Jump to content

most acidic proton?


Akeane

Recommended Posts

Thank you for your reply!

 

I understand that you need to look at the stability of the resulting conjugate base to determine which is the most acidic proton. To do this, you need to consider the type of atom the proton is attached to (the more electronegative, the better), whether there are resonance structures that can delocalize the charge, whether there is the possibility of induction, and finally, the type of orbital.

 

According to these criteria, I narrowed it down to the hydrogens attached to either C4 or C5 on the ring.I chose one attached to C5 because it is closest to the pi bond between the carbon and the oxygen, and the resulting negative charge could be delocalized by the oxygen. However, the answer key indicates that it should be a hydrogen attached to C4. I do see that the pi bond between two carbons in the ring can help to delocalize the negative charge, but I do not see why this trumps what I described earlier, especially since the oxygen is electronegative.

 

Any help in clarifying these concepts for me would be greatly appreciated!

Link to comment
Share on other sites

  • 3 weeks later...

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
×
×
  • Create New...

Important Information

We have placed cookies on your device to help make this website better. You can adjust your cookie settings, otherwise we'll assume you're okay to continue.