[dearka666@gmail.com]

Hello
I was doing my assignment for one of my chemistry classes and I just wanted to double check my answers. If anything seems odd please reply back telling me to double check my answers.
Thanks!

Most acidic to least acidic


e>a>b>d>c

Most basic to least basic


d>a>b>c

[Hunter2]

I would say E>A>B>D>C

and D>C>B>A

[clarkstill]

I agree with the first set. For the second I'd say:

d>b>c>a

The primary aliphatic amine is obviously the most basic. Then pyridine, since the sp2 lone pair is not involved in aromaticity and therefore relatively un-stabilized; in pyrrole, protonation requires loss of aromaticity, so it's definitely less basic than pyridine. Finally the amide, since the carbonyl is a very effective electron-withdrawing group, so the nitrogen lone pair isn't really available for protonation (in fact protonation occurs on oxygen, but only at very acidic pH).

[Hunter2]

I agree with that.

[siddy29]

I love how clarkstill explained it. It makes perfect sense. Can anyone tell me where aniline would lie here in terms of basicity?

[pgk]

Aniline's basicity is between pyrrole and pyridine. But attention, the basicity of ring- substituted anilines depends on the electron donor/attracting effect of the substituents, as well their position towards the amine group (o-, m-, p-). Of, course, the same are valuable for pyridine and pyrrole.