Each of the following compounds is reduced with LiAlH4, and the product is then shaken with C6H5SO2Cl and aqueous KOH. For which compounds is the final mixture NOT a clear solution of an alkali-soluble sulfonamide?

JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc016

Each of the following compounds is reduced with $LiAlH X_{4}$ , and the product is then shaken with $C X_{6} H X_{5} SO X_{2} Cl$ and aqueous $KOH$ . For which compounds is the final mixture NOT a clear solution of an alkali-soluble sulfonamide?

CH X_{3} CN

is reduced to the primary amine

CH X_{3} CH X_{2} NH X_{2}

, whose sulfonamide has an acidic N-H and dissolves in alkali.

CH X_{3} CONHCH X_{3}

gives the secondary amine

CH X_{3} CH X_{2} NHCH X_{3}

whose sulfonamide is insoluble in alkali.

CH X_{3} CON (CH X_{3}) X_{2}

gives a tertiary amine, which does not react, and

C X_{6} H X_{5} NO X_{2}

gives azobenzene, which has no N-H and does not react.