Question

The most acidic proton and the strongest nucleophilic nitrogen in the following compound

respectively, are

• A. $N^a-H;N^b$
• B. $N^b-H;N^c$
• C. $N^a-H;N^c$
• D. $N^c-H;N^a$

Answer 1

Answer: (B)

In the given compound most acidic proton will be $N^b—H$. This is because its conjugate base will get resonance stabilised and the most nucleophilic nitrogen will be $N^c$. This is because the lone pair of electrons present on this $N$ is localised over $s{p}^3$ -hybrid orbital.