An organic compound [ X ] reacts with H ₂ / Pd - BaSO ₄ to give compound [ Y ] which reduces Tollen's reagent and undergoes Cannizzaro's reaction. On rigorous oxidation of [Y] in presence of KMnO ₄ / H ⁺ Phthalic acid is the product obtained. What is [ X ] ?

Step-by-step solution

The reaction of an organic compound [X] with H₂/Pd-BaSO₄ (Rosenmund reduction) indicates that [X] is an acid chloride ( R-COCl ). The product [Y] obtained from this reduction is an aldehyde ( R-CHO ). Since [Y] reduces Tollen's reagent and undergoes Cannizzaro's reaction, [Y] must be an aromatic aldehyde (as it lacks -hydrogens). Rigorous oxidation of [Y] with KMnO₄/H⁺ yields phthalic acid. Phthalic acid is benzene-1,2-dicarboxylic acid. This implies that the starting material [X] must be an ortho-substituted benze