Comments on: Electrophilic Aromatic Substitutions (2) – Nitration and Sulfonation https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/ Wed, 28 Sep 2022 19:51:58 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-634601 Thu, 04 Aug 2022 15:55:37 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-634601 In reply to PRISHA JAIN.

The answer to the challenge is to sulfonate first, which will go on the para position. Then perform chlorination which will go ortho. Then heat with acid to remove the para sulfonyl group.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-634600 Thu, 04 Aug 2022 15:54:39 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-634600 In reply to Aditya Datey.

The rate of reaction of C6D6 versus C6H6 has been studied but the influence of D is less than 1% on the reaction rate.

There are no conventional deuterium isotope effects in EAS since the rate-determining step of EAS reactions is breakage of the C-C pi bond and not the second step (re-aromatization)

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-629632 Fri, 10 Jun 2022 22:11:35 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-629632 In reply to priya.

Use sulfonation to put an SO3H group on the para position, then perform your EAS, and finally, remove the SO3H

]]> By: priya https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-628441 Fri, 27 May 2022 05:44:31 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-628441 what is the answer to the challenge? how to get only o isomer without any para isomer?

]]> By: Nitration: Definition, Reaction, Examples, and Mechanism https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-622860 Wed, 16 Mar 2022 05:21:23 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-622860 […] Masterorganicchemistry.com […]

]]> By: Eric Mwiti https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-599608 Wed, 07 Apr 2021 06:21:38 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-599608 Good work.It’s helpful to undergraduate students.

]]> By: Aditya Datey https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-582269 Tue, 14 Jul 2020 06:44:32 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-582269 Does Rate of reaction also depend on the speed with which C-H bond is broken, What if we use C6D6 instead of C6H6 in Nitration?

]]> By: Rookie https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-580315 Mon, 18 May 2020 08:26:01 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-580315 Which one to pick between options – SO3 and HSO3+ ?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-580254 Sat, 16 May 2020 03:27:29 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-580254 In reply to Rookie.

Yes, protonated SO3 is the electrophile. Acids (and Lewis acids) tend to make electrophiles even more electrophilic.

]]> By: Rookie https://www.masterorganicchemistry.com/2018/04/30/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation/#comment-580246 Fri, 15 May 2020 19:35:11 +0000 https://www.masterorganicchemistry.com/?p=11541#comment-580246 My textbook says “the electrophilic reagent used in sulfonation of benzene is SO3”, but going by the exact mechanism, isn’t the electrophile SO3H?

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