Question

Which is more acidic, 3-nitrophenol or 2-nitrophenol and why? Which is more basic, benzyl amine or aniline and why? Which is more basic, triethylamine or diethylamine and why?

Answer 1

2-nitrophenol is more acidic than 3-nitrophenol

benyl amine is more basic than aniline

dimethylamine is more basic than triethylamine

Step-by-step explanation

Mesomeric effect stabilizes the anion formed when hydrogen of the the -OH group in the 2-nitrophenol is lost. This mesomerism is most pronounced at the 2 and 4 position.

Stronger bases have more available lone pair of electrons. The lone pair of electrons in aniline is delocalized over the ring. Hence it is unavailable for protonation while the lone pair on benzyl amine is available for protonation

Diethylamine is a stronger base because it has a balance of both inductive electron donation by alkyl groups, and solvation of the conjugate acid unlike triethylamine. Hence Diethylamine is a stronger base than triethylamine