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Ether

From Wikipedia, the free encyclopedia Jump to: navigation, search This article is about a general class of organic compounds. For other uses, see Aether.

The general structure of an ether Ethers ( /ˈiːθər/) are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'.[1] A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether" (CH3-CH2-OCH2-CH3). Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages in carbohydrates and lignin.

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1 Structure and bonding 2 Nomenclature o 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 8 External links

[edit] Structure and bonding

The term glycol is reserved for low to medium range molar mass polymer when the nature of the end-group. for example CH3-CH2-O-CH3 is methoxyethane. is a trivial usage. ethers are named using the general formula "alkoxyalkane". so -OCH3 would be considered a "methoxy-" group. ether is classified into two types: 1) Simple ethers or symmetrical ethers 2) Mixed ethers or asymmetrical ethers [edit] Nomenclature The names for simple ethers (i. Methyl phenyl ether is anisole. The crown ethers are examples of low-molecular weight polyethers.e. it is described as an alkoxy substituent. however. The aromatic ethers include furans." Ethyl methyl ether (CH3OC2H5). The bonding of oxygen in ethers. because it was originally found in aniseed. thus the hydrogens alpha to ethers are more acidic than in simple hydrocarbons. Acetals (α-alkoxy ethers R-CH(-OR)-O-R) are another class of ethers with characteristic properties. "ethyl methyl ether" in the example above. [edit] Polyethers Polyethers are compounds with more than one ether group. e. those with none or few other functional groups) are a composite of the two substituents followed by "ether. Polyether generally refers to polymers which contain the ether functional group in their main chain." but was once called sweet oil of vitriol. Some toxins produced by dinoflagellates such as brevetoxin and ciguatoxin are in a class known as cyclic or ladder polyethers. very common ethers acquired names before rules for nomenclature were formalized. and water is similar. Diethyl ether is simply called "ether.5° and C-O distances of about 140 pm. Depending on the groups at R and R'. IUPAC rules are often not followed for simple ethers.g. The barrier to rotation about the C-O bonds is low. In the IUPAC nomenclature system. The nomenclature of describing the two alkyl groups and appending "ether". The simpler alkyl radical is written in front. alcohols. Oxygen is more electronegative than carbon. which is usually a hydroxyl group.Ethers feature C-O-C linkage defined by a bond angle of about 104. They are far less acidic than hydrogens alpha to carbonyl groups (such as in ketones or aldehydes). Aliphatic polyethers . As for other organic compounds. still matters. so CH3-O-CH2CH3 would be given as methoxy(CH3O)ethane(CH2CH3). the hybridization at oxygen is sp3. The term "oxide" or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties. In the language of valence bond theory. diphenylether (C6H5OC6H5). If the ether is part of a more complex molecule.

as the van der Waals interactions of the extended carbon chain dominates over the presence of hydrogen bonding.4-dioxane are miscible in water because of the more exposed oxygen atom for hydrogen bonding as compared to aliphatic ethers. . however. hemiacetals (R-CH(-OH)-O-R). and the CO dipoles do not cancel out. Ethers are slightly polar. or amides of comparable structure. [edit] Related compounds Many classes of compounds with C-O-C linkages are not considered ethers: Esters (R-C(=O)-OR). carboxylic acid anhydrides (RC(=O)-O-C(=O)R). The C-O-C bond angle in the functional group is about 110°. Cyclic ethers such as tetrahydrofuran and 1. [edit] Physical properties Ether molecules cannot form hydrogen bonds with each other. esters. in the boiling points of the ethers and their isometric alcohols becomes lower as the carbon chains become longer. the presence of two lone pairs of electrons on the oxygen atoms makes hydrogen bonding with water molecules possible. Ethers are more polar than alkenes but not as polar as alcohols. However.Name of the Name of the polymers with low to polymers with high medium molar mass molar mass Polyoxymethylene Paraformaldehyde (POM) or polyacetal or polyformaldehyde Polyethylene oxide Polyethylene glycol (PEO) or (PEG) polyoxyethylene (POE) Polypropylene oxide Polypropylene glycol (PPO) ou (PPG) polyoxypropylene) (POP) Polytetramethylene glycol (PTMG) or Polytetrahydrofuran Polytetramethylene (PTHF) ether glycol (PTMEG) Aromatic polyethers Preparation Repeating unit Examples of trade names Delrin from DuPont Carbowax from Dow Step-growth polymerisation of -CH2Oformaldehyde Ring-opening polymerization of -CH2CH2Oethylene oxide Anionic ringopening -CH2CH(CH3)Opolymerization of propylene oxide Terathane Acid-catalyzed from Invista ring-opening and polymerization of CH2CH2CH2CH2OPolyTHF tetrahydrofuran from BASF The phenyl ether polymers are a class of polyethers containing aromatic cycles in their main chain: Polyphenyl ether (PPE) and Poly(p-phenylene oxide) (PPO). The difference. resulting in a relatively low boiling points compared to those of the analogous alcohols.

