Below is a Fischer Esterification reaction. Benzoic acid is refluxed in an exces

Question

Below is a Fischer Esterification reaction. Benzoic acid is refluxed in an excess amount of ethanol with a sulfuric acid catalyst

1. After the quench, the product must be isolated from the reaction mixture. Suppose diethyl ether is added to the quenched reaction mixture. What layer is on the top and what layer is on the bottom (organic or aqueous)? Why?

2. Using your knowledge of acid/base chemistry, what species will be present in the organic layer?

3. What species will be present in the aqueous layer?

4. If leftover starting materials are present, can they be removed via acid/base extraction in the workup? Explain

Explanation / Answer

When the reaction takes place, the products will be containing Ethyl Benzoate, Unreacted Benzoic acid and ethyl alcohol

. Ethyl Benzoate and majority of Benzoic acid are soluble in diethyl ether and they will be parts of organic layer. This is the top layer. Since ethyl alcohol is soluble in water, it will be in aqueous layer.

Yes. They can be. The addition of sodium bi carbonate, the benzoic acid gets ionized to sodium benzoate which is even more water soluble and the H2SO4 will be converted to sodium sulfate which is also higly soluble in the water This along with water solubel ethanol will be the aqueous layer while the Organic layer will be rich in Ethyl Benzoate. several washings of aqueous layer with ether gives traces of Ethyl Benzoate,

Related Questions

Navigate

• Browse (All)
• Browse B
• Subjects

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