Badges: 11
Report Thread starter 5 years ago
So i'm doing a question which asks out of pyrrole and pentadiene which is more acidic.
I know that pentadiene becomes aromatic on deprotonation, but I am unsure about pyrrole.
I think the N atom will be sp2 hybridised but I am not sure whether that means there can be resonance of the negative charge or not.
I want to say that pyrrole would be stronger due to the better electronegativity of N/lower energy sp2 orbital but again I'm not sure if pyrrole has no resonance if that would be better than the aromatic cyclopentadiene.

So basically: is resonance possible in the pyrrole conjugate base, if yes/no, why/why not? And then which one is stronger and why?

Second question:
Acidity of the attached two compounds - I want to say electronegativity of O atom is greater therefore more stabilised conjugate base for pyridone, but apparently this is wrong.

Thanks for your help!

Quick Reply

Attached files
Write a reply...
new posts
to top
My Feed

See more of what you like on
The Student Room

You can personalise what you see on TSR. Tell us a little about yourself to get started.


Should there be a new university admissions system that ditches predicted grades?

No, I think predicted grades should still be used to make offers (598)
Yes, I like the idea of applying to uni after I received my grades (PQA) (735)
Yes, I like the idea of receiving offers only after I receive my grades (PQO) (351)
I think there is a better option than the ones suggested (let us know in the thread!) (79)

Watched Threads

View All