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When aniline is forcefully subjected to severe extended sulfonation using concentrated sulfuric acidAmines Chemistry Question

Question

When aniline is forcefully subjected to severe extended sulfonation using concentrated sulfuric acid at high temperatures ($180-200^\circ C$), the final stable product is sulfanilic acid. In what specific unique structural form does this molecule predominantly exist?

Answer: C

💡 Solution & Explanation

Sulfanilic acid contains both a strongly basic amino group ($-NH_2$) and a powerfully acidic sulfonic acid group ($-SO_3H$) within the same molecule. An internal acid-base proton transfer permanently occurs, shifting the acidic proton to the basic nitrogen, forming a highly stable, highly polar dipolar salt known as a zwitterion ($^+H_3N-C_6H_4-SO_3^-$).

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