Spring Cleaning

7:30 AM

@orthocresol Nice job! I've now decided to reopen that question.

4 hours later…

Q: Can someone confirm and/or correct my logic regarding this mechanism?

11:04 AM

Hmm... I wonder if the time is ripe to reopen the homework policy discussion.

anyway...

In the picture, Ethyl 2-oxocyclopentanecarboxylate (I) reacts with ethyl 2-(4-chloromethylphenyl)propionate (II) in the presence of KOH in hot DMF to afford ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionate (III), which is then hydrolyzed and decarboxylated by treatment...

^ think this is too broad, but don't want to unilaterally close

3 hours later…

2:11 PM

@orthocresol Let's give ourselves a little Christmas present...

anyway...

Should we consider changing the name of this chat and the process involved? Maybe clean up the meta post a little?

@orthocresol I don't know. I have many questions about that reaction... I can't actually imagine that this would happen like this...

why wouldn't (I) decarboxylate right away given the reasonably strong KOH?

hmm, I think leaving the name is fine but that meta post sure could use some updating

wouldn't (II) form a much better carbanion at the ester end?

(I) has two carbonyls, hence more acidic; not sure about the KOH decarboxylation. It can happen and I guess the exact conditions determine everything, but aren't stated here.

hmm, although I think usually decarboxylation is done under acidic conditions

hmmm, it seems pretty broad, and the answer only 'answers' the last step

@orthocresol yeas, you're right Mechanism for decarboxylation

well, I would not object to closing it, but I don't see much need to do it either

2:42 PM

fair enough, I'm not particularly fussed about closing it

@orthocresol hmm, maybe a brand new meta post might be better...

and then close the old one as a dupe of new one

@orthocresol If it's going to explicitly, intentionally be an ongoing effort, rather than a localized push, then I think a new meta post is probably warranted.

And a different name would probably be wise, too, to emphasize its differing nature.

"Spring Cleaning" == Time-localized full-court press to do cleanup

"{Some Other Name}" == Low-key, ongoing cleanup effort

Four Seasons Cleaning

that sounds like a vacancy at a Chinese restaurant

LOL

quite.

I like 'spring cleaning' because it has a positive ring to it

and doesn't overtly say that we're getting rid of "bad" things

although maybe i'm thinking too much...

2:57 PM

@orthocresol Ah, ok, so "Chem.SE Crap Tossing" is out?

Dump Emptying, too, I'm afraid. :)

i guess i'm just afraid of deleting somebody's qquestion and then they awake from their 2-year long dormancy and get all upset that we implied their question was bad (although it probably wasn't all that great if we deleted it).

@orthocresol But what are the odds that such a person will specifically remember a particular question?

probably overthinking it though

3:06 PM

I suppose if they only asked one thing, maybe.

But, really, would they know that it was removed by human action, rather than some automated system?

As a SE newbie, I probably would have assumed it just got scrubbed automatically somehow.

Yes, they can view their own deleted qns from their profiles.

IIRC

Ahhh, indeed

Well, they could always petition a mod to undelete it, I guess?

Though that doesn't really ameliorate the potential emotional hit

@orthocresol not really i think... the own deleted post should only show the recent stuff to the ordinary user

I get your point about having a positive spin on everything, it makes sense to focus the effort on that

I mean i recently posted a few questions and we managed to salvage the most of them...

mmhmm, yeah. I'm not sure about the deleted questions, there was some change a while ago but I never followed particularly closely

← 2 messages moved from The Periodic Table

;)

well, i'm going to take my leave for now, my nose is acting up, but i'll have a think about it

at least we definitely agree that we need a mew neta post