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Benzyne Mechanism

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  • Two mechanisms have been proposed for nucleophilic aromatic substitution, one of which involves a benzyne as the intermediate and, therefore, is called benzyne mechanism.





    Step 1:



    Step 2:



    Step 3:



    Step 1 requires a very strong base.  Thus, for the benzyne mechanism to be operant, the medium must be very strongly basic.

    see also SNAr mechanism