Question 7.SSE.15: An organic compound A, C8H4O3, in dry benzene in the presenc......
An organic compound A, C_8H_4O_3 , in dry benzene in the presence of anhydrous AlCl_3 gives compound B. The compound B on treatment with PCl_5 , followed by reaction with H_2/Pd (BaSO_4) gives compound C, which on reaction with hydrazine gives a cyclic compound D (C_{14}H_{10}N_2) . Identify A,B,C and D. Explain the formation of D from C.
[IIT, 2000]
\begin{matrix} \overset{C_6H_6}{\underset{AlCl_3}{\xrightarrow {\hspace{2 cm}} }} \\\\\\\\\\\\\\\ \end{matrix} 
\begin{matrix} \overset{PCl_5}{\xrightarrow {\hspace{2 cm}} } \\\\\\\\\ \end{matrix} 
\begin{matrix} \overset{H_2-Pd }{\underset{BaSO_4}{\xrightarrow {\hspace{2 cm}} }} \\\\\\\\\ \end{matrix}
or 
\begin{matrix} \overset{H_2N.NH_2}{\xrightarrow {\hspace{2 cm}} } \\\\\\\\\ \end{matrix} 