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EtherFrom Wikipedia, the free encyclopedia
This article is about a general class of organic compounds. For the specific solvent known as "ether",
seediethyl ether.For other uses, seeAether.
The general structure of an ether
Ethers/ir/are a class oforganic compoundsthat contain an ethergroupanoxygenatomconnected
to twoalkylorarylgroups of general formula ROR'.[1]
A typical example is
thesolventandanestheticdiethyl ether,commonly referred to simply as "ether" (CH3-CH2-O-CH2-CH3).
Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages
incarbohydratesandlignin.
Contents
[hide]
1 Structure and bonding
2 Nomenclatureo 2.1 Polyethers
o 2.2 Related compounds
3 Physical properties
4 Reactions
o 4.1 Ether cleavage
o 4.2 Peroxide formation
o 4.3 Lewis bases
o 4.4 Alpha-halogenation
5 Synthesis
o 5.1 Dehydration of alcohols
o 5.2 Williamson ether synthesis
o 5.3 Ullmann condensation
o 5.4 Electrophilic addition of alcohols to alkenes
o 5.5 Preparation of epoxides
6 Important ethers
7 References
http://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Aether_(disambiguation)http://en.wikipedia.org/wiki/Aether_(disambiguation)http://en.wikipedia.org/wiki/Aether_(disambiguation)http://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Atomhttp://en.wikipedia.org/wiki/Atomhttp://en.wikipedia.org/wiki/Atomhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Arylhttp://en.wikipedia.org/wiki/Arylhttp://en.wikipedia.org/wiki/Arylhttp://en.wikipedia.org/wiki/Ether#cite_note-1http://en.wikipedia.org/wiki/Ether#cite_note-1http://en.wikipedia.org/wiki/Ether#cite_note-1http://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Anesthetichttp://en.wikipedia.org/wiki/Anesthetichttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Carbohydratehttp://en.wikipedia.org/wiki/Carbohydratehttp://en.wikipedia.org/wiki/Carbohydratehttp://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Ether#Structure_and_bondinghttp://en.wikipedia.org/wiki/Ether#Structure_and_bondinghttp://en.wikipedia.org/wiki/Ether#Nomenclaturehttp://en.wikipedia.org/wiki/Ether#Nomenclaturehttp://en.wikipedia.org/wiki/Ether#Polyethershttp://en.wikipedia.org/wiki/Ether#Polyethershttp://en.wikipedia.org/wiki/Ether#Related_compoundshttp://en.wikipedia.org/wiki/Ether#Related_compoundshttp://en.wikipedia.org/wiki/Ether#Physical_propertieshttp://en.wikipedia.org/wiki/Ether#Physical_propertieshttp://en.wikipedia.org/wiki/Ether#Reactionshttp://en.wikipedia.org/wiki/Ether#Reactionshttp://en.wikipedia.org/wiki/Ether#Ether_cleavagehttp://en.wikipedia.org/wiki/Ether#Ether_cleavagehttp://en.wikipedia.org/wiki/Ether#Peroxide_formationhttp://en.wikipedia.org/wiki/Ether#Peroxide_formationhttp://en.wikipedia.org/wiki/Ether#Lewis_baseshttp://en.wikipedia.org/wiki/Ether#Lewis_baseshttp://en.wikipedia.org/wiki/Ether#Alpha-halogenationhttp://en.wikipedia.org/wiki/Ether#Alpha-halogenationhttp://en.wikipedia.org/wiki/Ether#Synthesishttp://en.wikipedia.org/wiki/Ether#Synthesishttp://en.wikipedia.org/wiki/Ether#Dehydration_of_alcoholshttp://en.wikipedia.org/wiki/Ether#Dehydration_of_alcoholshttp://en.wikipedia.org/wiki/Ether#Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Ether#Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Ether#Ullmann_condensationhttp://en.wikipedia.org/wiki/Ether#Ullmann_condensationhttp://en.wikipedia.org/wiki/Ether#Electrophilic_addition_of_alcohols_to_alkeneshttp://en.wikipedia.org/wiki/Ether#Electrophilic_addition_of_alcohols_to_alkeneshttp://en.wikipedia.org/wiki/Ether#Preparation_of_epoxideshttp://en.wikipedia.org/wiki/Ether#Preparation_of_epoxideshttp://en.wikipedia.org/wiki/Ether#Important_ethershttp://en.wikipedia.org/wiki/Ether#Important_ethershttp://en.wikipedia.org/wiki/Ether#Referenceshttp://en.wikipedia.org/wiki/Ether#Referenceshttp://en.wikipedia.org/wiki/File:Ether-(general).pnghttp://en.wikipedia.org/wiki/File:Ether-(general).pnghttp://en.wikipedia.org/wiki/File:Ether-(general).pnghttp://en.wikipedia.org/wiki/File:Ether-(general).pnghttp://en.wikipedia.org/wiki/Ether#Referenceshttp://en.wikipedia.org/wiki/Ether#Important_ethershttp://en.wikipedia.org/wiki/Ether#Preparation_of_epoxideshttp://en.wikipedia.org/wiki/Ether#Electrophilic_addition_of_alcohols_to_alkeneshttp://en.wikipedia.org/wiki/Ether#Ullmann_condensationhttp://en.wikipedia.org/wiki/Ether#Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Ether#Dehydration_of_alcoholshttp://en.wikipedia.org/wiki/Ether#Synthesishttp://en.wikipedia.org/wiki/Ether#Alpha-halogenationhttp://en.wikipedia.org/wiki/Ether#Lewis_baseshttp://en.wikipedia.org/wiki/Ether#Peroxide_formationhttp://en.wikipedia.org/wiki/Ether#Ether_cleavagehttp://en.wikipedia.org/wiki/Ether#Reactionshttp://en.wikipedia.org/wiki/Ether#Physical_propertieshttp://en.wikipedia.org/wiki/Ether#Related_compoundshttp://en.wikipedia.org/wiki/Ether#Polyethershttp://en.wikipedia.org/wiki/Ether#Nomenclaturehttp://en.wikipedia.org/wiki/Ether#Structure_and_bondinghttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Carbohydratehttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Anesthetichttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Ether#cite_note-1http://en.wikipedia.org/wiki/Arylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Atomhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Aether_(disambiguation)http://en.wikipedia.org/wiki/Diethyl_ether 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8 External links
Structure and bonding[edit]
Ethers feature C-O-C linkage defined by a bond angle of about 110 and C-O distances of about 140 pm.
