Show all the steps to how 3-chloroaniline can synthesis from benzene ?

1 Answer
Aug 9, 2018
  1. nitration of benzene
  2. chlorination of nitrobenzene
  3. reduction of nitro group


Here's what the question is asking:
Summary of Question - Dr. K

The synthesis will involve adding 2 substituents to the benzene ring. In this case, we'll need to consider the order of substitution.

  • Cl is an ortho-para director . That means, if Cl is first added to benzene, the next substituent will be placed in the ortho/para position. That, will not work since, in the desired product, #NH_2# is meta to Cl.
  • That means, we'll need to add Cl last.
  • #NH_2# is also an ortho-para director , so that means we can't add Cl after forming aniline.

An alternative we can consider is:

  1. First add nitro group (#NO_2#) to the benzene ring to form nitrobenzene through nitration of benzene.
  2. Since nitro group is a meta director , we can then add Cl through chlorination .
  3. After that, we can reduce the #NO_2# group to #NH_2# group.

Here's a possible synthesis you can consider:
Synthesis of m-chloroaniline from benzene - Dr. K