Question
Which among the following compounds has highest solubility in water?
Which among the following compounds has highest solubility in water?
A. Phenol
Solubility of organic compounds in water depends on their ability to form hydrogen bonds with water molecules, the size of the hydrophobic part, and the lattice energy of the solid. 1. Phenol forms strong intermolecular hydrogen bonds with water, making it quite soluble (solubility 8.3 g/100 mL ). 2. p-Cresol contains an additional hydrophobic methyl (-CH_3) group, which increases the non-polar character and decreases its solubility compared to phenol (solubility 1.9 g/100 mL ). 3. o-Nitrophenol exhibits intramolecular hydrogen bonding (chelation). This restricts its ability to form intermolecular hydrogen bonds with water, resulting in very low solubility (solubility 0.2 g/100 mL ). 4. p-Nitrophenol can form intermolecular hydrogen bonds with water. However, due to its higher molecular mass and strong intermolecular interactions in the solid state (high lattice energy), its solubility is lower than that of phenol (solubility 1.6 g/100 mL ). Therefore, phenol has the highest solubility in water among the given compounds. Answer: Phenol
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