[Astrokel]

Hi good day all,

my question is how to synthesize propoxybenzene to 4-nitro-2-propoxyphenylamine? well the question specific in 2 steps and identify the intermediate compound. It also says the reactivity of propoxybenzene is similiar to that of phenol

I'm thinking to do nitration first with con. HNO₃ and H₂SO₄ reflux room temperature. And then do Sn, concentrated HCl, reflux followed by NaOH(aq) to liberate the salt.

But my problem is, if i do the nitration, it will direct to 2,4,6 no? That is what my notes said. Also if i did the reduction, both NO₂ will be reduced. How to selectively reduced 1 of the N₂O to NH₂ while keeping the other nitro group?

If i am not being clear let me know, thanks!

[macman104]

It says specifically in 2 steps only?

[Astrokel]

yes

I believe the reason why they mentioned reactivity of propoxybenzene is similar to that phenol is because we only study a few of phenol substiution reactions. One of it is nitration(aqueous and concentrated), and bromination(inert and aqueous). However i am still clueless

[Astrokel]

The question is in part d), ignore my writings! Actually, this is A level chemistry paper 3 i had two days ago, although the exam is over but since i will never get back my paper so i wouldn't know the answer might as well ask here. Also i have classmates asking about this because it might come out something smiliar for paper 2 next week.

thanks alot

ps: it says 5-nitro but is in 4 position, right? it that a mistake?