Talk:Condensation reaction

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Merge suggestion

I agree. I see no logical reason to have a second article named Condensation (organic chemistry). Probably the person who started it was not aware that this article already exists. Dirac66 (talk) 02:25, 29 March 2008 (UTC)

I agree user Dirac is perfectly right, though a redirection page ought to remain. I maintain that in the Condensation article we ought to have some reference to chemical condensation. From The Chemical Age etc a new definition was found, which I shall fully reference asap. LouisBB (talk) 13:19, 29 March 2008 (UTC)

On further reading it has become clear that The Chemical Age etc reference is not up to date, but has its definition become invalide?

• In polymerisation there is often no loss of a small molecular weight substance,
• Endo-condensation and exo-condensation are not acknowledged by the new definition, whilst there are examples for both in The chemical age ... book. For endo-condensation the conversion of suberone to tropane, and for exo-condensation the conversion of anthraquinone to benzanthrone.

Further, the question remains, what new title ought we choose? I do not know of inorganic chemistry examples, so I would prefer the Condensation(organic chemistry) title. Perhaps a lectoral decision is needed on these issues. LouisBB (talk) 22:04, 29 March 2008 (UTC)

My comments on the above: 1.The main point I think is to have this information on one page instead of two. A redirect page for the second title is a good idea.

2.For the title I see two reasons to prefer Condensation Reaction: a) The word Reaction makes clear that we are not talking about the condensation of a vapour to a liquid, as in distillation (a very common procedure in laboratory organic chemistry). b) There are inorganic examples as well as organic, for example the formation of silicates and polyphosphates as stated in the article.

3.If you want opinions on the definition in The Chemical Age, it would be best to quote it here. I for one do not know this source book.

4.There are two types of polymerization reactions - see the article on polymerization. Condensation or step-growth polymerizations usually involves loss of a small molecule, with some exceptions such as polyurethane. Addition or chain-growth polymerizations usually do not, but they are not the subject of the article. In any case this is not relevant to the question of whether to merge.

5.The endo/exo question is a specialized topic which might be included at the end of the article, but again this is not relevant to the question of whether to merge. Dirac66 (talk) 23:49, 29 March 2008 (UTC)

No strong feelings which way, I agree merging, and I don't think anybody is arguing against it so far. Now with a note in the Condensation article the existence of this subject is obvious and it can be found easily. If there is a redirect from the other title even better. LouisBB (talk) 23:53, 2 April 2008 (UTC)

OK, I have carried out the merge. I transferred all the text from Condensation (organic chemistry) to Condensation reaction, and placed a redirect at Condensation (organic chemistry). I then divided the new text in two, with the definitions in the introduction and the examples at the end. Both sections require editing to eliminate duplication etc.

Also I have now read the Chemical Age definition. I hadn't realized this reference was quite so old - much has changed in chemistry since 1924. The terms exo- and endo- have other meanings now, especially in stereochemistry. I'll check a more recent organic chem text to see if this distinction is maintained under another name. Also, the statement that condensation is "almost exclusively used for those reactions in which union is effected between carbon atoms" is certainly not true today (if it was in 1924), as many examples involves formation of esters, and amides or peptides.

More editing to come soon. Dirac66 (talk) 20:35, 3 April 2008 (UTC)

Suggested plan for merged introduction

First, the "endo" and "exo" mentioned by LouisBB are now called "intramolecular" and "intermolecular" respectively, and are unrelated to what is now called endo-exo isomerism. Since the use of "endo" and "exo" in this sense is quite archaic (the reference cited dates from 1924), I propose to distinguish the two types of condensation using the modern terms. I also propose to eliminate mention of the 1924 reference - I did ask above to see it but I didn't know it was that old.

With this in mind, I suggest we use the 1994 IUPAC definition to which we can add the distinction between the intermolecular and intramolecular condensations, using the modern terminology. We can also note that intramolecular forms a ring, and add a second example, perhaps formation of a lactone.

