Why ethers only undergo cleavage with strong acids and not with weaker acids?

1 Answer
anor277
Feb 6, 2017

Basically because the #C-O# bond is strong........

Explanation:

As far as anyone knows the oxygen, as the most basic site of the ether, #R-O-R#, is protonated by an acid, #HX#, to give #R-O^(+)H-R# and #X^(-)#. This weakens the #C-O# bond such that it may cleaved by (say) a water molecule to give #2xxROH#.

The stronger the acid, #HX#, the weaker the #H-X# bond, and the more likely it is to cause hydrolysis of the ether moiety.

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