Comments on: The SN2 Mechanism https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/ Fri, 18 Oct 2024 19:46:36 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-712062 Fri, 18 Oct 2024 19:46:36 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-712062 In reply to Aadity.

Published rates indicate that the rate of reaction for methyl halides is roughly 30 times the rate for primary halides (e.g. benzyl chloride) assuming the nucleophile is the same. That’s the rough difference in rates.

]]> By: Aadity https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-711820 Thu, 17 Oct 2024 15:55:28 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-711820 Thanks for this post! How can we compare the rate of SN2 for chloroethane and benzyl chloride?

]]> By: Molecular Manipulation: The Phenomena of Stereoselectivity – Natural Sciences MRes Students https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-696342 Mon, 10 Jun 2024 11:43:05 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-696342 […] Ashenhurst, J. (2024) The SN2 mechanism, Master Organic Chemistry. Available at: https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/ […]

]]> By: Madhav Mittal https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-693960 Fri, 17 May 2024 14:56:34 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-693960 According to the organic chemistry textbook by Clayden, Warren and Greeves,
Alpha halo ketones undergoes the fastest SN2 in the world!!
James, can you please pour some light over this?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-692431 Tue, 30 Apr 2024 19:35:19 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-692431 In reply to Madhav Mittal.

OK, thank you for visiting the side Madhav and I am glad you find it useful. Please let me know if you see any mistakes / typos. James

]]> By: Madhav Mittal https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-692371 Tue, 30 Apr 2024 04:54:27 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-692371 James , you are just awesome and the best.
The most accurate ,easy to understand and concise explanation of each and every topic.
Thanks a ton.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-680739 Tue, 26 Dec 2023 03:13:16 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-680739 In reply to Paolo Brocca.

“Chirality center” is an approved IUPAC term. https://goldbook.iupac.org/terms/view/C01060 .

The reason I dislike stereocenter in this context is that it also applies to the carbon atoms on double bonds capable of cis/trans isomerism. For that reason I choose not to use it here.

For the audience of this website I personally see no problem with shortening “chirality center” to “chiral center” since pretty much everyone knows that it means a carbon with four different substituents.

]]> By: Paolo Brocca https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-680294 Thu, 21 Dec 2023 05:11:38 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-680294 “chiral center” is a completely wrong expression. No center could ever be chiral. Chirality owns only to object/ molecules,not to atoms. That carbon is a stereocenter.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-670015 Tue, 05 Sep 2023 18:44:17 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-670015 In reply to Daksh Fluorosulphale.

The transition state contains a partial bond and it is not really appropriate to use hybridization terminology to describe it.

]]> By: Daksh Fluorosulphale https://www.masterorganicchemistry.com/2012/07/04/the-sn2-mechanism/#comment-669339 Thu, 31 Aug 2023 15:19:42 +0000 https://www.masterorganicchemistry.com/?p=5333#comment-669339 What will be the hybridization of the transition state in biomolecular substitution reaction (SN2)? Is it sp3 or sp2?

Thank you!

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