Question #44353

Consider the following reaction sequence starting from 3-methylaniline: $\text{3-Methylaniline} \xrightarrow{\text{1. } PhSO_2Cl, \text{ pyridine}} \textbf{P} \xrightarrow{\text{2. } Br_2, CH_3COOH} \textbf{Q} \xrightarrow{\text{3. } 70\% \text{ } H_2SO_4, \Delta} \textbf{R}$ $\textbf{R} \xrightarrow{\text{4. } NaNO_2, HCl, 273 \text{ K}} \textbf{S} \xrightarrow{\text{5. } CuCN, KCN, \Delta} \textbf{T} \xrightarrow{\text{6. } \text{DIBAL-H (1 eq), } -78^\circ\text{C, then } H_2O} \textbf{U}$ Identify the major product $\textbf{U}$.