Talk:Enol

Image of MOs

I've created Image:Enolate-pi-MOs.png, a drawing of the pi molecular orbitals of enolate anions, based on a similar diagram in Clayden (p. 528).

If anyone wants to write a little about the structure and bonding of enolates, it might be a nice illustration to use.

Ben (talk) 23:28, 26 October 2008 (UTC)[reply]

It is very unclear which bondings are showed on what moments. This article is not about molecular orbitals. Without an appropiate explanation it does not make any sense.--Wickey-nl (talk) 10:04, 1 April 2010 (UTC)[reply]

Actually the molecular orbitals are pretty clear. And what is more they are far more correct than the long debunked concept of so-called "resonance" that the article drops on people's plates as if it were the divine truth.... You are right that the article is not about molecular orbitals. Unfortunately it is about debunked science instead... Jcwf (talk) 18:37, 6 October 2010 (UTC)[reply]

Except the resonance article goes to great lengths to explain that that is just a way of thinking that is not correct and can give misleading results. It's still a useful, albeit simplified, way to consider enol(ate)s. That article discusses resonance as being extreme fictional cases, with reality being somewhere in between. Isn't that what MO says also?--"one point something" bond-orders, "some negative charge" on each end, etc.? It's definitely true that the electrons don't "resonate back and forth" (some sort of instantaneous equilibrium between two structures), but it's also true (as far as I read) that nobody above novice level really believes that is what "resonance" actually means anyway, despite using the term and drawing one or another structure when trying to illustrate that there is "some negative charge" on a certain atom. Not quite sure where I'm going with this, except that I disagree with banishing all mention of resonance as a rejected pile of phlogiston. It's a useful and "comfortable" way of examining certain aspects of a complicated situation and accurately explains many basic reactions, as long as its limitations and the resulting incorrect implications are remembered. DMacks (talk) 06:00, 8 October 2010 (UTC)[reply]

References needed?

Indeed, this lemma does not explicitly contain references. If you like to, you can add a list of basic organic chemistry textbooks. The subject is that basic, it does not need any references. As an example: I think, discussing the forms of the verb "to be" in english also will be very legitimate, without any obvious reference. T.vanschaik (talk) 21:03, 28 March 2009 (UTC)[reply]

I'll have to disagree on this on two points: first, chemistry is an experimental science and a statement cannot be considered factual unless someone who has done the experiment can confirm it, and second, even "basic" theories can be and are regularly challenged in chemistry. --Vuo (talk) 09:09, 29 March 2009 (UTC)[reply]

File:Enol.png Nominated for Deletion

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Move extensive explanation on MO description

I propose that the extensive explanation employed on this page be moved to the three-center four-electron bond page, while keeping the explanation here summarized as the explanation applies to all three-center four-electron bonds and somewhat draws attention away from the other more important sections on enols.--Officer781 (talk) 07:59, 27 September 2012 (UTC)[reply]

As there has been no response, I have shifted the explanation as planned.--Officer781 (talk) 13:40, 26 October 2012 (UTC)[reply]

Moving a primary source here

…because in this very fundamental (introductory) area of OChem there is absolutely no need for a primary source to appear,^[1] especially not as a sole source for a basic point. Here is the source, which can be added back, at another article, or in other more sophisticated discussions.

^ W. Caminati, J.-U. Grabow (2006). "The C_2v Structure of Enolic Acetylacetone". Journal of the American Chemical Society. 128 (3): 854–857. doi:10.1021/ja055333g. PMID 16417375.

What this article needs are text clarifications based on:

(i) advanced textbooks, and perhaps the best undergraduate OChem texts, like Clayden et al, [1], and after that,
(ii) available monographs and review articles.

There is no need for a JACS citation here, to make a basic point. It reflects a poor pedagogic approach, and lacks consideration for the audience that this article draws. Cheers, Le Prof Leprof 7272 (talk) 17:58, 16 July 2015 (UTC)[reply]

Moving web source here

…because in this important and fundamental area of OChem there is absolutely no reason for such a poor quality source to appear,^[1] especially not as a sole source for a basic point, given the rich secondary literature on this subject. Here is the source will be added back as external links or further reading, once a good citation is found for the introductory point in question.

^ Chemistry of Enolates and Enols - Acidity of alpha-hydrogens

As noted above, this article needs text revision based on advanced textbooks, and best undergraduate OChem texts like Clayden et al, [2], see above. Note, this websource cites Reusch at MSU, Taber at the OChem Protal, Carey and Sundberg (no date or page numbers), and the very least we can do is extract from and cite these 3 reasonable sources, completely.

Finally, such a source is not immediately being placed, because the text to which this was attached is extremely subpar, not even reflecting mediocre college chemistry material, and so its ultimate sourcing must be accompanied by a hard re-edit. Spending time attaching things to the text, as is, would be throwing good money after bad.

