Multiple hydride shifts 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.
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.