N
NotQuiteSure
Guest
How do you determine basicity of a lone pair? Like which is more basic? On the oxygen atom or the nitrogen atom? I am getting a ton of mixed answers from my professor and from the book, is there a website I can look on or does anybody have solid rules for what to look for first, second, third, etc when looking for the most basic lone pair?
I was working on several problems of finding the most acidic proton in the molecule. I can answer that very well. Looking at the elements, resonance, inductive effects, and hybridization around the atom. And seeing periodic trends as most priority when determining the strongest.
Then I started doing problems where it asked to find the most basic electron lone pair. So i started doing some of these and my ochem professor told us on this one molecule that the lone pair on the oxygens were most basic because they could have more resonance of the + charge when you drew the conjugate acid. A few problems in the book don't even mention stuff about resonance and go straight to the fact that nitrogen is less electronegative than oxygen so it is going to be a stronger base. I'm not sure What I should be looking for first when determining basicity?
Bottom line, Finding the acidic proton seems more straightforward than finding the most basic lone pair. finding the most basic lone pair seems to be based off of two things resonance and electronegativity of the atom so how do i know when to use what?
I was working on several problems of finding the most acidic proton in the molecule. I can answer that very well. Looking at the elements, resonance, inductive effects, and hybridization around the atom. And seeing periodic trends as most priority when determining the strongest.
Then I started doing problems where it asked to find the most basic electron lone pair. So i started doing some of these and my ochem professor told us on this one molecule that the lone pair on the oxygens were most basic because they could have more resonance of the + charge when you drew the conjugate acid. A few problems in the book don't even mention stuff about resonance and go straight to the fact that nitrogen is less electronegative than oxygen so it is going to be a stronger base. I'm not sure What I should be looking for first when determining basicity?
Bottom line, Finding the acidic proton seems more straightforward than finding the most basic lone pair. finding the most basic lone pair seems to be based off of two things resonance and electronegativity of the atom so how do i know when to use what?