Chapter 27, Problem 70IAE

Interpretation Introduction

(a)

Interpretation:

Name and structure of the benzene derivative with molecular formula ${\text{C}}_{\text{8}}{\text{H}}_{\text{10}}$ and that forms three monochlorination products if treated with ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$ should be determined.

Concept introduction:

In presence of ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$ as reagent only, ring substitution occurs. This proceeds via electrophilic aromatic substitution. Since methyl group attached serves as electron releasing, it directs the chlorine electrophile to ortho and more preferably to the para position.

Interpretation Introduction

(b)

Interpretation:

Name and structure of the benzene derivative with molecular formula ${\text{C}}_9{\text{H}}_{\text{10}}$ and that forms single monochlorinated product if treated with ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$ should be determined.

Concept introduction:

In presence of ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$ as reagent only, ring substitution occurs. This proceeds via electrophilic aromatic substitution. Since methyl group attached serves as electron releasing hence it directs the chlorine electrophile to ortho and more preferably to the para position.

Interpretation Introduction

(c)

Interpretation:

Name and structure of the benzene derivative with molecular formula ${\text{C}}_9{\text{H}}_{\text{10}}$ and that forms four monochlorinated product if treated with ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$ should be determined.

Concept introduction:

In presence of ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$ as reagent only ring substitution occurs. This proceeds via electrophilic aromatic substitution. Since methyl group attached serves as electron releasing hence it directs the chlorine electrophile to ortho and more preferably to the para position.