Comments on: The SN1 Mechanism https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/ Fri, 26 Apr 2024 18:47:38 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-644412 Fri, 16 Dec 2022 09:29:22 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-644412 In reply to Manan.

For something like t-butyl bromide going to t-butyl alcohol, there is no possibility of forming stereoisomers, so the question of retention or inversion becomes a non-issue.

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By: Manan https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-644398 Fri, 16 Dec 2022 05:43:05 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-644398 If after nucleophilic attack, the carbon is not a chiral centre, then wont it just give us a retained configuration product?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-634612 Thu, 04 Aug 2022 18:59:08 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-634612 In reply to StillStudying.

That is a very interesting paper.

I would not say that the SN1 doesn’t apply to secondary alkyl halides *at all* but let’s just say they are much less important than they appear to be.

Let’s just say that the whole teaching of SN1/SN2/E1/E2 is pretty muddled, and has been this way for quite some time. If you take introductory organic you would come away thinking that organic chemists spend a great deal of their time trying to plan out SN1/Sn2/e1/e2 reactions whereas in reality the ratio of published SN2 and E2 reactions vs SN1 and E1 reactions is at least 100:1. Even then the SN2 is best done on primary substrates to avoid side reactions.

It’s a mess. I’m glad someone has gone back and looked through the original Ingold/Hughes papers, because they are the basis for a lot of what is taught.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-631414 Mon, 27 Jun 2022 19:31:58 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-631414 In reply to Steven Tanjaya.

You’ll likely only ever see HBr if you are performing substitution reactions on alcohols. The purpose is to turn the poor leaving group OH into the good leaving group H2O, and then, depending on whether the substrate is primary (SN2) tertiary (SN1) or secondary (ask your instructor, answers vary!) you will obtain the resulting substitution product.

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By: Steven Tanjaya https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-631305 Sat, 25 Jun 2022 01:23:04 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-631305 I’m still learning about electrophilic sub/elim reactions, and your website is a blessing! I’ve got one question regarding the fast method to determine a reaction is SN1 or SN2. Let’s say that Br- is the leaving group. It’s said that if a nucleophilic substitution reaction has an acid (in this case HBr) as its product, then it’s a SN1 reaction. On the other hand, if a nucleophilic substitution reaction has a anion (in this case Br-), then it’s a SN2 reaction. I’m sure this method is useful and heuristic, but whether it be SN1 or SN2, shouldn’t the leaving group Br- not able to form HBr (as it’s a weak conjugate base)? I assume you wrote H3O+ Br- to show this, but I might be wrong. Would you please give some clarification on this? Thank you!

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By: StillStudying https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-629553 Fri, 10 Jun 2022 05:06:30 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-629553 Hey James, I recently came across this paper: http://dx.doi.org/10.1021/ed086p519
Does this mean that the SN1 mechanism is not applicable for secondary alkyl halides at all? If so, please make a post explaining why (I’m still a student, and don’t really understand the paper)

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By: Differences Between sn1 and sn2 - QuestionsCity https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-623012 Fri, 18 Mar 2022 23:10:54 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-623012 […] 01: https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/Resource 02: […]

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By: What Is Organic Chemistry? | Buy online from UK chemical suppliers https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-587904 Wed, 11 Nov 2020 10:04:27 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-587904 […] Substitution 1 reactions involve nucleophiles or bases. Reactions in this category will happen under two conditions: when a weak nucleophile or base is present, and when there’s a molecular fragment on the carbon chain. There are three steps involved in Sn1: […]

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By: What Is Organic Chemistry? https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-587902 Wed, 11 Nov 2020 09:00:54 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-587902 […] Substitution 1 reactions involve nucleophiles or bases. Reactions in this category will happen under two conditions: when a weak nucleophile or base is present, and when there’s a molecular fragment on the carbon chain. There are three steps involved in Sn1: […]

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/07/13/the-sn1-mechanism/#comment-580243 Fri, 15 May 2020 15:17:34 +0000 https://www.masterorganicchemistry.com/?p=5409#comment-580243 In reply to Afifa Idrees.

I’m not sure what details you mean by “all necessary details”, but even a limited reading of that would neglect issues like stereochemistry, etc. So the answer would be no.

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