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In an online test, the following question was asked:

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The answer to this question was:

enter image description here

I totally agree with the answer, as $\ce{OCH_3}$ is an EDG, hence it will tend to form meta product in this reaction.


While reading NAS on Master Organic Chemistry, I came up to this article:

enter image description here

This article says that $\ce{OCH_3}$ behaves similar to $\ce{CF_3}$, but I can't figure out the possible reason. Any help is appreciated!


Related (unanswered) question: Nucleophilic substitution in aromatic compounds

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    $\begingroup$ 1) although the use here is technically correct, usually "nucleophilic aromatic substitution" refers to SNAr mechanism. 2) for a benzyne mechanism, resonance effects do not matter, only inductive. This is covered in typical organic chemistry textbooks. $\endgroup$ – orthocresol Aug 4 at 15:53
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Normally during a nucleophillic aromatic substitution reaction one of oxygen's lone pairs would delocalize across the ring, the existence of a triple bond here prevents this from happening so oxygen actually ends up acting like an EWG.

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  • $\begingroup$ " the existence of a triple bond here prevents this" - Can you please elaborate? $\endgroup$ – rv7 Aug 5 at 5:38

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