Join WhatsApp Icon JEE WhatsApp Group
Question 47

Identify the product formed (A and E)

image

The starting compound is p-nitrotoluene.

On bromination with $$Br_2$$, the $$-CH_3$$ group acts as an ortho/para director and the $$-NO_2$$ group acts as a meta director. Both groups direct the incoming bromine to the same position, giving product A as 2-bromo-4-nitrotoluene.

Reduction with $$Sn/HCl$$ converts the nitro group into an amino group, forming product B (2-bromo-4-methylaniline).

Treatment with $$NaNO_2/HCl$$ at $$273-278\text{ K}$$ converts the amino group into the corresponding diazonium salt, giving product C.

Reaction with $$H_3PO_2/H_2O$$ replaces the diazonium group by hydrogen (deamination), yielding product D as o-bromotoluene.

Oxidation with $$KMnO_4/KOH$$ followed by acidic workup $$H_3O^+$$ converts the benzylic $$-CH_3$$ group into $$-COOH$$ without affecting the bromine substituent.

Thus, product E is o-bromobenzoic acid (2-bromobenzoic acid).

Therefore,

• Product A = 2-bromo-4-nitrotoluene

• Product E = 2-bromobenzoic acid

Hence, the correct option is $$\boxed{\text{Option B}}$$.

Get AI Help

Video Solution

video

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