Question #44924

Benzene undergoes electrophilic aromatic substitution with \ce{Cl_2 / FeCl_3} to give \textbf{A}, which upon nitration with a mixture of conc. \ce{HNO_3} and conc. \ce{H_2SO_4} yields \textbf{P} as the major isomer. \textbf{P} is then subjected to two different reaction pathways:

\textbf{Pathway 1:}

1. \ce{Sn / HCl}, then \ce{NaOH(aq)} $\rightarrow$ \textbf{Q}
2. \ce{NaNO_2 / HCl}, $273-278\text{ K}$ $\rightarrow$ \textbf{R}
3. \ce{CuCN / KCN}, $\Delta$ $\rightarrow$ \textbf{S}
4. \ce{CH_3MgBr}, dry ether, then \ce{H_3O^+}, $\Delta$ $\rightarrow$ \textbf{T}

\textbf{Pathway 2:}

1. \ce{LiAlH_4} (excess), dry ether, $\Delta$, then \ce{H_2O} $\rightarrow$ \textbf{U}

Identify the major products \textbf{T} and \textbf{U}.