Talk:Electrophilic aromatic substitution

VERY INFORMATIVE

This article is simply awesome!

Proposed merger with Electrophilic substitution

I oppose the complete merger of this page with the other. Electrophilic aromatic substitution (EAS) is simply the commonest example of electrophilic substitution, but it is important enough (one of the top ten organic reactions IMHO) to warrant its own page. However I accept that the current page on electrophilic substitution is almost totally concerned with electrophilic aromatic substitution, and that page is in fact a much better page. I would like to see the content from Electrophilic substitution moved here, then new content written on the topic of electrophilic substitution in general. This should cover the 53 electrophilic substitution reactions which are NOT aromatic substitutions, as listed in Jerry March's Advanced Organic Chemistry (5th ed, Wiley), as well as describing EAS. Examples include things like alpha halogenation of carbonyl compounds, nitrosation of active methylene compounds, etc. Walkerma 04:56, 14 July 2005 (UTC)

I did propose the merger and I agree with Walkerma that a content switch is the better solution and not the just the merge, do any guidelines exist for this type of edit? If ES officially merges to EAS then EAS is the main article and ES a redirect. EA can then start all over with new content starting with the first two lines of EA or something like that V8rik 16:30, 14 July 2005 (UTC).

I suppose I also oppose merging the two completely, since EAS is a quite rich topic. The EAS page would be perfect for diagrams that make clear(er) the reasons why certain groups activate the ring and others deactivate it. I do hope I haven't stepped on any toes by substantially updating the EAS article - now that I look at the diagram again, it isn't the best... Ataru 8 August 2005

• • we agree on the content switch and not the merge, will try to implement this 48 hours from now, so any suggestions wellcome. the new pics are LARGE. try using a thumb, also see Arene substitution patterns for explanation on ortho, meta, para, do not have to repeat everything 10 times. V8rik 23:02, 2 August 2005 (UTC)

• • Well, drat. I looked for ortho/meta/para and didn't see it anywhere. Thanks... I'll let you handle the merge; if you can size the diagrams appropriately, have at it. Ataru 2 August 2005 (How do you get the dang timestamp?)

reshuffle with electrophilic substitution

collected all the material from both pages and merged. tried to keep most of the previous edits in one piece but not always possible. All 5 main reactions have their separate pages so plenty of room there for additions, there is also a page called activating group you might consider. Also try consider downsizing the pics. V8rik 20:14, 4 August 2005 (UTC) (by the way thats 4 tilde signs in a row)

I like the material, but I'm not sure the diagrams will work off to the right where they are, especially if there are more in the future. Nice job though, thanks... Ataru 00:33, 6 August 2005 (UTC)

Diagrams

I still like the diagrams, and I like all the new content, but they don't seem to fit very nicely together... Ataru 23:08, 5 May 2006 (UTC)

What is the meaning of these abominations

This page is great except for one thing! Why should anyone learn these reactions?? What are they used for in industries, what is the main functions of the products of these various reactions? Who invented the reactions, where is the human angle?

I really do hate learning abstract reactions that seem distant to human endevour.

Ipso substitution

I have created a section on ipso substitution. Sadly I cannot do structures at the moment :-(

lewis acid used

the lewis acid used for the generation of electrophile in aromatic halogenation is usually AlX₃

Sidhu 2201 (talk) 13:49, 20 November 2009 (UTC)

addition of animation

Dear Contributors for EAS, Next semester, I would like my students to create animations for various reaction mechanisms and post them onto Wikipedia to take advantage of the additional media that Wikipedia now allows in order to further the public's understanding of chemistry and to explore new avenues for their learning. The videos/animations will be very similar to the animation posted here in this page as an example. Thoughts and suggestions? Thank you. MichChemGSI (talk) 07:20, 31 December 2010 (UTC)

• Hi MichChemGSI, I am all for it, great idea. On the other hand the current animation would be not acceptable. Way too fast and details too small, it is a demo right? Can you perhaps have it displayed on the talk page for this discussion? V8rik (talk) 16:25, 31 December 2010 (UTC)

• • sure! here's the animation:

    

    Animation of a general electrophilic aromatic substitution

    yeah, i'm working on a version that is slower and larger. I'll wait for more input before I post another animation. MichChemGSI (talk) 02:04, 1 January 2011 (UTC)

i'm thinking of also adding labels like reagent, products, electrophile, etc. MichChemGSI (talk) 02:06, 1 January 2011 (UTC)

