Question

Two major organic products are formed in the reaction of p-chlorotoluene with sodium amide. draw the structure of both products.

Answer 1

Amide ion is a very strong base that makes a nucleophilic aromatic substitution reaction, but here the aryl halide lacks an electron-withdrawing substituent. so the reaction occurs via elimination-addition sequence, not addition-elimination reaction by removal of H proton and Cl with the formation of triple bond (Benzyne) then addition of NH₃ in which NH₂ may be added on the same site as Cl or the site we removed H from it