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What is the reaction mechanism for the acid-catalyzed cleavage of an ether? Provide the step-by-step process and the structures of the intermediate compounds involved in the reaction.

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ago by (310 points)
The acid-catalyzed cleavage of an ether is a reaction in which an ether is converted into two alkyl halides in the presence of a strong acid and a halide ion. The general reaction mechanism involves the following steps:1. Protonation of the ether:The first step in the reaction is the protonation of the ether by the strong acid  HX, where X is a halide ion . The lone pair of electrons on the oxygen atom of the ether interacts with the hydrogen atom of the acid, forming a bond and resulting in a protonated ether.R-O-R' + HX  R-O H -R' + X^-2. Nucleophilic attack by the halide ion:The protonated ether is now more electrophilic due to the positive charge on the oxygen atom. The halide ion  X^-  acts as a nucleophile and attacks one of the alkyl groups  R or R'  connected to the oxygen atom. This leads to the formation of a new carbon-halogen bond and the breaking of the carbon-oxygen bond, resulting in the formation of an alkyl halide and a hydroxyl group.R-O H -R' + X^-  R-X + R'-O-H3. Proton transfer:The hydroxyl group  R'-O-H  is a poor leaving group, so it undergoes protonation by the strong acid  HX  to form a better leaving group, water  H2O .R'-O-H + HX  R'-O H -H + X^-4. Nucleophilic attack by the halide ion:The halide ion  X^-  acts as a nucleophile again and attacks the remaining alkyl group  R'  connected to the oxygen atom. This leads to the formation of a new carbon-halogen bond and the breaking of the carbon-oxygen bond, resulting in the formation of another alkyl halide and water as a leaving group.R'-O H -H + X^-  R'-X + H2OOverall, the acid-catalyzed cleavage of an ether results in the formation of two alkyl halides  R-X and R'-X  and water  H2O  as the byproduct.
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