Comments on: Bond Strengths And Radical Stability https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/ Wed, 28 Sep 2022 20:41:25 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-565946 Wed, 02 Oct 2019 19:28:29 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-565946 In reply to Aditya Gupta.

Yes, you are correct that alkyl iodides are not prepared directly through free-radical halogenation because the H-I bond is much weaker than the C-H bond.

]]> By: Aditya Gupta https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-565940 Wed, 02 Oct 2019 18:04:26 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-565940 Hey, as u mentioned in the section (8) ,the Iodine free radical is most stable. But if I’m not wrong alkyl iodides are not prepared using this mechanism as the free radical formed (Of Iodine) forms I2 molecule. Thank You !!

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-556558 Thu, 20 Jun 2019 04:28:14 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-556558 In reply to Vaishu.

Higher electron affinity of nitrogen versus carbon due to greater electronegativity.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-556557 Thu, 20 Jun 2019 04:25:59 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-556557 In reply to Ben.

Probably about the same. Trivial difference.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-556556 Thu, 20 Jun 2019 04:25:24 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-556556 In reply to Philip.

Where did you get that fluorine radical is more selective? Running reactions with fluorine radicals is not for the faint of heart…

]]> By: Philip https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-511718 Tue, 25 Apr 2017 05:52:58 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-511718 Thank you, sir. But what about I–I and F–F, 36 kcal/mole and 38 kcal/mole, BDE’s respectively. Apparently, their radicals have same behaviour but it turns out they don’t. Fluorine free radical is more selective, but Iodine reacts with any Hydrogen. Am I wrong? Why does that happen?

]]> By: Vaishu https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-476759 Fri, 02 Sep 2016 06:48:33 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-476759 Why is methyl radical more stable than NH2 in factor 4

]]> By: Ben https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-454929 Mon, 18 Apr 2016 16:34:00 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-454929 Can someone help me the order of stability of tertairy carbo free radical.
Eg: 3
methyl groups vs three ethyl groups

]]> By: Timothy Pillow https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-366801 Thu, 19 Feb 2015 05:28:32 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-366801 James, i have 2 questions
Firstly: free radicals decrease in stability as we reduce the amount of hybridization? This seems totally counter intuitive; you’d expect that sp would be much more stable because the radical is closer to the nucleus due to 50% s character… why is this?
Secondly: adjacent lone pairs stabilize a radical? woah, this one totally blew my mind; you’d expect electronic repulsion/increased electron density to destabilize the radical?
Thanks, and glad you liked the mnemonic (i created it for my physical organic test tomorrow :/

]]> By: James https://www.masterorganicchemistry.com/2013/08/14/bond-strengths-radical-stability/#comment-366771 Thu, 19 Feb 2015 03:29:18 +0000 https://www.masterorganicchemistry.com/?p=7477#comment-366771 In reply to Timothy Pillow.

Thanks Tim!

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