Chapter 23, Problem 23.10YT

Interpretation Introduction

Interpretation:

The given resonance structures are for the arenium ion produced when ${\text{NO}}_{\text{2}}{}^{\text{+}}$ attaches ortho to the ${\text{CH}}_{\text{3}}$ group in $\text{m-nitrotoluene}$. The most stable and least stable resonance structures are to be identified. Overall, whether this arenium ion is more stable or less stable than the one in Equation 23-24 is to be determined.

Concept introduction:

The resonance structure where ${\text{C}}^{\text{+}}$ is adjacent to the electron withdrawing group is the least stable structure. The structure where ${\text{C}}^{\text{+}}$ is adjacent to the electron donating group is the most stable resonance structure.