[xshadow]

Hi...I think that it  could also happen the B pathway.
So I may get a mixture..



According to us has it sense?
Thanks!


Think H2/Ni or  Zn/HCl  reductions are better here...

[sjb]

Is nucleophilic attack on a benzene ring favourable?

[xshadow]

Is nucleophilic attack on a benzene ring favourable?

Usually not...
Buy I've studied that could happen when I have an halide a strong electron withdrawing group on the ring (carbonyl,NO2...)

[spirochete]

What you're describing (addition/elimination mechanism for NAS) can only happen if the electron withdrawing group is in the ortho or para position relative to the leaving group. In these cases, you can create a resonance stabilized anion intermediate where the negative charge/lone pair is delocalized onto the electronegative atom in the electron withdrawing group.