Finally note that I have integrated the Applications section (from this article) and the list of examples (from the merged content). Dirac66 (talk) 02:04, 4 April 2008 (UTC)

Thank you Dirac66. I agree with all you have done and the view that some more editing is needed. (eg Ref1=Ref3, and the first para is repeated) I agree with the idea of getting rid of the ancient reference, BUT proof is needed that the statement, "condensation always includes the release of a low molecular weight substance" is valid (I always knew it that way, and the reference I quoted was a surprise to me as well) unless an internal condensation can occur without that? The deletion idea is supported by the fact that with the old meaning there is no sense in the two different types of polymerisation. LouisBB (talk) 06:53, 4 April 2008 (UTC)

OK, I have now revised the intro as above. I looked at your examples and decided to use the Dieckmann condensation as an intramolecular example. The article on Dieckmann condensation has a good figure which I copied into this article; the only problem is that the title does not appear for some reason.

As for the phrase "with or without elimination", I have never seen this in more modern texts. It appears the 1924 reference may have been including addition or complexation reactions. I think it is best not to refer to such old sources except for historical articles. Dirac66 (talk) 17:46, 8 April 2008 (UTC)

Nice merge work, and opening illustrations, @Dirac66:, please note, my criticisms are not leveled at the early work, but that so little has been done to build on your foundation. Cheers. Le Prof 73.210.155.96 (talk) 18:44, 29 March 2017 (UTC)

Name?

Why is it called a condensation reaction? —Preceding unsigned comment added by 208.102.33.163 (talk) 00:31, 5 January 2009 (UTC)

The word "condensation" implies that something is lost in the process. In this type of reaction a small molecule such as water, HCl, etc. is lost. The product of interest therefore weighs less than the reactants. The small molecule makes up the difference of course, but is usually considered uninteresting. Dirac66 (talk) 01:32, 5 January 2009 (UTC)

The explanation by Dirac66 is incorrect. It is called a "condensation" because the first identified condensation reactions, which were dehydration reactions, produced water vapor, which formed condensation when it came in contact with cool glass. A test for condensation reactions was to place a watch glass on top of a flask and see if condensation formed on it. [unsigned entry]

See closing paragraph, by this author, this date. While the unsigned entry is largely historically correct and relevant, as an unsourced statement, it is of no help to the article. Moreover, in truth, the early observations of condensation may have also had a more general understanding of the term, because water, while the most common condensation reaction byproduct to mist up a watch glass, was unlikely the only one. Le Prof. 73.210.155.96 (talk) 18:41, 29 March 2017 (UTC)

biochemical replacement reactions: condensations?

The enzyme cystathionine gamma-synthase works by "β-replacement" (a proton abstraction leads to the elimination of the substituent at the β-carbon, leading to a nucleophilic attack on the latter by the second substrate and thus forming the new molecule). From Wikipedia I gather that β-replacement is a biochemical term (esp. in terms of PLP cofactor) and different from what chemists call replacement, hence the quotes. The wiki for the aforementioned enzyme also calls it a condensation: is it despite non being a substitution? --Squidonius (talk) 23:47, 25 June 2013 (UTC)

Assessment comment

The comment(s) below were originally left at Talk:Condensation 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.

Rated "high" as high school/SAT biology content (dehydration synthesis redirects here) - tameeria 19:43, 22 February 2007 (UTC)

Last edited at 19:43, 22 February 2007 (UTC). Substituted at 12:09, 29 April 2016 (UTC)

Vote of little or no confidence

This article is not trustworthy. Trust at WP comes from sources. The list of synthetic reactions is unsourced—how do we know it is representative of what an expert would present, that it does not contain poor or incorrect examples, or omit important ones? The fact that none of the polymerisation reactions referred to elsewhere in the article are listed in the Applications—when one does a solid-supported peptide or oligonucleotide laboratory synthesis, are they no longer condensations?—suggests, (a) that people presented what they could wikilink to, and (b) that this compilation is an off-top-of-head (literally, stream of thought) WP editors' list.

