Which of the following specific aryl halides predictably undergoes nucleophilic substitution primari β Haloalkanes 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
π‘ 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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