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Phenol is treated with Con.H2SO4 to gives a product 'X" which on treatment with Con.HNO3 gives compound 'Y'. The compounds 'X' and 'Y' are respectively

  • A.Phenol-2- sulphonic acid and 2-nitrophenol
  • B.Phenol-2-sulphonic acid and 4-nitrophenol
  • C.Phenol-2-sulphonic acid, mixture of 2-nitrophenol and 4-nitrophenol
  • D.Phenol-2,4-disulphonic acid, mixture of 2-nitrophenol and 4-nitrophenol
  • E.Phenol-2,4-disulphonic acid and picric acid

Answer: E

X and Y are Phenol-2,4-disulphonic acid and picric acid.

Concentrated sulphuric acid sulphonates the activated phenol ring at both the ortho and para positions, giving phenol-2,4-disulphonic acid. Treating this with concentrated nitric acid replaces the sulphonic acid groups by nitro groups and nitrates the remaining ortho position, giving 2,4,6-trinitrophenol, picric acid.

This route is used because direct nitration of phenol with concentrated nitric acid oxidises much of it. A mixture of 2- and 4-nitrophenol comes from dilute nitric acid on phenol itself, not from the sulphonic acid with concentrated acid.

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