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Topic: Assigning chiral centres - R/S??  (Read 3049 times)

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Offline maverick1996

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Assigning chiral centres - R/S??
« on: May 15, 2016, 12:26:28 PM »
Hey!

Can somebody confirm the chiral centre is R in this molecule?


Thanks

Offline kriggy

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Re: Assigning chiral centres - R/S??
« Reply #1 on: May 15, 2016, 12:38:10 PM »
I think its S. O is priority 1, isopropyl is 2 and ethyl is 3 and the rotation is counterclockwise

Offline maverick1996

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Re: Assigning chiral centres - R/S??
« Reply #2 on: May 15, 2016, 04:50:32 PM »
But the Hydrogen is on a wedged bond so the molecule has to be rotated so its on a hashed as lowest priority has to be pointing back - thus making the clockwise and therefore R

Please correct me if I'm wrong

Thanks

Offline spirochete

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Re: Assigning chiral centres - R/S??
« Reply #3 on: May 15, 2016, 04:58:14 PM »
You are correct, Maverick. You can also bypass the visual rotation you describe and think to yourself "if the #4 priority is going toward from viewer (on a wedge), then the rule are reversed".

The only time when you can't use the same trick would be when the #4 priority is on a line (in the plane of the page, or computer screen, etc). Then you would have to consider a 3-D visualization, or use a more elaborate trick.

Offline kriggy

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Re: Assigning chiral centres - R/S??
« Reply #4 on: May 16, 2016, 01:10:45 AM »
But the Hydrogen is on a wedged bond so the molecule has to be rotated so its on a hashed as lowest priority has to be pointing back - thus making the clockwise and therefore R

Please correct me if I'm wrong

Thanks

Of course, I forgot to rotate  :-[

Offline maverick1996

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Re: Assigning chiral centres - R/S??
« Reply #5 on: May 16, 2016, 07:24:55 AM »
You are correct, Maverick. You can also bypass the visual rotation you describe and think to yourself "if the #4 priority is going toward from viewer (on a wedge), then the rule are reversed".

The only time when you can't use the same trick would be when the #4 priority is on a line (in the plane of the page, or computer screen, etc). Then you would have to consider a 3-D visualization, or use a more elaborate trick.

Yeah I have heard about this trick but our Prof wants us to rotate the molecule otherwise we won't get full marks

But thanks

Offline AWK

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Re: Assigning chiral centres - R/S??
« Reply #6 on: May 16, 2016, 08:03:44 AM »
Such rotation is very easy. You rotate molecule along horizontal axis in the plane of picture by 180 degree. Then C- - -O bond (downward) will be upward and C to hydrogen - downward. That's all.
AWK

Offline Babcock_Hall

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Re: Assigning chiral centres - R/S??
« Reply #7 on: May 16, 2016, 12:34:28 PM »
I find it helpful to rotate around the axis of one bond, usually a bond that is in the plane of the paper.  The rotation can be chosen in such a way that the lowest priority group is in the back.
EDT
In this case the bond between the central carbon atom and R2 is rotating.
« Last Edit: May 16, 2016, 03:22:32 PM by Babcock_Hall »

Offline maverick1996

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Re: Assigning chiral centres - R/S??
« Reply #8 on: May 16, 2016, 12:51:34 PM »
Thanks for all your help


Yeah this is relatively easy - some people got different answers so I just wanted to check


Thanks again

Offline OCSaviour

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Re: Assigning chiral centres - R/S??
« Reply #9 on: May 16, 2016, 01:27:15 PM »
You can use Jsmol software. It helps a lot to understand how rotation changes the spatial arrangement of the atoms/groups.

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