I had a question in a recent test which asked me to pick the compound that would react fastest with $\ce{HBr}$ with the options being:
- p-nitrobenzyl alcohol
- p-chlorobenzyl alcohol
- benzyl alcohol
- p-methoxybenzyl alcohol
The answer was p-methoxybenzyl alcohol.
Now what I don't understand is that $\ce{HBr}$ would produce nucleophilic $\ce{Br-}$, which would be looking to attack a region of electron deficiency. In that case option (1) p-nitrobenzyl alcohol would the right answer because the nitro group is an electron withdrawing group, thus making the ring more electron deficient.
Could someone please explain as to why this logic fails?