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Dehydration Of 2 Methylcyclohexanol Formal Report

2958 words - 12 pages

IntroductionA dehydration reaction of an alcohol results in an alkene. This type of reaction requires an alcohol, an acid catalyst and heat. Generally strong concentrated acids, like sulfuric acid and phosphoric acid, are used as the acid catalyst.The acid catalyst protonates the alcohol, to make a much better leaving group. Weakest bases make the best leaving groups, so once the alcohol is protonated the leaving group leaves and produces in a carbocation and water. In order to form the double bond, one of the beta hydrogens, hydrogens on a carbon adjacent to the carbocation, must be removed or eliminated. Therefore, another name for a dehydration reaction is beta elimination. Water acts as a nucleophile and attacks the carbocation, removing a beta hydrogen; the electrons from the C-H bond move to make a C-C pi-bond. The general mechanism is displayed by equation (1.0)Equation (1.0) shows a reaction with a primary alcohol. Usually primary alcohols form primary carbocation. However, primary carbocations are too unstable to form as intermediates, so they can undergo a rearrangement or E2 mechanism. A rearrangement occurs when an alkyl group or a hydrogen on the neighboring carbon of the carbocation shift to delocalize the positive charge to result in a more stable carbocation. A rearrangement almost always occurs whenever a carbocation can form a more stable molecule. An E2 mechanism means that the reaction is an elimination and the rate-determining step is bimolecular, two species are involved in one step of the mechanism. If the alcohol in equation (1.0) were to undergo an E2 mechanism then the beta hydrogen would be eliminated (the nucleophile would attack the electrophilic carbocation), C-C pi bond would be formed, and the leaving group would leave all in the rate determining step.Additionally, equation (1.0) only shows one product, which is not true for all alcohols. Certain alcohols can produce more than one product when they undergo dehydration, such as 2-methylcyclohexanol, structure shown on right. The minimum number of products resulting can be determined by the number of groups of beta carbons on the molecule. For example, after the alcohol is protonated and leaves, the carbocation will have two groups of beta hydrogens, so 2-methylcyclohexanol will have at least two products as a result of beta elimination. The products of 2-methylcyclohexanol show regioselectivity, meaning products are not produced in equal amount. Zaitsev's rule can predict which product will be the major, most favored product. Zaitsev's rule states that the more substituted alkene will the favored product; the double bond containing the most non-hydrogen substituents will be the major product.In this lab, 2-methylcyclohexanol will undergo a dehydration with the acid-catalyst, phosphoric acid. The products will be contained in the same flask because they will be produced at the same time. Gas chromatography will be used to separate the mixture of products into its...

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