User talk:Culdrum2

I saw your edits on electrophilic aromatic substitution. The new scheme mixes two concepts that probably should be separate. The mechanism involves addition of the electrophile to give the benzenium cation, which is delocalized, that later dissociates H+. The resonance structures are ways to represent the benzenium ion. They are not part of the mechanism. --Smokefoot (talk) 19:20, 18 March 2026 (UTC)

Thanks for the feedback. While resonance structures aren't part of a mechanism, I've been taught and think it is a good thing to show resonance structures for key intermediates. I imagine the page is primarily used by students trying to learn about the topic and including the resonance structures will be useful to them.

How would you change the figure? Culdrum2 (talk) 19:37, 18 March 2026 (UTC)

You might be correct that students use Wikipedia a lot, hence our reminder that most such reactions are not undergrad-org-lab-like acid chloride chem, but alkenes + arene with solid acids and the like. Another group of likely readers are technicians in industry seeking perspectives on the real world. But who knows who is reading?

I recommend taking out the resonance structures. Students will be confused to see resonance structures as part of a mechanism. Distinct ideas. While you are at it, minimize the white space problem. Wiki-chem likes denser images with no words. --Smokefoot (talk) 20:29, 18 March 2026 (UTC)

Do you think it is better now? Culdrum2 (talk) 20:59, 18 March 2026 (UTC)

The electrophilic chem scheme is pretty. But the reality is different probably. The majority of C-C bond forming reactions of arenes involve alkylation with alkenes, not alkyl chlorides. No contest. Zeolites (aluminosilicates) would be the catalysts, not AlCl3. But alkyl chlorides are apparently used sometimes as are ketones (Bisphenol-A) and alcohols. Acylation? Anhydrides are the reagents of choice. These perspectives are not mine, but from Ullmann's Encyclopedia of Industrial Chem and the related Kirk-Othmer series. A number of books on industrial will provide similar info. For some reason, our students are fixated on RCl/RCOCl + ArH, which is well intentioned and tidy.--Smokefoot (talk) 14:09, 19 March 2026 (UTC)

Quite a few C-C bond forming reactions also involve transition metal catalysis as well.

For the examples you mentioned, if you were to collate a few exemplar reactions I would happily collate them into a figure. Culdrum2 (talk) 12:43, 20 March 2026 (UTC)

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Always the bearer of uninteresting news am I. Your scheme for making carboxylic acids is very tidy and the way many teach, but it is very misleading. They are made by oxidations, not of ROH but ArCH3 (terephthalic). Oxidants: HNO3, O2, Cl2. Alkylcarboxylic acids are made by oxidation of RCHO (from hydroformylation, I am guessing). Of course the big one, acetic acid is produced by carbonylation of MeOH (Cativa process). Hydrocarboxylation of C=C is also common. Probably the most common carboxylation is effected in photosynthesis by rubisco. These scheme is correct that fatty acids are made by hydrolysis. Carbonation of organometallics? Ans from Ullmann's Encyclopedia: "reacting carbon dioxide with an aryl Grignard reagent or an aryl lithium compound ... is of limited use.." Probably way too expensive. One need to be skeptical of the chem one gets in school. The real world operates differently.--Smokefoot (talk) 16:23, 24 March 2026 (UTC)

> Cativa process - see previous paragraph

> Hydroformylation then oxidation - see previous paragraph

> Benzillic oxidations - see previous paragraph

Most, if not all, of your criticism here is that these methods aren't appropriate for industrial use and guess what, this why it is in the laboratory methods and not the industrial routes. Culdrum2 (talk) 17:18, 24 March 2026 (UTC)

My point is that the scheme re-emphasizes lab-scale methods, some of which are barely used in the real world.

The knowledge implicit in designing your scheme is truly impressive. Few people appreciate those routes, much less can depict them. I also used to think that way too. Tidy. But then, bingo, it dawned on me ... Commercial routes inform readers about life around them - possible pollution sources, likely feedstocks, suitable training helpful for employment. One can appreciate the huge challenges in biomass-to-chemicals. When people know real routes, then they better understand why petroleum is so central. Oh well, good luck. --Smokefoot (talk) 21:16, 24 March 2026 (UTC)