ochem2 lab 3 - Khoi Nguyen Lab 3 Title Friedel-Crafts...

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Khoi Nguyen 9-24-07 Lab 3 Title : Friedel-Crafts Alkylation: Formation of 1,4-di- t -butyl-2,5-dimethoxybenzene Introduction In this experiment, a Friedel-Crafts alkylation will be performed. In a Friedel-Crafts alkylation, a carbocation intermediate is generated, which then acts as the electrophile in an electrophilic aromatic substitution. The reactants are 1,4-dimethoxybenzene and t-butyl carbocation, which is generated from the reaction of t-butyl alcohol with sulfuric acid. The product will be 1,4-di- t -butyl-2,5-dimethoxybenzene. Generation of t-butyl carbocation: Friedel-Crafts alkylation: The benzene ring is activated towards electrophilic aromatic substitution because of the two electron-donating methoxy groups. Two molar equivalents of t-butyl alcohol are used to encourage disubstitution. Also, the resulting tetrasubstituted benzene will not undergo further alkylation because it is too sterically hindered. Table of Reagents mol. wt. (g/mol) mp (°C) density (g/mL) 1,4-dimethoxybenzene 138.17 57 t -butyl alcohol 74.12 0.79
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