- Plural of ether
Ether is a class of organic compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl or aryl groups — of general formula R–O–R. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether" (ethoxyethane, CH3-CH2-O-CH2-CH3).
Physical propertiesEther molecules cannot form hydrogen bonds among each other, resulting in a relatively low boiling point comparable to that of the analogous alcohols. However, the differences in the boiling points of the ethers and their isometric alcohols become smaller as the carbon chains become longer, as the hydrophobic nature of the carbon chain becomes more predominant over the presence of hydrogen bonding.
Ethers are slightly polar as the R - C - O - C - Z bond angle in the functional group is about 110 degrees, and the C - O dipole does cancel out. Ethers are more polar than alkenes but not as polar as alcohols, esters or amides of comparable structure. However, the presence of two lone pairs of electrons on the oxygen atoms makes hydrogen bonding with water molecules possible, causing the solubility of alcohols (for instance, butan-1-ol) and ethers (ethoxyethane) to be quite dissimilar.
Cyclic ethers such as tetrahydrofuran and 1,4-dioxane are totally miscible in water because of the more exposed oxygen atom for hydrogen bonding as compared to aliphatic ethers.
Ethers can act as Lewis bases. For instance, diethyl ether forms a complex with boron compounds, such as boron trifluoride diethyl etherate (BF3.OEt2). Ethers also coordinate to magnesium in Grignard reagents (RMgBr).
NomenclatureIn 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.
Ethers are not to be confused with the following classes of compounds with the same general structure R-O-R.
Primary, secondary, and tertiary ethersThe terms "primary ether", "secondary ether", and "tertiary ether" are occasionally used and refer to the carbon atom next to the ether oxygen. In a primary ether this carbon is connected to only one other carbon as in diethyl ether CH3-CH2-O-CH2-CH3. An example of a secondary ether is diisopropyl ether (CH3)2CH-O-CH(CH3)2 and that of a tertiary ether is di-tert-butyl ether (CH3)3C-O-C(CH3)3.
Dimethyl ether, a primary, a secondary, and a tertiary ether.
PolyethersPolyethers are compounds with more than one ether group. While the term generally refers to polymers like polyethylene glycol and polypropylene glycol, low molecular compounds such as the crown ethers may sometimes be included.
SynthesisEthers can be prepared in the laboratory in several different ways.
- R-OH +
R-OH → R-O-R + H2O
- This direct reaction requires drastic conditions (heating to 140 degrees Celsius and an acid catalyst, usually concentrated sulfuric acid). Effective for making symmetrical ethers, but not as useful for synthesising asymmetrical ethers because the reaction will yield a mixture of ethers, making it usually not applicable:
- 3R-OH + 3R'-OH → R-O-R + R'-O-R + R'-O-R' + 3H2O
- Conditions must also be controlled to avoid overheating to 170 degrees which will cause intramolecular dehydration,a reaction that yields alkenes. In addition, the alcohol must be in excess.
- R-CH2-CH2(OH) → R-CH=CH2 + H2O
- Such conditions can destroy the delicate structures of some functional groups. There exist several milder methods to produce ethers.
- R-O- +
→ R-O-R + X-
- This reaction is called the Williamson ether synthesis. It involves treatment of a parent alcohol with a strong base to form the alkoxide anion 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 does not work if R is aromatic like in bromobenzene (Br-C6H5), however, if the leaving group is separated by at least one carbon from the benzene, the reaction should proceed (as in Br-CH2-C6H5). Likewise, this method only gives the best yields for primary carbons, as secondary and tertiary carbons will undergo E2 elimination on exposure to the basic alkoxide anion used in the reaction due to steric hindrance from the large alkyl groups. Aryl ethers can be prepared in the Ullmann condensation.
- Nucleophilic Displacement of Alkyl halides 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 SN2 mechanism.
- HO-C6H5 + OH- → O--C6H5
- O--C6H5 + R-X → R-O-C6H5
Cyclic ethers which are also known as epoxides can be prepared:
Reactions| Ethylene oxide |The smallest cyclic ether. |- | |Dimethyl ether |An aerosol spray propellant. |- ||Diethyl ether |A common low boiling solvent (b.p. 34.6°C). |- | | Dimethoxyethane (DME) | A high boiling solvent (b.p. 85°C): |- | | Dioxane | A cyclic ether and high boiling solvent (b.p. 101.1°C). |- | | 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 |Cyclic polyethers that are used as phase transfer catalysts. |- | | Polyethylene glycol (PEG) | A linear polyether, e.g. used in cosmetics: |}
- ILPI page about ethers.
- An Account of the Extraordinary Medicinal Fluid, called Aether, by M. Turner, circa 1788, from Project Gutenberg
ethers in Arabic: إيثر
ethers in Catalan: Èter
ethers in Czech: Ethery
ethers in Danish: Æter (kemi)
ethers in German: Ether
ethers in Estonian: Eetrid
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ethers in French: Éther-oxyde
ethers in Korean: 에테르 (화학)
ethers in Italian: Eteri
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ethers in Latin: Aether (chemica)
ethers in Latvian: Ēteri
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ethers in Macedonian: Етер
ethers in Dutch: Ether (chemie)
ethers in Japanese: エーテル (化学)
ethers in Norwegian: Eter (kjemi)
ethers in Norwegian Nynorsk: Eterar
ethers in Polish: Etery
ethers in Portuguese: Éter
ethers in Romanian: Eter
ethers in Russian: Простые эфиры
ethers in Slovenian: Eter
ethers in Serbian: Етар (хемија)
ethers in Finnish: Eetteri
ethers in Swedish: Etrar
ethers in Vietnamese: Ete
ethers in Ukrainian: Прості ефіри
ethers in Chinese: 醚