Chapter 23, Problem 23.7YT

Interpretation Introduction

Interpretation:

The curved arrow notation for the conversion of one resonance form to another resonance form of chlorine substituted ortho arenium ion intermediates is to be shown. How many atoms in the second resonance form lack the octet is to be determined. The arrow along $\text{C}-\text{Cl}$ bond is to be drawn to represent the inductive effect, and its impact on the stability of positive charge in the intermediate is to be explained.

Concept introduction:

The curved arrow shows the flow of $\text{π}$ electrons in the resonance form. The atom or a group having nonbonding electron pair donates its lone pair and participates in resonance, thus having electron donating resonance effect and referred as ortho/para directing groups. The inductively electron withdrawing group pulls the bonding electron away and destabilizes the positive charge, which increases the positive charge on benzene ring, and is, therefore, called deactivating group.