Talk:Aldol condensation

Mechanism & products

I'm trying to work through the first example to get the side products drawn, but it doesn't seem very obvious. Am I missing something, or should this example be replaced with a clearer one or have some explanation added?

aldol condensation

I am reluctant to dismiss the examples given for this reaction, however, I do not believe they are very helpful for anyone wishing to see an example of the reaction listed in the title. Perhaps the examples could remain listed, but in the first case, it should be prefaced as an example of an unusual method for a mixed or crossed aldol reaction. It is several reactions combined for which aldol condensation would not readily come to mind from the reactants and products.

The second example contains a factual error related to the abstract posted. They are different. Either the abstract is in error or the wiki is in error. If decompostion were to also occur, the products of that decomposition have been been provided. However, the abstract doesn't suggest a decompostion occurs.

The third example contains a buried example of an aldol reaction. Again, I would doubt the average person interested in an aldol condensation could even pick out the named reaction.

Hopefully, either the orginators of the wiki would sef-edit their contribution appropiately or I should anticipate that an expert in the field of organic chemistry would see fit to simply delete these examples as rare or poorly relating to the original topic.

71.169.70.15 17:18, 11 December 2006 (UTC)

Overly technical

Like many articles on scientific matters on Wikipedia, I think this page is overly concentrated on the technical, and not providing enough content for the general person. Perhaps improving the introduction might be worthwhile. FrozenPurpleCube 23:21, 21 April 2007 (UTC)

• (RfC response from a "general person") While reading the article, the first question that occurred to me was, "is it even possible to reduce this information into 'layman's terms'?" Honest question. The "perfect article" may be understandable and self-contained, but what if the topic is so specific that these aspects are impossible? The final bullet on "perfection" is that it "may not be attainable". — Demong ^talk 06:51, 27 April 2007 (UTC)

Also, under what circumstances will someone unfamiliar with intermediate chemistry be reading an article called "Aldol condensation"? Other than responses to random RfCs. — Demong ^talk 07:52, 27 April 2007 (UTC)

Indeed, in theory, it may not be attainable to make the whole article understandable. That doesn't mean it shouldn't be tried, or at least given an honest look at doing it as best as one can. This is especially true for the introduction. You may not succeed with the whole article. I can't imagine anything where you can't make the first sentence meaningful by at least expressing some history and real-world usage. And one never knows why someone will read a given article on Wikipedia. People's browsing habits may lead them in all sorts of directions, not to mention the random article feature. That's why it's important to give a clear and understandable context that is as informative as possible. I see no reason not to do so. FrozenPurpleCube 14:10, 27 April 2007 (UTC)

"Aldol condensations are important in organic synthesis and integral part of university level organic chemistry, providing a good way to form carbon–carbon bonds and demonstrate fundamental reaction mechanisms"... are there practical applications besides teaching university-level chemistry? — Demong ^talk 18:29, 27 April 2007 (UTC)

Good question. I'd like to article to share the answer to that myself. If not, perhaps explaining why it's important to demonstrate carbon-carbon bonds or describing some fundamental reaction mechanisms might help. FrozenPurpleCube 18:49, 27 April 2007 (UTC)

We now explicitly mention the Robinson annulation as a practical use of an aldol condensation. One of the whole points of Orgo at the undergrad level is to learn about reaction mechanisms (intro had previously excessively muddled the ideas of "good mechanistic example" with "good bond-forming". DMacks 19:29, 30 April 2007 (UTC)

It's not "demonstrate carbon bonds" it's synthesize carbon bonds, and demonstrate fundamental mechanisms. It's right there three lines above your own comment. Aldol's are important because, IIRC, selective creation of C-C bonds are one of the more difficult things to achieve and this mechanism lets you do so brilliantly. --Belg4mit 20:24, 12 May 2007 (UTC)

• Wikipedia does not work like that, if you are unfamiliar with the content the reader is expected to thread back to organic reaction, chemical reaction (this article offers a basic explanation) or even chemistry. I notice that you make a career in providing context tags but I will only explain myself here. V8rik 19:21, 22 April 2007 (UTC)

I am not aware of any rules or policies that say an article has no responsibility to provide context or explanation. I am however, aware of things such as WP:PERFECT which clearly state

• is understandable; it is clearly expressed for both experts and non-experts in appropriate detail, and thoroughly explores and explains the subject.
• is nearly self-contained; it includes essential information and terminology, and is comprehensible by itself, without requiring significant reading of other articles.

