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I don't think that "step 3" (deprotonation step) is necessary for SN1. This implies that all SN1 should have a deprotonation step, which is not true. Absurdpoet 18:38, 7 July 2015 (UTC)
"Nuclophiclic attack": is that "nucleophilic attack"? The Anome 22:00 7 Jun 2003 (UTC)
Should SN1 and SN2 have some kind of link to each other? Or could they be combined? -- Gregoe86 06:37, 27 November 2005 (UTC)
Just for the sake of completeness, I’ve started adding in mechanistic diagrams of nucleophilic substitution and elimination reactions that include electron movement. I’m attempting to do these diagrams to enhance the existing example mechanisms already written by Walkerma. Please let me know if I’ve missed something in them. Thanks. -- AirMonk 20.23 9 Dec 2005 (UTC)
-Diagram-
Is it just me or is the diagram incorrect, the overall reaction quotes the Tert-Butyl-Bromide correctly but in the first step is written incorrectly?
SN1 stands for substitution -nucleophilic-first order [not unimolecular,an older term] similarly,SN2 is substitution-nucleophilic-second ordernot bimolecular] E1 and E2 are defined similarly in terms of order and not molecularity —Preceding unsigned comment added by 59.88.36.151 ( talk) 18:17, 7 October 2008 (UTC)
In case of arenes, SN1 reaction is ruled out as the the phenyl cation is too unstable to carry SN1 reaction. (Hence haloarenes prefer SN2 reactions). However it is not mentioned in the topic here. It is very important. Exceptions should be mentioned. Valchemishnu Valchemishnu 12:58, 26 May 2011 (UTC) — Preceding unsigned comment added by Valchemishnu ( talk • contribs)
My Chemistry Professor at UCSB was disturbed by a textbook illustration "proving" SN1 hydrolysis of halide as a straight line graphed through a series of non-linear points (statistically inconclusive confidence level in the data). ("Thiry caliber pencil" in military terms; common for scientists to fudge research results to get published.) She had several students redo the results with newer lab equipment and published. However the SN1 rubbish is still peddled in undergrad textbooks. This implies that e.g. 2-BromoButane will racemize in a non-reactive polar solvent say NaBr in DMSO ith first order kinetics also but that is not the case. Kinetics are actually somewhere between SN1+ and SN2-. Admittedly this an easy simplification for high school or freshman Chemistry. Shjacks45 ( talk) 19:35, 21 September 2013 (UTC)
Yeah because DMSO favors SN2 in that situation, of course you're going to get both situations. Secondary SN1 is a bit controversial, but this isn't data. — Preceding unsigned comment added by 168.156.42.7 ( talk) 15:59, 20 July 2016 (UTC)
The comment(s) below were originally left at Talk:SN1 reaction/Comments, and are posted here for posterity. Following several discussions in past years, these subpages are now deprecated. The comments may be irrelevant or outdated; if so, please feel free to remove this section.
A very good article. The main suggestion I would make is to add an energy profile diagram for a reaction to show the transition states and intermediate states. Also explanation of the mechanics behind these states (e.g. what is the molecular arrangement during the first peak? Why is the carbocation more stable than these?) would help.
