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Topic: Enantiomers, yes or no  (Read 6153 times)

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Offline Rutherford

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Enantiomers, yes or no
« on: August 16, 2012, 07:27:20 AM »
Is there a method to determine if these compounds are enantiomers or not? I had a hard time rotating those molecules in my head.

Offline sjb

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Re: Enantiomers, yes or no
« Reply #1 on: August 16, 2012, 07:45:08 AM »
Is there a method to determine if these compounds are enantiomers or not? I had a hard time rotating those molecules in my head.

Make models? Try naming them?

Offline Rutherford

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Re: Enantiomers, yes or no
« Reply #2 on: August 16, 2012, 08:16:33 AM »
I tried but I don't know how to rotate the molecules that have the H atom on the top. They should be on the back because of the lowest priority.

Offline fledarmus

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Re: Enantiomers, yes or no
« Reply #3 on: August 16, 2012, 08:18:07 AM »
Naming them requires that you mentally rotate them so that the hydrogen is in the back.

Make models. Make models. Make more models.

Offline Rutherford

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Re: Enantiomers, yes or no
« Reply #4 on: August 16, 2012, 10:43:56 AM »
I improvised somehow, and only practice is needed now. Solved, A)same compound (R,R); B)enantiomers.

Offline discodermolide

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Re: Enantiomers, yes or no
« Reply #5 on: August 16, 2012, 10:47:08 AM »
I improvised somehow, and only practice is needed now. Solved, A)same compound (R,R); B)enantiomers.

Have you got a models set? You can get them cheap.
Or use cocktail sticks and olives, cherries etc. Then you can break the bonds by eating the atoms!
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline fledarmus

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Re: Enantiomers, yes or no
« Reply #6 on: August 16, 2012, 11:05:14 AM »
Or gumdrops and toothpicks, or my personal favorite, those mini colored marshmallows  :D

Do they still have those? Either gumdrops or mini colored marshmallows, I mean...  ???

Offline Rutherford

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Re: Enantiomers, yes or no
« Reply #7 on: August 16, 2012, 11:30:40 AM »
I improvised somehow, and only practice is needed now. Solved, A)same compound (R,R); B)enantiomers.

Have you got a models set? You can get them cheap.
Or use cocktail sticks and olives, cherries etc. Then you can break the bonds by eating the atoms!

Sticks and plasticine  :D.

Offline discodermolide

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Re: Enantiomers, yes or no
« Reply #8 on: August 16, 2012, 11:35:58 AM »
I improvised somehow, and only practice is needed now. Solved, A)same compound (R,R); B)enantiomers.

Have you got a models set? You can get them cheap.
Or use cocktail sticks and olives, cherries etc. Then you can break the bonds by eating the atoms!

Sticks and plasticine  :D.

Prefer cocktail sticks etc.
At least you can eat your mistakes and nobody will ever know.

Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Rutherford

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Re: Enantiomers, yes or no
« Reply #9 on: August 16, 2012, 01:32:10 PM »
Now a tougher problem: http://orgchem.chem.uconn.edu/courses/243f97-rs-pract-04.html
Why is in (i) the C atom that has an OH group attached R? The H atom is towards me, the OH group is away, if I exchange those two shouldn't I get the S configuration?

Offline discodermolide

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Re: Enantiomers, yes or no
« Reply #10 on: August 16, 2012, 01:37:36 PM »
Now a tougher problem: http://orgchem.chem.uconn.edu/courses/243f97-rs-pract-04.html
Why is in (i) the C atom that has an OH group attached R? The H atom is towards me, the OH group is away, if I exchange those two shouldn't I get the S configuration?

Yes you get the (S) configuration.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Rutherford

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Re: Enantiomers, yes or no
« Reply #11 on: August 16, 2012, 02:17:07 PM »
Okay, then it is a mistake. Thanks.

Offline Babcock_Hall

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Re: Enantiomers, yes or no
« Reply #12 on: August 16, 2012, 07:17:00 PM »
One way to "rotate" a molecule on paper is to hold one bond constant (making it the axis of rotation), and spinning the other three groups as if they were a propeller.  This way you can always put the H in the back.  I like models very much, but I have sometimes found this trick to be handy.

Offline james_a

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Re: Enantiomers, yes or no
« Reply #13 on: August 17, 2012, 01:53:14 PM »
The fastest way is this:

After double checking to see that they have the same connectivity, determine (R) and (S) for each stereocenter. Enantiomers will always have opposite (R)/(S) values.

This is far, far simpler and faster than making models or doing bond rotations.

Offline Babcock_Hall

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Re: Enantiomers, yes or no
« Reply #14 on: August 17, 2012, 05:41:44 PM »
The purpose of building models or of rotating them on paper is to facilitate the R,S assigment process.

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