In the reaction of an ether with a hydrogen halide (HX), the positive hydrogen ion replaces one of the alkyl groups attatched to the oxygen; but why does this happen, isn't the hydrogen ion a better leaving group than the carbocation?

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    $\begingroup$ The leaving group takes the electron pair with it when the colavent bond breaks. Neither the proton nor the carbocation are the leaving group. The protonated alkoxy oxygen is the leaving group. $\endgroup$ – Ben Norris Dec 16 '18 at 21:17
  • $\begingroup$ @Ben Norris I just wanted to know whether a hydrogen ion replacing alkyl group is more feasible or an alkyl group replacing a hydrogen is more feasible. $\endgroup$ – SLADE Dec 17 '18 at 6:14

Yes it is, but that protonation is entirely reversible; the H+ comes off and goes on all the time. Occasionally the alkyl group comes off, that is not reversible and drives the reaction forward.

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