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Ethers are cleaved only by acids and not by bases. |
Answer» Solution :The C-O-C BOND in ethers like the C-OH bond in alcohols is quite STRONG. In order to weaken it, the OXYGE atom must be protonated. A subsequent nucleophilic attack by a strong nucleophile such as `BR^(-)` or `I^(-)` ion on the less hindered carbon atom of the protonated `C-underset(H)underset(|)overset(+)(O)-C` bond brings about the cleavage of ethers to form an alcohol and an alkyl halide. for example.  On the other hand, bases cannot weaken the C-O-C bond because ethers themselves being Lewis bases are not ATTACKED by strong bases such as `OH^(-)` or `H^(-)` (from `LiAlH_(4)`) ion. In other words, bases cannot cleave ethers. |
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