Chemistry Question on Aldehydes, Ketones and Carboxylic Acids

Question

Compound $( A ), C_8H_9Br$ gives a white precipitate when warmed with alcoholic $AgNO_3$ . Oxidation of $(A)$ gives an acid $(B)$ , $C_8H_6O$ 4. $(B)$ easily forms anhydride on heating. Identify the compound $(A)$ .

Answer 1

Solution

Compound A gives a precipitate with alcoholic AgNO,, so it
must contains Br in side chain. On oxidation, it gives $C_8H_6O_4$ ,
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