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Topic: Compound Naming Question (Vinyl Halide)  (Read 5162 times)

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Offline shannonlute

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Compound Naming Question (Vinyl Halide)
« on: December 15, 2013, 02:01:33 PM »
Can anyone tell me what the attached rendering of a vinyl halide is named, assuming the X stands for bromine. I did a Heck reaction in class and I got the cis-oriented bromine species from my aryl halide starting material, but I'm not sure what it's named.

Thanks!
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Offline discodermolide

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Re: Compound Naming Question (Vinyl Halide)
« Reply #1 on: December 15, 2013, 02:27:07 PM »
Have you any ideas?
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Offline shannonlute

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Re: Compound Naming Question (Vinyl Halide)
« Reply #2 on: December 15, 2013, 02:29:07 PM »
Well, it was synthesized from 2-bromoiodobenzene and acrylic acid, so maybe something with phenyl in the name or propanoic acid, since that's the common name for acrylic acid?

Other than that, I have no clue.
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Offline shannonlute

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Re: Compound Naming Question (Vinyl Halide)
« Reply #3 on: December 15, 2013, 02:36:02 PM »
Oh, and I think it's in the Z orientation, because the alkene chain and the bromine are on the same side...
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Offline discodermolide

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Re: Compound Naming Question (Vinyl Halide)
« Reply #4 on: December 15, 2013, 02:38:27 PM »
Well it is an acrylic acid, but in the E configuration. So define the bromobenzene bit and define where it sits on the acrylic acid.
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Offline shannonlute

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Re: Compound Naming Question (Vinyl Halide)
« Reply #5 on: December 15, 2013, 02:45:45 PM »
Thank you so much for your time!! Chem Draw said it's in the E configuration, too. Can you explain the difference to me, if it's not too much?

Is it that the R groups are on opposing sides of the alkene? I was thinking of it in terms of the benzene, but it goes by the alkene, right? I think that's where I messed up...
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Offline shannonlute

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Re: Compound Naming Question (Vinyl Halide)
« Reply #6 on: December 15, 2013, 02:49:20 PM »
I know it's really close to 2-(bromophenyl) propionic acid, except that it has an alkene in it. How do I name the alkene?
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Offline discodermolide

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Re: Compound Naming Question (Vinyl Halide)
« Reply #7 on: December 15, 2013, 02:54:21 PM »
E means Entgegen in german, i.e. opposite. Z means zusammen in german, i.e. together, that is E = trans, Z = cis.
We already said it was an acrylic acid, so what is the numbering?
If you have ChemDraw then you have the name, because I have it as well!
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Offline Borek

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Re: Compound Naming Question (Vinyl Halide)
« Reply #8 on: December 15, 2013, 03:26:07 PM »
I learned recently that Z means they are on ze zame zide :)
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Offline discodermolide

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Re: Compound Naming Question (Vinyl Halide)
« Reply #9 on: December 15, 2013, 03:39:06 PM »
Yes, zusammen means together, so the groups are on the same side. Like Man and Wife, zusammen, but unlike C=C not fixed and sometimes Z becomes E!
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Offline shannonlute

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Re: Compound Naming Question (Vinyl Halide)
« Reply #10 on: December 15, 2013, 04:07:19 PM »
Okay, I think I've figured it out...

(E) 2-bromophenyl propenoic acid?
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Offline discodermolide

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Re: Compound Naming Question (Vinyl Halide)
« Reply #11 on: December 15, 2013, 04:10:12 PM »
Where is the 2-bromophenyl located on the propenoic acid, the 2position or the 3 position?
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Offline shannonlute

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Re: Compound Naming Question (Vinyl Halide)
« Reply #12 on: December 15, 2013, 04:33:48 PM »
(E)-3-(2-bromophenyl)propenoic acid
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Offline discodermolide

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Re: Compound Naming Question (Vinyl Halide)
« Reply #13 on: December 15, 2013, 10:03:23 PM »
Yes, that's fine.
I would have used acrylic acid, (E)-3-(2-bromophenyl)-acrylic acid.
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Offline clarkstill

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Re: Compound Naming Question (Vinyl Halide)
« Reply #14 on: December 16, 2013, 11:17:04 AM »
(E)-2-bromocinnamic acid
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