[mreff555]

Question

In the Nitration of m-xylene through aromatic electrophilic substitution, where would the NO2 most likely attach?

Here is my rationalization: Since both methyl groups are O/P directors it would be more likely to attach to carbons 2, 4 and 6. Additionally, Carbons 4, and 6 produce 2 sp2 stabilized resonance structures to carbon 2's 1 stabilized structure. So I would think 4 and 6 would be about equal with 2 being the runner up?
Did I miss anything?

[sjb]

I'd think that additions to 2 and 4 (and 6, but that's the same as 4, really) would give the same number of resonance hybrids, but electronics is not the only thing that can affect a reaction pathway....

[ufalynn88]

I think nitration at carbon 2 would not be favored due to sterics. to me 4 and 6 would be produced equally.

[aldoxime_amine]

Wouldn't temperature make a difference,i.e, kinetic or thermodynamic competition..?