Which of the following compounds $(i)$ and $(ii)$ will not react with a mixture of $NaBr$ and $H_{2}SO_{4}$? Explain why?
$(i)$ $CH_{3}CH_{2}CH_{2}OH$
$(ii)$ Phenol (as shown in the image)

(II) Compound $(ii)$,which is phenol,will not react with a mixture of $NaBr$ and $H_{2}SO_{4}$.
In phenol,the $C-O$ bond acquires partial double bond character due to resonance between the lone pair of electrons on the oxygen atom and the benzene ring.
This makes the $C-O$ bond much stronger and shorter,making it difficult to break the bond to replace the $-OH$ group with a $-Br$ atom.
In contrast,primary alcohols like $(i)$ $(CH_{3}CH_{2}CH_{2}OH)$ readily undergo substitution reactions with $NaBr$ and $H_{2}SO_{4}$ to form alkyl bromides.