0:00
Hello everyone.
00:01
Today we're doing chapter 19, problem 16, and this problem asks us to rank the compounds in each of the groups in order of increasing acidity.
00:08
And just like how we did in problem 14 of this chapter, we determined that the better acid is going to have the more stable conjugate base.
00:17
So what does that mean? that means that when it loses its proton, its conjugate base is going to be stabilized either by putting a negative charge on an electronegative atom or by stabilizing the negative charge through resonant structures, having multiple resonance structures and such that.
00:30
The negative charge will move on to different nucleases throughout the molecule.
00:36
So if you look at a, we see that we have this acetic acid.
00:43
We have this other type of acid here.
00:51
Then we have another acid here.
01:00
So we see that obviously the proton is going to be lost, is the most acidic proton, being the carboxylic acid proton.
01:08
And what happens is that once it's lost, that we're going to have a negative charge on this oxygen that can be stabilized through resonance for all three of these.
01:16
So all three of these will have the same level of resonance stability.
01:20
But what happens after that? so what we need to investigate is that now, because for all of these, we will have a negative charge on this electronegative atom, and then we can have a resonance stabilization forming two resonance bonds or two resident structures with the negative charge on this oxygen atom, we need to investigate other factors.
01:42
What else can make this proton more acidic? well, the proximity of electron withdrawing groups or electronegative atoms can pull electron density away from the hydrogen nucleus towards its own nucleus, and thus making this proton more electron poor and susceptible for abstraction by either bases or nucleophile.
02:05
So it can be easily ripped off, more easily ripped off.
02:08
So if you see in this molecule, we see that we have this carbicilgazinia, this alcohol.
02:17
So this alcohol being oxygen is electron withdrawing.
02:22
So we can say that we'll have electron density being pulled towards this alcohol nucleus, making this carbicilic acid less electron rich, and therefore making this proton more susceptible to electro, to abstraction or to being ripped off, and therefore making it more acidic.
02:41
So not only that, what having this electronegative atom in close proximity to the conjugate base will also stabilize the conjugate base because not only is the the conjugate base going to be stabilized by two resident structures having the negative charge on this oxygen or on this oxygen but now some of that electron density of that full negative charging be shared through inductive pull of electron density towards this alcohol group here so we know that auction is more electronegative than sulfur so we know that the pulling effect of this molecule can be greater than this molecule even though they're same number of carbons away.
03:16
So we can say out of these two, this molecule is going to be more acidic because it has a more stable conjugate base.
03:23
So we can just say this is going to be the most acidic.
03:28
Now sulfur is not really that electron negative.
03:33
So actually sulfur with its lone pair electrons might actually donate electron density towards the conjugate base and actually it will form kind of a negative charge over here and we'll have a negative charge up here.
03:46
So we have two charges, two like charges in close proximity, so it's not that favorable.
03:53
So we can actually say that even though there will be electron pull of electron density towards this sulfur atom, there might also be some opposing effect that might occur, but it's not really likely.
04:07
So we'll just stick our discussion to the electron effect of the sulfur group, the electron pulling effect of the sulfur group, of the style group to stabilize the conjugate base.
04:20
So now we've determined what is going to be the second and the lowest level of acidity.
04:26
So if we look at the remaining two options, well, we have this acetic acid and we have this acid here.
04:31
So acetic acid, what is it stabilized by? well, it's stabilized by two forces, having negative charge on an electronegative atom, such as this oxygen, and moving this negative charge onto this oxygen over here, so it has resonance structure...