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The Wurtz Reaction: Coupling Alkyl Halides to Form C-C Bonds

Introduction The Wurtz reaction is a fundamental organic transformation that enables the formation of new carbon-carbon bonds through the coupling of alkyl halides with sodium metal. This classical reaction, discovered by Charles-Adolphe Wurtz in 1855, remains an important tool in synthetic organic chemistry, particularly for the synthesis of alkanes and the construction of larger carbon frameworks. Definition and Overview The Wurtz reaction is defined as the coupling of two alkyl halides mediated by sodium metal: $$2 \text{R-X} + 2 \text{Na} \rightarrow \text{R-R} + 2 \text{NaX}$$ Where: R = alkyl group X = halogen (Cl, Br, or I) Na = sodium metal Mechanism The Wurtz reaction proceeds through a radical mechanism involving two main steps: Step 1: Formation of Alkyl Radical Sodium metal transfers an electron to the alkyl halide: $$\text{R-X} + \text{Na} \rightarrow \text{R}^{\bullet} + \text{Na}^{+}\text{X}^{-}$$ Step 2: Carbon-Carbon Bond Formation Two al...

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