JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Amongst the following the most basic compound is
- Abenzylamine
- Baniline
- Cacetanilide
- Dp-nitroaniline
View written solutionFree
Correct answer: A
-
Concept of basicity in amines
Basicity depends on the availability of the lone pair on nitrogen for donation to a proton.
- Greater availability of the lone pair stronger base.
- If the lone pair is delocalized by resonance, basicity decreases.
- Electron-withdrawing groups also decrease basicity.
-
Examine each option
(A) Benzylamine,
- The amino group is attached to a group, not directly to the benzene ring.
- Therefore, the lone pair on nitrogen is not conjugated with the aromatic ring.
- It behaves like an aliphatic amine, so it is fairly basic.
(B) Aniline,
- Here, is directly attached to the benzene ring.
- The lone pair on nitrogen is delocalized into the benzene ring by resonance.
- Hence, the lone pair is less available for protonation.
- So aniline is less basic than benzylamine.
(C) Acetanilide,
- This is an amide derivative.
- The nitrogen lone pair is strongly delocalized toward the carbonyl group:
- Due to this strong resonance, the lone pair is much less available.
- Therefore, acetanilide is very weakly basic.
(D) -Nitroaniline
- Like aniline, the nitrogen lone pair is delocalized into the benzene ring.
- Additionally, the group is a strong electron-withdrawing group by both and effects.
- This further decreases electron density on nitrogen.
- Hence, -nitroaniline is less basic than aniline.
-
Order of basicity
From the above analysis: and acetanilide is the least/basicity is very low due to amide resonance.
So the most basic compound is:
-
Option check
- A: benzylamine — correct
- B: aniline — less basic due to resonance
- C: acetanilide — very weak base due to amide resonance
- D: -nitroaniline — even less basic due to group
Therefore, the correct answer is A.
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