Join WhatsApp Icon JEE WhatsApp Group
Question 47


Identify A and B in the following sequence of reaction:

image

In side-chain chlorination of toluene using $$Cl_2/h\nu$$, chlorine substitutes the benzylic hydrogen atoms to form $$Ph-CH_2Cl$$, $$Ph-CHCl_2$$, or $$Ph-CCl_3$$ depending on the extent of chlorination. Subsequent hydrolysis replaces chlorine atoms with hydroxyl groups.

Option A is incorrect because $$Ph-COCl$$ cannot be formed in the first step. The reagents $$Cl_2/h\nu$$ only cause free-radical chlorination and do not introduce an oxygen atom or generate a carbonyl group.

Option C is incorrect because hydrolysis of $$Ph-CH_2Cl$$ produces $$Ph-CH_2OH$$ (benzyl alcohol). Formation of $$Ph-CHO$$ (benzaldehyde) is not possible from an intermediate containing only one chlorine atom.

Option D is incorrect because hydrolysis of $$Ph-CHCl_2$$ first forms the unstable gem-diol $$Ph-CH(OH)_2$$, which loses water to give $$Ph-CHO$$ (benzaldehyde). Formation of $$Ph-COOH$$ (benzoic acid) requires the intermediate $$Ph-CCl_3$$, not $$Ph-CHCl_2$$.

Option B is correct because $$Ph-CHCl_2$$ (benzal chloride) on hydrolysis forms the unstable gem-diol $$Ph-CH(OH)_2$$, which dehydrates to yield $$Ph-CHO$$ (benzaldehyde).

Therefore, the correct sequence is:

$$Ph-CHCl_2 \rightarrow Ph-CHO$$

Hence, Option B is the correct answer.

Get AI Help

Create a FREE account and get:

  • Free JEE Mains Previous Papers PDF
  • Take JEE Mains 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 Topicwise Questions

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