There is also the featured article criteria to consider, which says

• "Comprehensive" means that the article does not neglect major facts and details.

And Wikipedia:Article development

Start your article with a concise lead section or introduction defining the topic at hand and mentioning the most important points. The reader should be able to get a good overview by only reading the lead, which should be between one and four paragraphs long, depending on the length of the article. See Wikipedia:Lead section.

Remember that, although you will be familiar with the subject you are writing about, readers of Wikipedia may not be, so it is important to establish the context of your article's subject early on.

among other things. Instead of commenting on me (WP:NPA), why don't you try improving this article? It would be much more effective. Thus I will re-add the clean-up templates since the concerns I expressed are unfixed. FrozenPurpleCube 20:48, 25 April 2007 (UTC)

I don't think this article is overly technical at all (but then I do have a background in chemistry). Could the intro use some polishing? Sure. But you are wrong to expect that every single article related to organic chemistry should itself include a crash course in organic chemistry. --Belg4mit 20:24, 12 May 2007 (UTC)

Not overly technical

This is a really good page. It is not overly technical it uses the appropiately language to describe an Aldol Condensation. I am not sure how you intend it to be improved. Are you suggesting that a summary of organic chemistry is included in every organic reaction in Wikipedia? This seems redudant and not a good use of energy. I would appriciate if you would repond to this before replacing the context tag. M stone 21:44, 25 April 2007 (UTC)

Why didn't you ask before removing the clean-up template? I'd have appreciated it if you tried to talk with me instead of reverting my concerns. It's very unproductive to go through this not once, but twice. Therefore I will re-add the templates, and try to explain my concerns. The biggest is that if you're not an organic chemist, you'll come into this article and have no idea what these reactions are used for. What do they matter? What is their importance in organic chemistry? Why are they included in University-level chemistry courses? It's easy to say "Well, any organic chemist would understand this" but wait, not all Wikipedians are chemists. Having the introduction to the page accessible is very important, and sadly often ignored in science articles. I can't see how this is a good page, but if you think it is, feel free to put it through a peer review. FrozenPurpleCube 03:43, 26 April 2007 (UTC)

Sentence with 3 cites added to explain why aldol is important in orgo. DMacks 05:20, 26 April 2007 (UTC)

Well, I'm sure you meant well, but did you consider writing the introduction at a level more appropriate for the average user? Perhaps you might explain some of the synthetic reactions, or carbon-carbon bonds. You may wish to consider WP:PERFECT's suggestions. I'm sorry, but I just don't consider your edits effective at remedying my concerns. Care to try improving them? FrozenPurpleCube 05:30, 26 April 2007 (UTC)

No. If you don't know what organic chemistry is, there's really no use trying to explain a specific type of organic reaction. The lead specifically explains the importance and utility in several respects and provides citations that support them if someone wants to learn more details about exactly how this fits into the larger picture. I agree with M.Stone...it's pretty obtuse to demand that an article about a technical subject contain a full treatment of how it fits into the larger picture, rather than saying it briefly and then linking to the more general article(s). Otherwise we may as well just have one huge "organic chemistry" page that has a section about every reaction instead of specific reaction pages. DMacks 05:46, 26 April 2007 (UTC)

It's not at all obtuse, I think it's quite wise. Right now, I'd say this article has no use for anybody who doesn't already know what it is. Trying to make a better article is important, just waving it off with the excuse that "you need to read elsewhere first" is missing the point of being a general purpose encyclopedia. Articles should be clear and approachable. This isn't it. Sadly, that's a common problem on many Science-related articles. Since I think there's more than one person involved, I'll put it on RFC. FrozenPurpleCube 05:49, 26 April 2007 (UTC)

The assertions of importance/context that you seem to find insufficient in the lead are essentially cloned from that of the Aldol reaction, a page which was deemed to be WP:FA status. The present article is essentially a subset, followup, or variant of that page, so it seems to me "enough" to state the same general issues (which are still applicable) and then link back to the parent article. Will wait for others to weigh in... DMacks 06:24, 26 April 2007 (UTC)

Yes, I've seen that. Note what it says in the lead:

