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What is the mechanism of the acid-catalyzed cleavage of cyclic ethers, specifically the cleavage of tetrahydrofuran in the presence of aqueous HCl?

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The acid-catalyzed cleavage of cyclic ethers, such as tetrahydrofuran  THF , in the presence of aqueous HCl involves a series of steps that ultimately lead to the opening of the ether ring and formation of the corresponding alcohol and alkyl halide products. The mechanism for this reaction can be described as follows:1. Protonation of the ether oxygen:In the first step, the lone pair of electrons on the oxygen atom of the tetrahydrofuran interacts with the HCl, resulting in the protonation of the oxygen. This forms an oxonium ion  a positively charged oxygen atom  and a chloride ion  Cl- .2. Nucleophilic attack by the chloride ion:The chloride ion, which is a good nucleophile, attacks one of the carbon atoms adjacent to the positively charged oxygen atom. This results in the breaking of the carbon-oxygen bond and the opening of the cyclic ether ring.3. Deprotonation of the oxonium ion:The positively charged oxygen atom in the intermediate formed in the previous step is then deprotonated by a water molecule, which acts as a base. This step generates an alcohol and an alkyl chloride as the final products.Overall, the acid-catalyzed cleavage of tetrahydrofuran in the presence of aqueous HCl results in the formation of an alcohol and an alkyl chloride. The reaction proceeds through a series of protonation, nucleophilic attack, and deprotonation steps, ultimately leading to the opening of the cyclic ether ring.
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