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When do lone pairs on nitrogen contribute to aromaticity?
@Nothing Yes, the green nitrogen is $\mathrm{sp^2}$ hybridized for the reasons you mention.
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1-Bromo-4-tert-butylbenzene reaction with NaNH2
Sorry, I'm not following. The aryne intermediate can only produce products by addition to either end of the "triple" bond. This would yield products with the substituent oriented either $meta$ or $para$ to the $t$-butyl group, no $ortho$ product would be formed. Further, there is no isobutylene or silica catalyst, as claimed in your referenced patent, present in this reaction.
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1-Bromo-4-tert-butylbenzene reaction with NaNH2
How would $ortho$ product ever form?
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