Pyrrolidine: Achiral or chiral?

[ochemstudent]

Hi everyone, this is my first time posting to this website.

I'm just trying to study for organic chemistry, and I've been having a little trouble trying to grasp the concept of chiral/achiral.

The book talks about pyrrolidine,C4H9N, and it asks whether or not pyrrolidine could be used to isolate the racemic form of ibuprofen. I know that if it was achiral then it could not be used because it would result in identical R and S forms and produce a racemic mixture. I am currently trying to determine whether pyrrolidine is achiral or chiral. It seems like it has symmetry around the nitrogen atom, but I am unsure of whether that counts?

I'm very confused and any advice would help! Thank you in advance!

For reference, pyrrolidine looks like this!
http://www.chm.bris.ac.uk/webprojects2001/gerrard/gifs/pyrrolidine-s-o.gif

 

[Zefram]

Hello and welcome to the forum! Chirality is a fundamental concept in organic chemistry and it can be a bit confusing at first. Pyrrolidine is indeed a chiral molecule, meaning it exists in two non-superimposable mirror image forms, also known as enantiomers. In order for a molecule to be chiral, it must have a chiral center, which is a carbon atom bonded to four different groups. In the case of pyrrolidine, the nitrogen atom is the chiral center.

The symmetry around the nitrogen atom does not affect the chirality of pyrrolidine. In fact, the presence of symmetry can sometimes make it more difficult to determine chirality. However, in this case, if you look at the structure of pyrrolidine, you can see that the four groups attached to the nitrogen atom are not the same, therefore making it chiral.

As for using pyrrolidine to isolate the racemic form of ibuprofen, you are correct in your understanding that an achiral molecule cannot be used for this purpose. Since pyrrolidine is chiral, it can be used to separate the R and S enantiomers of ibuprofen, resulting in a pure enantiomer. I hope this helps clarify things for you. Good luck with your studies!