Question

Which of the following mechanisms best describes electrophilic aromatic substitution of benzene with bromine?

a) SN1 Mechanism
b) SN2 Mechanism
c) Electrophilic Addition
d) Electrophilic Aromatic Substitution

Answer 1

Electrophilic aromatic substitution is the mechanism that best describes electrophilic aromatic substitution of benzene with bromine. In this mechanism, a strong electrophile captures electrons from the benzene ring, forming an unstable intermediate. The ring eliminates a proton instead of a nucleophile adding to the cation.

Step-by-step explanation:

The mechanism that best describes electrophilic aromatic substitution of benzene with bromine is electrophilic aromatic substitution. In this mechanism, a strong electrophile, such as bromine, captures electrons from the benzene ring, forming an unstable intermediate. The loss of aromaticity is energetically unfavorable, so instead of a nucleophile adding to the cation, the ring eliminates a proton. This reaction is commonly used in halogenation reactions where a -H on benzene is substituted with a halogen (-Cl or -Br), as shown in the example.