Chapter 24: Phenols
Base Hydrolysis of Chlorobenzene
Reaction type : Nucleophilic Aromatic Substitution
Summary
This is a useful industrial method for the synthesis of phenol.
Reagents : Usually NaOH, 350
o
C followed by an acidic work-up to neutralise the phenoxide.
The reaction occurs via the
elimination-addition mechanism
via a
benzyne
intermediate.
Elimination of HCl creates the benzyne that then undergoes
addition
of H
2
O to produce the phenol.
QUESTION
Can you recall how you make chlorobenzene ?
ANSWER
©
Dr. Ian Hunt
, Department of Chemistry