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Topic: How to assign configuration, R or S of this molecular?  (Read 16798 times)

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Offline Congenial

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How to assign configuration, R or S of this molecular?
« on: March 15, 2007, 10:15:12 AM »
This molecular  has no plane of symmetry and is chiral.  How to define it as R or S?  I can find the answer in any textbook.


Offline alphahydroxy

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Re: How to assign configuration, R or S of this molecular?
« Reply #1 on: March 15, 2007, 11:11:55 AM »
OK, unless I'm having a dense moment, this is a meso compound, exhibiting axial chirality

There is a good page on this here:

http://www.cem.msu.edu/~reusch/VirtualText/symmetry/symmtry.htm



Offline movies

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Re: How to assign configuration, R or S of this molecular?
« Reply #2 on: March 15, 2007, 12:00:23 PM »
Well, it's not meso because meso compounds are achiral.

This is a case of a chiral axis though.

Offline alphahydroxy

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Re: How to assign configuration, R or S of this molecular?
« Reply #3 on: March 16, 2007, 03:43:18 AM »
Well, it's not meso because meso compounds are achiral.

This is a case of a chiral axis though.

oops   :-[    a momentary lapse ;)

Offline nats

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Re: How to assign configuration, R or S of this molecular?
« Reply #4 on: March 28, 2007, 07:47:55 PM »
Can anyone please tell me how to find R\S configuration for 2-D structures?

Offline madscientist

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Re: How to assign configuration, R or S of this molecular?
« Reply #5 on: March 28, 2007, 07:52:12 PM »
if you look at the picture it is actually a Wedge-dash projection which you can visualise as 3D. Wedges are in the foreground (closest to you), while dashes are in the background (furthest from you).

Hope this helps, i am trying to do some R,S stuff at the momment too and its pretty confusing.
The only stupid question is a question not asked.

Offline nats

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Re: How to assign configuration, R or S of this molecular?
« Reply #6 on: March 28, 2007, 08:40:43 PM »
Thanks madscientist :) I understood when wedges and hashes are given....but I m confused when simple structue with all four single bonds are given without specifying which one is in front and which one in back.....for e.g. CH3-CBrH-CBrH-COOH, this is given and I am asked R/S configuration of C(2) and C(3)....plzzz *delete me*

Offline madscientist

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Re: How to assign configuration, R or S of this molecular?
« Reply #7 on: March 28, 2007, 10:07:23 PM »
Try to think about steric factors, i.e. the atoms are going to be as far away from each other as possible.
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Offline Custos

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Re: How to assign configuration, R or S of this molecular?
« Reply #8 on: March 29, 2007, 08:02:46 PM »
Thanks madscientist :) I understood when wedges and hashes are given....but I m confused when simple structue with all four single bonds are given without specifying which one is in front and which one in back.....for e.g. CH3-CBrH-CBrH-COOH, this is given and I am asked R/S configuration of C(2) and C(3)....plzzz *delete me*
There is no way of knowing the R/S configuration of carbons 2 and 3 from a molecular formula as given. They could be either. If the question doesn't specify which bonds are in front or behind (ie. doesn't specify the absolute stereochemistry) how can you possibly determine whether the centre is R or S?

Offline alphahydroxy

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Re: How to assign configuration, R or S of this molecular?
« Reply #9 on: March 30, 2007, 12:01:23 PM »

There is no way of knowing the R/S configuration of carbons 2 and 3 from a molecular formula as given. They could be either. If the question doesn't specify which bonds are in front or behind (ie. doesn't specify the absolute stereochemistry) how can you possibly determine whether the centre is R or S?
Quote

I think maybe the question is essentially "draw the R and S isomers of the following molecule...

try this page for understanding the assignment of stereochemistry:

http://tinyurl.com/yqlzw2


Offline madscientist

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Re: How to assign configuration, R or S of this molecular?
« Reply #10 on: March 31, 2007, 02:30:17 AM »
Correct me if im wrong, but I think the structure shown in the initial post by congenial contains no stereo (chirality) centres and therefore R & S configurations don't apply. Is this correct?
« Last Edit: March 31, 2007, 02:36:03 AM by madscientist »
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Offline Dan

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Re: How to assign configuration, R or S of this molecular?
« Reply #11 on: March 31, 2007, 06:45:28 AM »
Is this correct?

I would have thought so yes.
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Offline Alexander

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Re: How to assign configuration, R or S of this molecular?
« Reply #12 on: March 31, 2007, 09:24:28 AM »
This molecular  has no plane of symmetry and is chiral.  How to define it as R or S?  I can find the answer in any textbook.


and why is it chiral?
to be chiral. carbon atom must be bonded with 4 different groups or atoms. there are no 4 different groups
whenever people agree with me, I always feel I must be wrong

Offline Congenial

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Re: How to assign configuration, R or S of this molecular?
« Reply #13 on: April 01, 2007, 06:55:40 AM »
Quote
and why is it chiral?
to be chiral. carbon atom must be bonded with 4 different groups or atoms. there are no 4 different groups
Quote

It is chiral! To be chiral, it is not necessary that a molecular have a chiral center, it can also have a chiral axis or a chiral plane. This is a case of chiral axis. I have found the solution to this question from the website:

http://chemistry.umeche.maine.edu/CHY556/Config1.html

So A is S, B is R


Offline movies

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Re: How to assign configuration, R or S of this molecular?
« Reply #14 on: April 03, 2007, 01:57:27 PM »
Yes, an asymmetric carbon is not a requirement for chirality.  The structure shown in the first post is R.

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