Concept:Resonance stabilization of aniline and its conjugate acid determines their relative basicity.
Explanation:In aniline (
C6H5NH2), the lone pair on nitrogen delocalizes into the aromatic ring via resonance, providing significant stabilization.
In the anilinium ion (
C6H5NH3+), the lone pair is used to bond with
H+, so it cannot delocalize — resonance stabilization is much weaker.
Thus, anilinium ion is less resonance stabilized than aniline.
Evaluating other options:
Option A: Aliphatic amines are stronger bases than
NH3; aromatic amines (like aniline) are weaker. The statement is reversed.
Option B: Gabriel phthalimide synthesis works only with alkyl halides, not aryl halides; hence it cannot prepare aniline.
Option D: Sec-butylamine (
CH3CH(NH2)CH2CH3) has a chiral carbon (C-2) and can be optically active; the nitrogen atom's achirality does not negate that.
Answer:Option C is the correct statement.