• The aldol reaction is an important carbon-carbon bond formation reaction in organic chemistry.[1][2][3] In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals.[4][5][6] Sometimes, the aldol addition product loses a molecule of water during the reaction to form an α,β-unsaturated ketone. This is called an aldol condensation. The aldol reaction was discovered independently by Charles-Adolphe Wurtz[7] and by Alexander Porfyrevich Borodin in 1872. Borodin observed the aldol dimerization of 3-hydroxybutanal from acetaldehyde under acidic conditions. The aldol reaction is used widely in the large scale production of commodity chemicals such as pentaerythritol[8] and in the pharmaceutical industry for the synthesis of optically pure drugs. For example, Pfizer's initial route to the heart disease drug Lipitor (INN: atorvastatin), approved in 1996, employed two aldol reactions, allowing access to multigram-scale quantities of the drug.[9][10]

I'm sure you think the first sentence is ok. I'm not sure it's ideal, but at least the rest of the introduction provides some further context to it. No such attempt was made here on this page. FrozenPurpleCube 06:38, 26 April 2007 (UTC)

First, there is no "average reader". Seeing that in an argument always makes me cringe. The expected audience depend vastly on the topic. Many scientific topics are really not likely to be of interest to six-year old kids, and others are of interest only to people at the PhD level. This particular topic is more or less "college level", and it is reasonably written for that level. Anyone who is not completely ignorant of organic chemistry will be able to take something from it. Of course it's not perfect. It may be incomplete in some respects, and perhaps it's even possible to make it a bit more accessible. However, slapping on a template and running away doesn't help. If you can improve it, do it (WP:SOFIXIT). If not, the people who know may eventually do it. But slapping on a template tends to alienate the few people who actually know about the topic and have put efforts into it. This is Not a Good Thing. Some of them take it as an insult; like saying they have done a shitty job and putting it in flashing lights at the top of the article. No wonder Citizendium discourages the use of templates. ;-) A more diplomatic and constructive alternative IMO would be to mention your concerns politely in the talk page instead of slapping on a template. The real authors of the article are less likely to feel insulted that way and will be more likely to listen. As an aside, the WP:PERFECT page you link to doesn't seem to be an accepted guideline, or at least it doesn't say so on the page. All the comments in its talk page seem to be complaints. --Itub 08:46, 26 April 2007 (UTC)

Well, the argument that "I don't have to explain this any better since if you knew enough, you'd have understood it" makes me cringe. So does that adding cleanup templates insults people. It makes me feel like I'm being insulted because I think there's something to be concerned here. No, I'm not surprised people feel insulted when they're told a page needs work. That's a common problem, which will happen regardless of how it's done (on talk pages or templates). People get possessive, people hate to see criticism of their work. This doesn't mean there isn't a problem with the page itself. And just because there might be a problem, doesn't mean the editors did anything wrong. It means....the page needs work.

In this case, I'd still like some further context to explain this reaction. Simply saying it's important isn't as good as saying something as to what it's important for. You can say "If you aren't completely ignorant of organic chemistry, you will be able to take something from it" but pardon me for saying "Hey, wait, what if you are?" FrozenPurpleCube 12:27, 26 April 2007 (UTC)

The real problem is that there are very few people with the necessary knowledge to edit some scientific topics (although this article is certainly not one of the most esoteric). Alienating them can only hurt Wikipedia. I'm not being hypothetical here, V8rik is one of our greatest contributors for Wikipedia chemistry articles and he's so sick of these templates, and similar bureaucratic practices, that he's refusing to edit certain articles anymore (I hope he'll eventually reconsider after things cool down). And thank you, but I would rather take one V8rik over 1000 template-slapping editors any day. Regarding your last question, if you are completely ignorant of organic chemistry, you are asking for something impossible. There is no way an article in a reasonably advanced scientific topic can be "self-contained" enough and comprehensive enough so that you can understand it. Go and read organic reaction, carbonyl, ketone, aldehyde, nucleophile, enolate, base, or whatever it takes first (or even better, a textbook. Reading encyclopedia article is not always the best way of learning a completely new topic. That's why encyclopedias are generally used for reference and not as tutorials). You can't expect to jump straight into a topic as specific as this one and understand everything if you have no background. --Itub 12:52, 26 April 2007 (UTC)