3 34. Important reactions are listed below. [edit] Peroxide formation When stored in the presence of air or oxygen. ethers tend to form explosive peroxides.[3] Depending on the substituents. ketals. i. when an ether is used as a solvent. In addition to avoiding storage conditions likely to form peroxides. [RO(H)CH3]+Br-. not to distill it to dryness. e. Solubility in 1 liter of Ether Structure (°C) (°C) H2 O Dimethyl ether CH3-O-CH3 -138. and aldehydes. Some ethers rapidly cleave with boron tribromide (even aluminium chloride is used in some cases) to give the alkyl bromide.0 Miscible Dioxane O(C2H4)2O 11. and acetals are unrepresentative classes of ethers and are discussed in separate articles).g. b. they are cleaved by mineral acids such as hydrobromic acid and hydroiodic acid. it is recommended.4 66.0 70 g CH3CH2-ODiethyl ether -116.[2] [edit] Ether cleavage Although ethers resist hydrolysis.45 [edit] Reactions Structure of the polymeric diethyl ether peroxide Ethers in general are of low chemical reactivity. Hydrogen chloride cleaves ethers only slowly. such as diethyl ether peroxide. strong base. Methyl ethers typically afford methyl halides: ROCH3 + HBr → CH3Br + ROH These reactions proceed via onium intermediates.p. but they are more reactive than alkanes (epoxides.p. metal catalysts. .4 69 g CH2CH3 Tetrahydrofuran O(CH2)4 -108.e. The reaction is accelerated by light.8 101.5 -23. some ethers can be cleaved with a variety of reagents.3 Miscible Dipole moment (D) 1.14 1. as any peroxides that may have formed.74 0.Selected data about some alkyl ethers m.30 1.

i.OEt2). [edit] Alpha-halogenation This reactivity is akin to the tendency of ethers with alpha hydrogen atoms to form peroxides. and crown ethers.e. Such reactions must compete with dehydration of the alcohol: R-CH2-CH2(OH) → R-CH=CH2 + H2O The dehydration route often requires conditions incompatible with delicate molecules. will become concentrated in the last few drops of liquid." For instance. usually sulfuric acid. [edit] Lewis bases Ethers serve as Lewis bases and Bronsted bases. [edit] Synthesis Ethers can be prepared in the laboratory in several different ways. diethyl etherate (BF3. . Suitable leaving groups (X) include iodide. diethyl ether forms a complex with boron trifluoride. Chlorine gives alpha-chloroethers. Ethers also coordinate to Mg(II) center in Grignard reagents. The method is effective for generating symmetrical ethers. Several milder methods exist to produce ethers. It involves treatment of a parent alcohol with a strong base to form the alkoxide. bind alkali metal cations strongly. The reaction is catalyzed by acids. Diethyl ether is produced from ethanol by this method. Polyethers. [edit] Williamson ether synthesis Nucleophilic displacement of alkyl halides by alkoxides R-ONa + R'-X → R-O-R' + NaX This reaction is called the Williamson ether synthesis. followed by addition of an appropriate aliphatic compound bearing a suitable leaving group (R-X). Cyclic ethers are readily generated by this approach. but not unsymmetrical ethers. cryptands. [edit] Dehydration of alcohols The Dehydration of alcohols affords ethers: 2 R-OH → R-O-R + H2O at high temperature This direct reaction requires elevated temperatures (about 125 °C).being less volatile than the original ether. Strong acids protonate the oxygen to give "onium ions. including many antibiotics.

