Electrophilic substitution : Since - NO2 group is deactivating and m-directing, electrophilic substitution (halogenation, nitration and sulphonation) in simple aromatic nitro compounds (e.g. nitrobenzene) is very difficult as compared to that in benzene. Hence vigorous reaction conditions are used for such reaction and the new group enters the m-position.
(a) 
(b) 
(c) 
Although nitrobenzene, itself undergoes electrophilic substitution under drastic conditions, nitrobenzene having activating groups like alkyl, - OR, - NH2 etc. undergoes these reactions relatively more readily.
Sym-trinitrobenzene (TNB) is preferentially prepared from easily obtainable TNT rather than the direct nitration of benzene which even under drastic conditions of nitration gives poor yields.
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