key term - Ethyl acetate

Definition

Ethyl acetate is an organic compound that belongs to the ester functional group, characterized by its sweet, fruity aroma and common use as a solvent in various applications. It is formed through the reaction of ethanol and acetic acid, making it a significant compound in both the laboratory and industrial settings. Ethyl acetate plays a key role in reactions such as the Claisen condensation, where it acts as both a reactant and solvent, and is integral to the understanding of ester chemistry.

5 Must Know Facts For Your Next Test

1. Ethyl acetate has a boiling point of about 77 °C, making it a relatively volatile solvent commonly used in organic reactions.
2. It is widely utilized in the production of nail polish removers, glues, and food flavorings due to its pleasant odor and effective solvent properties.
3. In the Claisen condensation, ethyl acetate can serve as both a nucleophile and a solvent, facilitating the formation of β-keto esters.
4. Ethyl acetate is produced on a large scale through both direct esterification and via the alcoholysis of acetic anhydride.
5. This compound is biodegradable and considered less toxic compared to other organic solvents, which makes it a favorable choice in various applications.

Review Questions

• How does ethyl acetate function in the Claisen condensation reaction, and what are its contributions to the overall reaction mechanism?
  • In the Claisen condensation reaction, ethyl acetate acts as both a reactant and a solvent. When treated with a strong base, ethyl acetate can undergo deprotonation to form an enolate ion, which then attacks another molecule of ethyl acetate. This results in the formation of a β-keto ester. Its role as a solvent helps stabilize the reactive intermediates during the reaction process.
• Discuss the significance of ethyl acetate's properties as an ester in comparison to other functional groups like aldehydes and ketones.
  • Ethyl acetate, as an ester, exhibits unique properties such as a sweet fruity aroma and lower polarity compared to aldehydes and ketones. These characteristics make it highly useful as a solvent and flavoring agent. While aldehydes typically have stronger odors and can be more reactive, ethyl acetate's stability allows it to be used safely in various applications. Its lower boiling point also facilitates its use in processes requiring quick evaporation.
• Evaluate how understanding ethyl acetate's role in both laboratory and industrial settings reflects on its importance in organic synthesis and application development.
  • Understanding ethyl acetate's role in organic synthesis highlights its versatility as both a reactant in reactions like Claisen condensation and as a solvent for various chemical processes. In industrial settings, its widespread use in product formulations such as adhesives, coatings, and food flavorings showcases its practical applications. This duality emphasizes not just its chemical reactivity but also its significance in creating consumer products, ultimately impacting areas from pharmaceuticals to food science.

Related terms

Esterification:

A chemical reaction that forms an ester by combining an alcohol and a carboxylic acid, often catalyzed by an acid.

Claisen Condensation: A reaction between esters or ketones in the presence of a strong base that results in the formation of β-keto esters or β-dicarbonyl compounds.

Acetic Acid:

A colorless liquid organic compound that is the main component of vinegar and is used to produce ethyl acetate through esterification.