JEE Advanced 2018 · Paper 1, Chemistry question 16

Treatment of benzene with CO/HCl in the presence of anhydrous AlCl$_3$/CuCl followed by reaction with Ac$_2$O/NaOAc gives compound X as the major product. Compound X upon reaction with Br$_2$/Na$_2$CO$_3$, followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction of X with H$_2$/Pd-C, followed by H$_3$PO$_4$ treatment gives Z as the major product.