Ethers, which are organic molecules with the general formula , will also autoxidize with oxygen gas to form organic peroxides, which are very dangerous and explosive.
Ethers cleave in the presence of a haloacid (HBr, HCl, HI) to form alkyl halides (RX). This is known as acidic cleavage. Acidic cleavage is the breaking of a covalent bond using an acid. This reaction works with all ethers except for aryl ethers, such as phenyl ethers. Like alcohols, alkyl ethers are cleaved into alkyl halides using strong acids such as HI and HBr via a standard nucleophilic substitution reaction. In this reaction, the oxygen of the ether is protonated by the strong acid, creating a good leaving group. The nucleophilic halide then cleaves the ether bond, creating an alkyl halide and an alcohol. The alcohol is converted to an alkyl halide following the same mechanism. If either side of the ether is an aryl group, the aryl group will convert to an alcohol but will not further convert to an alkyl halide.
Summary of Ether Cleavage Reactions
|Type of Alkyl Group (R) on Ether ()||Product from Cleavage with Haloacid (HBr, HCl, HI)|
|Any alkyl group||Alkyl halide|
|Any aryl group||Aryl alcohol|