tbr orgo VII #19 (nucleophilicity of amine)

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angleslam08

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*need actual book* for this, don't have necessary image.

This is question with the 6 member ring fused with 5.....I get that 'c' is the most nucleophilic because of the resonance with it having minus charge on it, but I was a little unsure of how it is aromatic as said in explanation.

- Doesn't it only have 4 pi electrons (anti aromatic) to delocalize; the minus charge on the nitrogen and then the one double bond? They all seem to be sp2 so that fits, but i don't see how the actual delocalization works out in this case.


*another question: why is the O-H bond of the carboxyl group weaker than regular O-H as indicated by IR spectroscopy?

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