Acetic Acid, Which solvent works?

Cfq #8 student explanation

We have:

Acetic Acid

In this?

OR! Water

Or

Solubility occurs when the attractive forces are greater between the two molecules of two substances (A and B) than the attractive forces among the molecules of the pure substances A and B. But what does this really mean? Well, we are talking about intermolecular forces or the forces between molecules, not within them. So molecule A in this case lets calls Acetic Acid and molecules B could be: Our B can be glycerol tristearate or water Call water B and glycerol B and we will choose which one would the acetic acid be more soluble in. We first want to consider the properties of each molecule and what attractive forces could be at work between acetic acid and these two solvents between like
So we have acetic acid and water: As shown above both are polar molecules This is just to let you remember when we have mixed water and acetic acid and the next section is on acid and bases why not look at a relevant reaction that might help jog your memory of the solubility of acetic acid in water.

While we know acetic acid is a weak acid, it still has a dipole, as well does water. These dipoles arent transient like when dealing with a non-polar molecule and therefore when combined ( acetic acid and water) the attractive forces between the water molecules and the acetic acid molecules are stronger than the individual intermolecular forces if we just had acetic acid purely or water purely. There are various intermolecular forces at work: Dipole-dipole Partial charges of polar molcules H bonded to N, O, or F, and another N, O, or F Induced dipoles of polarizable molecules 25 5 40 10 HCl & HCl H2O & NH3 Xe & Xe

Hydrogen bond

London dispersion

40 0.05

While London dispersion forces are relatively weak we do have the hydrogen bonding and dipole-dipole interactions which are not weak. Therefore the interactions between A (acetic acid) and B (water) outweigh the intermolecular interactions if we just those pure substances this meaning

Acetic acid alone

water alone

add some acetic acid to water

Yay ! The intermolecular forces when I mix acetic and B occur in one phase and therefore acetic acid which is also polar! acid and water are stronger! Hence A a polar molecule is soluble in water

Note : cartoons are for fun, the equipment used and color of liquids are not to be taking to be correct or judged. Its a cartoon. Now to discuss Glycerol Tristearate and Acetic Acid.

As we can see we have the reaction of how we get Glycerol Tristearate, I thought this might be helpful to show you how these two polar molecules glycerol and steric acid come together to form a non-polar lipid glycerol Tristearate. Heres a link to read about non polar lipids.
http://chemed.chem.wisc.edu/chempaths/GenChem-Textbook/Nonpolar-Lipids-1018.html

This molecule has quite a lot of symmetry actually. One could deduce it is probably non polar or less polar simply from looking at the middle CH part of the molecule and evaluating the symetricalness from there.

If one doesnt see this and instead considers the esters to be polar, also take into account the long non polar hydrocarbon chains will probably outweigh the polarity of these regions. This molecule is less polar than acetic acid and less polar than water which is pretty easy to see. We know that like dissolves like. But beyond this , like said in the think book, the glycerols interaction with other molecules through London dispersion forces is larger than dipole forces (this means very weak dipole forces) . This is because there isnt a significant separation of charge in glycerol tristearate which would be needed in order to form a strong dipole-dipole interaction with another nonglycerol tristearate molecule such as acetic acid. The interactions that would occur within a glycerol tristearate and acetic acid mixture would mainly be London dispersion forces which would be relatively weak between these two molecules. Think about it. Think of it like this we have a beaker of glycerol tristearate. The induced or momentary dipoles within the glycerol tristearate would be weak and momentary. In comparison we have polar molecules of acetic acid in a beaker. These molecules have dipole-dipole interactions among themselves that are stronger than London dispersion forces alone. NOW back to the original idea of solubility To have solubility occur we need the attractive forces between the molecules of glycerol and acetic acid to be stronger than the attractive forces in each pure substance alone. How shall a substance such as glycerol tristearate with weak molecular forces when alone, and no strong dipole-dipole interactions, perform as a solvent when acetic acid which has strong dipole-dipole interactions when alone is dissolved in it!? Poorly, the attractive forces (London dispersion) between the acetic acid molecules and glycerol tristearate arent enough to overcome the forces within each pure substance. Weigh the option of acetic acid alone and with glycerol tristearate.

Choice A: Acetic acid molecules alone, nothing else, pure: dipole-dipole intermolecular forces Choice B: Acetic acid interaction with glycerol tristearate: London dispersion

London dispersion < dipole-dipole . Hence acetic acid has a low solubility in glycerol tristearate.