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Question
Why ortho-nitrophenol is steam volatile while para-nitrophenol is not?
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Solution
In o-nitrophenol, oxygen in the NO2 group forms an intramolecular hydrogen bond with hydrogen in the hydroxide group. While in the p-nitrophenol, oxygen in the NO2 group of one molecule forms an intermolecular hydrogen bond with hydrogen in the hydroxide group of another molecule.
Since intramolecular hydrogen bonds are weaker than intermolecular hydrogen bonds, o-nitrophenol is less steam volatile than p-nitrophenol.
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