The correct order of decreasing basic strength of the given amines is:
- N-ethylethanamine > ethanamine > N-methylaniline > benzenamine
- benzenamine > ethanamine > N-methylaniline > N-ethylethanamine
- N-methylaniline > benzenamine > ethanamine > N-ethylethanamine
- N-ethylethanamine > ethanamine > benzenamine > N-methylaniline
Answer
(1) N-ethylethanamine > ethanamine > N-methylaniline > benzenamine
Solution
Aliphatic amines are stronger bases than aryl amines because the lone pair on N of an aryl amine is delocalised into the ring.
In water, for ethyl amines: (C2H5)2NH (pKb = 3.00) > C2H5NH2 (pKb = 3.29).
Among aryl amines, the +I effect of the -CH3 group makes N-methylaniline (pKb = 9.30) slightly more basic than benzenamine (pKb = 9.38).
Order: N-ethylethanamine > ethanamine > N-methylaniline > benzenamine.
Answer: (1)