Reaction of aniline with \(HNO_3\) and conc. \(H_2SO_4\) at \(298 K\) will produce \(47\%\) of |
p-Nitroaniline o-Nitroaniline m-Nitroaniline 2,4-Dinitroaniline |
m-Nitroaniline |
The correct answer is option 3. m-Nitroaniline. The nitration of aniline with conc.nitric acid (\(HNO_3\)) and conc. sulfuric acid (\(H_2SO_4\)) at \(298 \, \text{K}\) involves the following considerations: 1. Aniline and Acids Reaction: Aniline (\(C_6H_5NH_2\)) is a basic compound. When treated with strong acids like concentrated sulfuric acid, the amino group (\(-NH_2\)) gets protonated to form the anilinium ion (\(C_6H_5NH_3^n+\)). 2. Electrophilic Aromatic Substitution: The nitration reaction is an electrophilic aromatic substitution where a nitro group (\(-NO_2\)) is introduced to the benzene ring. The presence of the protonated amino group (\(C_6H_5NH_3^+\)) significantly influences the position where the nitro group is introduced. The amino group in aniline (\(-NH_2\)) is an electron-donating group and typically directs electrophiles to the ortho and para positions relative to itself. However, when it is protonated to form the anilinium ion (\(-NH_3^+\)), it becomes an electron-withdrawing group. Electron-withdrawing groups direct electrophiles to the meta position on the benzene ring. Under the reaction conditions (strong acids and 298 K), the anilinium ion is the major species. The electron-withdrawing nature of the anilinium ion directs the nitro group to the meta position, resulting predominantly in the formation of m-nitroaniline. Therefore, the major product of the nitration of aniline under these conditions is m-nitroaniline, which accounts for the \(47\%\) mentioned in the problem. The protonated amino group directs the incoming nitro group to the meta position due to its electron-withdrawing effect. |