Haloalkanes and HaloareneshardMCQ SINGLE

Which of the following specific aryl halides predictably undergoes nucleophilic substitution primariHaloalkanes and Haloarenes Chemistry Question

Question

Which of the following specific aryl halides predictably undergoes nucleophilic substitution primarily via the high-energy elimination-addition benzyne mechanism?

Answer: A

💡 Solution & Explanation

Activated aryl halides possessing strongly electron-withdrawing groups (like $-NO_2$) perfectly positioned at the ortho or para positions undergo standard addition-elimination ($S_NAr$). However, unactivated or deactivated aryl halides lacking these precisely positioned stabilizing groups (such as $m$ -bromobenzotrifluoride) undergo substitution exclusively via the highly strained benzyne intermediate mechanism.

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