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General Mechanism of Electrophilic Aromatic Substitution

An organic co...

Question

An organic compound (A), $C_{8} H_{4} O_{3}$ in dry benzene in the presence of anhydrous ${A l C l}_{3}$ gives compound (B). The compound (B) on treatment with ${P C l}_{5}$ followed by reaction with $H_{2} / P d ({B a S O}_{4})$ gives compound (C) which on reaction with hydrazine gives a cyclised compound (D) $(C_{14} H_{10} N_{2})$ . Identify (A), (B), (C), and (D). Explain the formation of (D) from (C).

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Solution

When $^{'} C^{'}$ reacts with hydrazine gives compound $^{'} D^{'}$ with the removal of two molecules of water by $N H_{2} N H_{2}$ due to two $> C = O$ groups.

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