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Topic: Determining # of stereoisomers from IUPAC name and chiral centers  (Read 5051 times)

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Offline NeedHelp3

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I am trying to figure out...
Which compound has the fewest number of stereoisomers and which has the greatest number of stereoisomers?

A. 2-Bromo-3-chloro-4-hexen-1-ol

B. 2-Bromo-4-chloro-4-hexen-1-ol

C. 2-Bromo-5-chloro-4-hexen-1-ol

D. 2-Bromo-6-chloro-4-hexen-1-ol

E. 4-Bromo-5-chloro-4-hexen-1-ol

I am getting the same number of chiral centers for C and D (zero).  I don't think this is right :-\  I'm also struggling with the double bond, does that automatically make the carbon achiral? 

Offline Schrödinger

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Re: Determining # of stereoisomers from IUPAC name and chiral centers
« Reply #1 on: April 15, 2011, 01:35:14 PM »
A carbon atom is chiral only if it is attached to 4 different groups. So, a double bond automatically makes both the carbons achiral.

And number of chiral centers for C and D is 1, not zero.

"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
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Offline sjb

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Re: Determining # of stereoisomers from IUPAC name and chiral centers
« Reply #2 on: April 15, 2011, 04:42:46 PM »
A carbon atom is chiral only if it is attached to 4 different groups. So, a double bond automatically makes both the carbons achiral.

And number of chiral centers for C and D is 1, not zero.



True, but in some definitions (E)- and (Z)-but-2-enes are stereoisomers, as the atoms are arranged differently in space but have the same connectivity. You need to be careful here.

Offline Schrödinger

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Re: Determining # of stereoisomers from IUPAC name and chiral centers
« Reply #3 on: April 16, 2011, 12:50:49 AM »
True, but in some definitions (E)- and (Z)-but-2-enes are stereoisomers, as the atoms are arranged differently in space but have the same connectivity. You need to be careful here.
Yes, indeed.

But I wasn't talking about that. I was answering the OP's question regarding whether a double bond will make the carbon atom achiral or not :
I am getting the same number of chiral centers for C and D (zero).  I don't think this is right :-\  I'm also struggling with the double bond, does that automatically make the carbon achiral? 

I wasn't referring to the molecule's chirality/stereochemistry. As a matter of fact, all the compounds listed by the OP have double bonds that give atleast 2 different stereoisomers (E and Z). Again, I say atleast because I don't want to give away the exact number that arises due to the presence of chiral centers  ;)
"Destiny is not a matter of chance; but a matter of choice. It is not a thing to be waited for; it is a thing to be achieved."
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