In case of anisole, methylphenyl
oxonium ion, 
 is
formed by protonation of ether The
bond between O–CH3 is weaker
than the bond between O–C6H5
because the carbon of phenyl
group is sp
2 hybridised and there
is a partial double bond character CH3
C
CH3
CH3
O
H
+
CH3
slow
CH3
C
CH3
CH3
+ + CH OH
3
fast
CH3
C
CH3
CH3
CH3
C
CH3
CH3
+
+
I
–
I
Rationalised 2023-24
219
Alcohols, Phenols and Ethers
Therefore the attack by I
– ion breaks O–CH3 bond to form CH3I Phenols
do not react further to give halides because the sp
2 hybridised carbon
of phenol cannot undergo nucleophilic substitution reaction needed
for conversion to the halide