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Ethers are relatively unreactive compounds. The ether linkage is quite stable towards bases, oxidizing agents, and reducing agents. Therefore, we must remember that with respect to the ether linkage, ethers undergo just one kind of reaction. It is cleavage by acids :
R-O-R’ + HX → R-X + R’-OH R’ ¾X
Reactivity of HX : HI > HBr > HCl
Cleavage takes place only under quite extreme conditions, like in concentrated acids (usually HI or HBr) and high temperatures. A dialkyl ether produces, initially, an alkyl halide and alcohol. This alcohol may react further and form a second mole of alkyl halide. For example :
The oxygen of ether is basic, similar to the oxygen of alcohol. The initial reaction between ether and acid is no doubt, the formation of the protonated ether. Cleavage, then, involves the nucleophilic attack by a halide ion on this protonated ether, with the displacement of the weakly basic alcohol molecule.
Such a reaction usually occurs much more readily as compared to the displacement of the strongly basic alkoxide ion from the neutral ether.
Explanation:
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