User:ChefJeff41/Azo coupling/Benzene039 Peer Review

General info
ChefJeff41
 * Whose work are you reviewing?

Azo coupling - Wikipedia
 * Link to draft you're reviewing
 * User:ChefJeff41/Azo coupling - Wikipedia
 * Link to the current version of the article (if it exists)
 * Link to the current version of the article (if it exists)
 * Link to the current version of the article (if it exists)

Evaluate the drafted changes
(Compose a detailed peer review here, considering each of the key aspects listed above if it is relevant. Consider the guiding questions, and check out the examples of what feedback looks like.)

Lead
Has the Lead been updated to reflect the new content added by your peer? - The lead has only been updated slightly, as there is not a whole lot of new content added to begin with. For example, the line regarding azo compound synthesis with para substitution has been added in the lead, as it was addressed in the later section regarding azo C-coupling reactions. I would suggest that you may want to add something about the acidic workup in your lead, as this is also new content that you have added.

Does the Lead include an introductory sentence that concisely and clearly describes the article's topic? - The lead does mostly include a concise and clear introductory sentence. Since this clarity is already present from the previous article, it is reasonable that you have not made any alterations. One small suggestion I would make to the writing style of this article is that you could remove possible redundancies. For example, I don't think you have to mention that azo coupling is an "organic" reaction when you have already introduced the topic to be pertaining to organic chemistry.

Does the Lead include a brief description of the article's major sections? - For the most part, the lead only focuses on the reaction of azo coupling itself. It does not cover the uses of the reaction such as the entire section on azo dyes. I would suggest adding one or two sentences in the end of the leading paragraph that briefly mentions the application of dyes with regards to aromatic azo compounds.

Does the Lead include information that is not present in the article? - The article contains a vast majority of information that is present in the article, but does not explicitly cover that there is the present of two types of coupling: C and N-type. You could briefly mention in the introduction that these two types of azo coupling reactions exist (there's no need to go into detail", as these are two main subheadings in your article.

Is the Lead concise or is it overly detailed? - The lead is relatively concise, but very detailed in the sense that it scopes in on the azo coupling reaction more than any other subtopics. If you were to add another sentence or two regarding the applications of azo compounds (ie. as dyes) as I've stated above it would be a better balance.

Content
Strongest/Weakest Points: I would say that the strongest point of your article is how concise it is. You've done an excellent job not straying off topic and I believe it covers most of what it needs to. I would say then, that the weakest part of your topic is the fact that there is a lot of content added from older sources and that equity gaps are not addressed. The suggestions are elaborated upon further in the above answers.

Is the content added relevant to the topic? - Yes, the content added is relevant to the topic. From what is visible, it seems like you've just added that azo products can be obtained from an acid workup in the section under diazotization. In addition, it seems like you added another section explaining C-coupling for ortho and para positions. Both edits are relevant to each subtopic, and hence to each topic. I wonder, though, whether adding the section on acid workup was really necessary, since it doesn't add too much to the present information anyways.

Is the content added up-to-date? - No, I would say that the information is not the most up-to-date. The most recent published articles you've added is from 2017, but the oldest piece of information dates back to 1896 (the section from your azo N-coupling reactions subsection that talks about the production of triazenes). The rest of the articles you've added are closer to the 90's and early 2000's. I don't think the information you've added is necessarily wrong though, so I suggest you replace the old articles for some new ones.

Is there content that is missing or content that does not belong? - No, I don't think that there is content that is misplaced. For missing content, I am wondering if you could possibly add a subsection that talks about the history of azo compounds. It would be nice to explore how azo compounds were discovered and how it came into industrial use as dyes.

Does the article deal with one of Wikipedia's equity gaps? Does it address topics related to historically underrepresented populations or topics? - No, the article does not address these equity gaps. I would say that for these types of articles it is difficult to go into depth regarding equity, however one place where you couple implement this is in the subsection titled, "Uses of the reaction." When you talk about how aromatic azo compounds could be used as dyes you could possibly do some research and add some sections regarding how the use of these dyes affected certain populations in the world. Of course, you wouldn't want to go off topic so I would just add one or two lines near the end of the section.

