[bmilla35]

For a pre-lab exercise I have to show the mechanism for the nitration of chlorobenzene. I know that halogens are ortho/para deactivators, and that the nitronium ion must be formed my mixing sulfuric and nitric acid to form an electrophile, but just don't get the mechanism. As is the case in all of my organic chemistry whoas i'm probably just over thinking it. Hopefully someone can just give me that little bit of information I need to make sense of the situation.

Like always, any help is appreciated!

[bmilla35]

Actually, I had a lightbulb go out. The ortho/para attacks one more resonance structure, which means they're more stable?

[explosci]

Yes, the nitration of chlorobenzene gives either o or p-nitrochlorobenzene.  Harsher nitrating conditions give 2,4-dinitrochlorobenzene or 2,4,6-trinitrochlorobenzene.

[AWK]

http://depts.washington.edu/chemcrs/bulkdisk/chem238A_win05/notes_12_pt2.pdf