Wurtz reaction


This reaction is precisely parallel to the Wurtz Reaction in the aliphatic series, by which, for instance, n-butane can be obtained by the action of sodium on ethyl bromide.  [c.288]

All hydrocarbons prepared by th -. Wurtz reaction contain small quantities of unsaturated hydrocarbons. These may be removed by shaking repeatedly with 10 pier cent, of the volume of concentrated sulphuric acid until the acid is no longer coloured (or is at most extremely pale yellow) each shaking should be of about 5 minutes duration. The hydrocarbon is washed with water, 10 pier cent sodium carbonate solution, water (twice), and dried with anhydrous magnesium or calcium sulphate. It is then distilled from sodium two distillations are usually necessary  [c.236]

Two mechanisms have been proposed for the Wurtz reaction (compare Section III,7) and for the Wurtz-Fittig reaction. According to one, sodium reacts with the alkyl halide to produce a sodium halide and a free radical, which subsequently undergoes coupling, disproportionation, etc.  [c.508]

Williamson synthesis Wohl-Ziegler reaction Wolff rearrangement Wolff Kishner reduction Wurtz reaction Wurtz-Fittig reaction  [c.1211]

This reaction is precisely parallel to the Wurtz Reaction in the aliphatic series, by which, for instance, -butane can be obtained by the action of sodium on ethyl bromide.  [c.288]

As stated above, intermolecular coupling reactions between carbon atoms are of limited use. In the classical Wurtz reaction two identical primary alkyl iodide molecules are reduced by sodium. /i-Hectane for example, has been made by this method in 60%  [c.36]

A variant of the Wurtz reaction is the preparation of tetrabutyltin from activated magnesium chips, butyl chloride, and stannic chloride in a hydrocarbon mixture. Only a small amount of tetrahydrofuran is required for the reaction to proceed in high yield (86).  [c.68]

Coupling and Gyclization Reactions. An important process in organic chemistry is the coupling of alkyl haUdes to form longer-chain hydrocarbons. This process is classically referred to as the Wurtz reaction. Alkyl hahdes can be coupled using sodium metal in ethyl ether as the solvent, but the yields are normally low and the product impure. One of the most successful reagents for coupling alkyl hahdes is Ni(CO)4 (141)  [c.70]

This reaction, based on the Wurtz reaction, tends to go to completion and the yield of technically useful chlorosilane is low.  [c.820]

The coupling of alkyl halides 1 upon treatment with a metal, e.g. elemental sodium, to yield symmetrical alkanes 2, is called the Wurtz reaction. Aryl alkanes can be prepared by the Wurtz-Fittig reaction, i.e. the coupling of aryl halides with alkyl halides.  [c.304]

Cyclopropanes undergo a ready reaction with bromine to give 1,3-dibromopropane, and can in turn be formed from 1,3-dibromopropane by the Wurtz reaction. A variation  [c.137]

Elimination of halogen by sodium (Wurtz s reaction) gives a higher hydrocarbon.  [c.103]

Wurtz - Fittig reaction. The interaction of an aryl halide, alkyl hahde and sodium gives a reasonable yield of an alkyl aryl hydrocarbon, for example  [c.508]

Elimination of halogen by sodium (Wurtz s reaction) gives a higher hydrocarbon.  [c.103]

With Water. Wurtz was the first to obtain ethylene glycol by heating ethylene oxide and water in a sealed tube (1). Later, it was noted that by-products, namely diethjlene and triethylene glycol, were also formed in this reaction (50). This was the first synthesis of polymeric compounds of well-defined stmcture. Hydration is slow at ambient temperatures and neutral conditions, but is much faster with either acid or base catalysis (Table 8). The type of anion in the catalyzing acid is relatively unimportant (58) (see Glycols).  [c.453]

Another condensation method was investigated by Carothers and co-workers and reported in 1930. They reacted decamethylene dibromide with sodium in a Wurtz-type reaction but found it difficult to obtain polymers with molecular weights above 1300.  [c.206]

