Alkyl aryl ethers undergo cleavage at the alkyl-oxygen bond, leading to the formation of phenol and alkyl halide. This preference is due to the greater stability of the aryl-oxygen bond.
How does the cleavage of alkyl aryl ethers differ from dialkyl ethers, and what are the products obtained from the reaction?
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The cleavage of alkyl aryl ethers, which contain an aryl group (like phenyl) attached to the oxygen, often involves milder conditions compared to dialkyl ethers. Alkyl aryl ethers can be cleaved under relatively gentle conditions using a Lewis acid catalyst, such as aluminum chloride (AlCl₃). The Lewis acid facilitates the formation of an oxonium ion, leading to the cleavage of the C-O bond. The products obtained from the reaction are an aryl halide and an alcohol. The general reaction can be represented as:
Ar-O-R’+AlCl₃ → Ar-Cl+R’-OH + AlCl₃