phenols can be used to replace the alcohol. The phenoxide ion will then substitute the -X group in the alkyl halide. mercury trifluoroacetate (Hg(OCOCF3)2) is used as a catalyst for the reaction.bromide. geneating an ether with Markovnikov regiochemistry. However. this method only gives the best yields for primary halides. such as copper. In a related reaction. Such reactions generally require a catalyst.+ R-X → C6H5OR [edit] Ullmann condensation The Ullmann condensation is similar to the Williamson method except that the substrate is an aryl halide. alkyl halides undergo nucleophilic displacement by phenoxides. forming an ether with an aryl group attached to it in a reaction with an SN2 mechanism. tetrahydropyranyl ethers are used as protective groups for alcohols. The R-X cannot be used to react with the alcohol. bromobenzene (see Ullmann condensation below). Since phenols are acidic. Often. which is produced by oxidation of ethylene with oxygen.+ H2O C6H5-O. C6H5OH + OH. Using similar reactions. [edit] Electrophilic addition of alcohols to alkenes Alcohols add to electrophilically activated alkenes. Likewise. R2C=CR2 + R-OH → R2CH-C(-O-R)-R2 Acid catalysis is required for this reaction.→ C6H5-O. By the base intramolecular nucleophilic substitution of a halohydrin. 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. The most important epoxide in terms of industrial scale is ethylene oxide. [edit] Preparation of epoxides Main article: epoxide Epoxides are typically prepared by oxidation of alkenes. [edit] Important ethers . they readily react with a strong base like sodium hydroxide to form phenoxide ions.g. Other epoxides are produced by one of two routes:   By the oxidation of alkenes with a peroxyacid such as m-CPBA. This method usually does not work well for aryl halides (e. while maintaining the alkyl halide. or sulfonates.

6 °C).Ethylene oxide The smallest cyclic ether. 101. A common low boiling solvent (b. Anisole (methoxybenzene) An aryl ether and a major constituent of the essential oil of anise seed. one of the most polar simple ethers that is used as a solvent. [edit] . A potential renewable alternative fuel for diesel engines with a cetane rating as high as 56-57.1 °C).p. used in cosmetics and (PEG) pharmaceuticals. Polyethylene glycol A linear polyether. Crown ethers Cyclic polyethers that are used as phase transfer catalysts.p.g. Used as starting fluid for diesel engines. A high boiling solvent (b. An aerosol spray propellant.p. Dimethyl ether Diethyl ether Dimethoxyethane (DME) Dioxane Tetrahydrofuran (THF) A cyclic ether. and an early anaesthetic. 34. e. 85 °C): A cyclic ether and high boiling solvent (b.

1 Dehidrasi alkohol o 4. Untuk teknologi jaringan komputer.3 Sebagai basa Lewis 4 Sintesis o 4. cari Artikel ini berisi tentang sebuah golongan utama dari senyawa organik. lihat ethernet.3 Kondensasi Ullmann o 4.4 Adisi elektrofilik alkohol ke alkena o 4.[1] Contoh senyawa eter yang paling umum adalah pelarut dan anestetik dietil eter (etoksietana.Eter Dari Wikipedia bahasa Indonesia. Eter sangat umum ditemukan dalam kimia organik dan biokimia. dengan R dapat berupa alkil maupun aril. Struktur umum dari eter Eter adalah suatu senyawa organik yang mengandung gugus R—O—R'.1 Pembelahan eter o 3. CH3-CH2-O-CH2-CH3).2 Pembentukan peroksida o 3. lihat dietil eter. karena gugus ini merupakan gugus penghubung pada senyawa karbohidrat dan lignin.2 Sintesis eter Williamson o 4.5 Pembuatan epoksida 5 Beberapa eter penting 6 Referensi [sunting] Struktur dan ikatan .1 Struktur Serupa 2 Sifat-sifat fisika 3 Reaksi o 3. Untuk senyawa yang lebih spesifik. Daftar isi [sembunyikan]       1 Struktur dan ikatan o 1. ensiklopedia bebas Belum Diperiksa Langsung ke: navigasi.

