Question
Explain nitration of phenol in detail.
✓
Answer
→ Nitration: With dilute nitric acid at low temperature (298 K), phenol yields a mixture of ortho and para nitrophenols.
→ The ortho and para isomers can be separated by steam distillation. o-Nitrophenol is steam volatile due to intramolecular hydrogen bonding while p-nitrophenol is less volatile due to intermolecular hydrogen bonding which causes the association of molecules.
→ With concentrated nitric acid, phenol is converted to 2,4,6-trinitrophenol. The product is commonly known as picric acid. The yield of the reaction product is poor.
→ Nowadays picric acid is prepared by treating phenol first with concentrated sulphuric acid which converts into phenol-2,4-disulphonic acid, and then with concentrated nitric acid to get 2,4,6-trinitrophenol.
→ The ortho and para isomers can be separated by steam distillation. o-Nitrophenol is steam volatile due to intramolecular hydrogen bonding while p-nitrophenol is less volatile due to intermolecular hydrogen bonding which causes the association of molecules.
→ With concentrated nitric acid, phenol is converted to 2,4,6-trinitrophenol. The product is commonly known as picric acid. The yield of the reaction product is poor.
→ Nowadays picric acid is prepared by treating phenol first with concentrated sulphuric acid which converts into phenol-2,4-disulphonic acid, and then with concentrated nitric acid to get 2,4,6-trinitrophenol.
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