Question:
Which among the following compounds has highest solubility in water?
Which among the following compounds has highest solubility in water?
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Smaller hydrophobic groups and free OH hydrogen bonding with water favour solubility.
Updated On: Oct 1, 2026
- Phenol
- p-resol
- o-Nitrophenol
- p-Nitrophenol
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The Correct Option is A
Solution and Explanation
Step 1: Understanding the Concept:
Solubility of a phenol in water depends on how well it forms hydrogen bonds with water, and on the size of the non-polar part of the molecule.
Step 2: Detailed Explanation:
Phenol has one polar -OH group and a plain benzene ring. Its -OH can form hydrogen bonds with water freely, so it dissolves best of the four. Adding a methyl group (p-cresol) increases the non-polar part and lowers solubility.
Step 3: Why the other options are wrong.
p-Cresol (B) has an extra hydrophobic methyl group. o-Nitrophenol (C) forms an intramolecular hydrogen bond between OH and \(\text{NO}_2\), so its OH is not free to bond with water and it is much less soluble. p-Nitrophenol (D) has a large non-polar nitro-substituted ring and strong intermolecular attraction between its own molecules, so it dissolves less than phenol.
Final Answer:
Phenol has the highest solubility in water, option (A). \[ \boxed{\text{Phenol (A)}} \]
Solubility of a phenol in water depends on how well it forms hydrogen bonds with water, and on the size of the non-polar part of the molecule.
Step 2: Detailed Explanation:
Phenol has one polar -OH group and a plain benzene ring. Its -OH can form hydrogen bonds with water freely, so it dissolves best of the four. Adding a methyl group (p-cresol) increases the non-polar part and lowers solubility.
Step 3: Why the other options are wrong.
p-Cresol (B) has an extra hydrophobic methyl group. o-Nitrophenol (C) forms an intramolecular hydrogen bond between OH and \(\text{NO}_2\), so its OH is not free to bond with water and it is much less soluble. p-Nitrophenol (D) has a large non-polar nitro-substituted ring and strong intermolecular attraction between its own molecules, so it dissolves less than phenol.
Final Answer:
Phenol has the highest solubility in water, option (A). \[ \boxed{\text{Phenol (A)}} \]
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