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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc050

Which sequence is the most suitable for converting aniline into 4-nitroaniline as the major product?

  1. A followed by
  2. B; then at low temperature; then hydrolysis with aqueous acid or alkali
  3. Cdirect nitration with
  4. D; then ; then

Answer: B

Direct nitration gives anilinium ion chemistry, oxidation tar and a large meta fraction. Converting the amine into acetanilide first protects the nitrogen from protonation and oxidation and keeps an ortho/para director, so nitration gives mainly the para product. Hydrolysis of the amide then regenerates the free amine group.
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