I'm sorry if he's offended but while he may be one of the greatest contributors, if he's getting sick of good-faithed requests for article improvement, that's probably a problem he needs to work on himself, perhaps by being less possessive of pages, perhaps by examining his own attitudes. His words here and elsewhere indicate an attitude that is more like "How dare you say this page needs work" which indicates resentment that somebody might be concerned that a page should be reachable to more people. I'm sure it's quite likely that the number of people with the necessary knowledge to edit some topics may be rarer, and I'm sure some people may be offended when they're told their work is not quite good enough, but I just can't find it in me to blame myself for another person storming off in a huff because I suggest a page be more approachable. I did so politely and reasonably, so I'm not sure how it's wrong for me to have my concerns. There's a reason why it's important not to take things personally, or make things personal. It's easy to get upset, and there are times people do make inappropriate additions, but it's still important to take people's concerns seriously without getting outraged.

And I did slightly exaggerate my question, sorry. Complete ignorance is one extreme. Currently, this page is at the other, where as I see it, the only way you can fathom this article is if you knew what it was talking about already. I wish I knew enough to improve it, but I don't believe I do. Sorry. All I can do is say "Hey, I think you're overlooking the approachability of this page for the layman" . Nothing you, or anybody else has jumped in to say here has convinced me that you have done that. Rather the opposite. FrozenPurpleCube 13:09, 26 April 2007 (UTC)

Coment:"::There's no issue to address here. The article isn't a howto, as has been explained to FrozenPurpleCube several times in several places. He's waging a one person war against chess content on Wikipedia, but has little to no support for his positions. by Quale " (from Sicilian Defence) tells nearly everything you need to know what good-faithed requests really are.--Stone 18:32, 26 April 2007 (UTC)

Perhaps you need to consider whether this outside dispute has anything to do with this article, and whether it's constructive to attack me in this fashion rather than address the concerns I have. Just the fact that you'd even support the position Quale has taken doesn't convince me I'm wrong. That user's behavior regarding me has been hostile at best and harassment at worst. FrozenPurpleCube 19:41, 26 April 2007 (UTC)

And note, I'm sorry if it seems like I'm not Assuming Good Faith but I do consider this kind of position deplorable and highly detrimental to improving this article. Take this article on its own merits. If you're just looking me up to attack me, you're not going to improve this article. FrozenPurpleCube 19:44, 26 April 2007 (UTC)

Maybe it is too technical, if nobody up until now has recognized that the image used to depict the reaction incorrectly depicts an enol. One of the double-bonded carbons has to also be bonded to a hydroxyl group. 5, Dec 2011 — Preceding unsigned comment added by 173.85.47.101 (talk) 23:48, 5 December 2011 (UTC)

The first image in the article has a base written over the arrow (should definitely be cleaned up for pixelation and may as well just write "base" there...I agree that the overview image should be as non-technical as possible). That generates the enol as a reactive intermediate from the drawn starting material structures. Using this as the topic-image allows us to avoid needing to draw all the various different enol(ate) forms. If the enol itself were so stable that it were the actual available starting material, it would likely be to stable to react efficiently. DMacks (talk) 00:36, 6 December 2011 (UTC)

(Sorry, misread your concern..) No, I actually have no idea what image and problem you are seeing. The intro clearly and correctly states that the product is an "enone" not an "enol". The enol(ate) is a reactive intermediate that is formed and then reacts, it is not the final product and so it is not drawn in the simplified overview image at the start of the article. The mechanistic details are certainly important, and appear to be covered (correctly) in the next image? DMacks (talk) 00:40, 6 December 2011 (UTC)

Obligations

We're all volunteers here. While I can appreciate good-faith requests, I'll be damned if I have to cater to the whims of every reader.

I feel personally that we, as editors, have no such obligation. I'll write whatever I write. If you like it, fine and well. If you don't, and if I have the time, effort, motivation, I might give a shot. If I don't, you can do it yourself. Or not.

