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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&section=1http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=1http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=2http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=3http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=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&section=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_theoryhtt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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&section=4http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=4http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=5http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=5http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=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&section=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&section=6http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=6http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=7http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=7http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=7http://en.wikipedia.org/wiki/File:Diethylether_peroxide_chemical_structure.pnghttp://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=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

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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&section=13http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=13http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=14http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=14http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=15http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=15http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=15http://en.wikipedia.org/wiki/Ullmann_condensationhttp://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=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&section=16http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=16http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=17http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=17http://en.wikipedia.org/w/index.php?title=Ether&action=edit&section=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&section=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&section=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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