Draw the separation scheme for the esterification of acetic acid and isopropanol

Question

Draw the separation scheme for the esterification of acetic acid and isopropanol to yield isopropyl acetate. I don't need the mechanism but the separation scheme

Fischer Esterification: synthesis of an ester

So we began the experiment by adding 3.5ml of isopropanol and 3.7ml of acetic acid in a round bottom flask along with 1.0ml of sulfuric acid. This mixture went on the refluxing apparatus and was heated for 45 min. Once done it was then cooled and the extraction by the separatory funnel began. We rinsed the flask with 12ml of water and 16ml of diethyl ether and then transferred into the separatory funnel. We drained the aqueous layer. and the added 10ml of 5% sodium bicarbonate. We drained the aq layer again. The organic layer was then kept and a drying agent and then it was decanted for simple distillation. This organic layer was placed in a distilling flask in the distillation head. The first distilled fraction was diethyl ether. After the ether was collected we removed that flask and replaced it with a new one which would now contain the pure isopropyl acetate.

I have to do a product separation scheme but I'm not sure if its right this is what I have so far and I always have a hard time figuring out what goes in what layer.

Refluxing flask: isopropanol, acetic acid, and sulfuric acid

extraction by the separatory funnel add 12ml of water, 16ml of diethyl ether

organic layer: contains diethyl ether, isopropyl acetate. a portion of acetic acid

aqueous layer: water, sulfuric acid, portion of acetic acid

We take the organic layer which contains the diethyl ether, isopropyl acetate and trace water and extract it with 5%of sodium bicarbonate

Then use Na2SO4 to dry whatever water is left

This is when we start the simple distillation which will lead for the isopropyl acetate and diethyl ethers to form in different flasks I am assuming

So for the discussion, I just need to know which compounds are soluble in which layers, this should contain the chemical principles that allow for the compounds to separate. So please explain in detail

If you see anything wrong with my separation scheme please let me know

Explanation / Answer

After the workup, you are getting the isopropyl acetate and diethyl ethers in two different round bottom flask. It shows that your product is soluble in diethyl ether. So definitely organic layer contains your product. During workup, you washed with water and 5%of sodium bicarbonate to neutralize the solution from acetic acid and sulphuric acid. Water and diethyl ether have different polarity because of this they cant be miscible with each other. Water is kind of polar solvent while diethyl ether is non-polar in comparison with the water. It is well known that like dissolves like solvent. isopropanol, acetic acid, and sulphuric acid will be water soluble while isopropyl acetate will be diethylether soluble.

Related Questions

Navigate

• Browse (All)
• Browse D
• Subjects

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.