Question #44398

Phenol is treated with $CHCl_3$ and excess aqueous $NaOH$ at $340\text{ K}$. After complete consumption of $CHCl_3$, the resulting reaction mixture containing the sodium salt of the major product $P$ is divided into two equal aliquots, $X$ and $Y$. Aliquot $X$ is directly treated with aniline ($\ce{C6H5NH2}$) at $298\text{ K}$. Aliquot $Y$ is first adjusted to a pH of $4.5$ using dilute $HCl$, and then treated with aniline at $298\text{ K}$. Both mixtures are subsequently subjected to a standard mild aqueous workup. Identify the major organic products isolated from aliquots $X$ and $Y$, respectively.