of the essential oil of anise seed.
Crown ethers
Polyethylene glycol A linear polyether, e.g. used in cosmetics and (PEG) pharmaceuticals.