The barrier to rotation about the C-O bonds is low. The bonding of oxygen in ethers, alcohols, and water is
similar. In the language ofvalence bond theory,the hybridization at oxygen is sp3.
Oxygen is more electronegative than carbon, thus the hydrogens alpha to ethers are more acidic than in
simple hydrocarbons. They are far less acidic than hydrogens alpha to carbonyl groups (such as
inketonesoraldehydes), however.
Depending on the groups at R and R', ethers are classified into two types:
1. Simple ethers or symmetrical ethers; e.g.,Diethyl ether,dimethyl ether,etc.
2. Mixed ethers or asymmetrical ethers; e.g.,Methyl ethyl ether,Methyl phenyl ether,etc.
Nomenclature[edit]
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 isanisole,because it was originally
found inaniseed.Thearomaticethers includefurans.Acetals(-alkoxy ethers R-CH(-OR)-O-R) are
another class of ethers with characteristic properties.
In theIUPAC nomenclaturesystem, ethers are named using the general formula "alkoxyalkane", for
example CH3-CH2-O-CH3ismethoxyethane.If the ether is part of a more complex molecule, it is
described as an alkoxy substituent, so -OCH3would be considered a "methoxy-"group. The
simpleralkylradical is written in front, so CH3-O-CH2CH3would 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 atrivial usage.
Polyethers[edit]
Polyethers are compounds with more than one ether group.
Thecrown ethersare examples of low-molecular weight polyethers. Some toxins produced
bydinoflagellatessuch asbrevetoxinandciguatoxinare in a class known
as cyclicor ladderpolyethers.
Polyether generally refers topolymerswhich contain the ether functional group in their main chain. The
termglycolis reserved for low to medium rangemolar masspolymer when the nature of theend-
group,which is usually ahydroxylgroup, still matters. The term "oxide" or other terms are used forhigh molar mass polymer when end-groups no longer affect polymer properties.
http://en.wikipedia.org/wiki/Ether#External_linkshttp://en.wikipedia.org/wiki/Ether#External_linkshttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=1http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=1http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=1http://en.wikipedia.org/wiki/Valence_bond_theoryhttp://en.wikipedia.org/wiki/Valence_bond_theoryhttp://en.wikipedia.org/wiki/Valence_bond_theoryhttp://en.wikipedia.org/wiki/Ketoneshttp://en.wikipedia.org/wiki/Ketoneshttp://en.wikipedia.org/wiki/Ketoneshttp://en.wikipedia.org/wiki/Aldehydeshttp://en.wikipedia.org/wiki/Aldehydeshttp://en.wikipedia.org/wiki/Aldehydeshttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Methoxybenzenehttp://en.wikipedia.org/wiki/Methoxybenzenehttp://en.wikipedia.org/wiki/Methoxybenzenehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=2http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=2http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=2http://en.wikipedia.org/wiki/Anisolehttp://en.wikipedia.org/wiki/Anisolehttp://en.wikipedia.org/wiki/Anisolehttp://en.wikipedia.org/wiki/Aniseedhttp://en.wikipedia.org/wiki/Aniseedhttp://en.wikipedia.org/wiki/Aniseedhttp://en.wikipedia.org/wiki/Aromatichttp://en.wikipedia.org/wiki/Aromatichttp://en.wikipedia.org/wiki/Aromatichttp://en.wikipedia.org/wiki/Furanhttp://en.wikipedia.org/wiki/Furanhttp://en.wikipedia.org/wiki/Furanhttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/IUPAC_nomenclaturehttp://en.wikipedia.org/wiki/IUPAC_nomenclaturehttp://en.wikipedia.org/wiki/IUPAC_nomenclaturehttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Methoxyhttp://en.wikipedia.org/wiki/Methoxyhttp://en.wikipedia.org/wiki/Methoxyhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Trivial_namehttp://en.wikipedia.org/wiki/Trivial_namehttp://en.wikipedia