Chapter 18.5, Problem 13ATS

Interpretation Introduction

Interpretation For the given compounds, it should be predicted which compound will react more rapidly in an ${\text{S}}_{\text{N}}\text{1}$ process

Concept introduction:

• Unimolecular nucleophilic substitution reaction in organic chemistry is called ${\text{S}}_{\text{N}}\text{1}$ reaction.
• The first step of a ${\text{S}}_{\text{N}}\text{1}$ process is loss of leaving group, forming a carbocation.
• A five membered ring will be aromatic if it contains six $\text{π}$ electrons. In order to have six $\text{π}$ electrons, one of the carbon atoms must possess two electrons. It should be a carbanion.
• A seven membered ring will be aromatic if it contains six $\text{π}$ electrons. In order to have six $\text{π}$ electrons in a seven membered ring one of the carbon atom must possess an empty p orbital. This carbocation exhibits a continuous system of overlapping and p orbitals and has six $\text{π}$ electrons.
• Aromatic compounds are more stable than non-aromatic compound