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Topic: Conditions for cyclic compounds to show optical isomerism?  (Read 7597 times)

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Offline nishkarsh3

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Conditions for cyclic compounds to show optical isomerism?
« on: April 08, 2009, 03:06:50 PM »
What are the conditions for cyclic compounds to show optical isomerism?

Offline sjb

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #1 on: April 08, 2009, 03:16:42 PM »
What are the conditions for *any* compound to show optical isomerism?

Offline nishkarsh3

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #2 on: April 09, 2009, 09:33:51 AM »
4-bromo-4-chloro cyclopent-1-ene . It does not show optical isomerism. Why? Okay, it does not have chiral carbon. But a compound is optically active even if it does not have chiral carbon provided its mirror image does not super impose on the original image and I think that in this case the mirror image does not super impose.

Offline Squirmy

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #3 on: April 09, 2009, 11:46:53 AM »
Can you manipulate the mirror image (without breaking any bonds) to make the two images the same (i.e. superimposable)?

A model set might help you...try making the mirror image and see if you can super-impose the two.

Offline nishkarsh3

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #4 on: April 09, 2009, 11:55:10 AM »
I have already said that the images are not super imposable if we do not neglect the substituents.

Offline Squirmy

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #5 on: April 09, 2009, 12:27:57 PM »
I'm not asking you to neglect the substituents, and I believe you that the images are not super-imposable the way you have them drawn.

In reality, the molecules aren't static...they don't just sit there the way you have them drawn. Can you rotate one of them to make the images the same?

Offline sanderol

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #6 on: April 10, 2009, 10:11:52 AM »
you sure its not optically active?

Offline Squirmy

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #7 on: April 10, 2009, 11:42:39 AM »
Whether I'm "sure" should matter very little to you compared to understanding why I'm right or wrong.

Perhaps a simpler way to look at it: If you draw two identical structures of 4-bromo-4-chlorocyclopentene side by side, are they mirror images of each other or not?

Offline sanderol

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Re: Conditions for cyclic compounds to show optical isomerism?
« Reply #8 on: April 10, 2009, 12:24:07 PM »
missread in compound sorry. Squirmy is right.

mirror plane through C4 and C1=C2 bond

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