Suggest syntheses of mbromoaniline and pbromoaniline from be

Suggest syntheses of m-bromoaniline and p-bromoaniline from benzne.

Solution

1)

1. benzene to nitro benzene through nitration
2. nitro benzene to m-bromonitrobenzene by bromination
3. m-bromonitrobenzene to m-bromoaniline through halogenation in presence of Sn+HCl.

2)

C6H6 (benzene) + conc.HNO3 + conc.H2SO4 -------> C6H5-NO2 (nitrobenzene)
C6H5-NO2 + Sn + HCl -------->C6H5-NH2 (aniline)
C6H5-NH2 + (CH3CO)2O + CH3COOH -------->C6H5-NHCOCH3 (acetanilide) ...this reaction is known as acetylation reaction of amines)
C6H5-NHCOCH3 + Br2/CH3COOH ---------> Br-C6H4-NHCOCH3 (p-bromoacetanilide)
Br-C6H4-NHCOCH3 + H(+)/H2O --------> Br-C6H4-NH2 (p-bromoaniline or 4-bromoaniline)