Question:
Which of the following is least alkaline ?
Which of the following is least alkaline ?
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Electron withdrawing groups reduce the availability of the lone pair on nitrogen.
Updated On: Nov 12, 2026
- \(\text{O}_{2}\text{N-C}_{6}\text{H}_{4}\text{-NH}_{2}\)
- \(\text{CH}_{3}\text{O-C}_{6}\text{H}_{4}\text{-NH}_{2}\)
- \(\text{C}_{6}\text{H}_{5}\text{C}_{6}\text{H}_{4}\text{-NH}_{2}\)
- \(\text{C}_{6}\text{H}_{5}\text{NH}_{2}\)
Show Solution
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The Correct Option is A
Solution and Explanation
Step 1: Understanding the Concept
Basicity of an aromatic amine depends on how available the lone pair on nitrogen is. Electron-donating groups raise basicity and electron-withdrawing groups lower it.
Step 2: Effect of substituents
The nitro group withdraws electrons strongly by -I and -R effects, so the lone pair is pulled away. The methoxy group donates by resonance.
Step 3: Order
Methoxyaniline is more basic than aniline, which is close to the phenyl-substituted amine, and nitroaniline is the weakest base.
Final Answer:
Nitroaniline is the least basic. \[ \boxed{\text{(A) }\text{O}_{2}\text{N-C}_{6}\text{H}_{4}\text{-NH}_{2}} \]
Basicity of an aromatic amine depends on how available the lone pair on nitrogen is. Electron-donating groups raise basicity and electron-withdrawing groups lower it.
Step 2: Effect of substituents
The nitro group withdraws electrons strongly by -I and -R effects, so the lone pair is pulled away. The methoxy group donates by resonance.
Step 3: Order
Methoxyaniline is more basic than aniline, which is close to the phenyl-substituted amine, and nitroaniline is the weakest base.
Final Answer:
Nitroaniline is the least basic. \[ \boxed{\text{(A) }\text{O}_{2}\text{N-C}_{6}\text{H}_{4}\text{-NH}_{2}} \]
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