Amines

Hardchemistry

Aniline is a weaker base than cyclohexylamine mainly because:

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Aniline has higher molecular mass

Lone pair on nitrogen in aniline is delocalized by resonance

Cyclohexylamine forms intramolecular hydrogen bonding

Aniline is more soluble in water

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Subject: chemistry
Chapter: organic compounds containing nitrogen
Topic: amines
Difficulty: Hard
Year: 2025

Solution

Correct Answer:

Lone pair on nitrogen in aniline is delocalized by resonance

Basicity depends on the availability of the nitrogen lone pair for protonation. In aniline, this lone pair interacts with the aromatic ring and gets delocalized through resonance, reducing electron density on nitrogen and lowering basic strength. In cyclohexylamine, the lone pair remains localized and alkyl +I effect pushes electron density toward nitrogen, making protonation easier. Hence cyclohexylamine is stronger as a base.

This hard difficulty chemistry question is from the chapter organic compounds containing nitrogen, covering the topic of amines. It appeared in the 2025 exam.

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Amines

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