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Topic: Cyclohexane enantiomers or not  (Read 1792 times)

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Offline Rutherford

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Cyclohexane enantiomers or not
« on: February 20, 2013, 12:50:25 PM »
Are these two compound enantiomers or not? I said yes, the answer is no.
Although there is no chiral atom, these two compounds don't have symmetry and they are like an object and its image in the mirror. What is the real truth?
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Offline Dan

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Re: Cyclohexane enantiomers or not
« Reply #1 on: February 20, 2013, 01:06:16 PM »
Methylcyclohexane is achiral. It's easier to see the internal mirror plane if you draw it flat:

Ignore the fact that the picture says "chiral" - it is a bug (which has been reported).

C[C@H]1CCCCC1

Can you see the plane of symmetry?
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Offline Rutherford

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Re: Cyclohexane enantiomers or not
« Reply #2 on: February 20, 2013, 01:22:37 PM »
Yep, it passes though C atoms 1 and 4 and it is 90° in relation to the plane of cyclohexane. These are the same compound then. Thanks for the help.
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Offline Dan

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Re: Cyclohexane enantiomers or not
« Reply #3 on: February 20, 2013, 01:24:07 PM »
You're welcome
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