Chapter 6, Problem 6.68P

Interpretation Introduction

Interpretation:

The possible resonance structures are to be drawn for the given ion, and the order of the strongest to weakest resonance contributor is to be determined.

Concept introduction:

Resonance structures are alternate Lewis structures that can be drawn for a molecule or an ion. The overall charge on all the resonance forms must be the same. The contribution of all the resonance structures, to the resonance hybrid, is not equal. The lowest energy (more stable) resonance structure is the greatest resonance contributor to the hybrid. The stability of the resonance structure is governed by the following factors: greater number of atoms with octets, greater number of covalent bonds, and least number of formal charges. Further, the negative charge on the more electronegative atom and the positive charge on the least electronegative atom increase the stability of the resonance structure. The electron donating groups stabilize the positively charged atom, and the electron withdrawing groups stabilize the negatively charged atoms.