Question #44359

Compound $\textbf{X}$ is \ce{methyl 2-(2-bromophenyl)acetate}. It is subjected to two distinct reaction pathways to test functional group compatibility and reactive intermediates:

\textbf{Pathway A:} $\textbf{X}$ is treated with excess \ce{NaNH2} in liquid \ce{NH3} at $240\text{ K}$, followed by careful neutralization, to yield the major product $\textbf{P}$.

\textbf{Pathway B:} $\textbf{X}$ is first treated with excess \ce{LiAlH4} in dry THF at $298\text{ K}$ followed by aqueous workup to give intermediate $\textbf{Y}$. $\textbf{Y}$ is then treated with excess \ce{NaNH2} in liquid \ce{NH3} at $240\text{ K}$, followed by neutralization, to yield the major product $\textbf{Q}$.

Identify the structures of $\textbf{P}$ and $\textbf{Q}$.