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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Rutherford on August 16, 2012, 07:27:20 AM

Title: Enantiomers, yes or no
Post by: Rutherford 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.
Title: Re: Enantiomers, yes or no
Post by: sjb 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?
Title: Re: Enantiomers, yes or no
Post by: Rutherford 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.
Title: Re: Enantiomers, yes or no
Post by: fledarmus 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.
Title: Re: Enantiomers, yes or no
Post by: Rutherford 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.
Title: Re: Enantiomers, yes or no
Post by: discodermolide 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!
Title: Re: Enantiomers, yes or no
Post by: fledarmus 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...  ???
Title: Re: Enantiomers, yes or no
Post by: Rutherford 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.
Title: Re: Enantiomers, yes or no
Post by: discodermolide 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.

Title: Re: Enantiomers, yes or no
Post by: Rutherford 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?
Title: Re: Enantiomers, yes or no
Post by: discodermolide 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.
Title: Re: Enantiomers, yes or no
Post by: Rutherford on August 16, 2012, 02:17:07 PM
Okay, then it is a mistake. Thanks.
Title: Re: Enantiomers, yes or no
Post by: Babcock_Hall 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.
Title: Re: Enantiomers, yes or no
Post by: james_a 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.
Title: Re: Enantiomers, yes or no
Post by: Babcock_Hall 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.