During the complex benzyne mechanism, when the incoming nucleophilic species aggressively attaches t — Haloalkanes and Haloarenes Chemistry Question
Question
During the complex benzyne mechanism, when the incoming nucleophilic species aggressively attaches to a specific aromatic ring carbon atom that is directly immediately adjacent to the carbon originally bearing the leaving group, what is this specific fundamental phenomenon technically termed?
💡 Solution & Explanation
In the two-step elimination-addition benzyne mechanism, the highly transient intermediate cleanly features a localized triple bond. Because the nucleophile can symmetrically attack either carbon atom of this activated bond, attachment frequently correctly occurs at the adjacent position relative to the original halogen. This specific positional shift is classically defined as 'cine substitution'.