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Topic: Quick stereochemistry question: plane of symmetry  (Read 1638 times)

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Offline idllotsaroms

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Quick stereochemistry question: plane of symmetry
« on: October 20, 2013, 08:55:35 PM »
Hello, I was wondering if its possible to cut a molecule down its carbon backbone to produce a mirror image of itself to determine if it forms a racemate or not.

So would it be possible to say there is a mirror plane in this molecule:
 
that splits all those carbons and between the double bond? And therefore call the molecule achrial?

--Is it possible to say that the mirror plane is in the plane of the molecule and splits the molecule in half

Mod edit: img tags added. Dan
« Last Edit: October 21, 2013, 03:03:59 AM by Dan »

Offline discodermolide

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Re: Quick stereochemistry question: plane of symmetry
« Reply #1 on: October 20, 2013, 10:18:38 PM »
Think about the critera required for chirality, is that molecule chiral?
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Offline idllotsaroms

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Re: Quick stereochemistry question: plane of symmetry
« Reply #2 on: October 20, 2013, 11:05:33 PM »
No that molecule is not chiral (not 4 different groups). Sorry, I guess a better question would have been, why is the molecule racemic after bromide addition with water?

Offline discodermolide

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Re: Quick stereochemistry question: plane of symmetry
« Reply #3 on: October 21, 2013, 12:59:07 AM »
Because the carbonium ion can be quenched from either side, leading to a racemic product.
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