hibridisasi oksigen pada senyawa eter adalah sp3.3 -108. Eter lebih polar daripada alkena.4 66.74 Eter Dimetil eter Dietil eter Struktur CH3-O-CH3 CH3CH2-OCH2CH3 Tetrahidrofuran O(CH2)4 . nitrogen. namun tidak sepolar alkohol. Menurut teori ikatan valensi. ataupun amida. Walau demikian.   Senyawa aromatik seperti furan di mana oksigen adalah sebahagian daripada sistem aromatik. keberadaan dua pasangan elektron menyendiri pada atom oksigen eter. Senyawa dengan atom-atom karbon yang bersebelahan dengan oksigen terikat dengan oksigen. Sawar rotasi ikatan C-O sangatlah rendah.5 -23. sehingga hidrogen yang berada pada posisi alfa relatif terhadap eter bersifat lebih asam daripada hidrogen senyawa hidrokarbon. atau sulfur: o Ester R-C(=O)-O-R o Asetal R-CH(-O-R)-O-R o Aminal R-CH(-NH-R)-O-R o Anhidrida R-C(=O)-O-C(=O)-R [sunting] Sifat-sifat fisika Molekul-molekul eter tidak dapat berikatan hidrogen dengan sesamanya. [sunting] Struktur Serupa Eter tidak boleh disamakan dengan gugus-gugus sejenis berikut yang mempunyai stuktur serupa . Eter siklik seperti tetrahidrofuran dan 1.4-dioksana sangat larut dalam air karena atom oksigennya lebih terpapar ikatan hidrogen dibandingkan dengan eter-eter alifatik lainnya.0 69 g Larut pada semua perbandingan 1. Oksigen lebih elektronegatif daripada karbon. Beberapa alkil eter Titik lebur Titidk didih Kelarutan dalam 1 L Momen (°C) (°C) H2 O dipol (D) -138.Eter memiliki ikatan C-O-C yang bersudut ikat sekitar 110° dan jarak C-O sekitar 140 pm. sehingga mengakibatkan senyawa eter memiliki titik didih yang relatif rendah dibandingkan dengan alkohol. hidrogen ini kurang asam dibandingkan dengan alfa hidrogen keton.4 34.R-O-R.30 -116.14 1.0 70 g 1. walau demikian. ester. Eter bersifat sedikit polar karena sudut ikat C-O-C eter adalah 110 derajat.Eter dapat dipisahkan secara sempurna melalui destilasi. memungkinkan eter berikatan hidrogen dengan molekul air. sehingga dipol C-O tidak dapat meniadakan satu sama lainnya.

Eter juga berkooridasi dengan Mg(II) dalam reagen Grignard. diisopropil eter dan tetrahidrofuran jarang digunakan sebagai pelarut. dapat membentuk peroksida.8 101. yaitu [RO(H)CH3]+Br-. Oleh karena ini.Dioksana O(C2H4)2O 11. dan dipercepat oleh cahaya. Asam kuat dapat memprotonasi oksigen. walaupun ia lebih reaktif daripada alkana. misalnya dietil eter peroksida.3 Larut pada semua perbandingan 0. beberapa eter dapat dibelah menggunakan berbagai jenis reagen seperti basa kuat.45 [sunting] Reaksi Eter secara umumnya memiliki reaktivitas kimia yang rendah. Polieter (misalnya eter mahkoya) dapat mengikat logam dengan sangat kuat. [sunting] Pembentukan peroksida Eter primer dan sekunder dengan gugus CH di sebelah oksigen eter. Beberapa contoh reaksi penting eter adalah sebagai berikut.[3] Berganting pada substituennya. dietil eter dapat membentuk kompleks dengan boron trifluorida. menghasilkan "ion onium".[2] [sunting] Pembelahan eter Walaupun eter tahan terhadap hidrolisis. [sunting] Sebagai basa Lewis Eter dapat berperan sebagai basa Lewis maupun basa Bronsted. Beberapa jenis eter dapat terbelah dengan cepat menggunakan boron tribomida (dalam beberapa kasus aluminium klorida juga dapat digunakan) dan menghasilkan alkil bromida. dan aldehida. ia dapat dibelah oleh asam-asam mineral seperi asam bromat dan asam iodat. yaitu dietil eterat (BF3.OEt2). katalis logam. Reaksi ini memerlukan oksigen (ataupun udaara). Peroksida yang dihasilkan dapat meledak. [sunting] Sintesis Eter dapat disintesis melalui beberapa cara: [sunting] Dehidrasi alkohol Dehidrasi senyawa alkohol dapat menghasilkan eter: . Asam klorida hanya membelah eter dengan sangat lambat. Metil eter umumnya akan menghasilkan metil halida: ROCH3 + HBr → CH3Br + ROH Reaksi ini berjalan via zat antara onium. Contohnya.

