Cyclohexene: Hazards, Synthesis & Structure

Instructor: Korry Barnes

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

The focus of this lesson will be on a specific organic compound known as cyclohexene. Our primary topics of discussion will be on its structure, synthesis, and potential health hazards.

A Lab Experiment for Susan

It's the week before Susan's organic laboratory class and her instructor just sent out an email stating that the class is going to be conducting an experiment on cyclohexene when they meet the following week. Susan has heard of cyclohexene before in lecture but hasn't had to deal with it in the lab yet. As a pre-lab exercise, she decides to do some research on cyclohexene so she will be well prepared for her upcoming lab. Let's come along with Susan and learn about a some of the more important aspects of cyclohexene!

Structure of Cyclohexene

Let's start by taking a look at the structure of cyclohexene. Cyclohexene has a pretty simple structure. Its chemical formula is C6 H10. It is a six-membered carbon ring with a double bond in between two of the carbon atoms. When an organic compound has a carbon-carbon double bond we call it an alkene. This is the functional group of the molecule.

Structure of cyclohexene

Notice that the carbons in the ring have two hydrogens bonded to them except the carbons of the double bond or alkene, which only have one hydrogen each. This is because carbon can have a maximum of four bonds. Since the carbons of the alkene are connected by a double bond along with being connected to the other carbons in the ring, they can only accommodate one hydrogen. Cyclohexene is a clear, colorless liquid at room temperature with a sharp odor, so it should always be handled in a fume hood. It will float on water because it is insoluble in water and less dense than water.

Synthesis of Cyclohexene

Now that we know what the structure of cyclohexene looks like let's talk about how it's made synthetically since that might be part of Susan's upcoming experiment. By far the most common method of making cyclohexene is by taking cyclohexanol (cyclohexane with an -OH group attached to it) and treating it with an acid of some sort. When cyclohexanol is reacted with an acid it undergoes a reaction called a dehydration reaction, which means it loses a water molecule. The product of this dehydration process is actually cyclohexene itself!

Synthesis of cyclohexene from cyclohexanol by a dehydration reaction with an acid

It is important to realize that the only difference between cyclohexanol and cyclohexene is a water molecule, which again reinforces why this is called a dehydration reaction.

Hazards Associated with Cyclohexene

Now let's talk about a couple safety measures that you need to be aware of to work confidently and safely with cyclohexene in the lab. One of the most important things to realize about cyclohexene is that it is VERY flammable. For this reason, be sure never to work with cyclohexene anywhere near an open flame as it will combust and cause a fire extremely quickly.

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