Tone and Balance
Is the content added neutral? - Yes, the content is very neutral. I would say that the nature of the article itself can only be neutral to begin with, as it deals mainly with verified facts, not opinions. You've done a great job maintaining the same neutrality that the original author started.

Are there any claims that appear heavily biased toward a particular position? - No, there does not seem to be any claims that are biased.

Are there viewpoints that are overrepresented/underrepresented? - For the most part, it is not over or under representing any viewpoint. If anything, I would say that one thing you could potentially do to focus more on representation is that you could add one or two sections on the "Uses of the reaction" section regarding how different cultures make use of azo compounds. In particular, I think that there could be some information regarding the use of these dyes in different countries and cultures, as it seems the information currently present probably pertains mostly to the western synthesis and use of azo compounds. I am aware that the use of dyes date back centuries and across multiple civilizations, so I think there is some potential here for representation.

Does the content added attempt to persuade the reader in favor of one position or away from another? - No, the article does not persuade the reader in any way. Like I have mentioned above, you've done a great job maintaining neutrality!

Sources and References
Is all new content backed up by a reliable secondary source of information? - No, not all new content is backed up by a reliable source. For example, the new content regarding how azo products can also be made from acidic workup does not have a source (under subtitle, "Diazotization"). Regarding general content in the article:

"Diazonium salts are important synthetic intermediates that can undergo coupling reactions to form azo dyes and electrophillic substitution reactions to introduce functional groups" -> I see that there are hyperlinks present, however adding a source here would be helpful

"Prontosil, a first sulfa drug, was once produced by azo coupling. The azo compound is a prodrug that is activated in-vivo to produce the sufanilamide, which is active" -> I would probably add a citation here since you are stating historical facts.

Does the content accurately reflect what the cited sources say? (You'll need to refer to the sources to check this? - Yes, the content does reflect what the cited sources say.

Are the sources thorough - i.e. Do they reflect the available literature on the topic? - No, I would say that the sources are too few. There is much literature available on the topic of azo compounds and the applications regarding them, especially since a lot of the sources present are slightly outdated. Another source you can add is:

Androvič, L., Bartáček, J. & Sedlák, M. Recent advances in the synthesis and applications of azo initiators. Res Chem Intermed 42, 5133–5145 (2016). https://doi.org/10.1007/s11164-015-2351-4

You will have to change the above into ACS format.

Are the sources current? - No. Like stated previously, some of the sources date back to the 1900's. For example, the paper written by H.T. Clarke and W.R. Kirner dates back to 1922. I would suggest to at least replace the sources from the 20th century to ones from the 21st century.

Are the sources written by a diverse spectrum of authors? Do they include historically marginalized individuals where possible? - No, I would say most of the authors present are of European decent and are male, from the names listed. This is also probably due to the fact that the papers themselves date back to the early 2000's and 1900's, as historically marginalized groups were not given as much of a platform as they are given presently. I would suggest that in the process of finding more recent articles, you try to implement publications from multiple different areas around the world (i.e. perhaps Asia and South America), as now research in chemistry is far more diverse.

Are there better sources available, such as peer-reviewed articles in place of news coverage or random websites? (You may need to do some diffing to answer this.) - With regards to peer-reviewed articles, all the sources presented are peer-reviewed and are reliable sources to use in the article, so I do not have comments on that. When scoping for even better articles in the future, I would recommend that you to search for articles in reputable journals, such as Springer or ACS.

Check a few links. Do they work? - Yes, all links are working.

Organization
Is the content added well-written (i.e. is it concise, clear, and easy to read?) - The content added regarding acid workup is pretty clear in the subheading titled "Diazotization."

"When the para position (the Carbon directly..." <- I think this section that you added in the "Examples of azo C-coupling reactions" is slightly wordy, especially with the extra information you added in the brackets. I understand that this is likely because you tried to clarify the definition or "ortho" and "para" for a wider audience. If this is the case, I would recommend either taking out "ortho" and "para" and replacing them with the definitions you provided, or to hyperlink the "ortho" and "para" and to exclude the extra information in the brackets. I think you could also include a small image that points out these positions to help your case if you wish.

