Chapter 18, Problem 18.62P

Interpretation Introduction

Interpretation:

Benzene undergoes electrophilic aromatic substitution with anhydrides, compounds having the general structure (RCO)₂O, in a reaction that resembles Friedel-Crafts acylation and to draw a stepwise mechanism for the reaction of benzene with glutaric anhydride in the presence of AICl₃

Concept introduction:

The characteristic reaction of benzene is known as electrophilic aromatic substitution reaction-a hydrogen atom is replaced by an electrophile. Because of benzene has six pi electrons that delocalized in six p-orbitals that overlap above and below the plane of the benzene ring. These loosely held pi-electrons make the benzene ring electron rich, and so it reacts with electrophiles. Moreover because of benzene's six pi electrons satisfy Huckel's rule, benzene is especially stable ring. Reactions that keep the aromatic ring intact are therefore favored. A substituent in the benzene can affect the electrophilic aromatic substitution.

Friedel-Crafts acylation reaction is used to synthesis the acyl substituted benzene derivative.