balance all of chemical equations and calculation of theoretical yield(if applicable) with appropriate math of a mixture containing an organic acid...
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balance all of chemical equations and calculation of theoretical yield(if applicable) with appropriate math

of a mixture containing an organic acid and organic base and a neutral compound using acid/base extraction Lab. The steps are written.

1) have a 1:1 by mass mixture of benzoic acid, phenanthrene, and p-bromoaniline.


2) dissolve the mixture in 10mL of DCM or dichloromethane.

add the solution to a separator funnel.


3) add approximately 5mL of 3M of hydrochloric acid.

Two layers are noticeable.


4) cap the sep funnel and shake it to mix the two layers so the p-bromoaniline

that is in the dichloromethane layer will come in contact with the HCl and cause protonation.

The p-bromoaniline HCl salt will then migrate to the aqueous layer. vent it so the pressure does not build up too much.


5) add a few more drops of Dichloromehtane and watch where they go so to know which

layer is the Dichloromethane ayer and which layer is the aqueous layer.

You can see the drops fall to the bottom.


6) This makes sense because Dichloromethane has a greater density than water and is usually the bottom

layer.So I am going to label this bottom flask with an "N", which will be the neutral, organic, dichloromethane layer.

drain off the bottom layer being careful not to get any of the top layer.


7)label a second flask "A.E.", which will be the acidic extract or aqueous layer containing the HCl and the p-bromoaniline salt.

drain the solution into the flask, close the sep funnel, and add back the neutral Dichloromethane layer so extract it one more time to make sure I get all the p-bromoaniline


8) add approximately another 5mL of 3M HCl, cap the sep funnel, shake

drain off the bottom, neutral Dichloromethane layer, and then collect the top aqueous acidic extract layer.


9) pour back the neutral layer that should no longer contain p-bromoaniline, but still contains benzoic acid and phenanthrene.


10) To remove the benzoic acid, add approximately 5mL of 3M sodium hydroxide.

shake the sep funnel to facilitate the deprotonation of benzoic acid by sodium hydroxide, forming ionic sodium benzoate which will migrate to the aqueous layer.


11) as before, just to be safe, I will add a few drops of Dichloromethane. The DCM as expected is the bottom layer. label a new flask "B.E." for the base extracted aqueous layer.


12) First though, drain off the bottom, neutral Dichloromethane layer, and then collect the base extracted aqueous layer.

close the sep funnel and pour back in the neutral DCM layer, then extract it one more time with approximately five milliliters of the three molar sodium hydroxide solution. You can sort of see two layers on the sides of the sep funnel, but not in the middle.


13) add some more three molar sodium hydroxide to see if I can get the layers to be more noticeable.

Now drain off the bottom, neutral DCM layer and then collect the second portion of the base extracted aqueous layer. So now all three compounds should be separated.

The acidic extract should have the p-bromoaniline hydrochloride salt.

The basic extract should have the sodium benzoate.

And the neutral Dichloromehtane layer should still have the phenanthrene.

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