question_answer

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

A) Chlorination, nitration, reduction

B) Nitration, chlorination, reduction

C) Nitration, reduction, chlorination

D) Nitration, reduction, acetylation, chlorination, hydrolysis

Correct Answer: B

Solution :

[b] [a] When chlorination is done earlier than nitration, chlorobenzene formed at first step would introduce \[-N{{O}_{2}}\] group in ortho-position, not in w-position. [b] Again if \[-N{{O}_{2}}\] group is reduced earlier than the chlorination step, \[-N{{H}_{2}}\] group formed on reduction will again introduce -Cl in o-position.