Comments on: Deciding SN1/SN2/E1/E2 (1) – The Substrate https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/ Thu, 21 Mar 2024 09:49:11 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-587384 Tue, 03 Nov 2020 03:23:20 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-587384 In reply to Hina Mumtaz.

Here would be the thought process:
1) Secondary carbon. Can’t rule anything out at this stage.
2) Identity of nucleophile/base: Br(-). Good nucleophile (negatively charged), weak base. Rule out E2 because E2 needs a strong base. Rule out SN1/E1 because they operate with weak (generally neutral) bases. That leaves SN2.
3) So draw product of SN2 with inversion of configuration.

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By: Hina Mumtaz https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-587364 Mon, 02 Nov 2020 15:42:58 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-587364 ok so i have a question about what if in differentiating either an SN1 or an SN2 reaction lets say the substrate is a 6 carbon single chain on the 2nd carbon with a wedge of H and ladder on that same carbon with a Cl and a attacking nucleophile of Br-. how can you tell that this is an SN2?

For an Sn1 imagine a 5 carbon chain with carbon 2 has wedge of Br and ladder of H with nucleophile of Cl- how can you tell if its a SN1 reaction. like that what I’m having problem with. please let me know asap i have my exam on Thursday!

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-580662 Sat, 30 May 2020 02:09:49 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-580662 In reply to moreen.

You might want to look into the subject of “double inversion” :-) especially in basic conditions.

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By: moreen https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-580627 Thu, 28 May 2020 18:07:09 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-580627 hi, i was just wondering if a compound like (R) 2-bromopropan-1-ol was to undergo a substitution reaction with NaCN, and it resulted in the (R) configuration of the product with the bromine being substituted by the cyanide, which reaction mechanism does it do it by? SN1 or SN2?
can the compound undergo frontside attack by any mechanism because it is a secondary compound?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-555162 Mon, 13 May 2019 16:05:36 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-555162 In reply to Prakash.

Primary alkyl halide. Almost certainly an SN2 reaction.

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By: Prakash https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-554903 Wed, 08 May 2019 11:56:47 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-554903 Sir what product should I expect on treating ethylbromide with t butoxide. By the way great job on creating such a fabulous blog

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-552255 Wed, 10 Apr 2019 20:39:05 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-552255 In reply to jess.

Acid-base reactions on *heteroatoms* are fast, but that rule of thumb doesn’t really apply to the E2 reaction, where you’re breaking a C-H bond with accompanying change of hybridization on the carbon…

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-552254 Wed, 10 Apr 2019 20:38:18 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-552254 In reply to Aniket.

Well, these are the kinds of things that you have to weigh when evaluating these questions. Read on to parts 2 and 3.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-552253 Wed, 10 Apr 2019 20:37:56 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-552253 In reply to Kaavya.

The halogen would not have significant pi bond character. The answer is that the resulting carbocations would be very unstable.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/21/deciding-sn1sn2e1e2-1-the-substrate/#comment-552252 Wed, 10 Apr 2019 20:36:16 +0000 https://www.masterorganicchemistry.com/?p=6723#comment-552252 In reply to Ggh.

Primary allylic, yes. Primary alkyl halide, formation of the primary carbocation as an intermediate is unlikely. It’s possible to have concerted rearrangement reactions where migration of a neighboring group accompanies displacement of a leaving group, which is generally how these types of things happen.

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