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Key People:J. Fraser StoddartAlexander william Williamson...(Show more)Related Topics:ethyl ethermethyl tertiary butyl ethermethyl etherNerolin IItetrahydrofuran...(Show more)

ether, any kind of of a class of organic compounds defined by one oxygen atom bonded to two alkyl or aryl groups. Ethers are comparable in framework to alcohols, and both ethers and alcohols are similar in structure to water. In one alcohol one hydrogen atom of a water molecule is replaced by an alkyl group, whereas in one ether both hydrogen atom are changed by alkyl or aryl groups.

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At room temperature, ethers space pleasant-smelling colourless liquids. Relative to alcohols, ethers are typically less dense, are less soluble in water, and have reduced boiling points. They are reasonably unreactive, and also as a result they are advantageous as solvents because that fats, oils, waxes, perfumes, resins, dyes, gums, and also hydrocarbons. Vapours of details ethers are provided as insecticides, miticides, and also fumigants for soil.

Ethers are likewise important in medicine and also pharmacology, specifically for use as anesthetics. For example, ethyl ether (CH3CH2―O―CH2CH3), simply well-known as ether, was first used as a surgical anesthetic in 1842. Codeine, a potent pain-relieving drug, is the methyl ether of morphine. Due to the fact that ether is extremely flammable, it has actually largely been replaced by less-flammable anesthetics, consisting of nitrous oxide (N2O) and also halothane (CF3―CHClBr).

Ethyl ether is fantastic solvent for extractions and for a wide selection of chemical reactions. It is likewise used together a volatile beginning fluid for diesel engines and also gasoline engines in cold weather. Dimethyl ether is offered as a spray propellant and also refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that rises the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers that ethylene glycol are offered as solvents and plasticizers.


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Nomenclature of ethers

Common names of ethers simply provide the name of the 2 alkyl groups bonded to oxygen and include the native ether. The current practice is to list the alkyl teams in alphabet order (t-butyl methyl ether), however older names often list the alkyl teams in enhancing order of dimension (methyl t-butyl ether). If just one alkyl group is defined in the name, it implies two identical groups, as in ethyl ether for diethyl ether.

Systematic (IUPAC) names because that ethers use the more complex group together the root name, v the oxygen atom and also the smaller group named as an alkoxy substituent. Instances given over are ethoxyethane (diethyl ether), methoxyethane (methyl ethyl ether), 2-methoxy-2-methylpropane (MTBE), and also phenoxybenzene (diphenyl ether). The IUPAC nomenclature works well for compounds with extr functional groups, since the various other functional teams can be described in the source name.

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Physical nature of ethers

Ethers absence the hydroxyl teams of alcohols. Without the strongly polarized O―H bond, ether molecules cannot interact in hydrogen bonding with each other. Ethers do have actually nonbonding electron pairs on your oxygen atoms, however, and they can kind hydrogen bond with various other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The capability to type hydrogen binding with various other compounds makes ethers particularly great solvents because that a wide selection of organic compounds and also a surprisingly large number of inorganic compounds. (For much more information around hydrogen bonding, see chemical bonding: Intermolecular forces.)

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Because ether molecules cannot engage in hydrogen bonding with each other, they have actually much lower boiling points than do alcohols with similar molecular weights. For example, the boiling suggest of diethyl ether (C4H10O, molecular weight 74) is 35 °C (95 °F), yet the boiling suggest of 1-butanol (or n-butyl alcohol; C4H10O, MW 74) is 118 °C (244 °F). In fact, the boiling clues of ethers are lot closer come those the alkanes with comparable molecular weights; the boiling point of pentane (C5H12, MW 72) is 36 °C (97 °F), close come the boiling suggest of diethyl ether.

Complexes that ethers through reagents

The distinctive properties that ethers (i.e., that they space strongly polar, through nonbonding electron pairs yet no hydroxyl group) improve the formation and use of numerous reagents. For example, Grignard reagents cannot kind unless an ether is present to share its lone pair of electrons through the magnesium atom. Complexation the the magnesium atom stabilizes the Grignard reagent and also helps to save it in solution.

Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a advantageous reagent because that making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxicity gas that is inconvenient and hazardous to use. Borane forms stable complexes v ethers, however, and it is regularly supplied and also used together its liquid complicated with tetrahydrofuran (THF). Similarly, gaseous boron trifluoride (BF3) is an ext easily provided as the liquid complex with diethyl ether, referred to as BF3 etherate, fairly than together the toxic, corrosive gas.

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Crown ethers are specialized cyclic polyethers the surround particular metal ions to form crown-shaped cyclic complexes. They are named by making use of the parent name crown preceded by a number explicate the dimension of the ring and followed by the number of oxygen atom in the ring. In the crown-ether complex, the metal ion fits into the cavity that the crown ether and also is solvated through the oxygen atoms. The exterior the the complex is nonpolar, masked by the alkyl teams of the crown ether. Numerous inorganic salts deserve to be made dissolve in nonpolar necessary solvents through complexing them v an ideal crown ether. Potassium ions (K+) are complexed by 18-crown-6 (an 18-membered ring with 6 oxygen atoms), sodium ions (Na+) by 15-crown-5 (15-membered ring, 5 oxygens), and lithium ions (Li+) by 12-crown-4 (12-membered ring, 4 oxygens).

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In every of these crown-ether complexes, just the cation is solvated through the crown ether. In a nonpolar solvent, the anion is not solvated however is dragged into solution by the cation. These “bare” anions in nonpolar solvents can be much much more reactive 보다 they space in polar solvents that solvate and shield the anion. For example, the 18-crown-6 complex of potassium permanganate, KMnO4, disappear in benzene to offer “purple benzene,” through a ceiling MnO4− ion acting together a an effective oxidizing agent. Similarly, the bare −OH ion in salt hydroxide (NaOH), made dissolve in hexane (C6H14) through 15-crown-5, is a much more powerful base and also nucleophile than it is when solvated through polar solvents such as water or one alcohol.