See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Solution: Nucleophilic Aromatic Substitution ## Step 1: Identify the reaction type The reactant is a **chlorobenzene with an electron-donating group** ($-Cl$ at position 3, $-OCH_3$ at position 2). Treatment with $NH_2^-$ (strong nucleophile) indicates **nucleophilic aromatic substitution (SNAr)**. ## Step 2: Determine regioselectivity In SNAr reactions, the nucleophile attacks the carbon bearing the **best leaving group** (Cl in this case). However, the reaction is directed by the **electron-donating methoxy group** ($-OCH_3$). The $-OCH_3$ group activates ortho and para positions through resonance stabilization of the anionic intermediate. ## Step 3: Analyze directing effects - Position 2: **Ortho** to $-OCH_3$ (strongly activated) - Position 3: Bears the Cl (leaving group) - Position 4: **Para** to $-OCH_3$ (strongly activated) Since Cl is at position 3, nucleophilic attack occurs at **position 2** (ortho to $-OCH_3$, which is the most activated site adjacent to the leaving group at position 3). ## Step 4: Determine product structure Nucleophilic substitution of Cl at position 3 gives $-NH_2$ at position 3, producing: - $-OCH_3$ at position 2 - $-NH_2$ at position 3 **Answer: (C)** shows $-OCH_3$ at position 2 and $-NH_2$ at position 3, matching this regioselective outcome.