That sounds like a great idea but there is a general problem with .gifs in that they are either poor quality but small enough for dial up connections or too detailed but too large. Have you thought about making videos as .oggs and adding these instead? This would allow you to make bigger files as people would only have to load them if they wanted to look at them. (If you want help with graphics, the people over at Wikipedia:Graphic Lab may well be able to help). SmartSE (talk) 15:17, 3 January 2011 (UTC)

yes, i have noticed that most of the videos are .ogg. Can you lead me to a program that can convert my files to .ogg? or how to make .ogg files? I have pretty limited programing knowledge and am unfamiliar with this format. Thanks! MichChemGSI (talk) 15:54, 3 January 2011 (UTC)

update: ok so i have been working hard on how to make this not an animated gif and found a few resources referring to .ogv or .ogg. it seems as thought it is not very easy to convert GIFs to .OGV (please see here) because we have to first draw these in chem draw then transfer them to a program like GIMP, they will be saved as GIFs. ideas for how to make the GIFs better quality? or have i not found the right place to convert GIFs. There seems to be a command line option: see here, but as i'm not too familiar with coding, and we'd like this to be as easy as possible for the students. Thanks!MichChemGSI (talk) 20:38, 6 January 2011 (UTC)

This is a great idea. As a teacher myself, I see great value in students contributing to wikipedia (goes both ways). My comment on the animations is that it needs some captioning to explain what is going on.

As one of those guys from the Graphic Lab (and a chemist), I don't think there is a general way of animating reactions smoothly. This contributes to the lack of animated reaction mechanisms on the web in general. If you give up on smooth animations, powerpoint/keynote type of presentations actually do quite well in generating either video or GIF.

One option you have not mentioned is to show the front piece of the mechanism in an image-box, with the caption "click to see mechanism", and link it to the animated GIF.

BTW - you may want to get your students to try MarvinBeans. It's free for academic use (and wikipedia), and your students can contribute from home ;)

Jon C (talk) 20:05, 7 January 2011 (UTC)

Thanks for the suggestion Jon! Here's a new version using PP! This helped a great deal as I was able to also convert it to .ogg! Thoughts? I hope that it is slower!

Animation of a general electrophilic aromatic substitution

— Preceding unsigned comment added by MichChemGSI (talk • contribs) 23:22, 7 January 2011 (UTC)

This is no longer too fast to see, but still too fast for the reader to comprehend, especially if they haven't seen it before. The frame-rates can be higher so it's not nearly as jagged (aim for 30fps if PP supports it).

Animation of a general electrophilic aromatic substitution

I think a caption and color system is necessary - and it's probably useful for your students to have a template to work from, so the mechanisms are standardized across the whole wikipedia-scape. How much time do you have for the students to do this, and how much of your own time can you commit to working out the kinks? Jon C (talk) 04:16, 11 January 2011 (UTC)

• ogg looks great, I would opt for maximized use of color and captions , I support Jon C's suggestion to get everything standardised. Is it possible to do everything open source ? V8rik (talk) 18:28, 11 January 2011 (UTC)

I just realized after uploading that my .ogv is messed up - in the quicktime version it pauses at every point for a mouse-click, and that was lost during the conversion. While it's probably possible to do everything open-sourced (OpenOffice Presentation), MC-GSI may not want to force his/her student to install and use that. I think a template should be developed for PP, keynote, and OO.o for maximum compatibility; the template would use free fonts (e.g., helvetica), supports common animated symbols (e.g., reaction arrows and electron flow), and only standard functions (e.g., no magic move). It would be useful to have a central repository to host the source files so the completed mechanisms can be built upon and modified by others (I can help set that up if you wish). Jon C (talk) 19:11, 11 January 2011 (UTC)

• • I also agree with needing to adding color. I wanted to do a quick upload to figure out how to do the ogg conversion. We definitely have a plan on standardizing the formating for these. And I very much thank you for the great suggestions on how to format. The animation will be one part of the entire page that the students will be working on. They will for the most part commit about 2 hr/wk for 1/2 a semester just to the animation. And yes, I am committed to working out the kinks, I'd rather set aside a model/standard before the students start making the animations so that I don't have to retroactively fix theirs.

I am looking into how to make templates in PP, but can you clarify a few things in your comment?

