Fischer Esterification of Lauric Acid Lab Questions OCHt. What molar amount of b

Question

Fischer Esterification of Lauric Acid Lab Questions

OCHt. What molar amount of bydrochlorie acid is required for the Fischer esterification of lauric acid with ethanol to go to completion? Why was acetyl chloride/ethanol used as the sauree of hydrochloric acid instead of aqueous hydrochloric acid? Why was the majority of the ethanol boiled off prior to the extraction? Why was the reaction vial cooled to room temperature prior to the addition of diethyl ether? Why was sodium bicarbonate used during the isniatian of the product? What impurities were removed during the column chronarograpby?

Explanation / Answer

1. In Fischer esterification, acid is used as a catalytic amount (can say 0.05equivalent or few drops) just to protonate the carbonyl oxygen of carboxylic acid functionality. This increases the electrophilicity of carbonyl carbon atom towards incomming CH3CH2OH.

2. Acetyl chloride has more activated carbonyl group than simple carboxylic acid and former releases the side product HCl than can also catalyse the reaction.

3. In the esterification reaction under acidic condition, ethanol is used in excess, and it is removed before extraction because it has solubility in water and hence the mixture of ethanol+water can cause to dissolve the product. This will result as the loss of product through aqoeous layer during separation of organic and aqueous layers during extraction.

4. Because the diethyl ether is a low boiling solvent and if reaction mixture is hot, it will evaporate easily and also cause a high vapour pressure during extraction which is dangerous.

5. In order to neutralize the reaction mixture (acidic due to HCl) using NaHCO3 solution is required.

6. The non reacted acids can be removed through column chromatography.

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