Which of the following statements correctly describe the benzyne intermediate formed during the elim — Aromatic Hydrocarbons Chemistry Question
Question
Which of the following statements correctly describe the benzyne intermediate formed during the elimination-addition mechanism of nucleophilic aromatic substitution?
💡 Solution & Explanation
Benzyne is generated from unactivated aryl halides using strong bases ($NaNH_2$). It possesses a "triple bond" formed by the sideways overlap of two adjacent $sp^2$ orbitals. This overlap is weak and highly strained, making benzyne very reactive. However, the original $6\pi$ electron aromatic system remains intact and perpendicular to this new bond (C is false). Nucleophilic attack can occur at either carbon of the triple bond, leading to direct or cine-substitution.