.org/wiki/Trivial_namehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=3http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=3http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=3http://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/wiki/Dinoflagellatehttp://en.wikipedia.org/wiki/Dinoflagellatehttp://en.wikipedia.org/wiki/Dinoflagellatehttp://en.wikipedia.org/wiki/Brevetoxinhttp://en.wikipedia.org/wiki/Brevetoxinhttp://en.wikipedia.org/wiki/Brevetoxinhttp://en.wikipedia.org/wiki/Ciguatoxinhttp://en.wikipedia.org/wiki/Ciguatoxinhttp://en.wikipedia.org/wiki/Ciguatoxinhttp://en.wikipedia.org/wiki/Polymerhttp://en.wikipedia.org/wiki/Polymerhttp://en.wikipedia.org/wiki/Polymerhttp://en.wikipedia.org/wiki/Polyolhttp://en.wikipedia.org/wiki/Polyolhttp://en.wikipedia.org/wiki/Polyolhttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/End-grouphttp://en.wikipedia.org/wiki/End-grouphttp://en.wikipedia.org/wiki/End-grouphttp://en.wikipedia.org/wiki/End-grouphttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/End-grouphttp://en.wikipedia.org/wiki/End-grouphttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Polyolhttp://en.wikipedia.org/wiki/Polymerhttp://en.wikipedia.org/wiki/Ciguatoxinhttp://en.wikipedia.org/wiki/Brevetoxinhttp://en.wikipedia.org/wiki/Dinoflagellatehttp://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=3http://en.wikipedia.org/wiki/Trivial_namehttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Methoxyhttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/IUPAC_nomenclaturehttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/Furanhttp://en.wikipedia.org/wiki/Aromatichttp://en.wikipedia.org/wiki/Aniseedhttp://en.wikipedia.org/wiki/Anisolehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=2http://en.wikipedia.org/wiki/Methoxybenzenehttp://en.wikipedia.org/wiki/Methoxyethanehttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Aldehydeshttp://en.wikipedia.org/wiki/Ketoneshttp://en.wikipedia.org/wiki/Valence_bond_theoryhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=1http://en.wikipedia.org/wiki/Ether#External_links 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Aliphatic polyethers
Name of the
polymers with
low to medium
molar mass
Name of the polymers
with high molar massPreparation
Repeating
unit
Examples of
trade names
Paraformaldehyd
e
Polyoxymethylene(POM
) or polyacetal or
polyformaldehyde
Step-growth
polymerisationofformaldeh
yde
-CH2O-Delrin
fromDuPont
Polyethylene
glycol(PEG)
Polyethylene oxide
(PEO) or
polyoxyethylene (POE)
Ring-opening
polymerizationofethylene
oxide
-CH2CH2O-Carbowax
fromDow
Polypropylene
glycol(PPG)
Polypropylene oxide
(PPO) or
polyoxypropylene) (POP)
Anionicring-opening
polymerization ofpropylene
oxide
-
CH2CH(CH3)
O-
Polytetramethyle
ne glycol
(PTMG) or
Polytetramethyle
ne ether glycol
(PTMEG)
Polytetrahydrofuran(PT
HF)
Acid-catalyzed ring-opening
polymerizationoftetrahydrofuran
-CH
2CH
2CH2CH
2O-
Terathane
fromInvistaand PolyTHF
fromBASF
Aromatic polyethers
The phenyl ether polymers are a class of polyethers containing aromatic cycles in their main
chain:Polyphenyl ether(PPE) andPoly(p-phenylene oxide)(PPO).
Related compounds[edit]
Many classes of compounds with C-O-C linkages are not considered ethers:Esters(R-C(=O)-O-
R),hemiacetals(R-CH(-OH)-O-R),carboxylic acid anhydrides(RC(=O)-O-C(=O)R).
Physical properties[edit]
Ethermoleculescannot formhydrogen bondswith each other, resulting in relatively lowboiling
pointscompared to those of the analogousalcohols.The difference, however, in the boiling points of
the ethers and their isometric alcohols becomes lower as the carbon chains become longer, as the van
der Waalsinteractions of the extended carbon chain dominates over the presence of hydrogen
bonding.
