Identify the correct decreasing order of basicity for the following phenoxide derivatives: (i) (ii) (iii) (iv) (v)

Step-by-step solution

The basicity of a phenoxide ion is inversely proportional to its stability. Electron-donating groups (EDG) destabilize the anion and increase basicity, while electron-withdrawing groups (EWG) stabilize the anion and decrease basicity. Let us analyze the electronic effects of the substituents at the para position: (i) - OCH ₃ : Exhibits a strong +R effect and a weak -I effect. The +R effect dominates, making it a strong EDG. This strongly destabilizes the phenoxide ion, making it the strongest base. (ii) - CH ₃ : Ex