Skip to main content
Chemistry LibreTexts

Reactions of Acyl Chlorides with Alcohols

  • Page ID
    3796
  • \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)

    This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and alcohols.

    Ethanoyl chloride is taken as a typical acyl chloride. Any other acyl chloride will behave in the same way. Simply replace the \(CH_3\) group in what follows by anything else you want. Similarly, ethanol is taken as a typical alcohol. If you are interested in another alcohol, you can replace the \(CH_3CH_2\) group by any other alkyl group.

    The reaction between ethanoyl chloride and ethanol

    Ethanoyl chloride reacts instantly with cold ethanol. There is a very exothermic reaction in which a steamy acidic gas is given off (hydrogen chloride). Ethyl ethanoate (an ester) is formed.

    OrganicCore_AcidHalides44.png

    The mechanism

    The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by one of the lone pairs on the oxygen of an ethanol molecule.

    OrganicCore_AcidHalides11.png

    The second stage (the elimination stage) happens in two steps. In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off.

    OrganicCore_AcidHalides12.png

    That is followed by removal of a hydrogen ion by the chloride ion to give ethyl ethanoate and hydrogen chloride.

    OrganicCore_AcidHalides13.png

    Contributors

    Jim Clark (Chemguide.co.uk)


    This page titled Reactions of Acyl Chlorides with Alcohols is shared under a not declared license and was authored, remixed, and/or curated by Jim Clark.

    • Was this article helpful?