Question:medium

Which of the following is the most basic compound?

Show Hint

In benzyl amine the \( CH_2 \) separates \( NH_2 \) from the ring, so no resonance withdrawal; its lone pair stays fully available.
Updated On: Jul 10, 2026
  • Aniline
  • p-Nitro aniline
  • Benzyl amine
  • Acetanilide
Show Solution

The Correct Option is C

Solution and Explanation

Step 1: Rank basicity by how much the nitrogen lone pair is tied up by resonance or pulled by electron-withdrawing groups; a tied-up or pulled lone pair means weaker base.
Step 2: In aniline the lone pair spreads into the aromatic ring, lowering basicity relative to a plain alkyl amine. Adding a \( -NO_2 \) group (p-nitroaniline) drains electron density further, and turning the amine into an amide (acetanilide) locks the lone pair onto the carbonyl oxygen, the strongest deactivation of all.
Step 3: Benzyl amine keeps its nitrogen one carbon away from the ring. That insulating \( CH_2 \) blocks resonance with the ring, so its lone pair is as available as in an ordinary aliphatic amine.
Step 4: With the freest lone pair, benzyl amine accepts a proton most readily and is therefore the most basic of the four. Option (iii) is correct.
Was this answer helpful?
0