I have been asked to find the major product of the following reaction:
This is my thought process: the lone pairs of the oxygen atom connected to $\ce{-Et}$ are less delocalised than the other oxygen atom. So, that will abstract the $\ce{H^+}$ from $\ce{HI}$ leaving behind $\ce{I^-}$ and producing a positive charge on the oxygen atom. Now the oxygen atom will take up the bond pair electrons and $\ce{I^-}$ will form a bond in $\ce{S_{N}2}$ mechanism, producing $\ce{I-Ph-O-Ph}$ and $\ce{EtOH}$ as products.
But, the answer in the book states that:
The ether linkage will break as it does not have a double bond character due to the absence of resonance.
Why is the ether linkage breaking here? What does it mean by "it does not have a double bond character"?