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Here they considered -I effect of $\ce{OCH3}$ so carboanion is stable at orthroposition;

But $\ce{OCH3}$ also shows $\text{+M}$ effect if $\text{+M}$ is shown carboanion will be stable at meta position(generally in substitution reaction we give preference to $\text{+M > -I}$ of $\ce{OCH3}$).

But for this reaction NH2 in orthro position is not at all formed.

What is exactly happening in this reaction?

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  • $\begingroup$ carbon already has 8 valence electrons, so -och3 won't donate anymore electrons through +M (since resonance is impossible), we only consider -I here $\endgroup$ – Sunaina Das Jun 21 at 6:26
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    $\begingroup$ @Naren I think one explanation is that the carbanion is in the plane of the ring (in an sp2 orbital) while the delocalisation (+M effect) only occurs via p-orbitals perpendicular to the plane of the ring. So, the resonance does not affect the anion. $\endgroup$ – S R Maiti Jun 21 at 9:50

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