Ether is a class of chemical 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). Look up aether, ether in Wiktionary, the free dictionary. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... Properties For other meanings of Atom, see Atom (disambiguation). ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In the context of organic molecules, aryl refers to any member of the set of functional groups or substituents that are derived from a simple aromatic ring. ... For other uses, see Solvent (disambiguation). ... Anesthesia (AE), also anaesthesia (BE), is the process of blocking the perception of pain and other sensations. ... This article is about the chemical compound. ...

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. 3D (left and center) and 2D (right) representations of the terpenoid molecule atisane. ... An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ... Italic text This article is about the boiling point of liquids. ... This article does not cite any references or sources. ... In chemistry, hydrophobic or lipophilic species, or hydrophobes, tend to be electrically neutral and nonpolar, and thus prefer other neutral and nonpolar solvents or molecular environments. ...

Ethers are slightly polar as the C - O - C bond angle in the functional group is about 110 degrees, and the C - O dipole does not 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. Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ...

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. 1,4-Dioxane, often just called dioxane, is a clear, colorless heterocyclic organic compound which is a liquid at room temperature and pressure. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ...

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). A Lewis base is any molecule or ion that can form a new covalent bond by donating a pair of electrons. ... General Name, Symbol, Number boron, B, 5 Chemical series metalloids Group, Period, Block 13, 2, p Appearance black/brown Standard atomic weight 10. ... Boron trifluoride is the chemical compound with the formula BF3. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ...

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 methoxy(CH₃)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. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... Methoxyethane, also known as methyl ethyl ether, is a colorless gaseous ether with a medicine-like odor. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In chemistry, a trivial name (also common or vernacular name) is a non-systematic name. ...

Similar structures

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. Chemical structure of chemical structures that are not ethers selfmade by cacycle File links The following pages link to this file: Ether Categories: GFDL images ...

• 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

In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Furan, also known as furane and furfuran, is a heterocyclic organic compound, produced when wood, especially pine-wood, is distilled. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... This article is about the chemical element. ... A carboxylic acid ester. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... A hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and a amine attached to the same carbon atom: -C(OH)(NR2)-. R can be hydrogen or an alkyl group. ... Structure of anhydride. ...

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 (CH₃)₂CH-O-CH(CH₃)₂ and that of a tertiary ether is di-tert-butyl ether (CH₃)₃C-O-C(CH₃)₃. Chemical structure of diisopropyl ether Diisopropyl ether is an clear, colorless, and liquid secondary ether that is used as a solvent. ... Chemical structure of di-tert-butyl ether Di-tert-butyl ether is an clear, colorless, and liquid tertiary ether that is used as a solvent. ...

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. A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... Polyethylene glycol (PEG) and polyethylene oxide (PEO) are polymers composed of repeating subunits of identical structure, called monomers, and are the most commercially important polyethers. ... Polypropylene glycol or polypropylene oxide is the polymer of propylene glycol. ... Crown ethers are heterocyclic chemical compounds that, in their simplest form, are cyclic oligomers of ethylene oxide. ...

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 sulphuric 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.

• 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 procede (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 (Hg(OCOCF₃)₂ 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: In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule. ... This article does not cite any references or sources. ... This article does not cite any references or sources. ... H2O and HOH redirect here. ... H2O and HOH redirect here. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... In chemistry, nucleophilic substitution is a class of substitution reaction in which an electron-rich nucleophile attacks a molecule and replaces a group or atom, called the leaving group. ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. ... An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... A halide is a binary compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound. ... Williamson ether synthesis was developed by Alexander Williamson in 1850. ... This article does not cite any references or sources. ... Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit In... An anion is an ion with negative charge. ... A leaving group is an atom or molecule that detaches from an organic molecule, which, after detachment, is called the residual or main part. ... An iodide ion is an iodine atom with a −1 (negative one) charge. ... A bromide is a phrase, or person who uses phrases, which have been used and repeated so many times as to become either insincere in their meaning, or seem like an attempt at trying to explain the obvious. ... A sulfonate anion consists of sulfur double bonded to two oxygens and bonded to an R group and an oxygen anion. ... Bromobenzenes are a group of halobenzenes formed in a substitution reaction between bromine and benzene with a hydrogen bromide biproduct. ... The Ullmann condensation or Ullmann ether synthesis is a variation of the Ullmann reaction in which a phenol is coupled to an aryl halide to a diaryl ether in the presence of a copper compound. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-OH) attached to an aromatic hydrocarbon group. ... Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit In... Flash point Non-flammable. ... In chemistry, nucleophilic subsitution is a type of chemical reaction in which one nucleophile (electron donor) replaces another as a covalent substituent of some atom. ... In organic chemistry, an electrophilic addition reaction is an addition reaction where in chemical compound a pi bond is removed by the creation of two new covalent bonds. ... This article is about the chemical compound. ... This article is about the chemical compound. ... For other uses, see Acid (disambiguation). ... In chemistry and biology, catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance, called a catalyst, that is itself not consumed by the overall reaction. ... Late 19th-century photograph of Marknovnikov. ... Tetrahydropyran, or oxane, is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. ... A Protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction. ... An epoxide is a cyclic ether with only three ring atoms. ...

