Synthesis of Paracetamol

Question

A student accidentally mixed p-aminophenol with acetic acid instead of acetic anhydride, then an acid/base reaction ended up occurring. Which atom of p-aminophenol , the N or the O is more basic. Why?

Answer 1

N is more basic than O because it is less electronegative and is able to donate electrons more readily than O.

As a result, when acetic acid (an acid) is added to p-aminophenol, the -NH₂ group, which is basic, reacts faster with it in acid-base reaction yielding 4-acetamidophenol (or paracetamol) as the product.