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Question
p-Chloraniline and anilinium hydrochloride can be distinguished by
p-Chloraniline and anilinium hydrochloride can be distinguished by
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Solution
The correct option is D Carbylamine test
This is just the overall reaction. The base and chloroform give dichlorocarbene. The lone pair on aniline's nitrogen has a mild nucleophilic character. The lone pair attacks the dichlorocarbene, which is electron-deficient. This step is not possible in the case of anilinium chloride because the lone pair is no longer available for attacking the electrophile (dichlorocarbene). Of course, this assumes that anilinium chloride never gets to react with the base directly or else the substrate will be deprotonated to aniline.
Carbylamine test
This is just the overall reaction. The base and chloroform give dichlorocarbene. The lone pair on aniline's nitrogen has a mild nucleophilic character. The lone pair attacks the dichlorocarbene, which is electron-deficient. This step is not possible in the case of anilinium chloride because the lone pair is no longer available for attacking the electrophile (dichlorocarbene). Of course, this assumes that anilinium chloride never gets to react with the base directly or else the substrate will be deprotonated to aniline.
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