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E1 Reaction

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Introduction To transition from an alcohol to an alkene, the alcohol must be dehydrated with the help of an acid through a reaction known as an E1 mechanism.1 The first step of an E1 reaction is the formation of a carbocation intermediate. This carbocation is produced by the removal of a halogen or a substituted group.2 In this experiment, the hydroxy (OH ) group of the alcohol is removed and this produces the carbocation. The OH- group is removed due to the presence of phosphoric acid. The phosphoric acid is used in the process of adding an additional H+ to the OH- group on the alcohol and assists the OH- in leaving, making the reaction an acid catalyzed dehydration. Another reagent used along with phosphoric acid is heat, which is often used in acid catalyzed dehydration.1 The formation of the carbocation intermediate is followed by removal of a hydrogen that is taken up by a water molecule in the mixture, and this leads to the production of a hydronium (H3O+) ion.2 Carbocations are more stable when they are more substituted; therefore, tertiary carbocations are most stable. The last step of the reaction creates an alkene. When an alcohol is dehydrated through an E1 reaction, two alkene molecules are created. The slow step of this E1 reaction is the removal of the OH- group, which is known as the leaving group. Since the unimolecular rate-determining step is the slow step, this makes the reaction an E1 mechanism.1 The elimination of the alcohol leads to the production of

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