Ethers are slightly polar. The C-O-C bond angle in the functional group is about 110, and the C-O
dipoles do not cancel out. Ethers are more polar than alkenes but not as polar as alcohols, esters,
http://en.wikipedia.org/wiki/Paraformaldehydehttp://en.wikipedia.org/wiki/Paraformaldehydehttp://en.wikipedia.org/wiki/Paraformaldehydehttp://en.wikipedia.org/wiki/Polyoxymethylene_plastichttp://en.wikipedia.org/wiki/Polyoxymethylene_plastichttp://en.wikipedia.org/wiki/Step-growth_polymerisationhttp://en.wikipedia.org/wiki/Step-growth_polymerisationhttp://en.wikipedia.org/wiki/Step-growth_polymerisationhttp://en.wikipedia.org/wiki/Formaldehydehttp://en.wikipedia.org/wiki/Formaldehydehttp://en.wikipedia.org/wiki/Formaldehydehttp://en.wikipedia.org/wiki/Formaldehydehttp://en.wikipedia.org/wiki/DuPonthttp://en.wikipedia.org/wiki/DuPonthttp://en.wikipedia.org/wiki/DuPonthttp://en.wikipedia.org/wiki/Polyethylene_glycolhttp://en.wikipedia.org/wiki/Polyethylene_glycolhttp://en.wikipedia.org/wiki/Polyethylene_glycolhttp://en.wikipedia.org/wiki/Ring-opening_polymerizationhttp://en.wikipedia.org/wiki/Ring-opening_polymerizationhttp://en.wikipedia.org/wiki/Ring-opening_polymerizationhttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Dow_Chemical_Companyhttp://en.wikipedia.org/wiki/Dow_Chemical_Companyhttp://en.wikipedia.org/wiki/Dow_Chemical_Companyhttp://en.wikipedia.org/wiki/Polypropylene_glycolhttp://en.wikipedia.org/wiki/Polypropylene_glycolhttp://en.wikipedia.org/wiki/Polypropylene_glycolhttp://en.wikipedia.org/wiki/Anionic_addition_polymerizationhttp://en.wikipedia.org/wiki/Anionic_addition_polymerizationhttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Polytetrahydrofuranhttp://en.wikipedia.org/wiki/Polytetrahydrofuranhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Invistahttp://en.wikipedia.org/wiki/Invistahttp://en.wikipedia.org/wiki/Invistahttp://en.wikipedia.org/wiki/BASFhttp://en.wikipedia.org/wiki/BASFhttp://en.wikipedia.org/wiki/BASFhttp://en.wikipedia.org/wiki/Polyphenyl_etherhttp://en.wikipedia.org/wiki/Polyphenyl_etherhttp://en.wikipedia.org/wiki/Polyphenyl_etherhttp://en.wikipedia.org/wiki/Poly(p-phenylene_oxide)http://en.wikipedia.org/wiki/Poly(p-phenylene_oxide)http://en.wikipedia.org/wiki/Poly(p-phenylene_oxide)http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=4http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=4http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=4http://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Carboxylic_acid_anhydridehttp://en.wikipedia.org/wiki/Carboxylic_acid_anhydridehttp://en.wikipedia.org/wiki/Carboxylic_acid_anhydridehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=5http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=5http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=5http://en.wikipedia.org/wiki/Moleculehttp://en.wikipedia.org/wiki/Moleculehttp://en.wikipedia.org/wiki/Moleculehttp://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Van_der_Waals_forcehttp://en.wikipedia.org/wiki/Van_der_Waals_forcehttp://en.wikipedia.org/wiki/Van_der_Waals_forcehttp://en.wikipedia.org/wiki/Van_der_Waals_forcehttp://en.wikipedia.org/wiki/Van_der_Waals_forcehttp://en.wikipedia.org/wiki/Van_der_Waals_forcehttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/Moleculehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=5http://en.wikipedia.org/wiki/Carboxylic_acid_anhydridehttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=4http://en.wikipedia.org/wiki/Poly(p-phenylene_oxide)http://en.wikipedia.org/wiki/Polyphenyl_etherhttp://en.wikipedia.org/wiki/BASFhttp://en.wikipedia.org/wiki/Invistahttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Polytetrahydrofuranhttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Anionic_addition_polymerizationhttp://en.wikipedia.org/wiki/Polypropylene_glycolhttp://en.wikipedia.org/wiki/Polypropylene_glycolhttp://en.wikipedia.org/wiki/Dow_Chemical_Companyhttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Ring-opening_polymerizationhttp://en.wikipedia.org/wiki/Ring-opening_polymerizationhttp://en.wikipedia.org/wiki/Polyethylene_glycolhttp://en.wikipedia.org/wiki/Polyethylene_glycolhttp://en.wikipedia.org/wiki/DuPonthttp://en.wikipedia.org/wiki/Formaldehydehttp://en.wikipedia.org/wiki/Formaldehydehttp://en.wikipedia.org/wiki/Step-growth_polymerisationhttp://en.wikipedia.org/wiki/Step-growth_polymerisationhttp://en.wikipedia.org/wiki/Polyoxymethylene_plastichttp://en.wikipedia.org/wiki/Paraformaldehydehttp://en.wikipedia.org/wiki/Paraformaldehyde 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oramidesof comparable structure. However, the presence of two lone pairs of electrons on the
oxygen atoms makes hydrogen bonding with water molecules possible.
Cyclic ethers such astetrahydrofuranand1,4-dioxaneare miscible in water because of the more
exposed oxygen atom for hydrogen bonding as compared to aliphaticethers.
Selected d
Ether Structure m.p. (C)
Dimethyl ether CH3-O-CH3 -138.5 -23.
Diethyl ether CH3CH2-O-CH2CH3 -116.3 34.
Tetrahydrofuran O(CH2)4 -108.4 66.
Dioxane O(C2H4)2O 11.8 101.
