The Wurtz reaction is an organic chemical coupling reaction developed by Charles Adolphe Wurtz, which is used in organic chemistry and organometallic chemistry to synthesize higher alkanes by a reaction between two alkyl halides in the presence of sodium metal and dry ether solution. The reaction proceeds by an initial metal-halogen exchange, which is described with the following idealized stoichiometry: 2 R−X + 2 Na → R−R + 2 NaX. The carbon-carbon bond is formed in a nucleophilic substitution reaction in this reaction mechanism, which can be broken down into three steps. The Wurtz reaction is of little value except for intramolecular versions and is intolerant of a range of functional groups which would be attacked by sodium. The reaction is conducted in unreactive solvents such as ethers, and other metals have also been tested to effect the Wurtz-like couplings: silver, zinc, iron, activated copper, indium, as well as a mixture of manganese and copper chloride. A modification of the Wurtz reaction is known as the Wurtz-Fittig reaction, which involves alkyl and aryl halides.