Why does NO₂ direct meta but NO directs ortho-para in aromatic substitution?

[ddrplayboy]

The NO2 group directs meta with-deactivation in electrophilic aromatic substitution. The nitroso group - NO directs ortho-para with - deactivation. Write out the electroinc structures of - NO2 and -NO and explain the differences in behavior. Show all pertinent resonance forms for the addition of bromonium ino to form p-bromonitrosobenzene.
thanks for looking

 

[GoneRogue]

What is your question? We can't just answer your textbook question. What are you having trouble with in the problem?

 

[chem_tr]

First off, nitroso is written as -ONO. Please show where you are stuck; if you don't understand anything, be sure to post your question after you have studied to understand our responses.

 

[GCT]

Start by writing out the resonance structures for the aryl cation, "move the electrons around" as you have learned before, or should have. You should be able to notice why the nitroso group is supposed to direct ortho para ("supposed" since I haven't looked into this before). Ortho para with deactivation? doesn't ring a bell to me.

 

[movies]

Halides like bromine on the aromatic ring will direct ortho/para while deactivating the ring as well. To justify this observation you will need to consider two different effects.

 

[chem_tr]

First off, nitroso is written as -ONO. Please show where you are stuck; if you don't understand anything, be sure to post your question after you have studied to understand our responses.

Edit: Nitroso may also be in the form of N=O, as we are dealing with organic substances; inorganic nitroso compounds are written as -ONO.