Skip to main content
Library homepage
 
Chemistry LibreTexts

1° Amides can be converted to Nitriles with Thionyl Chloride

  • Page ID
    5892
  • \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)

    1o Amides can be converted to nitriles by reaction by dehydration with thionyl chloride.

    General reaction

    1.jpg

    Example 1:

    2.jpg

    Mechanism

    1) Nucleophilic attach on thionyl chloride

    3.jpg

    2) Leaving group removal

    4.jpg

    3) Deprotonation

    5.jpg

    4) Leaving group removal

    6.jpg

    Contributors

    Prof. Steven Farmer (Sonoma State University)


    1° Amides can be converted to Nitriles with Thionyl Chloride is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts.

    • Was this article helpful?