Phenol reacts with dilute nitric acid at low temperature, producing a mixture of ortho and para nitrophenols. Steam distillation is used to separate the isomers; o-nitrophenol is steam volatile due to intramolecular hydrogen bonding, while p-nitrophenol is less volatile due to intermolecular hydrogen bonding.
Describe the electrophilic aromatic substitution reaction of phenol with dilute nitric acid at low temperature, and what is the role of steam distillation in separating ortho and para nitrophenols?
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In the electrophilic aromatic substitution of phenol with dilute nitric acid at low temperature, phenol reacts with the nitronium ion (NO₂⁺), formed by nitric acid acting as an electrophile. This leads to the formation of ortho and para nitrophenols. Steam distillation is employed to separate ortho and para nitrophenols based on their different solubilities in water. At low temperatures, ortho-nitrophenol is less soluble than para-nitrophenol. Steam distillation allows the separation of the two isomers, as steam carries the more soluble para-nitrophenol while leaving the less soluble ortho-nitrophenol behind, facilitating isolation and purification of the products.