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I read from a source that 2-iodopropane undergoes iodoform reaction. What reaction mechanism is undergone here, and why does this happen?

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  • $\begingroup$ Mention the source. $\endgroup$ – Pritt says Reinstate Monica Apr 21 '17 at 14:24
  • $\begingroup$ Well, it was an online test for JEE Adv Prep $\endgroup$ – Aaron John Sabu Apr 21 '17 at 14:25
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Yes, Aaron.

It will.

Because Iodide is very good leaving group. In iodoform test, we use base... which will convert 2-iodopropane into propan-2-ol. The latter will give haloform the same way as ethyl alcohol and any other methyl ketone does! enter image description here

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  • $\begingroup$ Oxidation of isopropanol to acetone using halide? This isn't a common reaction $\endgroup$ – NotEvans. Apr 21 '17 at 19:09
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    $\begingroup$ Okay. How then would ethanol be giving haloform reaction... This is oxidation by halogen [NOT BY HALIDE]. Halogens are good oxidizing agents! $\endgroup$ – Che Mistry Apr 21 '17 at 19:11
  • $\begingroup$ Are you able to give a mechanism for the reaction? Or a source in the original literature oxidising isopropanol with just a halide/halogen? $\endgroup$ – NotEvans. Apr 21 '17 at 19:53
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    $\begingroup$ en.wikipedia.org/wiki/Haloform_reaction Go to mechanism section Reaction sequence 2 $\endgroup$ – Che Mistry Apr 21 '17 at 20:11
  • $\begingroup$ In that case, will any CH3CHX- group give the iodoform reaction? (X = halogen) $\endgroup$ – Aaron John Sabu Apr 22 '17 at 5:09

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