Imidazole

Chemistry Level 1

Which nitrogen is more acidic?

1 2 both are equally acidic nothing can be said

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Abhishek Singh by Abhishek Singh , 24, India

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2 solutions

Abhishek Singh
Oct 19, 2014

First one is most basic because it's lone pairs are not in conjugation because they are not in the plane of the π \displaystyle{\pi} orbitals of the s p 2 \displaystyle{sp^2} hybrid carbons of the ring. And so they are free to be donated!

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wrong It should be more basic ..!! or otherwise answer would be 2

Deepanshu Gupta - 6 years, 7 months ago

So it should be more basic isn't it. So how can it be acidic. A lone pair donor is a lewis base not a lewis acid

Ronak Agarwal - 6 years, 7 months ago

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Thanks. I have updated the answer so that those who said 2 were marked correct.

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Calvin Lin Staff - 6 years, 7 months ago

@Ronak Agarwal You can check the strength of the conjugate bases formed by protonating the nitrogen atoms.

Pratik Shastri - 6 years, 7 months ago

The compound becomes aromatic when a proton is pulled from second nitrogen

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