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A new contributor asked a question, Mechanism of ring formation of an epoxide under acidic aqueous conditions. It has "homework" written all over it. The original title ("did not understand the reaction mechanism,someone please explain") is vague, the question is a pasted image, followed by an all-caps cry for help. Usually, we would close this, but instead, prompted by a friendly nudge, the OP writes their thoughts in the comments. Two hours and 12 comments later, we have a much better idea of the thought process of the OP and of the problem structure.

Then, another new contributor posts an answer, and also addresses some of the issues raised in the comments. Alas, the answer is a pasted photo (not written on the classic paper napkin or back of the envelope, but close). The OP comments on the answer, and the second new contributor responds.

According to the rules of our site, none of this should have happened. The question should have been closed promptly before anyone answers. On the other hand, this is a gem. It shows you the misconceptions, the alternate reaction paths that should have been rejected, and a worked solution.

So what do we do as a community to preserve (rescue?) this question while encouraging folks to improve the utility of posts and encourage learners to think things through themselves?

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    $\begingroup$ +1 for gem preservation. $\endgroup$ – uhoh Apr 27 at 2:34
  • $\begingroup$ +1 for preserving such a good question. $\endgroup$ – Chakravarthy Kalyan Jun 9 at 10:39
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I may be reading your question more simply than intended but I would say:

1. Edit content from comments into question

Comments are meant to improve the question. If a user provides thought in the comments, the question should be updated.

2. Flag comments as "no longer needed"

These comments are now outdated noise and make it hard to figure out what is still of value.

3. Upvote (if it is worthy)

Lets be real a negative scored question is less likely to reopen than a positive scored one.

4. Nominate to Reopen

Editing automatically puts the question in a queue but doesn't automatically vote to reopen.

5.) Also a comment advocating reopening is often useful as it helps a reviewer see the merits of reopening more easily.

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  • $\begingroup$ Great, I did most of that. I only added the first comment of the OP into the question, though, because that was the status when asking the question. I did not know about flagging comments as "no longer needed", that is neat! $\endgroup$ – Karsten Theis Apr 18 at 15:47
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    $\begingroup$ You were not reading the question more simply than intended, and your is very helpful. I do wonder about the message to new contributors if their low quality questions magically get fixed and they get the desired answer. Offsetting this, I would guess the new contributor who answered the question learned something (or gained some self-confidence) by writing out the answer and showing it off to the world. $\endgroup$ – Karsten Theis Apr 18 at 15:58
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    $\begingroup$ @KarstenTheis feel free to flag comments outdated comments when ever you see them. An old Welcome to chem.SE comment from 4 years ago - flag it. $\endgroup$ – A.K. Apr 18 at 16:25
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While I agree with A.K.'s approach, I'd like to add a few things:

To me personally it doesn't matter if homework or not, I find it much more beneficial when there is context and an actual question to answer.

New users (especially) should be guided to edit their question as soon as possible, as this is a key feature of our site. In this very instance, the best path forward would have been to edit in the comment (now deleted) as soon as it appeared, and take it from there with further commenting (or answering). I believe that comment would have sufficed to keep that question in the positive range. (Side-note: I closed the question with the hammer, which I admit was a too drastic measure. I should have taken the time to do exactly what I just wrote.)

At this point it is important to prevent a conversation style thread. It is the goal of the site to have a Q&A that is concise, as this is most beneficial for future use. We are not a forum, you shouldn't have to look through every response to find the actual answer. If you have to read the comments, we basically failed making a useful Q&A. (More side-note: There is the feature to push comments to chat. That is only beneficial, if the question itself stays alive, and if the discussion is long enough to keep the chat-room visible. It is in the interest of all to try to avoid that.)

According to the rules of our site, none of this should have happened. The question should have been closed promptly before anyone answers. On the other hand, this is a gem. It shows you the misconceptions, the alternate reaction paths that should have been rejected, and a worked solution.

It is not really against the rules how this played out, but it is not ideal. The rules that you refer to are there to prevent more cleanup than necessary, they only set our own quality standards. It is a lot harder to clean up posts and make them useful for the future after the involved people are done with it. (Check the spring cleaning chat for more information.)

As a community, we need to see ahead and judge whether there is value in a question in the long term. If there is, we should make the Q&A as concise as possible, clean the comments, and retain the post.

There is nothing wrong with a little tutoring in the comments, we do that all the time, and it helps the OP in most cases, that doesn't necessarily mean the whole thing is worth retaining. If there is too much noise within the whole Q&A, it is unlikely to help anyone in the future. And then we eventually come around to cleaning that up manually ages after.

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    $\begingroup$ All this makes a lot of sense to me, especially adding the first comment by the OP into the question immediately if they don't edit the question themselves. What the back and forth in the comments showed my was that there was one misconception the OP kept coming back to (that the solvent would react with the carbocation earlier in the reaction pathway), but this is also documented in the OP's comment to the answer. I guess at this point I could write a second, Socratic answer, going down the various rabbit holes and then saying why it would be a bad idea. $\endgroup$ – Karsten Theis Apr 23 at 17:48

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