Reaction producing X (Electrophilic Aromatic Substitution): When toluene reacts with chlorine ($Cl_2$) in the presence of a Lewis acid catalyst like iron(III) chloride ($FeCl_3$) or iron ($Fe$), an electrophilic substitution reaction occurs on the benzene ring. The methyl group ($-CH_3$) is an ortho-para directing group. Therefore, the entering chlorine atom attacks the ortho and para positions relative to the methyl group, yielding a mixture of o-chlorotoluene and p-chlorotoluene . $C_6H_5CH_3 + Cl_2 \xrightarrow{FeCl_3} o-ClC_6H_4CH_3 + p-ClC_6H_4CH_3$

Reaction producing Y (Free Radical Substitution): When the reaction is carried out in the presence of light ($h\nu$) or heat, the conditions favour a free radical mechanism. This leads to substitution in the alkyl side chain (benzylic position) rather than the ring, similar to the halogenation of alkanes . The hydrogen atoms of the methyl group are replaced by chlorine atoms. Depending on the extent of reaction, mono-, di-, or tri-chlorinated products (benzyl chloride, benzal chloride, or benzotrichloride) are formed. Option 3 specifies trichloromethyl benzene (benzotrichloride), which is the product of exhaustive side-chain chlorination. $C_6H_5CH_3 + 3Cl_2 \xrightarrow{h\nu} C_6H_5CCl_3 + 3HCl$

Conclusion: X is the mixture of ring-substituted isomers (o and p-chlorotoluene), and Y is the side-chain substituted product (trichloromethyl benzene).