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Amines

Question
CBSEENCH12009196

Aniline is more soluble in aq. HCl than in water. Explain. 

Solution

Aniline does not undergo hydrogen bonding because of the presence of the benzene which is highly hydrophobic. therefore aniline is insoluble in water.
In the HCl the amine group becomes protonated (-NH3+) and the ionic  hence soluble in HCl.