Join WhatsApp Icon JEE WhatsApp Group
Question 67

The strongest conjugate acid will result from:

For substituted anilines, two electronic effects decide the stability of the protonated form (the anilinium ion):
1. Inductive effect (−I or +I): An electron-withdrawing (−I) group pulls electron density away from the positively charged nitrogen, dispersing the charge and stabilising the cation.
2. Resonance (−M or +M): A group that can withdraw electrons by resonance (−M) also delocalises and stabilises the positive charge.

Let us examine each substituent in the para position:

Case A: Aniline (no substituent)
No extra stabilising effect beyond the benzene ring. So its conjugate acid serves as the reference.

Case B: p-Methoxyaniline (−OCH3)
−OCH3 has a strong +M (electron-donating) effect, pushing electron density toward the ring. This increases electron density on nitrogen in the neutral base; once the base is protonated, that extra electron density destabilises the positive charge. Hence the conjugate acid is weaker than that of aniline.

Case C: p-Nitroaniline (−NO2)
−NO2 is a very powerful −I and −M group. Both effects withdraw electron density from the ring and ultimately from the protonated nitrogen. This delocalises and stabilises the positive charge on nitrogen, making the conjugate acid highly stabilised and therefore very strong.

Case D: p-Methylaniline (−CH3)
−CH3 is weakly +I and weakly +M (hyperconjugation). These donating effects slightly increase electron density, which destabilises the cation relative to aniline. So its conjugate acid is weaker.

Comparing all four, the conjugate acid of p-nitroaniline receives the maximum stabilisation due to the strong −I and −M effects of the nitro group. Hence it is the strongest conjugate acid among the given options.

Therefore, the correct choice is:
Option C which is: p-Nitroaniline

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