Question

4.imidazole has two nitrogen atoms, labeled as n3 and n1. please indicate which nitrogen is more basic. draw the products of protonating both nitrogen atoms and use this as part of your explanation.

Answer 1

$N_3$  is more basic than $N_1$ in imidazole.

Imidazole have two nitrogen attached in the ring at $N_1 and N_3$ .

This compound is an aromatic compound as it have $(4n+2)$π electrons which means lone pair electrons of $N_1$ nitrogen atom also takes part in π

system.

Thus when a proton attacks on this compound it easily attacks at $N_3$ rather than $N_1$.

After the attack of $H^{+}$ ion at $N_3$ the conjugate base thus formed is also aromatic and hence is more stable.

If the proton had attacked at $N_1$ the conjugate base would not be aromatic and its stability will decrease.

The reaction is shown in the image attached

To know more about protonation  

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