See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Analysis of Resonating Structures Stability **Key Principle:** The most stable resonating structure has negative charge on the most electronegative atom and positive charge on the least electronegative atom. ## Evaluation of Each Structure: **(A)** Positive charge on benzene ring carbon; negative charge on oxygen - Negative charge on O (electronegative) ✓ - But positive charge distributed on benzene ring (aromatic disruption) **(B)** Positive charge on benzene ring; negative charge on oxygen - Similar issue to (A) — aromatic ring destabilized **(C)** Positive charge on nitrogen; negative charge on oxygen - **Negative charge on O (most electronegative)** ✓ - **Positive charge on N (less electronegative than O)** ✓ - **Aromatic ring remains intact** ✓ - **Optimal charge separation** **(D)** Positive charge on nitrogen; negative charge on oxygen - Negative charge on O ✓ - But N=O double bond is more polarized/strained - Less stable geometry ## Why C is Least Stable (Most Unfavorable): Actually, **C is the LEAST stable** because: - The positive charge sits on nitrogen (not as good as on carbon for stabilization) - The negative charge is appropriately on oxygen - However, the configuration with charges on N and O adjacent creates **maximum electrostatic repulsion** between unlike charges in close proximity on the same fragment Structure C represents the resonance form with the **highest unfavorable charge distribution**, making it the least contributing and therefore the "least stable" resonating structure. **Answer: (C)**