The hydration of an alkene leads to the formation of an alcohol as a result of the acid-catalyzed addition of water to the double bond. This reaction mechanism is an equilibrium reaction as the forward reaction is the hydration of the alkene, and the reverse reaction is the dehydration of the alkene. Whether the equilibrium will favor the forward or reverse reaction is dependent on the conditions of the reaction. Excess water will drive the equilibrium forward as the double bond undergoes hydration. Conversely, removal of water will drive the equilibrium in the reverse direction as the alcohol undergoes dehydration. This experiment will focus on the hydration of norbornene to the product alcohol, exo-norborneol. Exo-norborneol is the thermodynamic product of the hydration of norbornene, whereas the kinetic product would be endo-norborneol.
The percent yield of the exo-norborneol produced will be calculated with
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The acid is necessary to deprotonate the norbornene. This deprotonation removes the double bond and creates a carbonation. Water then attacks this carbocation. This is followed by a deprotonation from another water molecule to reform the acid catalyst. Then, norborneol is formed. The process of acid-catalyzed hydration of an alkene to and alcohol has valuable properties with practical uses. Naturally, as an alkene, norbornene is not very reactive. It has a strong pi bond, and is also non-polar. However, by hydrating norbornene with the assistance of an acid-catalyst, norborneol is formed. Norborneol, being an alcohol, is much more reactive and has the potential to be further reacted to obtain a certain product. These products can have pharmaceutical uses, fragrant qualities, or become other chemical compounds used in the lab. Therefore, the reaction of an alkene to an alcohol is valuable due its ability to create the reactive intermediates for useful