I also suggest adding some information on how this reaction mechanism might be used - what are some of the important reactions/applications for which this reaction is employed? Finally, a 'substitution reactions' template (or something similar) might be handy to connect these reactions and concepts together. Richard001 00:34, 6 May 2007 (UTC) |
Last edited at 00:34, 6 May 2007 (UTC). Substituted at 05:11, 30 April 2016 (UTC)
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This
level-5 vital article is rated B-class on Wikipedia's
content assessment scale. It is of interest to the following WikiProjects: | |||||||||||
|
This article was the subject of an educational assignment in Spring 2015. Further details were available on the "Education Program:Mahidol University International College/ICCH336 (2015-16/T1)" page, which is now unavailable on the wiki. |
I don't think that "step 3" (deprotonation step) is necessary for SN1. This implies that all SN1 should have a deprotonation step, which is not true. Absurdpoet 18:38, 7 July 2015 (UTC)
"Nuclophiclic attack": is that "nucleophilic attack"? The Anome 22:00 7 Jun 2003 (UTC)
Should SN1 and SN2 have some kind of link to each other? Or could they be combined? -- Gregoe86 06:37, 27 November 2005 (UTC)
Just for the sake of completeness, I’ve started adding in mechanistic diagrams of nucleophilic substitution and elimination reactions that include electron movement. I’m attempting to do these diagrams to enhance the existing example mechanisms already written by Walkerma. Please let me know if I’ve missed something in them. Thanks. -- AirMonk 20.23 9 Dec 2005 (UTC)
-Diagram-
Is it just me or is the diagram incorrect, the overall reaction quotes the Tert-Butyl-Bromide correctly but in the first step is written incorrectly?
SN1 stands for substitution -nucleophilic-first order [not unimolecular,an older term] similarly,SN2 is substitution-nucleophilic-second ordernot bimolecular] E1 and E2 are defined similarly in terms of order and not molecularity —Preceding unsigned comment added by 59.88.36.151 ( talk) 18:17, 7 October 2008 (UTC)
In case of arenes, SN1 reaction is ruled out as the the phenyl cation is too unstable to carry SN1 reaction. (Hence haloarenes prefer SN2 reactions). However it is not mentioned in the topic here. It is very important. Exceptions should be mentioned. Valchemishnu Valchemishnu 12:58, 26 May 2011 (UTC) — Preceding unsigned comment added by Valchemishnu ( talk • contribs)
My Chemistry Professor at UCSB was disturbed by a textbook illustration "proving" SN1 hydrolysis of halide as a straight line graphed through a series of non-linear points (statistically inconclusive confidence level in the data). ("Thiry caliber pencil" in military terms; common for scientists to fudge research results to get published.) She had several students redo the results with newer lab equipment and published. However the SN1 rubbish is still peddled in undergrad textbooks. This implies that e.g. 2-BromoButane will racemize in a non-reactive polar solvent say NaBr in DMSO ith first order kinetics also but that is not the case. Kinetics are actually somewhere between SN1+ and SN2-. Admittedly this an easy simplification for high school or freshman Chemistry. Shjacks45 ( talk) 19:35, 21 September 2013 (UTC)
Yeah because DMSO favors SN2 in that situation, of course you're going to get both situations. Secondary SN1 is a bit controversial, but this isn't data. — Preceding unsigned comment added by 168.156.42.7 ( talk) 15:59, 20 July 2016 (UTC)
The comment(s) below were originally left at Talk:SN1 reaction/Comments, and are posted here for posterity. Following several discussions in past years, these subpages are now deprecated. The comments may be irrelevant or outdated; if so, please feel free to remove this section.
A very good article. The main suggestion I would make is to add an energy profile diagram for a reaction to show the transition states and intermediate states. Also explanation of the mechanics behind these states (e.g. what is the molecular arrangement during the first peak? Why is the carbocation more stable than these?) would help.
I also suggest adding some information on how this reaction mechanism might be used - what are some of the important reactions/applications for which this reaction is employed? Finally, a 'substitution reactions' template (or something similar) might be handy to connect these reactions and concepts together. Richard001 00:34, 6 May 2007 (UTC) |
Last edited at 00:34, 6 May 2007 (UTC). Substituted at 05:11, 30 April 2016 (UTC)
Hello fellow Wikipedians,
I have just modified one external link on SN1 reaction. Please take a moment to review my edit. If you have any questions, or need the bot to ignore the links, or the page altogether, please visit this simple FaQ for additional information. I made the following changes:
When you have finished reviewing my changes, you may follow the instructions on the template below to fix any issues with the URLs.
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(last update: 18 January 2022).
Cheers.— InternetArchiveBot ( Report bug) 03:19, 24 January 2018 (UTC)