solubility at pH 1

[inaccensa]

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Q- how would you compare the solubility of the foll molecules in an aq. sol at pH 1?
Benzoic acid, Aniline, phenol,diphenyl ether

Isn't the order of solubility Benzoic acid > phenol> Aniline > diphenyl ether

additionally, if I were given lets say, cis butene and trans butene. Trans will be more soluble since there is no dipole. is that correct?

WRT dicholromethane, it has net dipole, but its considered nonpolar,so its we would always solve such q's based on the assumption that the net dipole doesn't play any role.

 

[RogueUnicorn]

Q- how would you compare the solubility of the foll molecules in an aq. sol at pH 1?
Benzoic acid, Aniline, phenol,diphenyl ether

Isn't the order of solubility Benzoic acid > phenol> Aniline > diphenyl ether

additionally, if I were given lets say, cis butene and trans butene. Trans will be more soluble since there is no dipole. is that correct?

WRT dicholromethane, it has net dipole, but its considered nonpolar,so its we would always solve such q's based on the assumption that the net dipole doesn't play any role.

common ion effect.

also - anything with a net dipole moment is by definition polar. how that affects its solubility is a different question.

 

[inaccensa]

common ion effect.

also - anything with a net dipole moment is by definition polar. how that affects its solubility is a different question.

thanks. The presence of H+ decreases the solubility, but in general since acids are more soluble than alcohols, shouldn't the order go

Diphenyl Ether < benzoic acid<alchols<aniline

 

[RogueUnicorn]

aniline is a base. it should be most soluble in an acid. with bezoic acid vs phenol, i would think that the benzoic acid is more soluble due to the greater polarity & H-bond abilities

edit: my mistake, i read the < symbol backwards =p...

 

[inaccensa]

aniline is a base. it should be most soluble in an acid. with bezoic acid vs phenol, i would think that the benzoic acid is more soluble due to the greater polarity & H-bond abilities

edit: my mistake, i read the < symbol backwards =p...

So benzoic will still be more soluble. Although it does affect solubility, but not not to an extent will it increases solubility of acid over alcohol.

If this solution were basic, then will the trend go as
diphenyl ether < aniline< phenol <benzoic acid

 

[RogueUnicorn]

So benzoic will still be more soluble. Although it does affect solubility, but not not to an extent will it increases solubility of acid over alcohol.

i would think so, but i'm not 100% certain.

If this solution were basic, then will the trend go as
diphenyl ether < aniline< phenol <benzoic acid

yes, that's what i would expect absent any sort of context/hard data

 

[eric51]

common ion effect.

also - anything with a net dipole moment is by definition polar. how that affects its solubility is a different question.

Really has nothing to do with the common ion effect... It's really just knowing that things that have a charge (either negative or positive) will be water soluble. In acid (pH=1), the aniline, which is a base, will become protonated and have a charge of +1, thus, it will be very water soluble. The carboxylic acid will stay protonated in acid, and thus keep a 0 charge, making it relatively insoluble. Same with the phenol and ether. After that, it goes to ordering them by polarity. Acid is probably the most polar, followed by phenol, followed by ether.

 

[RogueUnicorn]

Really has nothing to do with the common ion effect... It's really just knowing that things that have a charge (either negative or positive) will be water soluble. In acid (pH=1), the aniline, which is a base, will become protonated and have a charge of +1, thus, it will be very water soluble. The carboxylic acid will stay protonated in acid, and thus keep a 0 charge, making it relatively insoluble. Same with the phenol and ether. After that, it goes to ordering them by polarity. Acid is probably the most polar, followed by phenol, followed by ether.

whether it is charged or not depends on acidity. which is another facet of solubility. which is affected by common ions. it's just a different way to look at it

 

[eric51]

whether it is charged or not depends on acidity. which is another facet of solubility. which is affected by common ions. it's just a different way to look at it

You are right that whether or not it is charged depends on the acidity (or basicity) of the sol'n, and that definitely effects solubility. But in this case, the common ion effect really has no relevance. The common ion effect is for predicting solubility of inorganic salts that have different cations but a common anion (or vice versa). So for example, you'd need to worry about the common ion effect when calculating the solubility of AgCl and HgCl2, because they both have Cl-, a common ion. This has no relevance to solubility of charged organic species though.

 

[inaccensa]

You are right that whether or not it is charged depends on the acidity (or basicity) of the sol'n, and that definitely effects solubility. But in this case, the common ion effect really has no relevance. The common ion effect is for predicting solubility of inorganic salts that have different cations but a common anion (or vice versa). So for example, you'd need to worry about the common ion effect when calculating the solubility of AgCl and HgCl2, because they both have Cl-, a common ion. This has no relevance to solubility of charged organic species though.

So you are saying that excess H+ in the solution has no relevance to solubility. So if the same Q were in a basic basic medium, then benzoic acid> phenol> aniline> ether? But either way, the solubility trends end up the same.

 

[eric51]

So you are saying that excess H+ in the solution has no relevance to solubility. So if the same Q were in a basic basic medium, then benzoic acid> phenol> aniline> ether? But either way, the solubility trends end up the same.

The excess of H+ only has relevance to the solubility in the sense that the organic base becomes protonated because of the H+ excess. Once the aniline is protonated and carries a charge, the H+ concentration really doesn't matter. And yes, that would be the correct order for a basic sol'n.

 

[RogueUnicorn]

You are right that whether or not it is charged depends on the acidity (or basicity) of the sol'n, and that definitely effects solubility. But in this case, the common ion effect really has no relevance. The common ion effect is for predicting solubility of inorganic salts that have different cations but a common anion (or vice versa). So for example, you'd need to worry about the common ion effect when calculating the solubility of AgCl and HgCl2, because they both have Cl-, a common ion. This has no relevance to solubility of charged organic species though.

common ion effect is another way to conceptualize leChat's principle, which directly affects essentially all processes, including the protonation/deprotonation of species. like i said, different ways to look at.

 

[eric51]

common ion effect is another way to conceptualize leChat's principle, which directly affects essentially all processes, including the protonation/deprotonation of species. like i said, different ways to look at.

I'd think of common ion effect more as a special case of LeChatlier's principle than another way to look at it. But this is really just an argument of semantics at this point, and is pretty pointless. I suppose we should just agree to disagree.

 

[RogueUnicorn]

I'd think of common ion effect more as a special case of LeChatlier's principle than another way to look at it. But this is really just an argument of semantics at this point, and is pretty pointless. I suppose we should just agree to disagree.

word.. we're just saying the same thing. in a different way =)