Which of the following is more basic than aniline?
- Benzylamine
- Diphenylamine
- Triphenylamine
- p-Nitroaniline
Answer
(1) Benzylamine
Solution
As per NCERT, in aniline the lone pair on nitrogen is delocalised over the benzene ring by resonance, so it is less available for protonation; aryl amines are weaker bases than ammonia and alkyl amines.
Benzylamine (C6H5CH2NH2): the -CH2- group separates N from the ring, so the lone pair is not delocalised ⇒ it behaves like an alkyl amine (pKb ≈ 4.7), far more basic than aniline (pKb = 9.38).
Diphenylamine and triphenylamine: the lone pair is delocalised over two / three rings ⇒ weaker bases than aniline.
p-Nitroaniline: the electron-withdrawing –NO2 group (−R, −I) further decreases basicity.
∴ Benzylamine is more basic than aniline.
Answer: (1)