Nitric acid not only nitrates but also oxidizes the highly reactive ring as well, with loss of much material as dark-coloured tar. Furthermore, in the strongly acidic nitration medium, the amine is converted into anilinium ion (NH3+); substitution is thus controlled not by the −NH2 group but by the −NH3+ group which, because of its positive charge, directs the entering group to the meta-position instead of ortho and para.