Other properties are:
The lower ethers are highly volatile and flammable.
Lower ethers also act asanaesthetics.
Ethers act as good organic solvents.
Reactions[edit]
Structure of the polymericdiethyl ether peroxide
Ethers are quite stablechemical compoundswhich do not react
withbases,activemetals,diluteacids,oxidising agentsandreducing agents.Generally, they are of
low chemicalreactivity,but they are more reactive thanalkanes(epoxides,ketals, and acetals are
unrepresentative classes of ethers and are discussed in separate articles). Important reactions are
listed below.[2]
Ether cleavage[edit]
http://en.wikipedia.org/wiki/Amidehttp://en.wikipedia.org/wiki/Amidehttp://en.wikipedia.org/wiki/Amidehttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/1,4-dioxanehttp://en.wikipedia.org/wiki/1,4-dioxanehttp://en.wikipedia.org/wiki/1,4-dioxanehttp://en.wikipedia.org/wiki/Aliphatichttp://en.wikipedia.org/wiki/Aliphatichttp://en.wikipedia.org/wiki/Aliphatichttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Dioxanehttp://en.wikipedia.org/wiki/Dioxanehttp://en.wikipedia.org/wiki/Anaestheticshttp://en.wikipedia.org/wiki/Anaestheticshttp://en.wikipedia.org/wiki/Anaestheticshttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=6http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=6http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=6http://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Metalhttp://en.wikipedia.org/wiki/Metalhttp://en.wikipedia.org/wiki/Metalhttp://en.wikipedia.org/wiki/Concentrationhttp://en.wikipedia.org/wiki/Concentrationhttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Oxidising_agenthttp://en.wikipedia.org/wiki/Oxidising_agenthttp://en.wikipedia.org/wiki/Oxidising_agenthttp://en.wikipedia.org/wiki/Reducing_agenthttp://en.wikipedia.org/wiki/Reducing_agenthttp://en.wikipedia.org/wiki/Reducing_agenthttp://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Alkaneshttp://en.wikipedia.org/wiki/Alkaneshttp://en.wikipedia.org/wiki/Alkaneshttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Ether#cite_note-Ullmann-2http://en.wikipedia.org/wiki/Ether#cite_note-Ullmann-2http://en.wikipedia.org/wiki/Ether#cite_note-Ullmann-2http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=7http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=7http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=7http://en.wikipedia.org/wiki/File:Diethylether_peroxide_chemical_structure.pnghttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=7http://en.wikipedia.org/wiki/Ether#cite_note-Ullmann-2http://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Alkaneshttp://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Reducing_agenthttp://en.wikipedia.org/wiki/Oxidising_agenthttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Concentrationhttp://en.wikipedia.org/wiki/Metalhttp://en.wikipedia.org/wiki/Reactivity_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=6http://en.wikipedia.org/wiki/Anaestheticshttp://en.wikipedia.org/wiki/Dioxanehttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Aliphatichttp://en.wikipedia.org/wiki/1,4-dioxanehttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Amide -
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Although ethers resist hydrolysis, their polar bonds are cloven by mineral acids such as hydrobromic
acid andhydroiodic acid.Hydrogen chloridecleaves ethers only slowly. Methyl ethers typically afford
methyl halides:
ROCH3+ HBr CH3Br + ROH
These reactions proceed viaoniumintermediates, i.e. [RO(H)CH3]+Br
-.
Some ethers undergo rapid cleavage withboron tribromide(evenaluminium chlorideis used in
some cases) to give the alkyl bromide.[3]
Depending on the substituents, some ethers can be
cloven with a variety of reagents, e.g. strong base.
Peroxide formation[edit]
When stored in the presence of air or oxygen, ethers tend to formexplosiveperoxides,such
asdiethyl ether peroxide.The reaction is accelerated by light, metal catalysts, and aldehydes.Inaddition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether
is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less
volatile than the original ether, will become concentrated in the last few drops of liquid.
Lewis bases[edit]
Ethers serve asLewis basesand Bronsted bases. Strong acids protonate the oxygen to give
"onium ions." For instance, diethyl ether forms a complex with boron trifluoride,i.e. diethyl
etherate (BF3.OEt2). Ethers also coordinate to Mg(II) center inGrignard reagents.Polyethers,
including manyantibiotics,cryptands,andcrown ethers,bind alkali metal cations strongly.
Alpha-halogenation[edit]
This reactivity is akin to the tendency of ethers with alpha hydrogen atoms to form peroxides.
Chlorine gives alpha-chloroethers.
Synthesis[edit]
Ethers can be prepared in the laboratory in several different ways.
