The Wurtz reaction, named after Charles-Adolphe Wurtz, is a coupling reaction in organic chemistry, organometallic chemistry and recently inorganic main group polymers, whereby two alkyl halides are reacted with sodium to form a new alkane:
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. 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.
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 SN2 reaction, forming a new carbon-carbon covalent bond.
R−M+ + R–X → R–R + M+X−
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