Question

p-Chloroaniline and anilinium chloride can be distinguished by:

• A. Sandmeyer reaction
• B. $NaHC{O}_3$
• C. $AgN{O}_3$
• D. Carbylamine test

Answer 1

The correct option is C $AgN{O}_3$

The key thing to realise here is that anilinium chloride is a salt, whereas p-chloroaniline is just an aromatic amine. So anilinium chloride will react with $AgN{O}_3$ to give a white precipitate of $AgCl$, but p-chloroaniline does not.
$C_6{H}_5\stackrel{\oplus }{N}{H}_3\stackrel{\ominus }{Cl}+AgN{O}_3\to C_6{H}_5\stackrel{\oplus }{N}{H}_{3}N{O}_3^{\ominus }+AgCl\downarrow$