Dehydration of alcohols[edit]
TheDehydrationofalcoholsaffords ethers:
2 R-OH R-O-R +H2Oat high temperature
[4]
This direct nucleophillic subsititution reaction requires elevated temperatures (about
125 C). The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for
http://en.wikipedia.org/wiki/Hydroiodic_acidhttp://en.wikipedia.org/wiki/Hydroiodic_acidhttp://en.wikipedia.org/wiki/Hydroiodic_acidhttp://en.wikipedia.org/wiki/Hydrogen_chloridehttp://en.wikipedia.org/wiki/Hydrogen_chloridehttp://en.wikipedia.org/wiki/Hydrogen_chloridehttp://en.wikipedia.org/wiki/Onium_compoundshttp://en.wikipedia.org/wiki/Onium_compoundshttp://en.wikipedia.org/wiki/Onium_compoundshttp://en.wikipedia.org/wiki/Boron_tribromidehttp://en.wikipedia.org/wiki/Boron_tribromidehttp://en.wikipedia.org/wiki/Boron_tribromidehttp://en.wikipedia.org/wiki/Aluminium_chloridehttp://en.wikipedia.org/wiki/Aluminium_chloridehttp://en.wikipedia.org/wiki/Aluminium_chloridehttp://en.wikipedia.org/wiki/Ether#cite_note-3http://en.wikipedia.org/wiki/Ether#cite_note-3http://en.wikipedia.org/wiki/Ether#cite_note-3http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=8http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=8http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=8http://en.wikipedia.org/wiki/Explosive_materialhttp://en.wikipedia.org/wiki/Explosive_materialhttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Aldehydehttp://en.wikipedia.org/wiki/Aldehydehttp://en.wikipedia.org/wiki/Aldehydehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=9http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=9http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=9http://en.wikipedia.org/wiki/Lewis_basehttp://en.wikipedia.org/wiki/Lewis_basehttp://en.wikipedia.org/wiki/Lewis_basehttp://en.wikipedia.org/wiki/Boron_trifluoridehttp://en.wikipedia.org/wiki/Boron_trifluoridehttp://en.wikipedia.org/wiki/Boron_trifluoridehttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Grignard_reagenthttp://en.wikipedia.org/wiki/Grignard_reagenthttp://en.wikipedia.org/wiki/Grignard_reagenthttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Cryptandhttp://en.wikipedia.org/wiki/Cryptandhttp://en.wikipedia.org/wiki/Cryptandhttp://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=10http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=10http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=10http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=11http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=11http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=11http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=12http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=12http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=12http://en.wikipedia.org/wiki/Dehydration_reactionhttp://en.wikipedia.org/wiki/Dehydration_reactionhttp://en.wikipedia.org/wiki/Dehydration_reactionhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Ether#cite_note-4http://en.wikipedia.org/wiki/Ether#cite_note-4http://en.wikipedia.org/wiki/File:Symm2.svghttp://en.wikipedia.org/wiki/Ether#cite_note-4http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Dehydration_reactionhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=12http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=11http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=10http://en.wikipedia.org/wiki/Crown_etherhttp://en.wikipedia.org/wiki/Cryptandhttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Grignard_reagenthttp://en.wikipedia.org/wiki/Boron_trifluoridehttp://en.wikipedia.org/wiki/Lewis_basehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=9http://en.wikipedia.org/wiki/Aldehydehttp://en.wikipedia.org/wiki/Diethyl_ether_peroxidehttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Explosive_materialhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=8http://en.wikipedia.org/wiki/Ether#cite_note-3http://en.wikipedia.org/wiki/Aluminium_chloridehttp://en.wikipedia.org/wiki/Boron_tribromidehttp://en.wikipedia.org/wiki/Onium_compoundshttp://en.wikipedia.org/wiki/Hydrogen_chloridehttp://en.wikipedia.org/wiki/Hydroiodic_acid -
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generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be
protonated, which would give a mixture of products. Diethyl ether is produced from ethanol by
this method. Cyclic ethers are readily generated by this approach. Elimination reactions
compete with dehydration of the alcohol:
R-CH2-CH2(OH) R-CH=CH2+ H2O
The dehydration route often requires conditions incompatible with delicate molecules.
Several milder methods exist to produce ethers.
Williamson ether synthesis[edit]
Nucleophilic displacementofalkyl halidesbyalkoxides
R-ONa + R'-X R-O-R' + NaX
This reaction is called theWilliamson ether synthesis.It involves treatment of a
parentalcoholwith a strongbaseto form the alkoxide, followed by addition of an
appropriate aliphatic compound bearing a suitableleaving group(R-X). Suitable
leaving groups (X) includeiodide,bromide,orsulfonates.This method usually does
not work well for aryl halides (e.g.bromobenzene(see Ullmann condensation
below). Likewise, this method only gives the best yields for primary halides.
Secondary and tertiary halides are prone to undergo E2 elimination on exposure to
the basic alkoxide anion used in the reaction due to steric hindrance from the large
alkyl groups.
In a related reaction, alkyl halides undergo nucleophilic displacement
byphenoxides.The R-X cannot be used to react with the alcohol.
However,phenolscan be used to replace the alcohol, while maintaining the alkyl
halide. Since phenols are acidic, they readily react with a strong baselikesodium
hydroxideto 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 anSN2mechanism.
C6H5OH + OH- C6H5-O-+ H2O
C6H5-O-+ R-X C6H5OR
Ullmann condensation[edit]
TheUllmann condensationis similar to the Williamson method except that
the substrate is an aryl halide. Such reactions generally require a catalyst,
such as copper.
