NaI in acetone is a classic Sn2 reaction, So why does 2-chloro-2-methypropane react here?(slowly at 55 Celsius) 5) Apparently Iodoethane doesn’t react here. What might be going on?

  • $\begingroup$ What sort of reaction could iodoethane produce ? $\endgroup$ – Maurice Feb 16 at 20:20
  • $\begingroup$ When you say iodoethane doesn't react what do you mean? Starting material is recovered or a different reaction occurs than the one you expected? $\endgroup$ – Waylander Feb 16 at 21:58
  • $\begingroup$ The t-Bu+ cation is pretty stable. Think this could have anything to do with it? $\endgroup$ – Waylander Feb 16 at 21:59
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    $\begingroup$ Let's assume iodoethane does react. How would you know? $\endgroup$ – matt_black Feb 17 at 14:23

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