See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Analysis of p-Nitrosonitrobenzene Resonating Structures **Stability Criteria for Resonating Structures:** - Minimize formal charges - Distribute negative charges on more electronegative atoms - Avoid placing like charges on adjacent atoms - Maintain aromaticity of the benzene ring **Evaluation of Each Structure:** **(A)** Positive charge on benzene ring carbon; negative charge on one N-O bond - Destabilizing: positive charge on $sp^2$ carbon **(B)** Both nitrogens bearing positive charges; negative charges on oxygens - Highly unstable: adjacent positive charges repel strongly **(C)** ✓ **Most stable** - N-nitroso group: $N^+=O$ with negative oxygen (formal charge distribution favorable) - N-nitro group: $N^+$ with two $O^-$ atoms (symmetric, distributes negative charge) - Negative charges reside on electronegative oxygen atoms - Positive charges on nitrogen atoms (less electronegative than O, acceptable) - No like charges adjacent; maximizes resonance stabilization **(D)** Negative charge on benzene ring; positive charge on nitrogen - Destabilizing: negative charge on carbon violates electronegative atom preference **Answer: (C)** is the most stable because it places all negative charges on oxygen atoms (most electronegative) and avoids unfavorable charge arrangements, while maintaining the aromaticity and resonance stability of the benzene ring.