Ethylamine is more basic than acetanilide.explain?

1 Answer
Feb 21, 2018

Well, you got an actual base versus an amide....

Explanation:

#"Ethylamine"#, #H_3C-CH_2NH_2# is an actual base...for which #pK_a=10.8# for the conjugate acid #H_3C-CH_2NH_2*HCl#...

On the hand, you got an acid derivative, an amide in acetanilide, #C_6H_5NHC(=O)CH_3#, for which the nitrogen lone pair is conceived to be delocalized over nine centres including the phenyl ring...

#C_6H_5stackrel(ddot)NHC(=O)CH_3harrC_6H_5stackrel(+)NH=C(-O^(-))CH_3#

...the amide is thus not a Bronsted base....