# Nucleophilic substitution in aromatic compounds

Predict the major product in following reaction:

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?

• Think about which species can act as electrophiles in EAS, would ammonia work? – AS_1000 Oct 30 '17 at 10:58
• @AS_1000 in my view $\ce{NH_2 ^{-}}$ acts as a nucleophile – user471651 Oct 30 '17 at 11:25
• Look up Meisenheimer intermediates rather than Wheland intermediates. The former are valid for nucleophilic aromatic substitutions. – Beerhunter Oct 30 '17 at 21:53
• Note that halides are weak EWG's. So, para product is preferred – Rahul Verma Aug 4 '19 at 14:32