Converting cyclohexanol to to cyclohexene

by Silky Jonsteen
(Lawrence, Ks)

The is an Organic elimination reaction. First we start my taking a solution of cyclohexanol, which is a cyclohexane ring with an alcohol functional group attached to it. Then we add sulfuric acid to the reaction. The acid will react with the alcohol group.

The acid will protanate the OH group, making it a H2O group. Which will leave the cyclohexane. This will form a carbocation which is unstable. The acid which gave up a proton will abduct a Hydrogen and that will form a double bond in the cyclohexane, converting it to cyclohexene.

This project is useful because, a double bond is easy to break and it is more reactive than a single bond. You can convert cyclohexene to many other products. This teaches you a basic organic reaction.

You can repeat this same procedure with other compounds that contain a leaving group. One which departs and make new compounds. Share them with your teachers, friends, family, neighbors. The fun part about this lab was using the condenser. You had to heat up the cyclohexanol and sulfuric acid so they could react with each other. Once they reacted the newly formed cyclohexene was converted to vapor form. This new substance was condensed from the sulfuric acid and moved to a different beaker.

The heated sulfuric acid
smelled bad. Like someone ate rotten eggs for breakfast, and now it's kickin' in. But on the whole, it was a
fun experiment.

Barry's Response - Could have been, Silky. Any organic chemists in the crowd?

For beginners - watch this cute introduction to chemical bonding:




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