• what do you mean by supports common animated symbols? (I originally planned on using Chemdraw (students have access to this, and c/p into PP)
• what are magic moves?
• It would be great if you could help me set up a repository! I also think that it would be a great idea to have it be modified by others (however, can the students upload to it after they are done? or request that it not be modified by others until the end of the semester? (I fear that my advisors on this project would like to and are concerned about assessessing the students' own work) MichChemGSI (talk) 15:47, 12 January 2011 (UTC)

12 hours is a pretty good time-frame for making the result detailed and pretty, especially if the groundwork is already laid down. After the templates are done, you'd probably want to get someone to give things a try to make sure it works well.

I still strongly recommend MarvinBeans as part of the workflow. If you don't already know, MarvinBeans is a java application (cross-platform), free for academic use, and contains the equivalent of ChemDraw, Chem3D, property calculators and more. The files it make are not locked into a proprietary .cdx. Most relevant to us (you ;)), all the atoms in the structure it draw are already colored.

Animated symbols: you'd like all the molecules/electron flows/arrows to come in and out the same way; leave to entropy, some will "dissolve" out while others will "explode". The easiest way is probably to prepare a "toolkit" page in your templates that already had the arrows/flows defined, so the students only need to copypasta it into the right position without needing to worry about the setup at all. (Same goes for fonts.)

Magic Move: it's a feature in KeyNote (OSX's presentation software), which smoothly blends two slides that has the same elements together. With vector images (and a skilled illustrator) it makes amazing presentations. I don't know if it's in PP/OO.o.

I'm thinking about somewhere like Launchpad/Bazaar for the repository. Even though we're not writing code, this is still useful because the versioning lets you step through the changes they've made and make sure the authenticity of the work. I strongly recommend that all the pieces be uploaded (i.e., not only the result video files, but also the intermediate PP/.keynote/OO.o and .mol/.cdx) Have you used a version control system before? Jon C (talk) 04:53, 13 January 2011 (UTC)

Thanks for your quick response! I do understand your push for MarvinBeans, but so not to overwhelm the students as they will be learning to code in Wikipedia for this semester, I think that I will stick with ChemDraw so that my advisors do not freak out. If it was me, i'd have them use it. but perhaps we can introduce the program after our first iteration of this project.

ok, so i might have to upload to the repository, will that be a problem with Wikipedia? (as i cannot move the pages of my students from their sandbox to the live page, I had this issue last semester). And I have never used a version control system so I am not familiar with how that works. MichChemGSI (talk) 20:02, 14 January 2011 (UTC)

Heya. I'm not sure if you want to upload the animations on behalf of your students, or if you want them to setup a personal account and upload it themselves (sounds like the latter though?) In any case, the repository and wikipedia would be separate uploads - your students wouldn't (shouldn't) do any uploading to Commons until The Old Ones have checked the make sure it's (at least) factually correct.

A version control system is most useful for text/code, but also a generally good way of making sure that there is a continuous history for the different components. (The history-keeping of wikipedia is in effect a versioning system.) It's useful for any kind of >20 page projects (e.g., I write my thesis and papers with Bazaar), especially when it involves multiple authors. Bazaar is the CVS for Launchpad and it's quite easy to use.

As with MarvinBeans, a CVS may not be something that you want to get your students to be involved in at the moment. (I presume there is probably also resistance from your prof to try all kinds of new things at once.) Do try to get them to produce things in open non-proprietary formats so the assets do not need to be replicated from scratch at another time.

There is a new "organic chemistry" Wikiprojects, and I've referred them to you. You may want to chime in there as well, since you know the scope and intents better than any of the other 6.9b people on earth :) Jon C (talk) 23:53, 14 January 2011 (UTC)

Aromatic Sulfonation

The Aromatic Sulfonation of Benzene will produce the compound Ph-SO₃H, not Ph-SO₂H. See also: Aromatic sulfonation, which is also linked in the article, in the same section where the wrong reaction is shown. — Preceding unsigned comment added by 134.147.5.29 (talk) 17:44, 15 January 2015 (UTC)

Seconded! -- UKoch (talk) 20:15, 4 October 2015 (UTC)

Bronsted base? I thought it was a Lewis base!

Um, is this edit correct? -- UKoch (talk) 21:16, 13 November 2015 (UTC)

On second thought, it doesn't seem wrong. It seems to be both a Bronsted base and a Lewis base. -- UKoch (talk) 17:35, 15 November 2015 (UTC)

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