Question

Which atom in the following compound is most likely to be protonated?

Short answer

Two sites can be protonated i.e. lone pair on nitrogen and lone pair on carbon.

Step-by-step solution

Protonation sites

As nitrogen has lone pair of electrons so it will attack on adjacent bond and make it double bond and nitrogen get positive charge and the double bond become single as carbon get negative charge.

Now H⁺ can attack on either nitrogen or carbon as both have negative charge.

Final answer

Two sites can be protonated i.e. lone pair on nitrogen and lone pair on carbon.