how can we obtain 3-nitro aniline from nitrobenzene?

Question

abb0t · Answer

Well, you might want to think about what nitro substituent is - ortho, meta, para director? electron w/drawing or donating?

mphetang · Answer

its electron withdrawing, so its a meta director...

abb0t · Answer

Knowing that, I would start by reducing nitrobenzene $\rightarrow$ aniline first. Then, nitrate the benzene to add nitrobenzene in meta position. Does that make sense?

mphetang · Answer

The thing is the amino group in aniline is electron donating, hence ortho-para directing, so if i reduce the nitro group to the amino group and then nitrate it, its gonna direct the new nitro group to the ortho/para positions, giving 2 and 4 nitro aniline, and not the desired 3 nitro aniline.

abb0t · Answer

nitrile group is electron withdrawing CN:

mphetang · Answer

nah, nitro, aniline is C6H6NH2, not CN: .So the amino group is electron donating.

abb0t · Answer

Are you sure? I think CN:$^-$ is EDG

mphetang · Answer

CN: is the nitrile(cyano) group, and -NO2 is the nitro group