Question

What ester is produced from the reaction of phenol and ethanoic acid?

Short answer

The ester produced is phenyl ethanoate.

Step-by-step solution

Understand Esterification

Esterification is a chemical reaction between an alcohol and a carboxylic acid to form an ester and water. In this reaction, phenol (an aromatic alcohol) reacts with ethanoic acid (acetic acid).

Identify Functional Groups

Phenol contains a hydroxyl group (-OH) attached to a benzene ring, while ethanoic acid contains a carboxyl group (-COOH). During esterification, the hydroxyl group of phenol will react with the carboxyl group of ethanoic acid.

Formation of the Ester

The hydroxyl group from phenol and the hydrogen part of the carboxyl group from ethanoic acid combine to release water (H₂O). The remaining oxygen from the carboxyl group bonds with the aromatic ring of phenol to form an ester linkage, creating phenyl ethanoate.

Naming the Ester

Esters are named by first identifying the alkyl group from the alcohol (phenyl, from phenol) and then naming the acid-derived portion (ethanoate, from ethanoic acid). Thus, the ester formed is called phenyl ethanoate.

Key concepts

Understanding Functional Groups

In chemistry, the term "functional group" refers to specific groupings of atoms within molecules that dictate how the molecules behave in chemical reactions. A functional group is a set of atoms bonded together in a precise configuration that always behaves the same way when part of different compounds. This predictability is key for chemists when they try to synthesize new molecules or understand how existing molecules will react.
The functional groups are often the "active" sites, meaning they are the portion of the molecule that typically participates in chemical reactions. Some common functional groups include hydroxyl (-OH), carbonyl (C=O), carboxyl (-COOH), and amino (-NH₂). Each of these functional groups displays a characteristic set of chemical behaviors.

• The hydroxyl group (-OH) is found in alcohols, which enables hydrogen bonding, making alcohols often soluble in water.
• The carboxyl group (-COOH) is present in carboxylic acids, lending acidic properties to the molecules.

In the esterification of phenol and ethanoic acid, the functional groups involved are critical. The hydroxyl group from phenol and the carboxyl group from ethanoic acid engage in a chemical reaction that produces an ester, specifically phenyl ethanoate.

Phenol: The Aromatic Alcohol

Phenol is an organic compound with the chemical formula C₆H₅OH. It is characterized by a hydroxyl group (-OH) directly bonded to a benzene ring. This classification makes phenol an aromatic alcohol. Its unique structure gives phenol several important chemical properties.
Despite being an alcohol, phenol differs from typical aliphatic alcohols due to its aromatic structure, which makes its hydroxyl group more reactive. This is because the oxygen atom in the hydroxyl group has a pair of electrons that can be shared with the benzene ring, enhancing its reactivity.
Phenol is particularly interesting in esterification reactions because, unlike aliphatic alcohols, its aromatic nature influences how it participates chemically.

• The -OH group in phenol allows for interactions with other molecules at a molecular level, supporting the formation of new compounds such as esters.
• Additionally, phenol showcases weak acidity due to the hydrogen in the hydroxyl group being loosely held.

Understanding phenol's role in reactions, like esterification, is key to how it transforms into different, more complex chemical structures.

The Basics of Ethanoic Acid

Ethanoic acid, more commonly known as acetic acid, is a carboxylic acid with the chemical structure CH₃COOH. It consists of a methyl group (CH₃-) linked to a carboxyl group (-COOH).
As a carboxylic acid, ethanoic acid exhibits acidity due to its carboxyl group. This group is reactive and is the site where many chemical reactions, including esterification, occur.
Ethanoic acid is pivotal in forming esters due to its ability to readily donate the hydrogen of the -COOH group in reactions.

• The carboxyl group offers a versatile bonding situation, participating in a variety of reactions, especially those forming long chains or cyclic structures.
• In nature, esters formed from ethanoic acid often have pleasant smells, contributing to flavors and fragrances.

In the esterification process with phenol, ethanoic acid reacts to form phenyl ethanoate. Here, it gives up a part of its structure to form water, facilitating the creation of the ester linkage crucial for ester formation.