Step 3:
Mechanism
Mechanism
Mechanism
Mechanism
Mechanism
However, when one of the alkyl group is a tertiary group, the halide
formed is a tertiary halide CH
C
CH +HI
CH OH +CH
C
I
3
3
3
3
CH3
CH3
CH3
CH3
O
It is because in step 2 of the reaction, the departure of leaving group
(HO–CH3) creates a more stable carbocation [(CH3)3C
+], and the reaction
follows SN1 mechanism 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