• By the oxidation of alkenes with a peroxyacid such as m-CPBA.
• By the base intramolecular nuclephilic substitution of a halohydrin.

A peroxy acid is an acid in which an acidic -OH group has been replaced by an -OOH group. ... Chemical structure of meta-chloroperoxybenzoic acid meta-Chloroperoxybenzoic acid (mCPBA) is a peroxy acid with chemical formula C7H5ClO3 and CAS number 937-14-4. ...

Reactions

Structure of the polymeric diethyl ether peroxide

Ethers in general are of very low chemical reactivity. Organic reactions are: Chemical structure of Diethyl ether peroxide selfmade by cacycle File links The following pages link to this file: Ether Categories: GFDL images ... Reactivity refers to the rate at which a chemical substance tends to undergo a chemical reaction in time. ...

• 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.

Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... Bromine tribromide, BBr3, is a liquid compound containing boron and bromine. ... It has been suggested that this article or section be merged into hydrogen bromide. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). ... Hydroiodic acid (sometimes also spelled hydriodic acid) is a highly acidic aqueous solution of hydrogen iodide (HI) (Concentrated solution is usually 48 - 57% HI). ... Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ... In chemistry, nucleophilic substitution is a class of substitution reaction in which an electron-rich nucleophile attacks a molecule and replaces a group or atom, called the leaving group. ... An epoxide is a cyclic ether with only three ring atoms. ... A peroxide is a compound containing an oxygen-oxygen single bond. ... Preparing C-4 explosive This article is concerned solely with chemical explosives. ... The general structure of an organic peroxide. ... Diethyl ether peroxides are a class of organic peroxides that slowly form in diethyl ether upon storage under air, light, or in the presence of metal by autoxidation. ... An aldehyde. ... For other uses of THF, see THF (disambiguation) Tetrahydrofuran is a heterocyclic organic compound. ... For other uses, see Solvent (disambiguation). ...

Important ethers

	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:

Chemical structure of Ethylene oxide selfmade by cacycle File links The following pages link to this file: Ether Categories: GFDL images ... “Oxirane” redirects here. ... Image File history File links This is a lossless scalable vector image. ... Dimethyl ether, also known as methoxymethane, oxybismethane, methyl ether, wood ether, and DME, is a colorless gaseous ether with an ethereal odor. ... Aerosol spray can Aerosol spray is a type of canister that sprays an aerosol when its button is pressed or held down. ... Image File history File links This is a lossless scalable vector image. ... This article is about the chemical compound. ... Chemical structure of Dimethoxyethane selfmade by cacycle File links The following pages link to this file: Ether Dimethoxyethane Categories: GFDL images ... Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent. ... Image File history File links No higher resolution available. ... 1,4-Dioxane, often just called dioxane, is a clear, colorless organic compound which is a liquid at room temperature and pressure. ... Image File history File links This is a lossless scalable vector image. ... For other uses of THF, see THF (disambiguation) Tetrahydrofuran is a heterocyclic organic compound. ... Image File history File links No higher resolution available. ... Anisole, also known as methoxybenzene, is a clear, colorless liquid with a pleasant smell similar to that of anise seed. ... An essential oil is a concentrated, hydrophobic liquid containing volatile aromatic compounds from plants. ... This article is about the Pimpinella species, but the name anise is frequently applied to Fennel. ... Image File history File links This is a lossless scalable vector image. ... Crown ethers are heterocyclic chemical compounds that, in their simplest form, are cyclic oligomers of ethylene oxide. ... A phase transfer catalyst or PTC in chemistry is a type of chemical compound, often a quaternary ammonium salt, which facilitates the migration of a particular chemical component in one phase into a other phase in a heterogeneous system. ... Chemical structure of polyethylene glycol selfmade by cacycle File links The following pages link to this file: Ether Polyethylene glycol Categories: GFDL images ... Polyethylene glycol (PEG) and polyethylene oxide (PEO) are polymers composed of repeating subunits of identical structure, called monomers, and are the most commercially important polyethers. ... “Make-up” redirects here. ...

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

In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... --> Flash point -45. ... A thioether (similar to sulfide) is a functional group in organic chemistry that has the structure R1-S-R2 as shown on right. ... The luminiferous aether: it was hypothesised that the Earth moves through a medium of aether that carries light In the late 19th century the luminiferous aether (light-bearing aether), or ether, was a substance postulated to be the medium for the propagation of light. ...

References

1. ^ International Union of Pure and Applied Chemistry. "ethers". Compendium of Chemical Terminology Internet edition.

IUPAC logo The International Union of Pure and Applied Chemistry (IUPAC) (Pronounced as eye-you-pack) is an international non-governmental organization established in 1919 devoted to the advancement of chemistry. ... Compendium of Chemical Terminology (ISBN 0-86542-684-8) is a book published by IUPAC containing internationally accepted definitions for terms in chemistry. ...

External links

• ILPI page about ethers.
• An Account of the Extraordinary Medicinal Fluid, called Aether, by M. Turner, circa 1788, from Project Gutenberg
• The Ether Monument at Boston Public Gardens