Comments on: PBr3 and SOCl2 https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/ Wed, 14 May 2025 18:05:06 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-740826 Wed, 14 May 2025 08:53:07 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-740826 In reply to Kabir Khan Gori.

The acid-base reaction is reversible, as protonated oxygen and HBr are within 4-5 pKa units. The SN2 reaction is not.

]]> By: Kabir Khan Gori https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-740807 Wed, 14 May 2025 06:49:18 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-740807 Why does Br- attack carbon and do SN2 when it can pick up the hydrogen on O+? What drives this?

]]> By: Dev https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-700122 Wed, 17 Jul 2024 14:04:10 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-700122 SOCL2 has Sni generally and does Sn2 in presence of pyridine

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-688134 Mon, 18 Mar 2024 17:39:26 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-688134 In reply to ua_kaliya0p.

Yes. Although this specific topic is not taught consistently throughout courses and textbooks. I wrote about this here, https://www.masterorganicchemistry.com/2014/02/10/socl2-and-the-sni-mechanism/

]]> By: ua_kaliya0p https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-687789 Fri, 15 Mar 2024 11:51:30 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-687789 Secondary alcohols show retention when treated with SOCl2 alone, it proceeds through SNi mechanism. Am I right? If yes, then why is the mechanism shown here different?

]]> By: Kashyap Patel https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-686265 Thu, 29 Feb 2024 16:09:24 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-686265 Why exactly does reacting SOCl2 or PCl3 prevent rearrangement in 2* alcohols? Arent these groups as good or better at leaving than H2O+ groups?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-642025 Tue, 08 Nov 2022 09:52:16 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-642025 In reply to Anshu Apoorva.

No, because that would have to involve backside attack on an sp2 hybridized carbon (and in the middle of the ring, besides)

]]> By: Lexi https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-639450 Tue, 04 Oct 2022 08:23:21 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-639450 The way the Mechanisms are explained it’s pretty easy to understand

]]> By: Anshu Apoorva https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-603969 Thu, 29 Jul 2021 04:43:42 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-603969 What will happen if we add these reagents to phenol? Can we get Halobenzene.

]]> By: Dr.Debasish Jana https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-539012 Fri, 05 Oct 2018 18:38:07 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-539012 In reply to James.

It’s right….it is SNi mechanism….but here it is written SN2

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