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Topic: how can double bonded carbons be a chiral center?  (Read 3768 times)

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Offline iScience

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how can double bonded carbons be a chiral center?
« on: December 30, 2013, 10:23:55 AM »
i have a silly question: so a chiral center has four distinct groups on it. but if that's the case, how can any carbon with a double bond be a chiral center? the maximum number of distinct groups you can have on it is three.

example:



how is the top carbon of the hexene a chiral center?

Offline discodermolide

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Re: how can double bonded carbons be a chiral center?
« Reply #1 on: December 30, 2013, 10:28:09 AM »
The top carbon of the ring is not a chiral centre.
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Offline iScience

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Re: how can double bonded carbons be a chiral center?
« Reply #2 on: December 30, 2013, 10:35:33 AM »
this compound only has one chiral center which is at the bottom of the ring right?

also, it is in fact impossible for a double bonded carbon to be a chiral center right?

Offline discodermolide

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Re: how can double bonded carbons be a chiral center?
« Reply #3 on: December 30, 2013, 10:39:32 AM »
The chiral centre is at the bottom of the ring. The only one in this system. If you hydrogenate the top C=C then the top ring carbon will then be chiral.
Allenes can be chiral and they contain double bonds, but that is a special case.
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Offline iScience

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Re: how can double bonded carbons be a chiral center?
« Reply #4 on: December 30, 2013, 11:34:01 AM »
even if the top is hydrogenated, i thought a chiral center required four different groups. a double bond means that two of the groups are the same doesn't it? so how can i get four distinct groups?

Offline discodermolide

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Re: how can double bonded carbons be a chiral center?
« Reply #5 on: December 30, 2013, 12:02:19 PM »
Draw the molecule without the top double bond and you should see that that C has 4 different substituents.

O=C1C[C@@H](C(C)=C)CCC1([H])C

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