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  4. Phenol on reaction with dilute nitric acid, gives two products. Which method will be most effective for large scale separation ?

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Q. Phenol on reaction with dilute nitric acid, gives two products. Which method will be most effective for large scale separation ?

JEE MainJEE Main 2022Organic Chemistry – Some Basic Principles and Techniques

Solution:

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Para product has higher boiling point than ortho as intermolecular $H$-bond is possible in former, where as intramolecular $H$-bond is possible in ortho product.
Steam distillation can separate them as ortho product is steam volatile.