Question:
Which of the following compounds has lowest solubility in water?
Which of the following compounds has lowest solubility in water?
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Intramolecular H-bonding (o-isomer) decreases water solubility and increases volatility compared to intermolecular H-bonding (p-isomer).
Updated On: Apr 30, 2026
- Phenol
- p-Cresol
- o-Nitrophenol
- p-Nitrophenol
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Verified By Collegedunia
The Correct Option is C
Solution and Explanation
Step 1: Concept
Solubility in water depends on the ability to form intermolecular hydrogen bonds with water.
Step 2: Hydrogen Bonding Analysis
- Phenol and p-Nitrophenol form strong intermolecular H-bonds with water. - o-Nitrophenol undergoes **intramolecular** hydrogen bonding (chelation).
Step 3: Effect on Solubility
Because the $-OH$ group in o-nitrophenol is involved in an internal bond, it is less available to bond with water molecules.
Step 4: Conclusion
This makes o-nitrophenol the least soluble and most steam-volatile.
Final Answer:(C)
Solubility in water depends on the ability to form intermolecular hydrogen bonds with water.
Step 2: Hydrogen Bonding Analysis
- Phenol and p-Nitrophenol form strong intermolecular H-bonds with water. - o-Nitrophenol undergoes **intramolecular** hydrogen bonding (chelation).
Step 3: Effect on Solubility
Because the $-OH$ group in o-nitrophenol is involved in an internal bond, it is less available to bond with water molecules.
Step 4: Conclusion
This makes o-nitrophenol the least soluble and most steam-volatile.
Final Answer:(C)
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