Arrange the following compounds in increasing order of solubility in water:
$C_{6} H_{5} N H_{2}, {(C_{2} H_{5})}_{2} N H, C_{2} H_{5} N H_{2}$

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Solution

The increasing order of solubility in water is $C_{6} H_{5} N H_{2} < {(C_{2} H_{5})}_{2} N H < C_{2} H_{5} N H_{2}$ .
The lower aliphatic amines are soluble in water because they are capable of forming hydrogen bonds with water. However, solubility decreases with increase in molar mass of amines due to increase in size of the hydrophobic alkyl part.
The extent of hydrogen bonding in secondary alcohols is lower than the extent of hydrogen bonding in primary amines.
Hence, the solubility of secondary amines is lower than the solubility of primary amines.
Aromatic amines are water insoluble due to larger hydrocarbon part which tends to retard the formation of hydrogen bonds.

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