Oxidation of Ethanol: Equation, Product & Mechanism

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

What happens when ethanol is oxidized? In this lesson, we will be learning about the chemical equation associated with the oxidation of ethanol, what product is formed, and how the reaction happens by studying the mechanism.

The Power of Oxidizers

Have you ever heard of a laundry detergent called OxiClean? It's widely advertised on most TV channels and usually, the commercials are up-beat with the presenter demonstrating how powerful the detergent is at removing tough stains on clothes. It never fails that the term 'oxidizing' comes up during the commercial because that's the company's claim to fame on their product.

What does it actually mean to oxidize something though? In our lesson today we are going to be learning about a specific oxidation reaction, the oxidation of ethanol. Over the course of our discussion, we will be looking at the chemical equation of the reaction, what specific product is formed, and finally how the reaction happens via the mechanism. Let's oxidize!

The Chemical Equation of the Oxidation

Let's get started by first introducing the concept of oxidation itself. Often times in organic chemistry, oxidation is thought of as both the gain of oxygen atoms or carbon-oxygen bonds. When ethanol is oxidized, it actually gains an oxygen atom and two additional carbon-oxygen bonds. In order for an oxidation reaction to occur it probably doesn't come as a surprise to you that we need an oxidizing agent.

There are a plethora of oxidizing agents available to organic chemists but probably one of the most common agents for this case is chromic acid. Chromic acid is an inorganic reagent that is particularly good at oxidizing alcohols and other types of functional groups. When ethanol is reacted with chromic acid the alcohol groups in ethanol are converted to carboxylic acid functional groups.

The chemical equation of the oxidation of ethanol with chromic acid

Notice that ethanol has only one carbon-oxygen bond but in the product, there is a new oxygen atom and a new carbon-oxygen double bond. This is how we know an oxidation event has taken place! A carboxylic acid functional group always has a carbon-oxygen double bond and a hydroxyl group (-OH) bonded to the same carbon.

The Product of the Oxidation of Ethanol

At this point, we know that ethanol will undergo an oxidation reaction with chromic acid acting as the oxidizing agent to give a carboxylic acid as the product. But is there anything special about the product? Actually, there is! The product of an ethanol oxidation reaction is a compound known as acetic acid. That may not mean much to you at first, but acetic acid is the main component of vinegar, used in everything from ketchup to salad dressing.

When ethanol is oxidized the product is acetic acid

Oxidation of Ethanol Reaction Mechanism

Let's now take a detailed look at the reaction mechanism to understand how the oxidation works.

Step 1

In the first step of the reaction, ethanol reacts with chromic acid to form what's called a chromate ester. Once the chromate ester is formed it then breaks down by reaction with a base to form an aldehyde.

The first step: an aldehyde is formed from an intermediate chromate ester

Step 2

At this point, you may be asking what's the deal with the aldehyde? Isn't the product a carboxylic acid? Indeed it is and the reaction still has some work to do. The aldehyde that was just formed doesn't stick around very long in the presence of the chromic acid, which is a very strong oxidizing agent.

In the second step, the aldehyde gets hydrated by a water molecule which results in two -OH groups being present on what once was our aldehyde.

The second step: the aldehyde is hydrated

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