Then regarding definitions—what is the usage/connotation of this term, that is the best starting point to write an article that might be used in teaching young readers? The fact that IUPAC says a thing, emphasising what it does, in some cases does not mean that the emphasis extends at all to practicing chemists [fill in your favourite head-in-the-clouds IUPAC example here], or that in this specific case, that the precisely accurate definition constitutes the best way to introduce and develop the subject (which is what we do here, very often, and how we help or fail to help chemistry instructors do the same). This would be resolved/captured by secondary source review. In my view, a high school training curriculum may limit examples to condensations releasing water (the historic basis set for the reactions, if you will), and if this is so, we may be mis-emphasising the broad, professional definition as the starting point for the article, over the connotation most often in play when young students are first reading. At the same time, the pedagogical connection between the chemical term condensation and the common meaning of the word is completely lost, given the current way the subject is developed. The adage of starting specific and familiar before generalising applies.

Otherwise, in 2017, after more than a decade of time on chemistry articles, here, there is no excuse to continue to allow this sort of article composition of organic chemistry articles. Every advanced ochem book covers this subject, as do all the good undergraduate texts (e.g., Claden). No further content should be allowed in this article, unless accompanied by a valid and complete (verifiable) citation. And say no to inserting any old happenstance class web page—yes only to good secondary or text sources. Enough of this WP:OR and just trust us writing.

Until then, a reader with no experience in real chemistry should have no confidence that any sentence of this is what they should be reading on the subject. Get ANY good university gen chem, ochem, or biochem textbook, or any good online source, and start there instead. It is scary that anyone, anywhere, rated this article as high in value (see last Talk entry). 73.210.155.96 (talk) 18:33, 29 March 2017 (UTC)

Proposed Edit

I think this page could benefit from some serious reorganization. I want to rewrite the intro paragraph, scrapping most of it, and provide a more comprehensive and coherent understanding of condensation reactions. I it would benefit from a more theoretical and generalized overview of this reaction type. For this section I like the current use of the IUPAC gold book, but I also want to use the Solomons and Fryhle ochem textbook 11th ed.

I was thinking of using the mechanism for the Claisen Condensation reaction for the mechanism section, as a general picture. The rest of the mechanism section would benefit from talking about how the mechanism might be different in different types of condensation reactions. I found an interesting book that goes over some mechanisms for several different types of condensation reactions ( Organic Reactions: Stereochemistry and Mechanism. Fourth Edition by PS Kalsi, 2006), other citations could include the Solomons&Fryhle ochem textbook.

Then for the application section, I think looking up some papers that are using condensation reactions in their research would be the most clear way to elucidate the utility of this class of reactions. One paper that I looked at that I thought could be interesting to cite is: 1) Efficient Synthesis of Dibenzo[a,c]cyclohepten-5-ones via a Sequential Suzuki−Miyaura Coupling and Aldol Condensation Reaction and finally an example of how prevalent these reactions are in everyday life by citing the retro-aldol reaction that is present in glycolysis. — Preceding unsigned comment added by Mm9656 (talk • contribs) 21:30, 21 November 2017 (UTC)

Disulfide formation is usually not a condensation process

I could be wrong, but this much is true: disulfide formation is not a condensation process. It is considered to be a redox process. If one wants t get into the intimate details, views can differ. --Smokefoot (talk) 15:42, 28 December 2017 (UTC)

Condensation Reaction is a broad term

The following discussion 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.

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Dear ::Smokefoot, I understand you have been trolling the chemistry edits by many of my classmates on wikipedia, I was unaware that you were the gatekeeper to the chemistry pages maybe that should be in the wikipedia training that I and all my classmates went through. To address your comment I would like to remind you of the dynamic nature of the condensation reaction. It is a term that at its simplest means any organic reaction in which a molecule of water is lost; however this can be expanded or limited depending on ones background and understanding. Also I think it is important to note that a redox reaction and a condensation reaction (in addition to many other reactions) are not mutually exclusive. I have done my best in trying to address the dynamic nature of this term in my edit through numerous examples of how condensation reactions can take place. The disulfide formation that I have cited from the biochemistry textbook is indeed a condensation reaction and I can send you screen shots of the book if that would be helpful for your understanding. If you would like to link my disulfide formation scheme to another page which describes in detail the various ways in which disulfide formation can take place I think that would be beneficial for all! I do not disagree that feedback is helpful and warranted on wikipedia, it is what helps to make it a more edifying and accurate experience for all. I do disagree with the act of pathological trolling in which you have engaged. Your tone and lack of empathy for the person on the other side of the computer results in what comes off as a hostile comment. I think your comment could have been improved by not using such definitive words such as "it is" "wrong" and "true". These serve to make the editor feel as though they have done a disservice in contributing. I also see that you try to limit your culpability in asserting the truth to your statement by saying that, "I could be wrong." This phrase is immediately rendered null and void by the following clause, "but this much is true." So in effect you have shown that you are aware of the humbling power of the phrase "I could be wrong" but have far too much pride to even let the phrase do the linguistic work that you wanted it to perform. Happy New Year! Mm9656 (talk) 11:18, 28 December 2017 (UTC)

