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o-Nitrophenol has a lower solubility in water than its m- and p-isomers mainly because:
- The melting point of o-nitrophenol is lower than that of the m- and p-isomers.
- o-Nitrophenol is more volatile in steam than the m- and p-isomers.
- o-Nitrophenol exhibits intramolecular hydrogen bonding.
- o-Nitrophenol exhibits intermolecular hydrogen bonding.
Correct answer: o-Nitrophenol exhibits intramolecular hydrogen bonding.
Solution
In o-nitrophenol the -OH and adjacent -NO2 form an intramolecular (chelate) hydrogen bond, so the molecule cannot hydrogen-bond effectively with water, lowering its water solubility. In the m- and p-isomers the groups are too far apart, so they hydrogen-bond with water and dissolve better.
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