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Question

What is the action of the nitrating mixture on phenol?
While separating O- and P- nitrophenol by steam distillation, Name the isomer which is steam volatile. Give reason.

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Solution

Phenol on reacting with nitrating mixture produces p-nitrophenol and o-nitrophenol.
p-Nitrophenol can undergo intermolecular hydrogen bonding and thus has a higher boiling point. But o-nitrophenol undergoes intramolecular hydrogen bonding. As a result, it has a lower boiling point and is steam volatile.
Thus, they can be separated by steam distillation.
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