Chapter 24: Phenols

Summary:

Phenol is derived from the old name for benzene (phene), to include the suffix that indicates it possesses a hydroxyl group (-ol).
CAUTION:  Students often confuse the word phenol (C₆H₅-OH) with phenyl (C₆H₅-).
Phenols can be obtained via substitution reactions, with the hydrolysis of diazonium salts being the most important laboratory method.
Phenols are acidic and are important intermediates in the preparation of aryl ethers, C₆H₅-OR

Phenols

• Nomenclature
• Structure
• Physical Properties
• Acidity
• Reactivity

• Overview
• Via Nucleophilic Aromatic Substitution of
• Benzene Sulfonic acid
• Chlorobenzene
• Acidic Oxidation of Cumene
• Hydrolysis of Diazonium salts

• Electrophilic Aromatic Substitutions
• Acylation of Phenols
• Carboxylation
• Preparation of Aryl Ethers
• Oxidation

• Electrophilic Aromatic Substitutions
• Reaction with HI and HBr
• The Claisen Rearrangement

• IR
• ¹H NMR
• ¹³C NMR
• UV-VIS
• Mass Spectrometry

• Sample problems

© Dr. Ian Hunt, Department of Chemistry