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20-September-2008 09:55:57 - Ether Redirected from Ethers This article is about a general class of organic compounds. For other uses, see Aether. The general structure for an ether The general structure for an 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'.1 A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as ether ethoxyethane, CH3-CH2-O-CH2-CH3. Contents 1 Physical properties 2 Nomenclature 3 Similar structures 4 Primary, secondary, and tertiary ethers 5 Polyethers 6 Organic reactions 6.1 Synthesis 6.2 Reactions 7 Important ethers 8 See also 9 References 10 External links Physical properties Ether 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 COC 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. Nomenclature 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 methoxyCH3OethaneCH2CH3. The nomenclature of describing the two alkyl groups and appending ether, e.g. ethyl methyl ether in the example above, is a trivial usage. Similar structures Not all compounds of the formula R-O-R are ethers. Not all compounds of the formula R-O-R are ethers. Ethers are not to be confused with the following classes of compounds with the same general structure R-O-R. Aromatic compounds like furan where the oxygen is part of the aromatic system. Compounds where one of the carbon atoms next to the oxygen is connected to oxygen, nitrogen, or sulfur: Esters R-C=O-O-R Acetals R-CH-O-R-O-R Aminals R-CH-NH-R-O-R Anhydrides R-C=O-O-C=O-R Primary, secondary, and tertiary ethers The 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 CH32CH-O-CHCH32 and that of a tertiary ether is di-tert-butyl ether CH33C-O-CCH33. Dimethyl ether A primary ether diethyl ether A secondary ether diisopropyl ether A tertiary ether di-tert-butyl ether Dimethyl ether, a primary, a secondary, and a tertiary ether. Polyethers Polyethers 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. Organic reactions Synthesis Ethers can be prepared in the laboratory in several different ways. Intermolecular Dehydration of alcohols: 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-CH2OH → R-CH=CH2 + H2O Such conditions can destroy the delicate structures of some functional groups. There exist several milder methods to produce ethers. Nucleophilic displacement of alkyl halides by alkoxides R-O- + R-X → 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 Electrophilic addition of alcohols to alkenes. R2C=CR2 + R-OH → R2CH-C-O-R-R2 Acid catalysis is required for this reaction. Often, Mercury trifluoroacetate HgOCOCF32 is used as a catalyst for the reaction, creating an ether with Markovnikov regiochemistry. Tetrahydropyranyl ethers are used as protective groups for alcohols. Cyclic ethers which are also known as epoxides can be prepared: By the oxidation of alkenes with a peroxyacid such as m-CPBA. By the base intramolecular nuclephilic substitution of a halohydrin. Reactions Structure of the polymeric diethyl ether peroxide Structure of the polymeric diethyl ether peroxide Ethers in general are of very low chemical reactivity. Organic reactions are: Hydrolysis. Ethers are hydrolyzed only under drastic conditions like heating with boron tribromide or boiling in hydrobromic acid. Lower mineral acids containing a halogen, such as hydrochloric acid will cleave ethers, but very slowly. Hydrobromic acid and hydroiodic acid are the only two that do so at an appreciable rate. Certain aryl ethers can be cleaved by aluminium chloride. Nucleophilic displacement. Epoxides, or cyclic ethers in three-membered rings, are highly susceptible to nucleophilic attack and are reactive in this fashion. Peroxide formation. Primary and secondary ethers with a CH group next to the ether oxygen easily form highly explosive organic peroxides e.g. diethyl ether peroxide in the presence of oxygen, light, and metal and aldehyde impurities. For this reason ethers like diethyl ether and THF are usually avoided as solvents in industrial processes Important ethers Chemical structure of ethylene oxide Ethylene oxide The smallest cyclic ether. Chemical structure of dimethyl ether Dimethyl ether An aerosol spray propellant. Chemical structure of diethyl ether Diethyl ether A common low boiling solvent b.p. 34.6°C. Chemical structure of dimethoxyethane Dimethoxyethane DME A high boiling solvent b.p. 85°C: Chemical structure of dioxane Dioxane A cyclic ether and high boiling solvent b.p. 101.1°C. Chemical structure of THF Tetrahydrofuran THF A cyclic ether, one of the most polar simple ethers that is used as a solvent. Chemical structure of anisole Anisole methoxybenzene An aryl ether and a major constituent of the essential oil of anise seed. Chemical structure of 18-crown-6 Crown ethers Cyclic polyethers that are used as phase transfer catalysts. Chemical structure of polyethylene glycol Polyethylene glycol PEG A linear polyether, e.g. used in cosmetics: See also Functional group Methoxy Petroleum ether, not an ether but a low boiling alkane mixture. Thioether, analogs of ethers with the oxygen replaced by sulfur. Luminiferous ether References December 2007 ^ International Union of Pure and Applied Chemistry. ethers. Compendium of Chemical Terminology Internet ion. External links ILPI page about ethers. An Account of the Extraordinary Medicinal Fluid, called Aether, by M. Turner, circa 1788, from Project Gutenberg v d e Functional groups Chemical class: Alcohol Aldehyde Alkane Alkene Alkyne Amide Amine Azo compound Benzene derivative Carboxylic acid Cyanate Disulfide Ester Ether Haloalkane Hydrazone Imine Isocyanide Isocyanate Ketone Oxime Nitrile Nitro compound Nitroso compound Peroxide Phosphoric acid Pyridine derivative Sulfone Sulfonic acid Sulfoxide Thioester Thioether Thiol Retrieved from http://en..org/wiki/Ether Categories: Ethers | Functional groupsHidden category: Articles needing additional references from December 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Català Česky Dansk Deutsch Eesti Español Esperanto Français í•œêµì–´ Italiano עברית Latina LatvieÅ¡u Magyar МакедонÑ?ки Nederlands 日本語 ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Polski Português Română РуÑ?Ñ?кий SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Suomi Svenska Tiếng Việt УкраїнÑ?ька ä¸æ–‡ This page was last modified on 1 August 2008, at 21:26
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