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Topic: Chirality of tans-but-2-ene  (Read 8795 times)

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Offline deutdeut

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Chirality of tans-but-2-ene
« on: January 17, 2007, 08:56:20 AM »
The compound does not have any chiral carbons, but since the image and the molecule itself cannot superimpose each other, they are enantiomers. But my book said that they are not, why?

Offline AWK

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Re: Chirality of tans-but-2-ene
« Reply #1 on: January 17, 2007, 09:03:49 AM »
Set mirror parallel to carbon skeleton
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Offline deutdeut

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Re: Chirality of tans-but-2-ene
« Reply #2 on: January 17, 2007, 09:19:59 AM »
Which carbon skeleton?

Offline Dan

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Re: Chirality of tans-but-2-ene
« Reply #3 on: January 17, 2007, 09:20:47 AM »
the mirror image is superimposable on the original structure.
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Offline deutdeut

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Re: Chirality of tans-but-2-ene
« Reply #4 on: January 17, 2007, 09:25:26 AM »
why?and how I cannot know that from the structure I drew?

Offline Dan

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Re: Chirality of tans-but-2-ene
« Reply #5 on: January 17, 2007, 09:26:08 AM »
see above, the mirror image is related to the original by a simple rotation
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Offline deutdeut

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Re: Chirality of tans-but-2-ene
« Reply #6 on: January 17, 2007, 09:36:10 AM »
I still can't understand the problem, can you explain a little bit more?
« Last Edit: January 17, 2007, 09:42:16 AM by deutdeut »

Offline Dan

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Re: Chirality of tans-but-2-ene
« Reply #7 on: January 17, 2007, 09:49:56 AM »
I'm afraid that the diagram is the best I can do without a model kit. I suggest you get a model kit, build the two structures and superimpose them.
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Offline AWK

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Re: Chirality of tans-but-2-ene
« Reply #8 on: January 17, 2007, 10:02:14 AM »
Which carbon skeleton?
Carbon skeleton of trans-butene is flat
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Offline deutdeut

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Re: Chirality of tans-but-2-ene
« Reply #9 on: January 17, 2007, 10:12:15 AM »
But the molecule itself is not a symmetric molecule, how can the image and molecule superimpose?

Offline AWK

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Re: Chirality of tans-but-2-ene
« Reply #10 on: January 17, 2007, 11:33:37 AM »
Trans-butene is a symmetric molecule. It shows a center of symmetry in the middle of a double bond.
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Offline english

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Re: Chirality of tans-but-2-ene
« Reply #11 on: January 21, 2007, 06:33:35 AM »
deutdeut, in general the best way to tell whether you can have chirality is if your carbon is bonded to 4 unique groups.

This isn't always the case, but it works the majority of the time.



One case in which this doesn't necessarily work is in the case of allenes.

For example, the allene penta-2,3-diene exhibits chirality even though it has no asymmetric centers:
« Last Edit: January 21, 2007, 06:45:17 AM by k.V. »

Offline AWK

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Re: Chirality of tans-but-2-ene
« Reply #12 on: January 22, 2007, 06:55:23 AM »
But allene is not flat!
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Offline english

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Re: Chirality of tans-but-2-ene
« Reply #13 on: January 22, 2007, 06:57:45 AM »
But allene is not flat!

Yeah I know.  Some dumb image from a chemical supply site.  I don't know how to get my own images from ChemSketch on here.

 ::)

Offline AWK

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Re: Chirality of tans-but-2-ene
« Reply #14 on: January 22, 2007, 11:14:06 AM »
[
Yeah I know.  Some dumb image from a chemical supply site.  I don't know how to get my own images from ChemSketch on here.

 ::)
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