[xshadow]

Hi

Accordind to us where will nitration  occour??


In A)  or B)
The A position is ortho instead para but  that benzene ring should be more activated thanks the OR group

From the other end the ring on the right is less activated but has the para position free (less steric hindrance)

Who """win"""?

[rolnor]

If you look in this table, its pretty clear that the alkoxy is so strong activating it will "winn" the race. It is important to controll the conditions or both positions will be nitrated.
https://en.wikipedia.org/wiki/Electrophilic_aromatic_directing_groups

[xshadow]

If you look in this table, its pretty clear that the alkoxy is so strong activating it will "winn" the race. It is important to controll the conditions or both positions will be nitrated.
https://en.wikipedia.org/wiki/Electrophilic_aromatic_directing_groups

Very helpful
Thanks

[xshadow]

in addition could  I say that if  I would have had a C=C between the two ring instead of  C-C , the -OMe could transfer its electron density till the other ring ---> so in that case also the other ring is activated and the SeAr could happen also at the orto position (less bulky + activated)

Can it be right ?

[Orcio_87]

True, but will not NO₂⁺ substitute also one of H⁺ in -CH=CH- chain between the two rings ?

[xshadow]

True, but will not NO₂⁺ substitute also one of H⁺ in -CH=CH- chain between the two rings ?

da you mean a double bond nitration?

[Meter]

True, but will not NO₂⁺ substitute also one of H⁺ in -CH=CH- chain between the two rings ?

Would it? I don't see the reaction described anywhere obvious and I'm also a little skeptical of the mechanism.

[xshadow]

True, but will not NO₂⁺ substitute also one of H⁺ in -CH=CH- chain between the two rings ?

Would it? I don't see the reaction described anywhere obvious and I'm also a little skeptical of the mechanism.

me too

I've seen something very strange about olefins nitration with organometallic and palldium.
But is not the case..

[Orcio_87]

Substition is unlikely, but addition of H⁺, NO₂⁺ and NO₃^-, HSO₄^- is possible.

[Meter]

Substition is unlikely, but addition of H⁺, NO₂⁺ and NO₃^-, HSO₄^- is possible.

How would that look? I'm well versed in the addition mechanisms of HX compounds, but I'm a little confused how it would work with nitric acid, for example. You form the nitronium ion, the π-bond attacks, and then what exactly adds to the carbocation? Water followed by deprotonation?

[Orcio_87]

I think that addition of H₂O (formation of alcohol) is unlikely in conc. H₂SO₄.

After addition of NO₂⁺ HSO₄^- should be attached as it is major counter-ion.