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Topic: Substituted cyclohexane configurations  (Read 2875 times)

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Offline Rutherford

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Substituted cyclohexane configurations
« on: November 11, 2012, 05:15:27 AM »
The molecule is attached.
1.How can I determine the absolute configurations of the three chiral atoms in this molecule? I don't know which substituent is under or above the plane.
2.Why is the name of this compound 1-bromo-3,4-dimethyl-cyclohexane and not 1,2-dimethyl-4-bromo-cyclohexane?

EDIT: I made a mistake. Now it is attached.
« Last Edit: November 11, 2012, 05:29:06 AM by Raderford »

Offline discodermolide

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Re: Substituted cyclohexane configurations
« Reply #1 on: November 11, 2012, 05:29:17 AM »
Wherever the molecule is it is called 4-bromo-1,2-dimethylcyclohexane according to ChemDraw.

Make a model of this compound and you will see what is up and what is down.
In your drawing it is not clear if the methyl and bromine are axial or equatorial, you drew them as straight bonds. See drawing.

« Last Edit: November 11, 2012, 05:50:05 AM by discodermolide »
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Offline Rutherford

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Re: Substituted cyclohexane configurations
« Reply #2 on: November 11, 2012, 05:38:59 AM »
What do you mean by model?

Offline discodermolide

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Re: Substituted cyclohexane configurations
« Reply #3 on: November 11, 2012, 05:41:43 AM »
Use balls and sticks to make a model of the compound . Then you will see what it looks like.
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Offline Rutherford

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Re: Substituted cyclohexane configurations
« Reply #4 on: November 11, 2012, 06:02:30 AM »
I didn't draw this and I don't have balls and sticks. I will try now, when they are equatorial by imagining.

Offline discodermolide

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Re: Substituted cyclohexane configurations
« Reply #5 on: November 11, 2012, 06:03:52 AM »
OK let's see what configuration you get.
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Offline Rutherford

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Re: Substituted cyclohexane configurations
« Reply #6 on: November 11, 2012, 06:20:39 AM »
Wow, this is tough. Somehow I got all S.When I look from above at cyclohexane, are carbon 1/6 and 3/4 in the same plane?

Offline discodermolide

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Re: Substituted cyclohexane configurations
« Reply #7 on: November 11, 2012, 06:29:16 AM »
That's correct, you got it.
See pic
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Offline Rutherford

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Re: Substituted cyclohexane configurations
« Reply #8 on: November 11, 2012, 06:49:44 AM »
Okay, this is solved then. Thanks.

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