extraction

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sv3

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Hi,

Just had a question regarding extraction (orgo). Searched for this and the dental folks obviously have a different view!

I've looked at TPR and Ek and both seem to like the technique that invovles using: A strong acid, a weak base, and a strong base. The strong acid and weak base can be used in a different order as long as the strong base is last. So i get all this.....but....why not make it 4 steps and use a weak acid first, then a strong acid in different steps in order to seperate out the strong and weak bases respectively. Where is my flaw?

thanks
steve

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From what I am reading from EK:
Step 1: Add strong acid to get rid of bases.
Step 2:Add base to deprotonate some of the strong acids you just added to protonate the bases
Step 3: Add strong base to eliminate the remaining weak acids.
 
What he is asking is why is this not a 4 step process, where step 1 is adding a weak acid to get rid of the strong bases. Then adding a strong acid to get rid of all of the weak bases.

I am wondering this too.
 
perhaps its just not as common as the three stepper? I just wanted to make sure nothing is wrong with the 4 stepper in case i need to use it some day.......like july 31st for example
 
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you might want to mention the compounds you're trying to separate if you want to get an informed reply. i have no idea what the compounds used in those examples are, so I can't tell you anything about the validity of a different protocol.
 
you might want to mention the compounds you're trying to separate if you want to get an informed reply. i have no idea what the compounds used in those examples are, so I can't tell you anything about the validity of a different protocol.

this is just a general question and im not exactly sure it matters what the compounds are other than knowing if they are strong or weak bases. I don't have a specific example. I am just wondering if there is something inherently wrong with using a 4 step process as I have not seen it in my prep books
 
I was going to ask the same question as sleepy. If you're trying to extract an aprotic substance from a bunch of other aprotic substances, an acid/base extraction method isn't really going to do anything for you.
 
this is just a general question and im not exactly sure it matters what the compounds are other than knowing if they are strong or weak bases. I don't have a specific example. I am just wondering if there is something inherently wrong with using a 4 step process as I have not seen it in my prep books

sigh, well, the problem is that you didn't give us any information about any of the compounds. anyway, since I used to teach for TPR, I vaguely remember that the hyperlearning book has a flowchart showing extraction with 4 compounds. they were something like this:

naphthalene (two fused benzene rings), some sort of benzoic acid, some sort of aniline derivative, and some sort of phenol derivative.

so the naphthalene has no significant acid/base properties. the benzoic acid derviative is a strong acid (relatively). the aniline derivative is a weak base. and the phenol derivative is a weak acid.

So they do something like, add a strong acid to pull the aniline into aqueous solution, then add a weak base to pull the benzoic acid into the water, then add a strong base to pull the phenol out. You're left with naphthalene in the organic layer.

so let's see what you're suggesting. you add a weak acid, but in this example, nothing comes out (since a weak acid wouldn't be good enough to protonate aniline), so you just wasted some (admittedly cheap) reagent and maybe 10 minutes of your time. Then you add a strong acid and you pull the aniline out. Then you add a weak base to pull the benzoic acid out, then a strong base to pull the phenol out. Is that what you're asking? Are you just saying that you add a weak acid as the first step, and then do the rest of the protocol like the review books are saying?

If that is what you're saying, there is no point to adding that extra step. It does absolutely nothing in this example. Now, if you had a strong base like ethylamine or something in solution, then yeah, you're going to need to add a weak acid sometime before you add a strong acid. The reason these books don't suggest a four step protocol is because there are only three steps necessary.

But I would strongly caution you against thinking about it like that. It sounds like you're attempting to memorize a protocol for doing solvent extraction (sorry if this is an incorrect observation, it just sounds like it), when you should just understand it. It's pretty simple. You're trying to separate compounds based on their acid/base properties. If the reagent you're adding will change the protonation state of a compound you're trying to extract so that you have a salt instead of a neutral compound, then the compound will be more soluble in the aqueous layer and will be found mainly in that layer. So if you have multiple ionizable compounds in your organic layer, you want to add your extraction reagents in an order that will allow only one compound to come into the aqueous layer at a time. If multiple compounds come into the aqueous layer at the same time, you may have separated them from the rest of the compounds, but you'll still need to separate those compounds from each other.
 
sigh, well, the problem is that you didn't give us any information about any of the compounds. anyway, since I used to teach for TPR, I vaguely remember that the hyperlearning book has a flowchart showing extraction with 4 compounds. they were something like this:

naphthalene (two fused benzene rings), some sort of benzoic acid, some sort of aniline derivative, and some sort of phenol derivative.

so the naphthalene has no significant acid/base properties. the benzoic acid derviative is a strong acid (relatively). the aniline derivative is a weak base. and the phenol derivative is a weak acid.

So they do something like, add a strong acid to pull the aniline into aqueous solution, then add a weak base to pull the benzoic acid into the water, then add a strong base to pull the phenol out. You're left with naphthalene in the organic layer.

so let's see what you're suggesting. you add a weak acid, but in this example, nothing comes out (since a weak acid wouldn't be good enough to protonate aniline), so you just wasted some (admittedly cheap) reagent and maybe 10 minutes of your time. Then you add a strong acid and you pull the aniline out. Then you add a weak base to pull the benzoic acid out, then a strong base to pull the phenol out. Is that what you're asking? Are you just saying that you add a weak acid as the first step, and then do the rest of the protocol like the review books are saying?

If that is what you're saying, there is no point to adding that extra step. It does absolutely nothing in this example. Now, if you had a strong base like ethylamine or something in solution, then yeah, you're going to need to add a weak acid sometime before you add a strong acid. The reason these books don't suggest a four step protocol is because there are only three steps necessary.

But I would strongly caution you against thinking about it like that. It sounds like you're attempting to memorize a protocol for doing solvent extraction (sorry if this is an incorrect observation, it just sounds like it), when you should just understand it. It's pretty simple. You're trying to separate compounds based on their acid/base properties. If the reagent you're adding will change the protonation state of a compound you're trying to extract so that you have a salt instead of a neutral compound, then the compound will be more soluble in the aqueous layer and will be found mainly in that layer. So if you have multiple ionizable compounds in your organic layer, you want to add your extraction reagents in an order that will allow only one compound to come into the aqueous layer at a time. If multiple compounds come into the aqueous layer at the same time, you may have separated them from the rest of the compounds, but you'll still need to separate those compounds from each other.

Perfect. thanks very much. your last paragraph confirmed what I was looking. I was thinking that the 3 step system for some reason was the prototype extraction and from what I've gathered based on your response, it will come down to what I need to seperate in the organic layer. As for the 4 steps, I just making sure nothing was inherently wrong with it if indeed a strong base was mixed into the organic layer. I've also realized that it seems Ek copies TPR or Kaplan alot, and thus that is why their examples are similar (btw you remembered the TPR example very well).

thanks again and sorry for the confusion. now i can start bio in peace.....
 
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