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Topic: Nomenclature when the stereogenic centre is on a substituent  (Read 2037 times)

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Offline HarryHagaren

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Nomenclature when the stereogenic centre is on a substituent
« on: November 03, 2018, 07:19:38 AM »
Hello everyone,
I found this molecule among the exercises I was given to in preparation for an organic chemistry test; the exercise asks me to give the right nomenclature, but I had some doubts because, unlike all the exercises and examples we've done so far, the stereogenic centre is not on the main hydrocarbon chain.
Here's the molecule with my two attempts:


In the upper attempt I wrote S without numbering it because that's how sometimes I see books writing molecules with only one possible stereogenic centre. I assumed it's because anyone reading that IUPAC name instantly knows the only possible molecule that can be drawn. So, is it a correct nomenclature?

In the lower attempt I tried numbering the configuration, but is it correct this way?
I assumed I had to put the (1S) inside the brackets of the substituent; a friend of mine told me he wrote it like 1S-(1-chloroethyl)-cyclopentane , but I think that is incorrect because the 1S outside the bracket would indicate that the Carbon 1 of the cyclopentane is stereogenic, which is not.

Are any of my attempts correct?

Offline chenbeier

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Re: Nomenclature when the stereogenic centre is on a substituent
« Reply #1 on: November 03, 2018, 12:39:09 PM »
I would call it 1S-1-Chloro-1-Cyclopentyl-ethane  or 1S-1-Cyclopentyl -1-ethylchloride to get of the problem what you described. But I would agree with your second naming. The 1S in brackets.

I found only without the S

http://www.chemspider.com/Chemical-Structure.30995317.html
« Last Edit: November 03, 2018, 12:56:40 PM by chenbeier »

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