Cheers, Le Prof Leprof 7272 (talk) 19:48, 16 July 2015 (UTC)[reply]

Moving image set here

…because the images are extremely subpar in composition, and the legends and text accompanying make clear this is an incomplete, likely student effort (in accuracy of detail and scope of content). In my view these images should not be returned unless the indicated bond angles and positioning of charges—which cry out with inexperience—are made to match a good advanced OChem textbook, precisely, and unless time is then committed to make the legends and text reflect the content of the same book. No chemical image can stand alone in its content at Wikipedia; chemical images always require legends and text that are expert in perspective, but tailored to a lay audience.

Keto-enol-tautomerism

Interconversion between keto form and enolate; deprotonation of the α-C-atom.	Enolate anion, described in terms of resonance. Left the carbanion.	Interconversion between enolate and enol; protonation of the enolate.

Otherwise, some of this content is redundant, as the alpha-label, and the carbanion and oxyanion resonance pairs already appear, and without the bond geometry, charge, and lone pair presentation issues. (If this appeared as a specific, sourced mechanism, with proper arrow pushing, then this would offer something distinct.) In short, there is nothing here that is necessary, or that would be considered acceptable as encyclopedic (perhaps anywhere else than here). Cheers, Le Prof Leprof 7272 (talk) 19:48, 16 July 2015 (UTC)[reply]

Need for EZ converage

Given the importance of E-/Z-enols in effecting stereochemical outcomes in Mukaiyama and other aldol reactions, there is a need in WP for making clear this absolute stereochemical nomenclature applies also to enols. Since it does not appear at the E-Z notation [sic.] article, perhaps it can be inserted here first, based on good references. See the Bridged compounds article for an already formatted citation of Clayden's OChem text, and Advanced Organic Chemistry. Part B: Reactions and Synthesis (5th ed.). Berlin, Germany: Springer Science & Business. 2010. pp. 64ff, esp. 67f and 98f, 82, 91, 88, 93. ISBN 0387683542. Retrieved 1 March 2016. {{cite book}}: Unknown parameter |authors= ignored (help) (another formatted and so ready citation)for material on E, Z- use in enolate reactions. Page numbers are not comprehensive, just a few examples. Le Prof Leprof 7272 (talk) 00:30, 3 March 2016 (UTC)[reply]

Merger proposal

I suggest that we merge Keto–enol tautomerism into this one. One cannot discuss enols without discussing the equilibrium, it seems. Enolates, however are a diff topic. Comments welcome.--Smokefoot (talk) 01:29, 28 August 2020 (UTC)[reply]

Clicking on a link for Keto–enol tautomerism just to be redirected to the Enol functional group can be confusing to someone learning about the topic. It may be more appropriate to merge Keto–enol tautomerism with the Tautomer article. Synpath (talk) 06:41, 1 September 2020 (UTC)[reply]

Merger proposal

The following discussion is closed. Please do not modify it. Subsequent comments should be made in a new section. A summary of the conclusions reached follows.

To redirect (applying WP:TNT) rather than merging on the basis of long-standing COI and a viewpoint not supported by the wider field. Klbrain (talk) 14:03, 16 March 2023 (UTC)[reply]

I suggest that we merge Stereochemistry of ketonization of enols and enolates into this one. Stereochemistry of ketonization of enols and enolates was created and developed by H.E.Zimmerman (deceased) basically to highlight his publications, so its a huge COI. Another problem is that ketonization takes a different more traditional meaning. --Smokefoot (talk) 19:06, 26 March 2022 (UTC)[reply]

As a walled garden promoting an unconventional view, with COI, written in technical language that isn't accessible for the readership, I suggest that we apply TNT and delete rather than merge. Klbrain (talk) 19:39, 1 January 2023 (UTC)[reply]

Do we want to put Stereochemistry of ketonization of enols and enolates up for AfD? Pinging @Smokefoot and Klbrain: Joyous! Noise! 04:24, 7 March 2023 (UTC)[reply]

Let's just make it a redirect, using the TNT you mentioned before. If we put it up for AfD, all sorts of opinionated do-gooders chime who know absolutely nothing about chemistry but are filled with advice. --Smokefoot (talk) 14:08, 7 March 2023 (UTC)[reply]

The discussion above is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

"Erlenmeyer rule" listed at Redirects for discussion

The redirect Erlenmeyer rule has been listed at redirects for discussion to determine whether its use and function meets the redirect guidelines. Readers of this page are welcome to comment on this redirect at Wikipedia:Redirects for discussion/Log/2023 August 7 § Erlenmeyer rule until a consensus is reached. 1234qwer 1234qwer 4 19:36, 7 August 2023 (UTC)[reply]

[1] W. Caminati, J.-U. Grabow (2006). "The C_2v Structure of Enolic Acetylacetone". Journal of the American Chemical Society. 128 (3): 854–857. doi:10.1021/ja055333g. PMID 16417375.

[2] Chemistry of Enolates and Enols - Acidity of alpha-hydrogens

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