Let's discuss the synthesis of ethyl butanoate in brief, so let's get started right now. Its chemical formula is CH3CH2CH2COOCH2CH3, and it is also known as ethyl butyrate or butyric ether. There are numerous ways to synthesize this volatile ethyl ester, which is frequently present in alcoholic beverages and can be created by yeast fermentation in addition to other methods. It is the ester in charge of a variety of scents, including those of apples, pineapples, blue cheese, and other foods.
You can see the significance of ethyl butanoate in this. First and foremost, it is more well-known due to the fact that it is an artificial flavoring ingredient that offers a variety of flavors, including orange, pineapple, mango, guava, bubble-gum, etc. It also works well in the manufacturing of cosmetic items. Similar to how it was used earlier, it is very useful in alcoholic drinks (such as martinis, daiquiris, etc.). As a plasticizer for cellulose, which is highly soft and flexible and can be regarded as being of excellent quality, and as a solvent in fragrance items. Ethyl butanoate can also be used to create a variety of different compounds, such as new 2-cyanopyrimidines and pyrido benzimidazole derivatives.
The topic of today's discussion will be the synthesis of ethyl butanoate using a haloalkane nucleophilic substitution process. I'll be using iodoethane for that. Look at this nucleophilic substitution reaction now. Simply An electrophile that is positively charged is attacked by a nucleophile that is negatively charged in a nucleophilic substitution reaction in order to replace a substrate. You can see the nucleophilic substitution reaction's reaction form in the image below. While the substrate could be positively or negatively charged electrically, the nucleophile could be either.
There are always two key considerations when discussing nucleophilic substitution reactions. SN1 AND SN2 reactions differ in that SN1 reactions are unimolecular—that is, they only depend on the reactant concentration—and take place in two steps, whereas SN2 reactions take place in just one step and depend on the concentrations of the substrate and the nucleophile.
The reaction below illustrates the nucleophilic substitution approach used to produce ethyl butanoate, which is the subject of my discussion today. For this, we use iodoethane, a haloalkane that also serves as a substrate in this reaction, as well as the conjugate base of butanoic acid (CH3CH2CH2COO), which acts as a nucleophile in our reaction. The final product we receive, along with iodine ion, is ethyl butanoate once the reaction begins to meet the parameters under favorable conditions. We may claim that our reaction is carried out by an SN2 mechanism because it is one step and depends on the final product as well as the conjugate base of butanoic acid and iodoethane.
We selected a haloalkane that contains iodine because it is simple to separate from a substrate that is carrying two electrons. Because it makes a powerful connection with the carbon atom, fluoride is the haloalkane exception. Furthermore, polar aprotic solvents with low dielectric constants or a hindered dipole end, such as tetrahydrofuran, dimethylsulfoxide, dimethylformamide, and acetone, are predicted to be better solvents for this reaction than polar protic solvents because the latter will hydrogen bond to the nucleophile and prevent it from attacking the carbon with the leaving group.
The final step in the synthesis of ethyl butanoate is the inversion of the chiral carbon configuration, which is accomplished when the connection between carbon and iodine breaks and the iodine anion is liberated.
In addition to the nucleophilic substitution reaction, ethyl butanoate can also be produced through other processes such as esterification, alcoholysis, acidolysis, interesterification, and other processes that you can see below along with their individual reactions. I'll now go into more detail about the esterification reaction. Fisher esterification is another name for the esterification reaction. Carboxylic acid and alcohol condense in the presence of a catalyst, producing ester and water as the byproducts. Now that the hydrogen ion will be produced later by the reaction of butanoic acid and ethanol in the presence of conc. H2S04, we can obtain ethyl butanoate and water as a byproduct.
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