3
$\begingroup$

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

$\endgroup$
2
  • $\begingroup$ Mention the source. $\endgroup$ Apr 21, 2017 at 14:24
  • $\begingroup$ Well, it was an online test for JEE Adv Prep $\endgroup$ Apr 21, 2017 at 14:25

1 Answer 1

3
$\begingroup$

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

$\endgroup$
6
  • $\begingroup$ Oxidation of isopropanol to acetone using halide? This isn't a common reaction $\endgroup$
    – NotEvans.
    Apr 21, 2017 at 19:09
  • 3
    $\begingroup$ 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, 2017 at 19:11
  • 1
    $\begingroup$ 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, 2017 at 19:53
  • 3
    $\begingroup$ en.wikipedia.org/wiki/Haloform_reaction Go to mechanism section Reaction sequence 2 $\endgroup$
    – Che Mistry
    Apr 21, 2017 at 20:11
  • 2
    $\begingroup$ Yes! Except that of CH3CHF-R $\endgroup$
    – Che Mistry
    Apr 22, 2017 at 13:06

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.