Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: moe6141 on October 18, 2012, 02:45:41 PM
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i found 21 consititutional isosmers, what about steriosime
and what is the total amount ( constitutional and sterio) of isomers of this compound?
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21 sounds rather a lot to me can you post some of the structures you came up with?
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21 sounds rather a lot to me can you post some of the structures you came up with?
Here's the eight NIST came up with:
Oxirane, (chloromethyl)- (C3H5ClO)
2-Propanone, 1-chloro- (C3H5ClO)
Propanoyl chloride (C3H5ClO)
Oxirane, (chloromethyl)- (C3H5ClO)
Oxirane, (chloromethyl)-, (R)- (C3H5ClO)
2-Chloro-2-propen-1-ol (C3H5ClO)
(S)-(+)-Epichlorohydrin (C3H5ClO)
3-chloro-2-propen-1-ol (C3H5ClO)
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I've got 21. So I apologise for my previous comment about it being too many. It's just amazing how many there are for such a "simple" compound.
@curiouscat:
I think your Oxirane (chloromethyl) is the same as epichlorohydrin
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I've got 21. So I apologise for my previous comment about it being too many. It's just amazing how many there are for such a "simple" compound.
@curiouscat:
I think your Oxirane (chloromethyl) is the same as epichlorohydrin
Right!
I'm trying now; still only at 10. 14 18 >:(
PS. Do any 1-Chloro-1-hydroxy compounds exist? Or are they always unstable. i.e. Can -OH and -Cl ever be attached to the same C atom?
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These compound decompose and you get the Aldehyde/Ketone and HCl.
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I don't think the stability is asked for here. The OP asks for the number of possible isomers. If they are stable or not is a different question.
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And what is the answer now. Of course I can draw these kind of molecules, but do they really exist?
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If they exist is not the question here the OP is asked for the number of isomers only. I get 21, including those "unstable ones".
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If they exist is not the question here the OP is asked for the number of isomers only. I get 21, including those "unstable ones".
Then I'm at 22! ;D
Unless I miscounted. :P
Maybe I'll try drawing them all and posting. :-\
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LOL, I'll have another count of mine, it's 19 now, I spotted two the same. I can post them as well.
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LOL, I'll have another count of mine, it's 19 now, I spotted two the same. I can post them as well.
Darn! How did you draw them up so fast? I'm still on my Molecule #2. :-[
Never mind; I'll only post the ones I had that you didn't. (Unless I mis counted too! :P)
PS. What software did you use to draw?
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I did it earlier, lol
This should have been a question of the month!
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LOL, I'll have another count of mine, it's 19 now, I spotted two the same. I can post them as well.
Aren't these the same? If so you are on 17! ;)
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FaOPHN.png&hash=28f0a973dcbc189c831f881b715039ab7343bc7c)
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If they exist is not the question here the OP is asked for the number of isomers only. I get 21, including those "unstable ones".
Ok, I must have messed something up because I drew up 22 excluding steroisomers!... {I never was good at the 3D stuff :P}
I'll post in a bit and then you guys can tear me apart. ;D
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The red boxed ones are cis and trans isomers of the enol.
Before anyone comments. I know that enols are in equilibrium with the keto form, the latter favoured.
But these are still isomers with that molecular formula.
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No, they are different, but the 3-chlorooxetanes are the same. I also have 2-chlorovinyl methyl ether (E and Z), 1-chlorovinyl methyl ether; and 3-chloropropanal, E and Z but-1-ene hypochlorite and but-2-ene hypochlorite, making 25
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What about these? Valid?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FYaU0T.png&hash=fbc43bdbd03f2019ad78221902555f49ce3998af)
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No, they are different, but the 3-chlorooxetanes are the same. I also have 2-chlorovinyl methyl ether (E and Z), 1-chlorovinyl methyl ether; and 3-chloropropanal, E and Z but-1-ene hypochlorite and but-2-ene hypochlorite, making 25
Damm, forgot the methyl ethers etc. Thanks.
Must have boggled my eyes and brain cell.
