Monday, September 19, 2011

Question on Basic Strength

In the molecule given below which of the three labelled nitrogen atoms will get protonated first when treated with an acid?



Answer:


Nitrogen atom labelled 2 will get protonated first because its conjugate acid will be stabilized by identical resonating structures.


Nitrogen atom labelled 3 is the least basic as the lone pair on that nitrogen atom will be used in making the 5 membered ring aromatic and will be unavailable for an acid.

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