Electrophilic addition of alcohols to alkenes[edit]
Alcohols add to electrophilically activatedalkenes.
http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=13http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=13http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=13http://en.wikipedia.org/wiki/Nucleophilic_displacementhttp://en.wikipedia.org/wiki/Nucleophilic_displacementhttp://en.wikipedia.org/wiki/Alkyl_halidehttp://en.wikipedia.org/wiki/Alkyl_halidehttp://en.wikipedia.org/wiki/Alkyl_halidehttp://en.wikipedia.org/wiki/Alkoxidehttp://en.wikipedia.org/wiki/Alkoxidehttp://en.wikipedia.org/wiki/Alkoxidehttp://en.wikipedia.org/wiki/Halidehttp://en.wikipedia.org/wiki/Halidehttp://en.wikipedia.org/wiki/Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Leaving_grouphttp://en.wikipedia.org/wiki/Leaving_grouphttp://en.wikipedia.org/wiki/Leaving_grouphttp://en.wikipedia.org/wiki/Iodidehttp://en.wikipedia.org/wiki/Iodidehttp://en.wikipedia.org/wiki/Iodidehttp://en.wikipedia.org/wiki/Bromidehttp://en.wikipedia.org/wiki/Bromidehttp://en.wikipedia.org/wiki/Bromidehttp://en.wikipedia.org/wiki/Sulfonatehttp://en.wikipedia.org/wiki/Sulfonatehttp://en.wikipedia.org/wiki/Sulfonatehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Phenoxidehttp://en.wikipedia.org/wiki/Phenoxidehttp://en.wikipedia.org/wiki/Phenoxidehttp://en.wikipedia.org/wiki/Phenolshttp://en.wikipedia.org/wiki/Phenolshttp://en.wikipedia.org/wiki/Phenolshttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Sodium_hydroxidehttp://en.wikipedia.org/wiki/Sodium_hydroxidehttp://en.wikipedia.org/wiki/Sodium_hydroxidehttp://en.wikipedia.org/wiki/Sodium_hydroxidehttp://en.wikipedia.org/wiki/SN2http://en.wikipedia.org/wiki/SN2http://en.wikipedia.org/wiki/SN2http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=14http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=14http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=14http://en.wikipedia.org/wiki/Ullmann_condensationhttp://en.wikipedia.org/wiki/Ullmann_condensationhttp://en.wikipedia.org/wiki/Ullmann_condensationhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=15http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=15http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=15http://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=15http://en.wikipedia.org/wiki/Ullmann_condensationhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=14http://en.wikipedia.org/wiki/SN2http://en.wikipedia.org/wiki/Sodium_hydroxidehttp://en.wikipedia.org/wiki/Sodium_hydroxidehttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Phenolshttp://en.wikipedia.org/wiki/Phenoxidehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Sulfonatehttp://en.wikipedia.org/wiki/Bromidehttp://en.wikipedia.org/wiki/Iodidehttp://en.wikipedia.org/wiki/Leaving_grouphttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Williamson_ether_synthesishttp://en.wikipedia.org/wiki/Halidehttp://en.wikipedia.org/wiki/Alkoxidehttp://en.wikipedia.org/wiki/Alkyl_halidehttp://en.wikipedia.org/wiki/Nucleophilic_displacementhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=13 -
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R2C=CR2+ R-OH R2CH-C(-O-R)-R2
Acidcatalysisis required for this reaction. Often, mercury
trifluoroacetate (Hg(OCOCF3)2) is used as a catalyst for the reaction,
generating an ether withMarkovnikovregiochemistry. Using similarreactions,tetrahydropyranyl ethersare used asprotective groupsfor
alcohols.
Preparation of epoxides[edit]
Main article:epoxide
Epoxidesare typically prepared by oxidation of alkenes. The most
important epoxide in terms of industrial scale is ethylene oxide, which
is produced by oxidation of ethylene with oxygen. Other epoxides are
produced by one of two routes:
By the oxidation of alkenes with aperoxyacidsuch asm-CPBA.
By the base intramolecular nucleophilic substitution of a
halohydrin.
Important ethers[edit]
Ethylene oxide
The smallestcyclic ether.
Also the simplestepoxide.
Dimethyl ether
Anaerosol spray
propellant.A potential
renewable alternative fuel
fordiesel engineswith
acetane ratingas high as
56-57.
Diethyl ether
A common lowboilingsolvent(b.p. 34.6
C) and an
earlyanaesthetic.Used asstarting fluid for diesel
engines. Also used as
arefrigerantand in the
manufacture ofsmokeless
gunpowder,along with useinperfumery.
