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Topic: stereochemistry problem  (Read 2204 times)

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Offline kriggy

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stereochemistry problem
« on: October 11, 2014, 02:24:36 PM »
Hi, i came around this assignment:


The question is, determine the reaction product and its stereochemistry. Well, the product is quite easy, its reation which leads to anti-markovnikov alcohol. But I cand find out the way how to determine the stereochemistry. I suppose both of the centers will have same configuration so its SS or RR. But how should I find out which one? I would think there will be both of them in mixture but im not sure.
Any help or hints appreciated.
Thank you :)

Offline C-hemCards

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Re: stereochemistry problem
« Reply #1 on: October 11, 2014, 02:43:35 PM »
This question is only asking for the relative stereochemistry (syn vs. anti), not the absolute stereochemistry (R or S at each chiral center). This is because neither the starting material or reagents have any chirality to begin with.

Sounds like you understand the reaction well, so you probably already know the answer.

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Offline kriggy

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Re: stereochemistry problem
« Reply #2 on: October 11, 2014, 02:51:32 PM »
so the answer is that its either SS or RR but we cant figure which exactly without any experiment?

Offline mjc123

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Re: stereochemistry problem
« Reply #3 on: October 11, 2014, 06:19:02 PM »
In the absence of chiral reagents, it will be an equal mixture of SS and RR.

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