PKaH values

Imidazoline is a simple cyclic amidine and its pKaH value is just what we expect, around 11. Imidazole, on the other hand, is less basic (p.fQtH 7.1) because both nitrogens are attached to an electron-withdrawing sp2 carbon. However, imidazole, with its two nitrogen atoms, is more basic than pyridine (pKaH 3.2) because pyridine only has one nitrogen on which to stabilize the positive... 

The pKaH values of sortie substituted pyridines are as follows. 

Predict the success or failure of these attempted nucleophilic substitutions at the carbonyl group. You should use estimated pK or pKaH values in your answer and, of course, draw mechanisms. 

---