Skip to main content
Chemistry LibreTexts

Wurtz reaction

  • Page ID
    68892
  • \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)

    Wurtz reaction is coupling of haloalkanes using sodium metal in solvent like dry ether

    \[2R-X + 2Na \rightarrow R-R + 2Na^+X^−\]

    The reaction consists of a halogen-metal exchange involving the free 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.

    \[R-X + M → R^{\cdot} + M^+X^−\]

    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.

    \[R^{\cdot} + M → R^−M^+\]

    The nucleophilic carbon of the alkyl anion then displaces the halide in an SN2 reaction, forming a new carbon-carbon covalent bond.

    \[R^−M^+ + R-X → R-R + M^+X^−\]


    Wurtz reaction is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

    • Was this article helpful?