Join WhatsApp Icon JEE WhatsApp Group
Question 37

In the following reaction, the reason why meta-nitro product also formed is:

image

The formation of such a large amount of the meta-nitro product is due to the strongly acidic conditions used during the nitration process. Under normal circumstances, the amine group attached to the benzene ring is a powerful activating group. Because the nitrogen atom has a lone pair of electrons, it pushes those electrons into the ring through resonance, which naturally directs any incoming electrophiles, like the nitro group, to the ortho and para positions. This is why you still see a significant amount of the para product forming in the reaction mixture, as a portion of the molecules react in their standard state.

However, the reagents used for this nitration, concentrated nitric acid and concentrated sulfuric acid, create an intensely acidic environment. Because the amine group on the aniline molecule is basic, it rapidly reacts with the abundant protons in this acidic mixture. This acid-base reaction protonates the amine group, converting it into an anilinium ion. This transformation is the crucial key to the puzzle because the nitrogen atom now holds a positive charge and no longer has a free lone pair of electrons to donate to the benzene ring.

Once converted into the anilinium ion, the functional group entirely changes its chemical personality. Instead of pushing electrons into the ring, the positively charged nitrogen acts as a strong electron-withdrawing group, pulling electron density away from the benzene ring through the inductive effect. Electron-withdrawing groups inherently deactivate the ortho and para positions much more heavily than the meta position. Consequently, the anilinium ions in the mixture direct the incoming nitro groups almost exclusively to the meta position, which perfectly explains why you end up with a massive forty-seven percent yield of the meta-nitroaniline product alongside the expected para product.

Thus the right answer is the formation of anilinium ion, which is option A.

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