My goal is to treat all editors more or less equally. But each semester, we receive a surge of content from students with a modest background in chemistry, who expect to be treated differently because they are doing homework, and who are in a hurry to drop a lot of content quickly. Almost always under the command of an instructor who has limited experience with Wikipedia. Hostility? no, but frustration, yes. Trolling? no, but defending the medium, absolutely! Do I make mistakes in style and content? yes. If you do not agree with a my edit or my comment, then override my edit or defend your viewpoint (as you do above), but don't attack me. I contribute because I want to, not because my teacher told me to.--Smokefoot (talk) 17:37, 28 December 2017 (UTC)

Smokefoot Last time I checked wikipedia is open source, non-profit organization. This means that anyone is welcome to edit it and add content. While having to sift through a large amount of student additions might be frustrating because of incorrect content or content that lacks depth, it is not right to defend the medium with snarkiness and hostility (there are several examples of snarky comments and hostility on the talk and sandbox pages of my classmates). It is your place to offer helpful and insightful critiques, to work with students and not to bash them on the talk pages by saying things like, "...But it appears that the student is not very interactive. Not very good content by this student." Many college chemistry students care deeply about the field of chemistry. Many of them might have also taken on a topic that is particularly interesting or meaningful to them therefore I think it appropriate to comment on these posts with empathy, objectivity, and to stray from saying negative things about the poster. Also, to say that just because we are doing this for a grade does means we don't care is a tragic oversimplification and I do not care to get into a philosophical debate with you about it. PLEASE STOP HARASSING STUDENTS, we are here to help. If we do not contribute in a way that you see fit refrain from saying negative things and offer possible modifications. Thanks Mm9656 (talk) 01:09, 29 December 2017 (UTC)

An editor might contribute here with the intent of helping, but if the edits are not helpful, what is one to do? Pat them on the head or treat them like other adults? Very, very rarely do students ask advice of any regular Wikipedia editor. The moment their class ends, they cease editing. If a student wants to learn, engage the editors here (like you are now), but on a technical level. So forget all the bad blood, and get back to arguing about content. Its fun. Here's an example: Maybe I should consider 2 RSH + O --> RSSR + H2O as a condensation? Maybe you should consider that cross coupling reactions are small change in the realm of organometallic catalysis? Get on with the damn science!--Smokefoot (talk) 04:31, 29 December 2017 (UTC)

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.

Description of Edit (12/28/2017)

So with this edit I created a more concise lead section which outlines what a condensation is and what it can look like. I also added to the mechanistic details section with two different types of mechanisms with supporting references. Finally I created an application section in which I cited some examples from recent literature in how condensation reactions are still being used today. Mm9656 (talk) 16:41, 28 December 2017 (UTC)

• Not acceptable, the existing content has been removed, the article now contains much less information than before. The article now contains zero internal links. The "Modern Synthetic Applications" section is not relevant. Propose immediate restoration of original article. V8rik (talk) 17:06, 28 December 2017 (UTC)
• V8rikHow about instead we workshop what we have here. The previous article had zero references. This contains several references to textbooks and journal articles and trusted sources. There are several mechanisms highlighting how this process works whereas there were zero before. What kind of internal links would you like to see that are not there? Also I feel like the modern application section is necessary for such a broad topic and provides scope. Mm9656 (talk) 17:39, 28 December 2017 (UTC)

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