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If I have aniline in acid and fuming $\ce{SO3}$, will it reversibly sufonate? I am worried that the nitrogen will be protonated and reduce the nucleophilicity of benzene ring to the point where sulfonation just isn't possible and instead you just get a salt? Or is it possible that you only get mono-sulfonation?

Here is my reaction scheme:

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  • $\begingroup$ See this question. Quoting: "Sulfonation [of aniline] is a reversible reaction. (However) The p-isomer, being more stable, does not get desulfonated easily. Hence, p-sulfanilic acid is the major product." $\endgroup$ Commented Jun 2, 2021 at 6:55

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It sulfonates on N first and then rearranges on heating to give sulfonation in the 4 position. JACS 68 (1946) 969

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