Join WhatsApp Icon JEE WhatsApp Group
Question 39

The reaction sequence(s) that would lead to o-xylene as the major product is(are)

The target molecule is $$o$$-xylene, i.e. $$1,2$$-dimethylbenzene. To obtain two methyl groups ortho to each other we must make sure that the para position is blocked before the second methyl group is introduced. The only sequence that does this efficiently is given in Option A.

Step 1 (Option A)
Starting compound: toluene. Treat it with conc. $$H_2SO_4$$ (≈ 20-30 °C).
The methyl group is an ortho/para director; however, sulphonation at this temperature is para-selective because of steric hindrance in the ortho positions.
Reaction: $$\underset{\text{toluene}}{C_6H_5CH_3} \xrightarrow[20-30^{\circ}\mathrm{C}]{H_2SO_4/SO_3} C_6H_4(CH_3)(SO_3H)\ (\text{major para})$$

Thus the para position is now occupied by $$SO_3H$$, while both ortho positions remain available.

Step 2 (Option A)
Carry out a Friedel-Crafts alkylation with $$CH_3Cl/AlCl_3$$.
Because the para position is blocked by $$SO_3H$$, the incoming $$CH_3^+$$ can enter only the ortho positions relative to the original methyl group.
Reaction: $$C_6H_4(CH_3)(SO_3H) \xrightarrow[AlCl_3]{CH_3Cl} C_6H_3(CH_3)_2(SO_3H)$$(methyl enters ortho).

Step 3 (Option A)
Desulphonate the ring by heating with dilute acid/steam.
$$C_6H_3(CH_3)_2(SO_3H)\ \xrightarrow[\text{steam}]{\Delta,\, H^+} C_6H_4(CH_3)_2 \;=\; o\text{-xylene}$$

The $$SO_3H$$ group is removed cleanly, leaving two adjacent methyl groups; hence the major product is $$o$$-xylene.

Why the other options fail
• Options that attempt two successive Friedel-Crafts methylations on benzene or on toluene without a temporary blocking group give a mixture in which the para isomer predominates (steric hindrance disfavors ortho).
• Options that introduce a meta-directing group (−NO2, −COOH, etc.) before the second methyl group place the second methyl meta, not ortho, to the first one.
• Any sequence that removes the first directing methyl group (e.g., through oxidation) loses regiocontrol.

Therefore only Option A supplies a blocking group at the para position, introduces the second methyl group ortho to the first, and finally removes the blocker to give $$o$$-xylene in high yield.

Final answer: Option A which is: $$\text{toluene} \; \xrightarrow{H_2SO_4} \; p\text{-toluenesulphonic acid} \; \xrightarrow{CH_3Cl/AlCl_3} \; o\text{-methyl-}p\text{-toluenesulphonic acid} \; \xrightarrow{\text{heat, H}_2O} \; o\text{-xylene}.$$

Get AI Help

Create a FREE account and get:

  • Free JEE Advanced Previous Papers PDF
  • Take JEE Advanced paper tests

JEE Quant Questions | JEE Quantitative Ability

JEE DILR Questions | LRDI Questions For JEE

JEE Verbal Ability Questions | VARC Questions For JEE

Free JEE DILR Questions

JEE Continuity & DifferentiabilityJEE LimitsJEE MatricesJEE Magnetism & Magnetic MaterialsJEE StatisticsJEE Wave OpticsJEE SolutionsJEE Inverse Trigonometric FunctionsJEE Carboxylic AcidsJEE Laboratory Experiments - XIJEE CirclesJEE Definite IntegrationJEE Binomial TheoremJEE Hydrocarbons - AromaticJEE Nitrogen-Containing CompoundsJEE Purification & CharacterisationJEE Electric Charges & FieldsJEE Ray OpticsJEE Organic Compounds with HalogensJEE Chemical ThermodynamicsJEE p-Block Elements (Groups 13-18)JEE Applications of DerivativesJEE DifferentiationJEE Electric Potential & CapacitanceJEE Rotational MotionJEE Hydrocarbons - AlkenesJEE Redox ReactionsJEE Heat TransferJEE Complex NumbersJEE Differential EquationsJEE Trigonometric FunctionsJEE d and f-Block ElementsJEE Work, Energy & PowerJEE Alcohols, Phenols & EthersJEE Aldehydes & KetonesJEE Atoms & NucleiJEE ElasticityJEE Straight LinesJEE GravitationJEE Hydrocarbons - AlkynesJEE Electromagnetic InductionJEE Sequences & SeriesJEE Electromagnetic WavesJEE WavesJEE Periodic Table & PeriodicityJEE Simple Harmonic MotionJEE Quadratic EquationsJEE ProbabilityJEE Dual Nature of Matter & RadiationJEE Current & ResistanceJEE Chemical Bonding & Molecular StructureJEE Practical Organic ChemistryJEE ElectrochemistryJEE EMF & Circuit AnalysisJEE Permutations & CombinationsJEE Chemical KineticsJEE Coordination CompoundsJEE BiomoleculesJEE Kinetic Theory of GasesJEE Vector AlgebraJEE Three Dimensional GeometryJEE Number SystemJEE Laws of MotionJEE Atomic StructureJEE Basic Principles of Organic ChemistryJEE EquilibriumJEE Alternating CurrentsJEE Fluid MechanicsJEE Kinematics - 1D MotionJEE Hydrocarbons - AlkanesJEE Surface TensionJEE Indefinite IntegrationJEE Conic SectionsJEE Kinematics - 2D MotionJEE DeterminantsJEE Magnetic Effects of CurrentJEE JEE 2D GeometryJEE Electronic DevicesJEE Units & MeasurementsJEE Sets, Relations & FunctionsJEE Basic Concepts in ChemistryJEE Laws of Thermodynamics
Ask AI