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Q. Compound (A), $C_{8}H_{9}Br$ gives a yellow precipitate when warmed with alcoholic $AgNO_{3}$. Oxidation o f (A) gives an acid (B), $C_{8}H_{6}O_{4}$ . (B) easily forms anhydride on heating. Identify the compound (A).

Haloalkanes and Haloarenes

Solution:

Compound A gives a precipitate with alcoholic $AgNO_{3}$, so it must contains Br in side chain. On oxidation, it gives $C_{8}H_{6}O_{4}$, which shows the presence of two alkyl chains attached directly with the benzene nucleus. Since compound B gives anhydride on heating, the two alkyl substituent must occupy adjacent (1,2) position. Thus, A must be
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and the reactions are as follows
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