JEE Main 2025 Jan 29 Shift 2, Chemistry Q20: Properties of Ether

An aryl alkyl ether cleaved by $HBr$ gives a phenol and an alkyl halide: the alkyl–O bond breaks because $S_{N}2$ attack of $B{r}^{-}$ on the $s{p}^3$ carbon is fast, while attack on the aromatic $s{p}^2$ carbon is essentially impossible.

For anisole, $PhOC{H}_3+HBr\to PhOH+C{H}_{3}Br$. The phenol oxygen is liberated as $-OH$.

The acetal in (1) hydrolyses back to benzaldehyde, not a phenol. The benzyl ethers in (3) and (4) cleave at the benzylic carbon to give a benzyl halide plus an alcohol, never a phenol, because there is no $Ar-O$ bond directly on the ring.

$\therefore$ Only anisole, option (2), yields a phenol.