Esters can be conveniently prepared by Fisher esterification, a nucleophilic substitution reaction in which a carboxylic acid is heated with an alcohol, in the presence of an acid catalyst, to make the ester. Note that the OH group of the carboxylic acid is replaced by an alkoxy group (OR’) from an alcohol, in the process kicking out a water molecule:
BACKGROUND
This experiment attempts to prepare isopentyl acetate (banana oil) from acetic acid and isopentyl alcohol (3-methyl-1-butanol). The reaction is catalyzed by sulfuric acid, but the catalyst affects only the rate of reaction, and not the extent of reaction. The desired product accumulates only if the equilibrium constant is favorable.
As it happens, the equilibrium constant for this reaction is rather small (~4) (comparing bond energies in the reactants and products will tip you off as to why the equilibrium constant is so small). Therefore, simply mixing equal amounts of the starting materials will convert only about 67% of the starting material into product.
If you recall Le Chatelier's principle, you may remember that there are two ways to adjust reagent concentrations to force isopentyl alcohol to become isopentyl acetate. One way is to remove product as it forms. The other way is to use a large excess of acetic acid. This experiment is based on the latter approach.
Because several of the components of this reaction are volatile (i.e. have relatively low boiling points), you would rapidly lose reactants and products if you were to simply heat the reaction in an open flask. Therefore, we will instead use a very common organic chemistry technique called refluxing, where a reaction mixture is heated and the gases so produced condensed in a long, water-cooled tube. This procedure, effected using a reflux condenser, results in the return of the condensed liquids back to the reaction flask. The arrangement of glassware you will use is shown in the Figure below.
Once the reflux part of the experiment is over, our desired banana oil product must be separated from the leftover liquids in the reaction flask. This separation will involve an initial liquid extraction, just as you have done in earlier experiments, followed by another technique, fractional distillation, to complete purification of the product.
Fractional distillation is a method for separating two or more liquids based on differences in their boiling points: the "fractions" are the individual components. All pure liquids have characteristic boiling points at atmospheric pressure which, in part, reflect the intermolecular interactions holding molecules together in the liquid phase. As a general rule, polar compounds have higher boiling points than non-polar ones, and larger molecules have higher boiling points than smaller ones with similar polarities. Therefore, since different components of a mixture will boil at different temperatures we can achieve separation by collecting fractions at different temperatures. When a mixture is heated to the point where the most volatile (the lowest boiling) component starts to boil, i.e. vaporizes from the mixture of liquids, the pure (single component) vapor can be condensed back to liquid form and separately collected using the fractional distillation apparatus shown in the experimental part below.
You will likely achieve both good separation and a good recovery of the banana oil if you carefully monitor the temperature during your distillation.
Esters can be conveniently prepared by Fisher esterification, a nucleophilic substitution reaction in which a carboxylic acid is heated with an alcohol, in the presence of an acid catalyst, to make the ester. Note that the OH group of the carboxylic acid is replaced by an alkoxy group (OR’) from an alcohol, in the process kicking out a water molecule: BACKGROUND This experiment attempts to prepare isopentyl acetate (banana oil) from acetic acid and isopentyl alcohol (3-methyl-1-butanol). The reaction is catalyzed by sulfuric acid, but the catalyst affects only the rate of reaction, and not the extent of reaction. The desired product accumulates only if the equilibrium constant is favorable. As it happens, the equilibrium constant for this reaction is rather small (~4) (comparing bond energies in the reactants and products will tip you off as to why the equilibrium constant is so small). Therefore, simply mixing equal amounts of the starting materials will convert only about 67% of the starting material into product. If you recall Le Chatelier's principle, you may remember that there are two ways to adjust reagent concentrations to force isopentyl alcohol to become isopentyl acetate. One way is to remove product as it forms. The other way is to use a large excess of acetic acid. This experiment is based on the latter approach. Because several of the components of this reaction are volatile (i.e. have relatively low boiling points), you would rapidly lose reactants and products if you were to simply heat the reaction in an open flask. Therefore, we will instead use a very common organic chemistry technique called refluxing, where a reaction mixture is heated and the gases so produced condensed in a long, water-cooled tube. This procedure, effected using a reflux condenser, results in the return of the condensed liquids back to the reaction flask. The arrangement of glassware you will use is shown in the Figure below. Once the reflux part of the experiment is over, our desired banana oil product must be separated from the leftover liquids in the reaction flask. This separation will involve an initial liquid extraction, just as you have done in earlier experiments, followed by another technique, fractional distillation, to complete purification of the product. Fractional distillation is a method for separating two or more liquids based on differences in their boiling points: the "fractions" are the individual components. All pure liquids have characteristic boiling points at atmospheric pressure which, in part, reflect the intermolecular interactions holding molecules together in the liquid phase. As a general rule, polar compounds have higher boiling points than non-polar ones, and larger molecules have higher boiling points than smaller ones with similar polarities. Therefore, since different components of a mixture will boil at different temperatures we can achieve separation by collecting fractions at different temperatures. When a mixture is heated to the point where the most volatile (the lowest boiling) component starts to boil, i.e. vaporizes from the mixture of liquids, the pure (single component) vapor can be condensed back to liquid form and separately collected using the fractional distillation apparatus shown in the experimental part below. You will likely achieve both good separation and a good recovery of the banana oil if you carefully monitor the temperature during your distillation.
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