Ortho-Nitrophenol is less soluble in water than p- and mNitrophenols b...
Compounds involved in chelation become non-polar.
Consequently such compounds are soluble in nonpolar solvents like ether, benzene etc. and are only sparingly soluble in water whereas meta and para isomers are more soluble in water & less soluble in non-polar solvents.
intra-molecular H-bonding
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Ortho-Nitrophenol is less soluble in water than p- and mNitrophenols b...
Explanation:
Ortho-nitrophenol (o-nitrophenol) is less soluble in water than p- and m-nitrophenols due to the presence of intramolecular hydrogen bonding.
Intramolecular Hydrogen Bonding:
Intramolecular hydrogen bonding occurs when a hydrogen atom is bonded to an electronegative atom (such as oxygen or nitrogen) and is also attracted to another electronegative atom within the same molecule. In the case of o-nitrophenol, the hydrogen atom of the hydroxyl group (OH) forms a hydrogen bond with the oxygen atom of the nitro group (-NO2) within the same molecule.
Effect on Solubility:
The presence of intramolecular hydrogen bonding in o-nitrophenol affects its solubility in water. When a compound is soluble in water, it means that it is able to form favorable interactions with water molecules through hydrogen bonding. However, in the case of o-nitrophenol, the intramolecular hydrogen bonding restricts the availability of the hydroxyl group for interaction with water molecules. This decreases the solubility of o-nitrophenol in water.
Comparison with p- and m-Nitrophenols:
On the other hand, p- and m-nitrophenols do not exhibit intramolecular hydrogen bonding because the hydroxyl group is not in close proximity to the nitro group. As a result, the hydroxyl group in p- and m-nitrophenols is more readily available for interaction with water molecules, leading to higher solubility in water compared to o-nitrophenol.
Other Factors:
The other options given in the question are not the correct explanations for the difference in solubility between o-nitrophenol and p- and m-nitrophenols. The volatility of a compound does not directly affect its solubility in water. Intermolecular hydrogen bonding and melting point differences also do not explain the observed difference in solubility.
Conclusion:
In summary, o-nitrophenol is less soluble in water than p- and m-nitrophenols due to the presence of intramolecular hydrogen bonding, which restricts the availability of the hydroxyl group for interaction with water molecules.
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