Why is aniline soluble in hydrochloric acid while it is insoluble in water ?
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Water is a polar solvent and it dissolved polar species. This is actually an acid-base reaction. Now in aniline, the nitrogen atom donates its lone pair to the acid and by forming a salt (ionic compound), it dissolves in water(aqueous HCl).
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Aniline is highly soluble in HCl.
- Aniline contains a hydrophobic benzene ring. That's why aniline does not make a hydrogen bond with water and become insoluble in water.
- On the other hand, aniline is a base and Hydrochloric acid is a strong acid. Thus aniline easily dissolves in HCl and form a protonated species by accepting a proton from HCl. Thus aniline is highly soluble in HCl.
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