What kind of reaction mechanism does the synthesis of banana oil involve?

What kind of reaction mechanism does the synthesis of banana oil involve?

The reaction mechanism involves initial protonation of the carboxyl group, nucleophilic attack by the hydroxyl, proton transfer, and loss of water followed by loss of the catalyzing acid to produce the ester. The process is thermodynamically controlled yielding the most stable ester product.

What happens in a Fischer esterification reaction?

Description: When a carboxylic acid is treated with an alcohol and an acid catalyst, an ester is formed (along with water). This reaction is called the Fischer esterification. Notes: The reaction is actually an equilibrium. The alcohol is generally used as solvent so is present in large excess.

Why is Fischer esterification in equilibrium?

The Fischer esterification reaction takes advantage of Le Chatelier’s principle to increase the amount of carboxylic acid that is esterified. The equilibrium is shifted towards products by using a large excess of the alcohol (it is used as the reaction solvent), and (in some cases) also removing water as it it formed.

Why was the esterification of isopentyl acetate successful?

In the experiment, the acetic acid was in excess and the isopentyl alcohol was the limiting reagent, therefore, the reaction depended on the amount of isopentyl alcohol available. This experiment was successful because the smell of bananas was achieved along with the percent yield attained of 61.9%.

How are esters formed in the Fischer esterification reaction?

Esters can also be formed by the reaction of the alcohol with the acid chloride rather than the acid itself. Or, the acid anhydride may be used instead of the acid. In this experiment, we will create the ester isopentyl acetate (banana oil) via the Fischer esterification reaction. Esters are an important group of carboxylic acid derivatives.

How is banana oil prepared by Fischer esterification?

In this laboratory experiment, you will prepare banana oil (isopentyl acetate) by the Fischer esterification of acetic acid and isopentyl alcohol (figure 3). The reaction will be catalyzed by the addition of sulfuric acid. Once the reaction is complete, a distillation will be performed to isolate the pure organic ester, which will be a liquid.

How is isopentyl acetate transferred to a flask?

The bicarbonate washings of the ester product are followed by a single 20-mL wash using distilled water to remove any bicarbonate ions that may still be mixed with product. After the water layer (bottom layer) is removed, the isopentyl acetate is transferred to an 100-mL round bottom flask (use 19/22 ground glass flask).

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