Does the content added have any grammatical or spelling errors? - I'm slightly confused about what's goin on with the first sentence under "Examples of azo C-coupling reactions," where it says:

"Many procedures have been described, which re." <- "re." what? What exactly is that supposed to mean (is it an unfinished sentence?).

Otherwise, there is the occasional comma missing for clarity of writing. For example, under "Examples of azo C-coupling reactions":

"Similarly beta-naphthol couples with..." <- there should be a comma after "similarly."

Is the content added well-organized (i.e. broken down into sections that reflect the major points of the topic?) - The content is well-organized. I would say you did a great job keeping each point relevant to its own section, and I think that the major points were definitely covered. The general logical flow is also good, except I would probably put the "Uses of the reaction" last so that the information can flow from "Diazotization" (more specific) to the different examples of reactions. In terms of the writing within each section, I would say that there is not much to comment on with flow. There are certain sections though, that would flow better if there were more information to accompany it. For example, the section regarding Pauly reaction tests under "Uses of the reaction" seems slightly out of place because there is only one sentence as its own individual idea.

Images and Media
I could not tell whether the images were added since the edits made were on the actual article so I decided to comment on them just in case (and for your own interest)

Does the article include images that enhance understanding of the topic? - Yes, the article does include images that enhance the topic's understanding. For example, the first image with the reaction mechanism of aniline and diazonium salt is very informative and appropriately sized. I would add that perhaps for the image regarding azo N-coupling, you can increase the sizing as the image is slightly too small to read. Increasing the sizing to take up an entire horizontal row like the other images is a suggestion I can make. Good inclusion of different reaction schemes!

Are images well-captioned? - The captioning for some images could use some work. For the first and second images there is no captioning (not sure if this is intentional). I think it would benefit if you could add a caption for both the images. For example:

"Reaction mechanism for the synthesis of solvent yellow 7."

In addition, the caption added for the last image can be improved. Instead of "Azo N-coupling," you could go for something slightly more descriptive. For example:

"Reaction of diazonium salt with primary and secondary amines."

Do all images adhere to Wikipedia's copyright regulations? - Yes, all images adhere to Wikipedia's copyright regulations.

Are the images laid out in a visually appealing way? - Yes, the images are laid out in a visually appealing way. I especially like how you spaced out the images quite well. Leaving each reaction scheme/mechanism to take up an entire horizontal section is a good choice. I think it is important to be able to see the images well if you are going to include them!

Overall Impressions
Overall Effects of Edits + Biggest Strengths and Weaknesses : Overall, the edits are done in a way that is effective and logical. In particular, you did an excellent job staying on topic with the new additional information, and you kept a good eye out for possible hyperlinks that can be fixed or added. For example, your section added on "ortho" and "para" substitutions in the lead and under "Examples of azo C-coupling reactions" provided better insight into the reaction mechanisms. I would say that overall, because you did not make any noticeably significant changes to the original article, the changes that your edits brought about were not incredibly impactful. Perhaps making some more big changes, such as adding another new section on the history of azo compounds, or adding more information onto an existing section like the Pauly reaction test, would allow the reviewer to see the changes more drastically. In addition, another weakness that I can identify for the edits, are that you can definitely benefit from adding more references to the article itself. This is not only pertaining to the points I have already mentioned, such as adding references in addition to the hyperlinks (for example, in the second sentence under "Diazotization"), but also to the fact that you can add more recent sources from 2015 onwards. Of course, this is just a rough guideline and anything that you can find that is more recent than the articles you have currently are also acceptable.

Does the topic fit the Target Audience? : The topic does in general, fit the target audience (I am thinking first year science undergraduate students). I would say that it is great with clarity for this audience in the most part, however some jargon could be cleared-up. For example, instead of saying "leaving a latent image in undegraded diazonium salt", I think you could leave that entire part out since the sentence makes sense without adding that level of detail and complexity. The sentence would then be:

".. the diazonium ion is degraded by light, which is made to react.."

Since your other more technical jargon such as "electrophilic aromatic substitution" are hyperlinked, I would say that it is more acceptable. However, if possible, I would try to reduce any more technical terms as I have demonstrated above, or replace them for something that a high-school level student could more easily understand.

Overall, I like the work you did and I think you can keep it up by increasing the quantity of your edits!

- Esther