Will $\ce{CF3I}$ show nucleophilic substitution? In other words, is the following reaction feasible? $$\ce{CF3I + NaOH -> CF3OH + NaI}$$

I know that $\ce{I-}$ is a pretty good leaving group. Also due to inductive effects, the carbon already has a $\delta+$ charge. So I think it should react, yet the answer in my textbook is telling me otherwise.

Are there any other effects that I am not considering?

  • 1
    $\begingroup$ The reaction may not be occurring because solvent may not be correct, as in polar protic or polar aprotic. $\endgroup$ Jul 7, 2020 at 12:33
  • $\begingroup$ If I'm not mistaken, said reaction does not take place because the three fluorine atoms so change the electronics of the system that trifluoromethyl iodide is not nearly as electrophilic as one might think. $\endgroup$
    – Zhe
    Jul 7, 2020 at 15:38
  • $\begingroup$ @Zhe Could you please elaborate. Is it that the fluorine atoms' electron pairs repel the incoming anion? $\endgroup$ Jul 9, 2020 at 6:13
  • $\begingroup$ No, I think it changes the energy of the σ* orbital. $\endgroup$
    – Zhe
    Jul 9, 2020 at 14:41


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