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Topic: Diastereotopic hydrogens  (Read 1637 times)

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Offline orgo814

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Diastereotopic hydrogens
« on: October 17, 2015, 04:09:14 PM »
I'm doing a problem involving methyl-cyclohexane. Supposedly the hydrogens para to the methyl group are diastereotopic? How can that be true. Even if I replaced one of those hydrogens with a deuterium (how I normally do it), it's not a chiral stereocenter. I would have that these were homotopic.
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Offline mjc123

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Re: Diastereotopic hydrogens
« Reply #1 on: October 17, 2015, 06:55:01 PM »
One is cis to the methyl and the other trans. Substitution gives configurational isomers.
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Offline Kate

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Re: Diastereotopic hydrogens
« Reply #2 on: October 17, 2015, 07:03:42 PM »
^^

Because it's cyclic and rotation is restricted, so the hydrogens are heterotopic.
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