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C. The Friedel-Crafts Acylation of Benzene

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    3769
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    This page gives you the facts and a simple, uncluttered mechanism for the electrophilic substitution reaction between benzene and ethanoyl chloride in the presence of an aluminium chloride catalyst.

     

    The electrophilic substitution reaction between benzene and ethanoyl chloride

     

    What is acylation?

    An acyl group is an alkyl group attached to a carbon-oxygen double bond. If "R" represents any alkyl group, then an acyl group has the formula RCO-. Acylation means substituting an acyl group into something - in this case, into a benzene ring.

    The most commonly used acyl group is CH3CO-. This is called the ethanoyl group. In the example which follows we are substituting a CH3CO- group into the ring, but you could equally well use any other alkyl group instead of the CH3.

     

    The facts

    The most reactive substance containing an acyl group is an acyl chloride (also known as an acid chloride). These have the general formula RCOCl.

    Benzene is treated with a mixture of ethanoyl chloride, CH3COCl, and aluminium chloride as the catalyst. A ketone called phenylethanone is formed.

     

     

    or better:

     

     

    The aluminium chloride isn't written into these equations because it is acting as a catalyst. If you wanted to include it, you could write AlCl3 over the top of the arrow.

     

    The formation of the electrophile

    The electrophile is CH3CO+. It is formed by reaction between the ethanoyl chloride and the aluminium chloride catalyst.

     

     

    The electrophilic substitution mechanism

     

    Stage one

     

     

    Stage two

     

     

    The hydrogen is removed by the AlCl4- ion which was formed at the same time as the CH3CO+ electrophile. The aluminium chloride catalyst is re-generated in this second stage.