Abstract: Friedel-Crafts reactions are used to attach alkyl groups to aromatic rings.

This requires the formation of a highly electrophilic carbocation, which will react with an aromatic in an electrophilic aromatic substitution reaction. Here we use the t-butyl carbocation to alkylate 1,4-dimethoxybenzene. A 77.2% yield was obtained through experimentation, this indicates that the reaction went as expected and its likely that there was little occurrence of sulfuric acid-dimethoxybenzene reactions nor eliminations from the t-butyl carbocation.

Background: Alkylation is the addition of an alkyl group to another organic stem molecule. In our case the highly reactive aromatic ring 1,4-dimethoxybenzene is the target aromatic species while t-butanol supplies the alkyl groups to be added.1,3 Cold, concentrated sulfuric acid is then added to the solution to dehydrate the t-butanol to form the requisite t-butyl carbocationan alkyl group.2,3 This is the first alkylation; there appear to be three total areas on the benzene ring that have the potential to become alkylated, but after the addition of two alkyl groups at opposite ends of the aromatic ring, the molecule becomes too sterically hindered for further substitution.3,5,6 The resultant 5-t-butyl-1,4-dimethoxycyclohexa-1,3-diene is deprotonated which opens the second site for alkylation.1,4 As mentioned above the bulkiness associated with the two alkyl groups now on the 1,4-dimethoxybenzene: the remaining two apparent sites of further alkylation will not react as the molecule is too sterically hindered to accommodate more bulky groups.2,3,4 The entire

reaction is performed at low temperatures to attempt to prevent unwanted side reactions between the concentrated sulfuric acid and the highly reactive aromatic ring nor polymerization of the t-butyl carbocation.1,5,6 Cumene, also known as isopropylbenzene, is made through Friedel-Crafts reaction and requires propylene to be the alkyl group to be added to a simple benzene ring.8 It is used as itself as a high-octane automotive fuel but is mostly oxidized and further treated to give rise to acetone and phenol.9 It is important because this is an industrial use of the technique that was performed in this experiment, showing that there is relevant need for this information, and also demonstrating the high degree of reliability of similar procedures.6,8,9 In the industrial production of Cumene it is important to note that industry methods require the use of phosphoric acid instead of the concentrated sulfuric acid, because of the temperature range of its activity and its reactivity with propylene.9 To keep the entire system in liquid phase the reaction takes place at about 30 atms, yet Cumene is still formed in the gas phase.8,9 Further alkylation is possible due to the fact that the molecule is not sterically hindered with only one bulky group, but the reaction is halted here because the desired product is simply the isopropylbenzene.