I am working on a lab assignment and we will be preparing isoamyl acetate this week. My question is, Why is the reaction mixture extracted with sodium bicarbonate and sodium chloride solution?

I know that it will be an acid/base reaction and I'm assuming the sodium bicarbonate will react with the acid to form carbonic acid, which I know decomposes into water and carbon dioxide. I'm not sure though of the role of sodium chloride and what happens to the acetic acid when it reacts with the sodium bicarbonate. I know it will lose the hydrogen but what happens to the rest of the molecule?

Any help is appreciated. Thanks!

Edit: title should say sodium chloride instead of HCl

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level 1
· 6y
The sodium bicarbonate extraction is used to remove the catalytic HCl as well as any excess acetic acid. After neutralization of the acid with bicarbonate, the remaining anions (Cl- and AcO-) will go into the aqueous phase.

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The NaCl wash is concucted to extract as much water as possible (from the previous extractions) out of the organic phase.

level 2
Op · 6y

Thank you! I have ome more question if you don't mind. Sulfuric acid is the acid used to prepare the ester. What is the point of adding HCl along with the sodium bicarbonate?

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level 1
· 6y
I'm not sure though of the role of HCl and what happens to the acetic acid

You're preparing isoamyl acetate which is an ester of isoamyl alcohol and acetic acid. If I remember correctly, the OH group on isoamyl alcohol forms a water molecule with the acidic hydrogen in acetic acid, and the rest forms the ester. I imagine the HCl is just a catalyst. I think sulfuric is more common, but I'm sure HCl would work too.

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Created Nov 8, 2010


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