Organic Chemistry / Predicting Protonation Sites
  • Solutions 3
Sign up for free to keep watching this solution

Solution: Below is the structure of rilpivirine, a promising new anti-...

Question

Below is the structure of rilpivirine, a promising new anti-HIV  drug that combats resistant strains of HIV. Its ability to side-step resistance will be discussed in the upcoming chapter.

(a) Identify the two most acidic protons in rilpivirine.

Video Transcript

Alright, so let's go ahead and figure out the two most acidic hydrogens that we have in this molecule, and guys it might be a little bit easy to see, right? Because we don't have that many atoms that have hydrogens to begin with, right? We would expect that maybe a carbon that can resonate, right? Would definitely be a good candidate but even better will be something more electronegative like a nitrogen, which we have plenty of here, right? And if we take a look there are only two nitrogens that have hydrogen on them in this molecule. So, here the only two are these right here this one and this one and guys if you look they can both resonate quite a lot if they lose that hydrogen and gain a negative charge, right? that extra lone pair, so guys actually the two most acidic protons are both these two, both of those are the two most acidic ones. Alright, so let's move on.