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The last two are the methyl ethers I mention, hadn't got as far as the chloromethyl vinyl ether you draw first.
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Damm, forgot the methyl ethers etc. Thanks.
And these?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FlKaIo.png&hash=1942387868307150f2fa94ec9b091c1b0bb681b7)
....and more (or am I violating any valency rules? ).
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2F3p7D4.png&hash=8052552dd3399c1f0b6da509f53ebcae56fe4229)
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erased
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Damm, forgot the methyl ethers etc. Thanks.
And these?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FlKaIo.png&hash=1942387868307150f2fa94ec9b091c1b0bb681b7)
....and more....
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2F3p7D4.png&hash=8052552dd3399c1f0b6da509f53ebcae56fe4229)
Of these, the chloropropanal has been listed. Can someone consolidate all the structures to date :) I think we are wasting a bit of time crossposting etc.
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I'll try and put it all together. Give me some time.
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Of these, the chloropropanal has been listed. Can someone consolidate all the structures to date :) I think we are wasting a bit of time crossposting etc.
Listed but not drawn. ;)
My bad. I'm too dumb to convert names to structures.
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Up to now I have 30, with everyone's suggestions. I'll wait and see if any more come in before I post the structures.
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Everyone above has forgotten the organic hypochlorites.(edit: oops, missed sjb's post) R-O-Cl well known but stinky. I made ethyl hypochlorite once back in the day.
Also R-Cl(+)-O(-) (organic chlorites) could be considered, but I am away from scifinder and can not even confirm the existence of this type of compound.
So that should add a pile more isomers
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I think sjb mentioned them, thanks. I'll have another look for my compilation.
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No, they are different, but the 3-chlorooxetanes are the same. I also have 2-chlorovinyl methyl ether (E and Z), 1-chlorovinyl methyl ether; and 3-chloropropanal, E and Z but-1-ene hypochlorite and but-2-ene hypochlorite, making 25
Sorry, this should be prop-1/2-enes for the hypochlorites. Can these be both O- and Cl- bonded to the carbon chain?
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Up to now I have 30, with everyone's suggestions. I'll wait and see if any more come in before I post the structures.
Post them (please :) ); otherwise it is hard to know which ones haven't been included.
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OK I now have 35, here they are. Probably still not finished! Everyone's suggestions included I hope.
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Great going discodermolide :)
Can we have the other cis and trans 2-chloro-3-methyloxiranes? Propanoyl chloride? And the organic chlorites 408 mentions?
Actually, perhaps we should stop here as I just noticed the OP hasn't come back...
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OK I'll not post anymore until the OP comes back.
I will include anymore suggestions and post them all tomorrow, is that OK?
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Great going discodermolide :)
Can we have the other cis and trans 2-chloro-3-methyloxiranes? Propanoyl chloride? And the organic chlorites 408 mentions?
Actually, perhaps we should stop here as I just noticed the OP hasn't come back...
It's still fun. :) Thanks @discoderm.
I tried marking the steroisomers (14 sets) ; so there seem 21 structural isomers. In case it helps....
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2F417Hi.png&hash=5a9c9485834eb1551fa3b6804aca3c8ff72427a0)
** Red box means structurally it is a redundant entity.
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These? My apologies if they've been mentioned before!!!
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FmYdb6.png&hash=1182e8a67ed79284a3113e208d01eaf05d9a4490)
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I don't think those are redundant, they are enantiomers and thus different. The others are cis/trans isomers.
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cyclopropyl hypochlorite
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cyclopropyl hypochlorite
Thank you.
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OK, there have been no more contributions, not even from the OP. My final tally is 37. They are pictured. Let me know about duplicates etc.
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OK, there have been no more contributions, not even from the OP. My final tally is 37. They are pictured. Let me know about duplicates etc.
Thanks! This is fascinating.
Next challenge might be to decide which ones are actually stable, known compounds...
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That's a different question >:D
I have no SciFinder access so I have no way of carrying out your suggestion in a reasonable fashion.