Editing Ether (section)

===Cleavage===
{{see also|Ether cleavage}}
Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and [[hydroiodic acid]]. [[Hydrogen chloride]] cleaves ethers only slowly. Methyl ethers typically afford [[methyl halide]]s:
:ROCH<sub>3</sub> + HBr → CH<sub>3</sub>Br + ROH
These reactions proceed via [[onium compounds|onium]] intermediates, i.e. [RO(H)CH<sub>3</sub>]<sup>+</sup>Br<sup>−</sup>.

Some ethers undergo rapid cleavage with [[boron tribromide]] (even [[aluminium chloride]] is used in some cases) to give the alkyl bromide.<ref>{{OrgSynth|author = J. F. W. McOmie and D. E. West|title = 3,3′-Dihydroxylbiphenyl|collvol = 5|collvolpages = 412|year = 1973|prep = CV5P0412}}</ref> Depending on the substituents, some ethers can be cleaved with a variety of reagents, e.g. strong base.

Despite these difficulties the chemical [[pulp (paper)|paper pulping]] processes are based on cleavage of ether bonds in the [[lignin]].