Attempted alkylation of benzene with 1 -chlorobutane in the presence of $\mathrm{AlCl}_{3}$ gave not only the expected butylbenzene, but also, as a major product, (1-methylpropyl)benzene. Write a mechanism for this reaction.
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This complexation activates the alkyl halide for electrophilic aromatic substitution. Show more…
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Aromatic compounds such as benzene react with alkyl chlorides in the presence of $\mathrm{AlCl}_{3}$ catalyst to yield alkylbenzenes. This reaction occurs through a carbocation intermediate, formed by reaction of the alkyl chloride with $\mathrm{AlCl}_{3}\left(\mathrm{R}-\mathrm{Cl}+\mathrm{AlCl}_{3} \rightarrow \mathrm{R}^{+}+\mathrm{AlCl}_{4}^{-}\right) .$ How can you explain the observation that reaction of benzene with 1 -chloropropane yields isopropylbenzene as the major product?
Benzene undergoes electrophilic aromatic substitution with anhydrides, compounds having the general structure (RCO}$_2$O, in a reaction that resembles Friedel-Crafts acylation. Draw a stepwise mechanism for the reaction of benzene with glutaric anhydride in the presence of AICl$_3$.
What product is formed when benzene is treated with each organic halide in the presence of AICl$_3$?
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