Exams › JEE Main › Chemistry

When toluene is treated with chlorine in the presence of FeCl3, product 'X' is formed. If the same hydrocarbon is chlorinated in sunlight, product 'Y' is obtained. Identify 'X' and 'Y'.

1. X = benzyl chloride, Y = o-chlorotoluene
2. X = m-chlorotoluene, Y = p-chlorotoluene
3. X = o- and p-chlorotoluene, Y = trichloromethylbenzene
4. X = benzyl chloride, Y = m-chlorotoluene

Correct answer: X = o- and p-chlorotoluene, Y = trichloromethylbenzene

Solution

With Cl2/FeCl3 (ionic conditions) toluene undergoes ring substitution giving o- and p-chlorotoluene (X). With Cl2 in sunlight (free-radical) the methyl side chain is chlorinated, ultimately to C6H5CCl3, trichloromethylbenzene (Y).

Related JEE Main Chemistry questions

• Arrange the following carbanions in decreasing order of basicity: (A) CH3CH2−, (B) CH2=CH−, and (C) HC≡C−.
• In acid-catalyzed hydration of alkenes, all alkenes except ethene generally give rise to which type of alcohol product?
• Which of the following organic compounds has the same hybridization as the carbon atom in its combustion product, CO2?
• What is formed when CH3MgX reacts with CH3C≡CH?
• Which of the following reagent sets can be used to convert propene into 1-propanol?
• When ethyne (H–C≡CH) is treated first with (1) NaNH2 in liquid NH3 and then with (2) CH3CH2Br, the product X is formed. If X is again subjected to the same two-step sequence, the product Y obtained is:

⚔️ Practice JEE Main Chemistry free + battle 1v1 →