Which reaction sequence would be best to prepare 3-chloroanilne from benzene?

Which reaction sequence would be best to prepare 3-chloroanilne from benzene?
  1. Chlorination, nitration, reduction
  2. Nitration, chlorination, reduction
  3. Nitration, reduction, chlorination
  4. Nitration, reduction, acetylation, chlorination, hydrolysis

Solution



(a) When chlorination is done earlier than nitration, chlorobenzene formed at first step would introduce $-$ $\mathrm{NO}_{2}$ group in ortho-position, not in $\mathrm{m}$ -position
(b) Again if $-\mathrm{NO}_{2}$ group is reduced earlier than the chlorination step, $-\mathrm{NH}_{2}$ group formed on reduction will again introduce $-\mathrm{Cl}$ in o-position ,

Asked in: JEE-TOPICTESTS-CHEMISTRY

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