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JEE Main levelSingle correct optionDifficulty 2 of 3nc155

Heating aniline hydrogensulfate at 453-473 K gives, after rearrangement, which product?

A2-aminobenzenesulfonic acid as the major product
B3-aminobenzenesulfonic acid
C4-aminobenzenesulfonic acid (sulfanilic acid), which exists as a zwitterion
DN-phenylsulfamic acid, $C X_{6} H X_{5} NHSO X_{3} H$ , which is stable at this temperature

Answer: C

Aniline hydrogensulfate on heating at 453-473 K rearranges to the para sulfonic acid, sulfanilic acid. It exists as the dipolar ion

H X_{3} N X^{+} - C X_{6} H X_{4} - SO X_{3} X^{-}

(zwitterion), which accounts for its high melting point and poor solubility in organic solvents.

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