Can we have multiple hydride or methanide shifts? Specially in the case where after first shift it becomes less stable and after the second shift it becomes more stable.

For example, the first step of acid catalysed dehydration of 3-methylbutan-1-ol. The step in which H+ is added to the hydroxy group and it departs leaving a carbocation.

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    $\begingroup$ Could you be more specific and provide an example. $\endgroup$ – user55119 Jul 10 '20 at 19:39
  • $\begingroup$ @user55119 Please check now, I have also stated an example. $\endgroup$ – Harrison Wells Jul 11 '20 at 11:44
  • $\begingroup$ @RahulVerma What about the example above? I'm telling to check the example written in the question. Can the carbonation have multiple Hydride shifts? $\endgroup$ – Harrison Wells Jul 11 '20 at 11:44
  • $\begingroup$ hydration or dehydration? $\endgroup$ – Safdar Faisal Jul 11 '20 at 11:44
  • $\begingroup$ @SafdarFaisal sorry dehydration i will correct it $\endgroup$ – Harrison Wells Jul 11 '20 at 11:45

Yours is a primary alcohol and it has $\beta$ hydrogen atoms also. Thus, it will undergo $\pu E2$ mechanism. In this mechanism removal of protonated hydroxyl group and $\beta ~\pu H$ happen at once (in a single step). Therefore, there will be no scope of hydride shifting.

You may compare this with the dehydration of neo-pentyl alcohol.


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