COMEDK2023Evening ShiftChemistryAminesActual
Select the strongest base from the given compounds: [A] p- NO ₂- C ₆ H ₄ NH ₂ [B] C ₆ H ₅- CH ₂- NH ₂ [C] m - NO ₂- C ₆ H ₄ NH ₂ [D] C ₆ H ₅ NH ₂
Options
- A[A]
- B[B]
- C[D]
- D[C]
Correct answer
B. [B]
Step-by-step solution
The basicity of amines is determined by the availability of the lone pair of electrons on the nitrogen atom for protonation. In p-nitroaniline [A] and m-nitroaniline [C], the - NO ₂ group is a strong electron-withdrawing group (EWG) that decreases the electron density on the nitrogen atom through both inductive (-I) and resonance (-M) effects, significantly reducing basicity compared to aniline [D]. In aniline [D], the lone pair of electrons on the nitrogen atom is in conjugation with the benzene ring, which decrea