When aniline is treated with a mixture of nitric acid and sulfuric acid, the expected nitration product
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When aniline is treated with a mixture of nitric acid and sulfuric acid, the expected nitration product (para-nitroaniline) is obtained in poor yield. Instead, the major product from nitration is meta-nitroaniline. Apparently, the amino group is protonated under these acidic conditions, and the resulting ammonium group is a meta-director, rather than an ortho-para director. Propose a plausible method for converting aniline into para-nitroaniline.
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