http://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Catalysishttp://en.wikipedia.org/wiki/Catalysishttp://en.wikipedia.org/wiki/Catalysishttp://en.wikipedia.org/wiki/Markovnikovhttp://en.wikipedia.org/wiki/Markovnikovhttp://en.wikipedia.org/wiki/Markovnikovhttp://en.wikipedia.org/wiki/Markovnikovhttp://en.wikipedia.org/wiki/Markovnikovhttp://en.wikipedia.org/wiki/Tetrahydropyranyl_etherhttp://en.wikipedia.org/wiki/Tetrahydropyranyl_etherhttp://en.wikipedia.org/wiki/Tetrahydropyranyl_etherhttp://en.wikipedia.org/wiki/Protective_grouphttp://en.wikipedia.org/wiki/Protective_grouphttp://en.wikipedia.org/wiki/Protective_grouphttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=16http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=16http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=16http://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Peroxyacidhttp://en.wikipedia.org/wiki/Peroxyacidhttp://en.wikipedia.org/wiki/Peroxyacidhttp://en.wikipedia.org/wiki/Meta-Chloroperoxybenzoic_acidhttp://en.wikipedia.org/wiki/Meta-Chloroperoxybenzoic_acidhttp://en.wikipedia.org/wiki/Meta-Chloroperoxybenzoic_acidhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=17http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=17http://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=17http://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/w/index.php?title=Cyclic_ether&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Cyclic_ether&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Cyclic_ether&action=edit&redlink=1http://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Aerosol_spray#Propellanthttp://en.wikipedia.org/wiki/Aerosol_spray#Propellanthttp://en.wikipedia.org/wiki/Aerosol_spray#Propellanthttp://en.wikipedia.org/wiki/Aerosol_spray#Propellanthttp://en.wikipedia.org/wiki/Diesel_enginehttp://en.wikipedia.org/wiki/Diesel_enginehttp://en.wikipedia.org/wiki/Diesel_enginehttp://en.wikipedia.org/wiki/Cetane_numberhttp://en.wikipedia.org/wiki/Cetane_numberhttp://en.wikipedia.org/wiki/Cetane_numberhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Anaesthetichttp://en.wikipedia.org/wiki/Anaesthetichttp://en.wikipedia.org/wiki/Anaesthetichttp://en.wikipedia.org/wiki/Refrigeranthttp://en.wikipedia.org/wiki/Refrigeranthttp://en.wikipedia.org/wiki/Refrigeranthttp://en.wikipedia.org/wiki/Smokeless_gunpowderhttp://en.wikipedia.org/wiki/Smokeless_gunpowderhttp://en.wikipedia.org/wiki/Smokeless_gunpowderhttp://en.wikipedia.org/wiki/Smokeless_gunpowderhttp://en.wikipedia.org/wiki/Perfumeryhttp://en.wikipedia.org/wiki/Perfumeryhttp://en.wikipedia.org/wiki/Perfumeryhttp://en.wikipedia.org/wiki/File:Diethylether_chemical_structure.svghttp://en.wikipedia.org/wiki/File:Dimethylether_chemical_structure.svghttp://en.wikipedia.org/wiki/File:Ethylene_oxide_chemical_structure.pnghttp://en.wikipedia.org/wiki/File:Diethylether_chemical_structure.svghttp://en.wikipedia.org/wiki/File:Dimethylether_chemical_structure.svghttp://en.wikipedia.org/wiki/File:Ethylene_oxide_chemical_structure.pnghttp://en.wikipedia.org/wiki/File:Diethylether_chemical_structure.svghttp://en.wikipedia.org/wiki/File:Dimethylether_chemical_structure.svghttp://en.wikipedia.org/wiki/File:Ethylene_oxide_chemical_structure.pnghttp://en.wikipedia.org/wiki/Perfumeryhttp://en.wikipedia.org/wiki/Smokeless_gunpowderhttp://en.wikipedia.org/wiki/Smokeless_gunpowderhttp://en.wikipedia.org/wiki/Refrigeranthttp://en.wikipedia.org/wiki/Anaesthetichttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/Cetane_numberhttp://en.wikipedia.org/wiki/Diesel_enginehttp://en.wikipedia.org/wiki/Aerosol_spray#Propellanthttp://en.wikipedia.org/wiki/Aerosol_spray#Propellanthttp://en.wikipedia.org/wiki/Dimethyl_etherhttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/w/index.php?title=Cyclic_ether&action=edit&redlink=1http://en.wikipedia.org/wiki/Ethylene_oxidehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=17http://en.wikipedia.org/wiki/Meta-Chloroperoxybenzoic_acidhttp://en.wikipedia.org/wiki/Peroxyacidhttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/wiki/Epoxidehttp://en.wikipedia.org/w/index.php?title=Ether&action=edit§ion=16http://en.wikipedia.org/wiki/Protective_grouphttp://en.wikipedia.org/wiki/Tetrahydropyranyl_etherhttp://en.wikipedia.org/wiki/Markovnikovhttp://en.wikipedia.org/wiki/Catalysishttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Alkene 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Dimethoxyethane(D
ME)
A high boiling solvent
(b.p. 85 C):
Dioxane
A cyclic ether and high
boiling solvent
(b.p. 101.1 C).
Tetrahydrofuran(TH
F)
A cyclic ether, one of the
most polar simple ethers
that is used as a solvent.
Anisole(methoxyben
zene)
An aryl etherand a major
constituent of theessential
oilofaniseseed.
Crown ethers Cyclic polyethers that areused asphase transfer
catalysts.
Polyethylene
glycol(PEG)
A linear polyether, e.g.
used
incosmeticsandpharmaceuticals.
References
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