Which of the following specific structural modifications to Aniline will reliably result in a measur — Amines Chemistry Question

💡 Solution & Explanation

Basicity is predictably decreased by electron-withdrawing groups (EWGs) and increased by electron-donating groups (EDGs). The $-NO_2$ group is an incredibly strong EWG (-I, -R) and severely decreases basicity. The $-Cl$ halogen is predominantly an EWG via its dominating -I effect (which outweighs its weak +R effect), steadily decreasing basicity. Alternatively, $-OCH_3$ (+R) and $-CH_3$ (+I, hyperconjugation) act as EDGs, which push electron density into the ring and definitively increase basicity.