wurtz reaction examples

Published by on November 13, 2020

And, it is very difficult to separate them in two individual compounds. A halide ion is displaced by alkyl anion from another molecule of alkyl halide. 3) When tert-butylhalides are subjected to Wurtz reaction, isobutylene is formed as the major product. In second step, second sodium atom release one more electron to the free radical and provide a carbonium ion. For example, In this reaction , two R groups are coupled by reacting RBr, RCl or RI with Na or K. The yields of the product are best for 1° alkyl halides (60%) and least for 3° alkyl halides (10%). Important Questions CBSE Class 10 Science. Mechanism Two: This mechanism used organo-metallic compound as intermediate and the reaction is performed in a solution. In other example, if two different type of alkyl halides are used in the reaction then a combination of three alkanes will be formed. Example of Wurtz Reaction. * The Wurtz reaction must be performed under anhydrous conditions because the alkyl free radical formed (see the mechanism) during the reaction is strongly basic and can abstract proton from water. is not prepared by using Wurtz reaction because the number of carbon atoms is every time double in production. [Note: Metal other than sodium, which can be employed in Wurtz reaction are Ag and Cu in finally divided state], The reaction involves the intermediate formation of free radicals. Wurtz reaction is used to ascend the homologous series through the preparation of higher alkanes containing even number of carbon atoms. Here, a large alkane molecule is developed by the joining two compound of alkyl halide and eradicate the halogen atoms in the form of sodium halide. The reaction shows productive results with primary alkyl iodides. The best yield of an alkane will be obtained when R and R are the same, i.e., when the alkane contains an even number of carbon atoms and is symmetrical. Alkyl halide in presence of dry ether medium when treated with sodium metal yields di-alkane. * Thus formed alkyl anion displaces halide ion from the second molecule of alkyl halide. A-1, Acharya Nikatan, Mayur Vihar, Phase-1, Central Market, New Delhi-110091. R-X + 2 Na + X-R🡪R-R + 2 Na-X (Basic reaction), R = alkyl group X =halogen (F, Cl, Br, I), Dry ether is used to provide anhydrous condition as moisture and sodium metal reacts strongly in the presence of water.Na + H2O —› NaOH + H2This reaction produce NaOH that reacts with alkyl halide to produce alcohol, R-X + OH¯ —› R-OHe.g. : CH3-Cl + Na —› CH3-CH3 + NaCl. * In case of alkyl and aryl fluorides as well as aryl chlorides, tetrahydrofuran is used as solvent instead of ether. Methane (CH4) is not prepared by using Wurtz reaction because the number of carbon atoms is every time double in production. Wurtz-Fittig reaction- A modification in Wurtz reaction is known as Wurtz-Fittig reaction. This reaction is considered as a SN2 reaction. That means the lowest alkane developed through Wurtz reaction is ethane. In case of Wurtz reaction, there exists a side reaction using which an alkene product is formed. The yields can be poor and with alkene contamination. The mechanism also used for the production of ethane and ethylene. Unsaturated hydrocarbons are also obtained. It fails with tertiary alkyl halides. Wurtz reaction aids in industrial preparation of alkanes. This mixture cannot be separated easily. If the reaction is between R-X and R'-X, it gives R-R and R'-R'- it will be difficult to separate the two products. The Wurtz reaction strictly needs anhydrous conditions as it forms alkyl free radical in the reaction; this free radical is a highly basic and can eliminate proton from water. Bicyclobutane was prepared this way from 1-bromo-3-chlorocyclobutane in 95% yield. Comment: Since the alkyl free radicals are formed, elimination side reactions leading to alkenes is also possible, especially with bulky alkyl groups, which require more activation energy during the nucleophilic substitution (SN2) step. This mechanism used organo-metallic compound as intermediate and the reaction is performed in a solution. That means the lowest alkane developed through Wurtz reaction is ethane. Looking further in the above reaction, it was found that in addition to the desired alkane R1-R2, there will also be present the alkanes R1-R1 and R2-R2. List of Name Reaction of Organic Chemistry consist of detail Reaction Mechanism of all name reactions of Organic Chemistry. all rights reserved. Wurtz reaction is a coupling reaction which is developed by Charles-Adolphe and used in organic chemistry and organometallic chemistry. Dry ether is used to provide anhydrous condition as moisture and sodium metal reacts strongly in the presence of water. Vapour phase is consider as a suitable phase for free radicals. REACTION: * In Wurtz reaction, two alkyl halide molecules are coupled in presence of sodium metal in anhydrous ether or Tetrahydrofuran to form a new carbon carbon bond and thus by giving a symmetrical alkane. So Wurtz reaction is not considered for the synthesis of alkanes with odd number of carbon atoms, as it provides a combination of non-separable alkanes. It is because the elimination is favored over SN2 mechanism. In such a case, if methyl and ethyl iodides are used to react with sodium then mixture of propane, butane and ethane will be formed, although it’s difficult to separate the alkanes from the mixture. Wurtz coupling is, however, useful in closing small, especially three-membered, rings. For example, it is intolerant of a range of functional groups. The best yield of an alkane will be obtained when R and R are the same, i.e., when the alkane contains an even number of carbon atoms and is symmetrical. 1) Ethane is formed when methyl chloride is treated with sodium metal in dry ether. It is not applicable for the synthesis of two dissimilar alkyl halides as the product of these could be a combination of alkanes that are not easy to separate.

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