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

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

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Answer 1 · 2017-02-06T14:08:29

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

Explanation:

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

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

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

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