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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc013

Which sequence is the best synthesis of 3-bromoaniline from benzene?

  1. A; then ; then
  2. B; then ; then
  3. C; then ; then
  4. D; then ; then

Answer: B

The nitro group is meta directing, so nitration must come first, then bromination gives 3-bromonitrobenzene, and finally reduces the nitro group to amine. Bromination first would place nitro ortho or para to bromine. Reducing first gives aniline, whose strongly activating would direct bromine to ortho and para positions.
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