Wurtz Reaction

$$2\text{R--X} + 2\text{Na} \xrightarrow{\text{Dry Ether}} \text{R--R} + 2\text{NaX}$$

Concept: Two molecules of alkyl halide react with metallic sodium in dry ether to form a symmetrical alkane containing double the number of carbon atoms present in the parent halide. Proceeds via free radical intermediate

Limitations:

• Methane ($$\text{CH}_4$$) cannot be prepared by this method because the reaction requires coupling two alkyl groups.
• Unsymmetrical alkanes ($$\text{R--R'}$$) give a mixture of three different alkanes ($$\text{R--R}$$, $$\text{R'--R'}$$, and $$\text{R--R'}$$), which are difficult to separate due to close boiling points.