1.

Which of the following ethers is cleaved even by hydrogen chloride at room temperature ?

Answer»

`C_(6)H_(5)-O-CH_(2)CH_(3)`
`CH_(3)CH_(2)-O-CH_(2)CH_(3)`
`(CH_(3))_(3)C-O-CH_(2)CH_(3)`
`(CH_(3))_(3)C-O-C(CH_(3))_(3)`

Solution :
Due to crowding in protonated ether (1), nucleophilic attack by `CI^(-)` ion does not OCCUR. Instead it undergoes cleavage to give `3^(@)`-butyl ALCOHOL and stable `3^(@)`-butyl carbocation which subsequently reacts with `CI^(-)` ion to form `3^(@)`-butyl chloride. Thus, it is the stability of `3^(@)`-carbocation which favours the cleavage of ether EVEN with HCl.


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