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Oxidation of Alcohols: Mechanism, Reaction & Conditions

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  • 0:04 Oxidation of Alcohols:…
  • 0:52 The Reaction and Conditions
  • 1:48 Oxidation Mechanism
  • 3:28 Lesson Summary
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Lesson Transcript
Instructor: Korry Barnes

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

How are alcohols oxidized and what are the products formed? In this lesson, we'll be learning about the mechanism behind the oxidation as well as the reaction conditions.

Oxidation of Alcohols: Background

Do you or someone you know have a swimming pool? Swimming pools can be a love-hate relationship to those that own them: they're great to enjoy on those hot summer days but they can also be a pain to keep clean and maintained. Speaking of maintenance, one of the main things a pool needs to stay clean is pool bleach, also known as sodium hypochlorite.

It actually turns out that pool bleach isn't just a good chemical for keeping swimming pools clean and tidy, it also has powerful oxidizing ability and is used for oxidizing organic compounds. In our current lesson, we're going to be learning about how sodium hypochlorite can be used to oxidize organic alcohols. Specifically, our goals will be to understand how the reaction mechanism works and also look at what reaction conditions are needed for the reaction.

The Reaction and Conditions

Let's get started by looking at what the reaction looks like and what conditions are needed. In general, an alcohol reacts with sodium hypochlorite in the presence of acetic acid to give a ketone as the final product. Since acetic acid is being used, it's important to realize that we are dealing with reaction conditions that are acidic. We will see the role of acetic acid a bit later in our discussion when we study the mechanism.

As an example let's use the oxidation of cyclohexanol as our model system. When cyclohexanol is exposed to sodium hypochlorite (NaOCl) and acetic acid, an oxidation reaction takes place that gives cyclohexanone as the product. In general when a secondary alcohol (secondary because the carbon with the -OH group contains one hydrogen) is oxidized, the product is always a ketone, which is an organic compound that contains a carbon-oxygen double bond.

Oxidation Mechanism

Now that we know what sodium hypochlorite does to alcohols, let's see exactly how the reaction mechanism works.

Step 1

In the first step of the reaction, a molecule of acetic acid reacts with sodium hypochlorite to form hypochlorous acid, which is the active oxidizing agent for the reaction.

Step 2

Now that the oxidizing agent has been formed, the next step is to use it in a reaction with cyclohexanol. Cyclohexanol accepts a hydrogen atom from sodium hypochlorite, and after this happens, the oxygen atom contains two hydrogen atoms and a formal positive charge. The hypochlorite anion is also formed from this reaction.

Step 3

In the third step of the mechanism, the hypochlorite ion that was just formed attacks the carbon bonded to the oxygen atom in cyclohexanol, and a water molecule gets ejected as what's called a leaving group. This is a very favorable process since when water leaves, the positive charge on oxygen is quenched, and it becomes neutral again in terms of charge.

Step 4

Here is the fourth and final step of the reaction mechanism in which the water molecule that was just ejected from cyclohexanol acts as a base and pulls off a hydrogen atom. Simultaneously, the chlorine-oxygen bond breaks to finally form the ketone and our final product!

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