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Topic: Stereochemistry and optical activity question  (Read 4718 times)

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Offline HoshiKagakushya

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Stereochemistry and optical activity question
« on: August 17, 2012, 06:55:16 PM »
Did I do this anywhere near correct?





Offline discodermolide

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Re: Stereochemistry and optical activity question
« Reply #1 on: August 17, 2012, 11:41:27 PM »
My neck can't remain at 90° for long enough to work out your drawings. Please repost it and make it bigger because I am half blind as well.
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Offline HoshiKagakushya

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Re: Stereochemistry and optical activity question
« Reply #2 on: August 18, 2012, 12:20:02 AM »
Better Picture of my work


Offline discodermolide

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Re: Stereochemistry and optical activity question
« Reply #3 on: August 18, 2012, 12:29:08 AM »
Question 4. The starting material has a chiral center in it so you get a mixture of diastereoisomers. The answer you gave is incorrect.
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Offline rrr_asd

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Re: Stereochemistry and optical activity question
« Reply #4 on: August 19, 2012, 02:46:06 PM »

Offline discodermolide

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Re: Stereochemistry and optical activity question
« Reply #5 on: August 19, 2012, 02:50:54 PM »
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Offline rrr_asd

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Re: Stereochemistry and optical activity question
« Reply #6 on: August 19, 2012, 02:58:24 PM »
Maybe, I'm wrong, but you claimed the opposite.
Question 4. The starting material has a chiral center in it so you get a mixture of diastereoisomers. The answer you gave is incorrect.

Offline discodermolide

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Re: Stereochemistry and optical activity question
« Reply #7 on: August 19, 2012, 03:02:44 PM »
Maybe, I'm wrong, but you claimed the opposite.
Question 4. The starting material has a chiral center in it so you get a mixture of diastereoisomers. The answer you gave is incorrect.


The OP's question was number 4 in the question sheet asking" what is the relationship between the products".
In the case of the acetylide addition you already have a chiral centre, therefore as the addition creates another one this produces a mixture of diastereoisomers, which is the answer he required.
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Offline rrr_asd

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Re: Stereochemistry and optical activity question
« Reply #8 on: August 19, 2012, 04:56:00 PM »
I'm sorry, I didn't notice the question about relationship between the products.
I thought that you mean that all answer is incorrect.
I agree with you that there will be a mixture of diastereoisomers.

Offline HoshiKagakushya

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Re: Stereochemistry and optical activity question
« Reply #9 on: August 19, 2012, 09:59:21 PM »
Thank you all so much.
Just to reiterate, the products of the ketone reaction are in fact enantiomers, but in the second reaction, the products are the two drawn rrr_asd and are diastereomers as stated by discodermolide.

The question also asks about optical activity. Would tit be accurate to state that the entantiomeric pair is a racemic mixture and no optical activity while the diastereomers do have optical activity?

Thanks you both so much for your wisdom. If you are familiar with kinetics, I have an unanswered question in the physical chem section :-)
« Last Edit: August 19, 2012, 10:11:48 PM by HoshiKagakushya »

Offline discodermolide

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Re: Stereochemistry and optical activity question
« Reply #10 on: August 19, 2012, 11:55:59 PM »
"The question also asks about optical activity. Would tit be accurate to state that the entantiomeric pair is a racemic mixture and no optical activity while the diastereomers do have optical activity"
[/quote]



Yes that would be correct. But the optical activity ov the diastereoisomers only comes from that one optically active position.
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