Practicing Success
Arrange the following three compounds in order of decreasing acidity |
B > A > C B > C > A C > B > A C > A > B |
B > A > C |
The correct answer is option 1. B > A > C. The given compounds are: Let us explain the acidity trend: A. Phenylammonium: It has no substituents attached to the phenyl group. The positive charge on the nitrogen is delocalized over the phenyl ring, providing some stability to the conjugate base. B. p-Nitrophenylammonium: The nitro group (\(NO_2\)) is electron-withdrawing due to its strong -I effect and moderately strong -M effect. This electron withdrawal enhances the positive charge on the nitrogen, stabilizing the conjugate base through resonance. C. p-Methylphenylammonium: The methyl group (\(CH_3\)) is weakly electron-donating due to its +I effect. It disperses electron density into the phenyl ring, making the positive charge on the nitrogen less stable and thus decreasing the acidity compared to the unsubstituted phenylammonium. So, considering these factors, the correct order of decreasing acidity is 1. B > A > C |