Gugus lepas tersebut dapat berupa iodida. Biasanya merkuri trifluoroasetat (Hg(OCOCF3)2) digunakan sebagai katalis. ia dapat bereaksi dengan basa kuat seperti natrium hidroksida. namun tidak dapat digunakan untuk menghasilkan eter tak simetris. Metode ini efektif untukn menghasilkan eter simetris. maupun sulfonat.+ H2O C6H5-O. Dietil eter dihasilkan dari etanol menggunakan metode ini.2 R-OH → R-O-R + H2O Reaksi ini memerlukan temperatur yang tinggi (sekitar 125 °C). misalnya tembaga. kecuali substratnya adalah aril halida.→ C6H5-O. yang diikuti oleh adisi pada senyawa alifatik terkait yang memiliki gugus lepas (R-X). RX tidak dapat digunakan untuk bereaksi dengan alkohol. Oleh karena fenol bersifat asam. [sunting] Pembuatan epoksida . bromida. [sunting] Sintesis eter Williamson Eter dapat pula dibuat melalui substitusi nukleofilik alkil halida oleh alkoksida R-ONa + R'-X → R-O-R' + NaX Reaksi ini dinamakan sintesis eter Williamson. Eter siklik dapat pula dihasilkan menggunakan metode ini. Reaksi ini menghasilkan rendemen reaksi yang tinggi untuk halida primer.+ R-X → C6H5OR [sunting] Kondensasi Ullmann Kondensasi Ullmann mirip dengan metode Williamson. Dalam reaksi lainnya yang terkait. membentuk ion fenoksida. Namun. Reaksi ini umumnya memerlukan katalis. Reaksi ini dikatalisis oleh asam. [sunting] Adisi elektrofilik alkohol ke alkena Alkohol dapat melakukan reaksi adisi dengan alkena yang diaktivasi secara elektrofilik. fenol dapat digunakan untuk menggantikan alkohol. Halida sekunder dan tersier sangat rawan menjalani reaksi eliminasi E2 seketika berpaparan dengan anion alkoksida yang sangat basa. menghasilkan alkoksida. biasanya asam sulfat. C6H5OH + OH. alkil halida menjalani substitusi nukleofilik oleh fenoksida. Ion fenoksida ini kemudian mensubstitusi gugus -X pada alkil halida. menghasilkan eter dengan gugus aril yang melekat padanya melalui mekanisme reaksi SN2. Metode ini biasanya tidak bekerja dengan baik dengan aril halida (misalnya bromobenzena). Reaksi ini melibatkan penggunaan alkohol dengan basa kuat. R2C=CR2 + R-OH → R2CH-C(-O-R)-R2 Katalis asam diperlukan agar reaksi ini dapat berjalan.

Eposida yang paling penting dalam industri adalah etilena oksida. 34. dan dulunya merupakan zat anestetik. Anisol (metoksibenzena) Merupakan eter aril dan komponen utama minyak esensial pada biji adas manis.p. 85 °C): Merupakan eter siklik dan pelarut pada suhu tinggi (b. Dimetil eter Dietil eter Dimetoksimetana (DME) Dioksana Tetrahidrofuran (THF) Eter siklik. Merupakan bahan bakar alternatif yang potensial untuk mesin diesel karena mempunyai bilangan cetan sebesar 5657. Merupakan propelan pada aerosol. Pelarut pada suhu tinggi (b. [sunting] Beberapa eter penting Etilena oksida Eter siklik yang paling sederhana.Artikel utama untuk bagian ini adalah: epoksida Epoksida biasanya dibuat melalui oksidasi alkena. . Melalui substitusi nukleofilik intramolekuler halohidrin.6 °C). Merupakan pelarut umum pada suhu rendah (b. yang dihasilkan melalui oksidasi etilena dengan oksigen.p.1 °C). salah satu eter yang bersifat paling polar yang digunakan sebagai pelarut. Epoksida lainnya dapat dihasilkan melalui dua cara:   Melalui oksidasi alkena dengan peroksiasam seperti Asam meta-kloroperoksibenzoat (mCPBA). Digunakan sebagai cairan starter kontak pada mesin diesel. 101.p.

Eter mahkota Polieter siklik yang digunakan sebagai katalis transfer fase. [sunting] . Polietilen glikol (PEG) Merupakan polieter linear. digunakan pada kosmetik dan farmasi.