Bromination of aniline: intermediates and controlling it to one bromine

1. A.
   Ortho sigma complex: $NH_{2}$ on C1, $sp^{3}$ carbon bearing H and Br at C2, positive charge at C3
2. B.
   Para sigma complex, iminium form: $C1 = \overset{+}{N}H_{2}$, $sp^{3}$ carbon bearing H and Br at C4
3. C.
   Meta sigma complex: $NH_{2}$ on C1, positive charge at C2, $sp^{3}$ carbon bearing H and Br at C3
4. D.
   Ortho sigma complex, iminium form: $C1 = \overset{+}{N}H_{2}$, $sp^{3}$ carbon bearing H and Br at C2

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1. A.
   ${Br}_{2} \mid {FeBr}_{3},H_{2}O(\Delta),NaOH$
2. B.
   $H_{2}{SO}_{4},{Ac}_{2}O,{Br}_{2},H_{2}O(\Delta),NaOH$
3. C.
   ${Ac}_{2}O,{Br}_{2},H_{2}O(\Delta),NaOH$
4. D.
   ${Ac}_{2}O,H_{2}{SO}_{4},{Br}_{2},NaOH$

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

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1. A.
   4-Bromoaniline ($-NH_{2}$ and $-Br$ para)
2. B.
   3-Bromoaniline ($-NH_{2}$ and $-Br$ meta)
3. C.
   2,4,6-Tribromoaniline
4. D.
   2,4-Dibromoaniline

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