Why does 3-bromopropanoic acid have least pKb value when compared to 3-chloropropanoic acid, 3-fluropropanoic acid and fluoroacetic acid?
The correct order of PKb is
fluoroacetic acid&gt; 3-fluoropropanoic acid&gt;3-chloropropanoic acid&gt;3-bromopropanoic acid.
To find the order of pKb, first find the order of pKa which can be found by checking the stability of negative charge on carboxylate anion once it donated proton.
Halogens are electron withdrawing groups. The halogen which will withdraw the most electron density will stabilise the anion the best. Fluorine, being the most electronegative withdraws the most electron density thus reducing the charge on oxygen and stabilising the anion, therefore having the least pKa and maximum pKb.