Monday, April 16, 2018

organic chemistry - Nucleophilic substitution in aromatic compounds



Predict the major product in following reaction:



Nucleophilic substitution in 1,4‐dichlorobenzene



In my view this reaction will proceed via benzyne intermediate and $\ce{NH2-}$ will act as a base and substitute one of the chlorine. After benzyne formation as $\ce{Cl}$ is ortho/para directing my view was that $\ce{NH2-}$ will attach to the meta position.


However, the answer key says overwise. Any ideas?




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