JEE Main levelSingle correct optionDifficulty 2 of 3g2081
Aniline dissolves readily in dilute aqueous HCl but acetanilide does not, because
Aacetanilide is a stronger base than aniline
Baniline is an acid and reacts with HCl as a Bronsted acid
Cacetanilide forms a covalent bond to chloride
Daniline (pKaH 4.6) is protonated to the water-soluble anilinium chloride, whereas the amide nitrogen is not appreciably basic
Answer: D
Protonation of aniline by dilute HCl gives CX6HX5NHX3X+ClX−, an ionic salt soluble in water. Acetanilide's lone pair is delocalised into C=O, so it is not protonated in dilute acid and remains insoluble.