Comments on: PBr3 and SOCl2 https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/ Wed, 17 Jul 2024 14:04:10 +0000 hourly 1 https://wordpress.org/?v=6.6.2 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

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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/

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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?

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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?

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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)

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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

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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.

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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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By: James https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-502530 Mon, 23 Jan 2017 22:09:30 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-502530 In reply to Gerlach.

That’s an excellent question and one that isn’t immediately obvious. One thing I neglected to add in the MsCl / TsCl example is that a weak base (e.g. pyridine) is usually added to mop up any HCl formed, which could prevent the substitution for occurring.
Another is that in the case of the PCl3, once the phosphorus attacks oxygen you could have formation of a partial P-O double bond, which would put a formal charge of +1 on oxygen and make it a better leaving group, more easily displaced by a halide.
I’m sorry if this seems like an unsatisfying answer!

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By: Gerlach https://www.masterorganicchemistry.com/2015/03/20/pbr3-and-socl2/#comment-502515 Mon, 23 Jan 2017 20:42:28 +0000 https://www.masterorganicchemistry.com/?p=8823#comment-502515 What accounts for the difference in step 2 btw this rxn and the mesylate/tosylate route for making alkyl halides from alcohols (i.e., why does the free Cl- deprotonate in the latter but substitute in the former)?

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