Badgering the editors here, demanding "improvements" just isn't the way. I would simply ignore a tag I didn't agree with. --Rifleman 82 18:51, 26 April 2007 (UTC)

And treating people's good-faithed concerns that there are problems with a page as a demand isn't a good idea either. If you don't care to fix it, well, certainly you're not obliged to fix it. Wikipedia is a volunteer-based system. That doesn't mean it shouldn't be fixed just because you don't care for the cleanup tag. FrozenPurpleCube 19:41, 26 April 2007 (UTC)

Possible corrections to technical complaints

I do not believe the article is too technical for the readers it targets; however, the inclusion of more human-interest information would be helpful for Random-button readers. Human-interest would include the discoverer(s) of this process, as well as specific examples of this reaction in chemical synthesis of recognizable products (ie drugs), or in cellular processes. These are hinted at, but not stated directly. Also, the article does not demonstrate the arrow mechanism of this reaction, nor does it cite or link examples of the arrow mechanism readily available online[1]. The reader targeted by this article would probably find the arrow mechanism helpful. DayBaye 04:57, 6 June 2007 (UTC)

The aldol condensation is most often discussed in the context of an aldol reaction, and that (featured article!) page has historical info and the full arrow-pushing mechanisms. Feel free to import whatever parts of that article would improve the one here. DMacks 05:18, 6 June 2007 (UTC)

I have changed it, but as I am still unfamiliar with wikipedia editing, would like someone to make sure it's okay! DayBaye 21:11, 6 June 2007 (UTC)

Looks reasonable to me. Thanks for improving this page! DMacks 21:23, 6 June 2007 (UTC)

Importance

I'm not sure how to go about rating articles, might look into. But I'd suggest that this is a topic of high importance. --Belg4mit 22:41, 6 June 2007 (UTC)

Response from RfC

I saw this page at the RfC list. I think this page is not overly technical (I do have a BS in biophysics/biochem). Is there a confusion between aldol condensation and aldol reaction? Maybe that's the point of confusion? Otherwise, the reaction diagrams are plentiful and clear, and the wording seems sufficient. Antelan ^talk 08:47, 17 June 2007 (UTC)

Please consider that there have been many changes to the article since the RfC. --Itub 09:15, 17 June 2007 (UTC)

Then the RfC accomplished its goal, I suppose? Congrats to all who have been working on the article, then. It looks good. Antelan ^talk 10:52, 17 June 2007 (UTC)

Thermodynamic Control, Kinetic Control and References

I would like the article to explain more about the thermodynamic and kinetic control neccessary for the aldol reaction since they are extremely important for what product you would obtain. I would also highly recommend people to read Advanced Organic Chemistry by Carey and Sundberg for more information regarding this topic. The Aldol Condensation reaction article in general is too brief and does not contain enough essential detail and references Zyvov 01:54, 28 October 2016 (UTC) Zyvov 01:35, 28 October 2016 (UTC) — Preceding unsigned comment added by Zyvov (talk • contribs)

Furthemore, a reference for the current definition for "aldol condensation" is desperately needed. Zyvov 01:54, 28 October 2016 (UTC)

Merge into Aldol reaction

I propose that this article be merged into the aldol reaction. The two articles are highly redundant. The topic is important. --Smokefoot (talk) 23:39, 29 December 2021 (UTC)

• Oppose simple merge. They are certainly related, but there appears to be tons to say about each independently. The stereochemistry of the first step is nearly a whole topic in its own right. Control of the subsequent stage, and its mechanism, is a different topic than the first stage, even if the second stage is "only" a follow-up to the second. The first stage is also a lead-in to the Claisen condensation, so I think it makes more sense to have one page for the first stage and then separate pages for the diverse followups and their resulting outcomes. It also makes it easier to map to wikidata and as targets of links from other pages. However, I would propose renaming aldol reaction to aldol addition (or aldol addition reaction) to clarify its scope. DMacks (talk) 00:37, 30 December 2021 (UTC)
• Or an alternate major overhaul to have a summary article about aldol reactions that is generally about the addition stage and subsequent possibilities (E1cb to make condensation, tetrahedral collapse to make Claisen--treating it as a pathway divergence, etc.), with each of those having their own more-detailed sub-article. One of my concerns with a simple merger is that Aldol reaction is already huge and full of details, and I don't want an in-depth article (really good info for grad students and beyond) to also spread to further breadth...too over-whelming for what is both an important topic and a topic that should be accessible (!= intimidating) for mid-level college students. One way to do that is to offload the full details of stereochemical outcome and control into a separate sub-article--Stereochemical control in aldol addition reactions really is a notable topic in its own right. DMacks (talk) 16:03, 30 December 2021 (UTC)

Closing merge proposal, given no support for a merge and no consensus for alternative proposal. Klbrain (talk) 11:49, 8 October 2022 (UTC)