Write structures of the products A, B, C, D, and E in the following scheme.

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Solution

In presence of $C l_{2} / F e C l_{3}$ , halogenation on benzene takes place on or the position to $C l$ , as $C l$ is o, p-directing group for electrophilic substitution.
On addition of $N a - H g / H C l$ Clemenson reduction takes place, which reduce carbonyl to alkane.
On addition of $H N O_{3}$ , nitration takes place at para-position because at ortho -I effect of $C l$ will deactivate.
On addition of sodium salt nucleophilic attack takes place on para to $N O_{2}$ as it is most deactivating group and ease the attack of nucleophilic.
On addition of $H_{2} / P d$ , reduction of $N O_{2}$ and alkene takes place which gives product E.

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Identify A, B, C, D, and E in the following schemes and write their structures:

B a C^{*} O_{3} + H_{2} S O_{4} \to X_{(g a s)}, (C^{*} d e n o t e s^{14})

C r O_{3}

S O C l_{2}

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