I was teaching the $S_N1$ mechanism to a friend. He asked a question a subtle question I can't shake off. Take a tertiary alkyl halide and aqueous sodium hydroxide. The first step is the formation of the carbocation. My friend asked how did the alkyl halide just do that all of a sudden. What about the presence of the $\ce{NaOH}$ made this compound do this if it doesn't even interact with it ( in the first step)? I first thought maybe it was just that the first step is something that is a feasible process, and that the alkyl halide would do (to an appreciable extent) that even without the $\ce{NaOH}$, but I am not sure.

Is my idea correct?

  • $\begingroup$ The solvation of the halide part led to energy being released which compensated for the bond being broken(which apparently seems "spontaneous") $\endgroup$ – Yusuf Hasan Mar 31 '19 at 9:33
  • $\begingroup$ So this would have happened even without the NaOH present? $\endgroup$ – Sal_99 Mar 31 '19 at 12:25
  • $\begingroup$ Heard of the term solvolysis if not look it up $\endgroup$ – Aditya Garg Mar 31 '19 at 13:33

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