Which sequence converts benzene into 3-bromoaniline?

A $HNO X_{3} / H X_{2} SO X_{4}$ ; $Sn / HCl$ ; $Br X_{2} / FeBr X_{3}$
B $Br X_{2} / FeBr X_{3}$ ; $HNO X_{3} / H X_{2} SO X_{4}$ ; $Sn / HCl$
C $HNO X_{3} / H X_{2} SO X_{4}$ ; $Br X_{2} / FeBr X_{3}$ ; $Sn / HCl$
D $HNO X_{3} / H X_{2} SO X_{4}$ ; $Sn / HCl$ ; $Br X_{2}$ water

Answer: C

Nitrobenzene is meta-directing, so bromination with Br2/FeBr3 gives 3-bromonitrobenzene; Sn/HCl then reduces the nitro group. If the amino group is made first it directs ortho/para, and if bromine is introduced first the nitro group enters ortho/para to Br. Br2 water on aniline gives 2,4,6-tribromoaniline.

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Which sequence converts benzene into 3-bromoaniline?

Answer: C

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