Poly-p-phenylene has been prepared in the laboratory by a variety of methods, including the condensation of p-dichlorobenzene using the Wurtz-Fittig reaction. Although the polymer has a good heat resistance, with decomposition  [c.584]

The synthetic applicability is rather limited, due to the various side-reactions observed, such as eliminations and rearrangement reactions. The attempted coupling of two different alkyl halides in order to obtain an unsymmetrical hydrocarbon, usually gives the desired product in only low yield. However the coupling reaction of an aryl halide with an alkyl halide upon treatment with a metal (the Wurtz-Fittig reaction) often proceeds with high yield. The coupling of two aryl halides usually does not occur under those conditions (see however below ) since the aryl halides are less reactive.  [c.305]

In addition to sodium, other metals have found application for the Wurtz coupling reaction, e.g. zinc, iron, copper, lithium, magnesium. The use of ultrasound can have positive effect on reactivity as well as rate and yield of this two-phase reaction aryl halides can then even undergo an aryl-aryl coupling reaction to yield biaryls.  [c.305]

Aliphatic hydrocarbons can be prepared by the reduction of the readily accessible ketones with amalgamated zinc and concentrated hydrochloric acid (Clemmensen method of reduction). This procedure is particularly valuable for the prep>aration of hydrocarbons wdth an odd number of carbon atoms where the Wurtz reaction cannot be applied with the higher hydrocarbons some secondary alcohol is produced, which must be removed by repeated distillation from sodium.  [c.238]

The Wurtz reaction, which reties on in situ formation of an active organosodium species, is also usefiil for preparing tetraorganotin compounds and is practiced commercially. Yields are usually only fair and a variety of by-products, including ditins, also form  [c.68]

Dehydration to 2-vinylthiophene is better achieved from 2-(2-thienyl) ethanol with powdered potassium hydroxide in the presence of copper than from 1-(2-thienyl) ethanol. a-Chloro-2-thienylpro-pane undergoes a Wurtz reaction with active iron to give 3,4-di-(2-thienyl) hexane in low yield, which has also been obtained through coupling with n-butyllithium.  [c.92]

In the case of an intramolecular Wurtz reaction less side-reactions are observed this variant is especially useful for the construction of strained carbon skeletons. For example bicyclobutane 5 has been prepared from l-bromo-3-chlorocyclobutane 4 in a yield of > 90%  [c.305]

Wurster process Wurster salts Wurtz-Fittigcoupling Wurtz-Fittig reaction Wurtzite  [c.1074]

Uses. Ethyl ether [60-29-7] has a wide range of uses in the chemical industry. It is a good solvent or extractant for fats, waxes, oils, perfumes, resins, dyes, gums, and alkaloids. When mixed with ethanol, ethyl ether becomes an excellent solvent for cellulose nitrate in the manufacture of guncotton (see Explosives and propellants), collodion solutions (see Membrane technology), and pyroxylin plastics (see Cellulose esters). Another important use is an extractant for acetic acid as well as other organic acids, eg, in the cellulose acetate and plastic industries to recover acetic acid from dilute aqueous systems. Ethyl ether is also used as a denaturant in several denaturant alcohol formulas. It has been used as a starting fuel for diesel engines and as an entrainer for dehydration of ethanol and isopropyl alcohol. It may be used as an anhydrous, inert reaction medium for the Grignard and Wurtz-Eittig reactions. Ethyl ether is used as a general anesthetic in surgery.  [c.428]

Another type of Grignard reaction is the alkylation with alkyl halides. Upon treatment of a Grignard reagent RMgX with an alkyl halide 5, a Wwrtz-like coupling reaction takes place.  [c.147]


See pages that mention the term Wurtz reaction : [c.236]    [c.1074]    [c.340]    [c.304]    [c.304]    [c.305]    [c.72]    [c.72]    [c.97]    [c.589]    [c.587]   
See chapters in:

Named organic reactions 2nd edition  -> Wurtz reaction


Textbook on organic chemistry (1974) -- [ c.236 , c.237 ]

Practical organic chemistry (1978) -- [ c.103 , c.288 ]

Plastics materials (1999) -- [ c.820 ]