Chapter 24: Phenols

Electrophilic Aromatic Substitution Reactions of Aryl Ethers

Reaction type: Electrophilic Aromatic Substitution

Summary

• Aryl ethers are potentially very reactive towards electrophilic aromatic substitution.
• This is because the alkoxy group, -OR,  is a strongly activating, ortho- / para- directing substituent (review)
• These reactions are essentially the same as those of the phenols (where R = H)
• Substitution typically occurs para to the alkoxy group unless the para position is blocked, then ortho substitution occurs.
• The strong activation often means that milder reaction conditions than those used for benzene itself can be used.
• Aryl ethers are so activated that polysubstitution can be a problem.

Related reactions

• Electrophilic Aromatic Substitutions reactions of Phenols
• Electrophilic Aromatic Substitutions reactions of Benzenes
• Electrophilic Aromatic Substitutions reactions of Anilines

© Dr. Ian Hunt, Department of Chemistry