Q.
Compound (A), C8H9Br gives a yellow precipitate when warmed with alcoholic AgNO3. Oxidation o f (A) gives an acid (B), C8H6O4 . (B) easily forms anhydride on heating. Identify the compound (A).
Compound A gives a precipitate with alcoholic AgNO3, so it must contains Br in side chain. On oxidation, it gives C8H6O4, 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
and the reactions are as follows