For this question, doesn't resonance stabilize the base as well and make it less basic (i.e., more stable)? Also, in the explanation it says that letter B has an electron withdrawing group. Is Dr. Romano referring to the benzene ring itself?
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Destroyer 2013 Orgo #21
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I was just working on this problem! I don't know if I took an erroneous approach to this problem, but I know benzene rings are resonance stabilized ------>more acidic. Choice A is the only one that does not have as many resonance structures as the others.
I thought NH2 is an electron donating group, I do not know why the answer key says withdrawing...
NH2 is an electron donating group when on a benzene ring because it contributes resonance with the lone pair. if there's no benzene/other resonance possibilities, then Nitrogen acts normal as an electronegative, and electron withdrawing, atom
Now you guys are confusing me too. I thought the questions is referring to the benzene ring as being electron withdrawing. Therefore it destabilizes the lone pair on the N from reacting on its own. Whereas in choice A it's still free to react.
Haha, WOW. I TOTALLY oversaw that NH2 group
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