REACTIONS OF BENZENE

The most common reaction of aromatic compounds is electrophilic

aromatic substitution. An electrophile reacts with an aromatic ring
and substitutes for one of the hydrogens.
For example: Consider the Bromination of Benzene

Reaction mechanism:
• Catalyst FeBr3 makes Br2 more electrophilic
by polarizing it into Br+ -FeBr4.
• Electron pair from benzene attacks positively
polarized Br, forming a new C-Br bond and
leaving a nonaromatic carbocation
intermediate.
• The base removes the H+ from the
intermediate and aromatic ring reforms.
Tutorial 2

1. Identify the reagents represented by the letters a-f.

2. Propose the detailed reaction mechanisms for each reactions a-f.