The cleavage of the C-O bond in ethers happens under drastic conditions with excess hydrogen halides. The reaction of a dialkyl ether yields two alkyl halide molecules.
Describe the conditions under which the cleavage of the C-O bond in ethers occurs, and what are the products obtained from the reaction of a dialkyl ether?
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The cleavage of the C-O bond in ethers typically occurs under acidic or acidic conditions. In the presence of an acid, such as concentrated hydrochloric acid (HCl) or sulfuric acid (H₂SO₄), dialkyl ethers undergo cleavage to form two alkyl halides. The reaction involves protonation of the ether oxygen, followed by the departure of a leaving group, leading to the formation of carbocation intermediates. Subsequent nucleophilic attacks by halide ions yield the alkyl halides. The general reaction can be represented as:
R-O-R’ + 2HCl → R-Cl + R’-Cl + 2H₂O