Analysis Of Cyclohexene

In the lab we produced cyclohexene by dehydrating cyclohexanol using H2SO4. This is an acid catalyzed E1 elimination reaction. The reaction is stabilized by polar protic solvents since it as an E1. A polar protic solvent speeds up the reaction which in turn makes more of the product. Since it was an E1, that means it was a unimolecular elimination. The overall reaction looks like this:

The first step is the protonation of the alcohol. Protonation starts at equilibrium when the alcohol starts to react with the H+ ions. To protonate the alcohol, cyclohexanol, we need H+ from the added H2SO4. When the H2SO4 was added, the H+ (from the acid) forms a bond with the O from the OH on the alcohol. One of the lone pairs from the O goes off and forms

This is why the equilibrium shifts to the right towards the products when heat and excess H+ is added. The more acid you have, the more H+ there are, which in turn makes more protonated alcohol and speeds up the reaction. The protonated alcohol is the key to this experiment, it is what decomposes to eventually form the product. The protonated alcohol is what goes through the elimination process. The protonated alcohol determines the rate of the reaction because it creates the carbocation and eventually the product cyclohexene. Without the protonated alcohol, there would be no

This would lead to a competition between the products and the elimination. The products are racemic S1 products, so the elimination portions of the reaction and the SN1 part of the reaction compete when a nucleophile is present. The flat state of the structure make it likely to racemize if a nucleophile was present. This racemization would cause competition in the formation of products from both the reaction types, elimination and SN1. However, since there is no nucleophile present for this experiment, there was no competition with racemic products due to a