Esterification: the synthesis of isoamyl acetate Objective To develop organic laboratory techniques, to synthesize isoamyl acetate (isopentyl acetate), familiarize ourselves with the reactions of carbonyl compounds, and to gain experience using Fourier Transform Infrared (FTIR) Spectroscopy to characterize the product of a reaction. Background The reaction of an alcohol with a carboxylic acid is a straightforward way to synthesize esters. Often these esters have an interesting aroma. Flavors in wines can be created in this way. Wines are rich in a variety of alcohols and acids. When the various acids and alcohols combine, they can form esters, which can add flavors to the wine. Two issues arise when one attempts to do these reactions in the laboratory. First, the reactions are equilibrium reactions. Second, esterification reactions are not particularly fast. O. + H2O eq. 1 ОН Но To encourage product formation the reaction must be driven to completion. An excess of one reagent is added to drive the consumption of the other reagent. Typically, the reagent that is added in excess is the less expensive reagent or the reagent that is more easily separated from the product. In this case, acetic acid is more easily removed from the oily product since acetic acid has a higher solubility in water. The reaction can also be driven to completion by the removal of one of the products, typically through distillation. The second problem, the low reaction rate, is solved by adding a catalyst. The catalyst is an acid. Since many protic acids can catalyze the reaction, the mechanism by which the catalyst acts is referred to as general-acid catalysis. Adding a proton to the reaction increases the rate of the reaction by making two crucial steps faster. First, the formation of the tetrahedral intermediate is encouraged because the carbonyl carbon of the acetic acid becomes more susceptible to nucleophilic attack. Second, the catalyst aids in the proton transfer steps that generate the leaving group. Н+ н, Н. H. H. -C. Но .C FR %3D C-R Но R'-O R'-O R'-O ОН 0-H R'-OH R'-OH H. H.
Esterification: the synthesis of isoamyl acetate Objective To develop organic laboratory techniques, to synthesize isoamyl acetate (isopentyl acetate), familiarize ourselves with the reactions of carbonyl compounds, and to gain experience using Fourier Transform Infrared (FTIR) Spectroscopy to characterize the product of a reaction. Background The reaction of an alcohol with a carboxylic acid is a straightforward way to synthesize esters. Often these esters have an interesting aroma. Flavors in wines can be created in this way. Wines are rich in a variety of alcohols and acids. When the various acids and alcohols combine, they can form esters, which can add flavors to the wine. Two issues arise when one attempts to do these reactions in the laboratory. First, the reactions are equilibrium reactions. Second, esterification reactions are not particularly fast. O. + H2O eq. 1 ОН Но To encourage product formation the reaction must be driven to completion. An excess of one reagent is added to drive the consumption of the other reagent. Typically, the reagent that is added in excess is the less expensive reagent or the reagent that is more easily separated from the product. In this case, acetic acid is more easily removed from the oily product since acetic acid has a higher solubility in water. The reaction can also be driven to completion by the removal of one of the products, typically through distillation. The second problem, the low reaction rate, is solved by adding a catalyst. The catalyst is an acid. Since many protic acids can catalyze the reaction, the mechanism by which the catalyst acts is referred to as general-acid catalysis. Adding a proton to the reaction increases the rate of the reaction by making two crucial steps faster. First, the formation of the tetrahedral intermediate is encouraged because the carbonyl carbon of the acetic acid becomes more susceptible to nucleophilic attack. Second, the catalyst aids in the proton transfer steps that generate the leaving group. Н+ н, Н. H. H. -C. Но .C FR %3D C-R Но R'-O R'-O R'-O ОН 0-H R'-OH R'-OH H. H.
Esterification: the synthesis of isoamyl acetate Objective To develop organic laboratory techniques, to synthesize isoamyl acetate (isopentyl acetate), familiarize ourselves with the reactions of carbonyl compounds, and to gain experience using Fourier Transform Infrared (FTIR) Spectroscopy to characterize the product of a reaction. Background The reaction of an alcohol with a carboxylic acid is a straightforward way to synthesize esters. Often these esters have an interesting aroma. Flavors in wines can be created in this way. Wines are rich in a variety of alcohols and acids. When the various acids and alcohols combine, they can form esters, which can add flavors to the wine. Two issues arise when one attempts to do these reactions in the laboratory. First, the reactions are equilibrium reactions. Second, esterification reactions are not particularly fast. O. + H2O eq. 1 ОН Но To encourage product formation the reaction must be driven to completion. An excess of one reagent is added to drive the consumption of the other reagent. Typically, the reagent that is added in excess is the less expensive reagent or the reagent that is more easily separated from the product. In this case, acetic acid is more easily removed from the oily product since acetic acid has a higher solubility in water. The reaction can also be driven to completion by the removal of one of the products, typically through distillation. The second problem, the low reaction rate, is solved by adding a catalyst. The catalyst is an acid. Since many protic acids can catalyze the reaction, the mechanism by which the catalyst acts is referred to as general-acid catalysis. Adding a proton to the reaction increases the rate of the reaction by making two crucial steps faster. First, the formation of the tetrahedral intermediate is encouraged because the carbonyl carbon of the acetic acid becomes more susceptible to nucleophilic attack. Second, the catalyst aids in the proton transfer steps that generate the leaving group. Н+ н, Н. H. H. -C. Но .C FR %3D C-R Но R'-O R'-O R'-O ОН 0-H R'-OH R'-OH H. H.
H+ catatylzes the esterification reaction of alcohols with carboxylic acids. Describe at least two ways the addition of H+ can increase the rate of the reaction. based on the image
Transcribed Image Text:Esterification: the synthesis of isoamyl acetate
Objective
To develop organic laboratory techniques, to synthesize isoamyl acetate (isopentyl acetate),
familiarize ourselves with the reactions of carbonyl compounds, and to gain experience
using Fourier Transform Infrared (FTIR) Spectroscopy to characterize the product of a
reaction.
Background
The reaction of an alcohol with a carboxylic acid is a straightforward way to synthesize
esters. Often these esters have an interesting aroma. Flavors in wines can be created in
this way. Wines are rich in a variety of alcohols and acids. When the various acids and
alcohols combine, they can form esters, which can add flavors to the wine. Two issues arise
when one attempts to do these reactions in the laboratory. First, the reactions are
equilibrium reactions. Second, esterification reactions are not particularly fast.
O.
+ H2O
eq. 1
ОН
Но
To encourage product formation the reaction must be driven to completion. An excess of one
reagent is added to drive the consumption of the other reagent. Typically, the reagent that
is added in excess is the less expensive reagent or the reagent that is more easily separated
from the product. In this case, acetic acid is more easily removed from the oily product since
acetic acid has a higher solubility in water. The reaction can also be driven to completion by
the removal of one of the products, typically through distillation.
The second problem, the low reaction rate, is solved by adding a catalyst. The catalyst is an
acid. Since many protic acids can catalyze the reaction, the mechanism by which the
catalyst acts is referred to as general-acid catalysis. Adding a proton to the reaction
increases the rate of the reaction by making two crucial steps faster. First, the formation of
the tetrahedral intermediate is encouraged because the carbonyl carbon of the acetic acid
becomes more susceptible to nucleophilic attack. Second, the catalyst aids in the proton
transfer steps that generate the leaving group.
Н+
н,
Н.
H.
H.
-C.
Но
.C
FR
%3D
C-R
Но
R'-O
R'-O
R'-O
ОН
0-H
R'-OH
R'-OH
H.
H.
Science that deals with the amount of energy transferred from one equilibrium state to another equilibrium state.
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