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Topic: stereochemistry  (Read 4273 times)

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Offline khim

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stereochemistry
« on: September 27, 2007, 07:00:54 AM »
I noticed (Internet chemistry sites, books, etc) that there are different opinions about the use of some terms. In particular I'd like to know what teachers say about the terms:
stereogenic center
chiral center
It is my opinion that the two terms cannot be used by students as having the same meaning.

Tks for reply

Offline movies

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Re: stereochemistry
« Reply #1 on: September 27, 2007, 01:26:40 PM »
You are correct, the two are not the same.  A stereogenic center is wherever you have stereochemistry.  That means, if you were to exchange any two groups about that center you would end up with a differect compount.  A chiral center is a stereogenic center which is also chiral (bonded to four different groups).

An example of a stereogenic center that is not a chiral center would be C-2 or C-3 in Z-2-hexene.

Offline khim

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Re: stereochemistry
« Reply #2 on: September 27, 2007, 06:36:50 PM »
Hi Movies,
thanks for your reply, we agree at all but unfortunately many colleagues of mine use the two terms indifferently. There are also many www sites of well known american Universities that follow this wrong criterion (see with google for example searching for stereochemistry).
Could you or somebody else suggests a strong support for our opinion? I normally cite the Eliel's book but it seems not to be enough!!!!! (sic)

Regards
khim

Offline movies

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Re: stereochemistry
« Reply #3 on: September 28, 2007, 02:26:15 AM »
Ha!  Eliel's book is the one that I would recommend citing as well!

You could always refer them to the IUPAC definitions as well.  Look up "stereogenic unit" and "chiral centre" on this site: http://www.iupac.org/publications/compendium/index.html

I think the confusion most likely arises from the fact that all chiral centers are stereogenic centers, but not all stereogenic centers are chiral centers.

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