In Wurtz reaction Higher alkanes are prepared using lower alkyl halides with sodium metal in presence of dry ether.

By this method aromatic hydrocarbons can also be prepared in the same manner. Only difference is that it is named as Fittig reaction.

Reactions involving both alkyl and aryl halides are called Wurtz-Fittig reaction

EXAMPLE: C₂H₅Cl + 2Na + C₂H₅Cl → C₄H₁₀ + 2NaCl

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The Wurtz reaction, named after Charles-Adolphe Wurtz, is a coupling reaction in organic chemistry, organometallic chemistry and recently inorganic main grouppolymers, whereby two alkyl halides are reacted with sodium to form a new carbon-carbon bond:

2R-X + 2Na → R-R + 2Na⁺X⁻

Other metals have also been used to effect the Wurtz coupling, among them silver, zinc, iron, activated copper, indium and a mixture of manganese and copper chloride.^[1] The related reaction dealing with aryl halides is called the Wurtz-Fittig reaction.This can be explained by the formation of free radical intermediate and its subsequent disproportionation to give alkene.

Mechanism

The reaction consists of a halogen-metal exchange involving the radical species R• (in a similar fashion to the formation of a Grignard reagent and then the carbon-carbon bond formation in a nucleophilic substitution reaction.)

One electron from the metal is transferred to the halogen to produce a metal halide and an alkyl radical.

R-X + M → R• + M⁺X⁻

The alkyl radical then accepts an electron from another metal atom to form an alkyl anion and the metal becomes cationic. This intermediate has been isolated in a several cases.

R• + M → R⁻M⁺

The nucleophilic carbon of the alkyl anion then displaces the halide in an S_N2 reaction, forming a new carbon-carbon covalent bond.

R⁻M⁺ + R-X → R-R + M⁺X⁻

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Wurtz Reaction

The Wurtz Coupling is one of the oldest organic reactions, and produces the simple dimer derived from two equivalents of alkyl halide. The intramolecular version of the reaction has also found application in the preparation of strained ring compounds:

Using two different alkyl halides will lead to an approximately statistical mixture of products. A more selective unsymmetric modification is possible if starting materials have different rates of reactivity  (see Wurtz-Fittig Reaction).

Mechanism of the Wurtz Reaction

Side products: