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Old 07-12-2012, 12:29 PM   #1
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Default Optically pure product


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I just finished DAT qVAULT orgo test #2 and there is one question that I can't seem to wrap my head around... The question asks, Which of the following reactions will give an optically pure product? And the answer is 2-chloro pentane reacting with NaCN... Can someone explain to me why this is the case?
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Old 07-12-2012, 12:34 PM   #2
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Does optically pure product refer to a product that only has ONE chiral center...?
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Old 07-12-2012, 12:36 PM   #3
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read the question wrong =P.. sorry

was reviewing my notes for chad at the same time and was on the optically inactive section XD

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Old 07-12-2012, 12:50 PM   #4
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No that's wrong.

Optically pure means it only has one enantiomer. Since this reaction undergoes sn2 -CN is a typical substitution nucleophile for sn2 chemistry then it forms the inverse product only. All the product will have one chiral center.

Basically you wont have a racemic mixture at all (when both enantiomers are in solution like sn1 chemistry does)
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Old 07-12-2012, 12:50 PM   #5
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But when you react 2-chloro pentane with NaCN, dont you get 2-methyl-1-pentamine, which has a chiral center at carbon #2?
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Old 07-12-2012, 12:51 PM   #6
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Quote:
Originally Posted by koreano View Post
Does optically pure product refer to a product that only has ONE chiral center...?
And optically INACTIVE is when the product is achiral (or meso, watch out for those!)
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Old 07-12-2012, 12:51 PM   #7
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I thought so... Thanks ah7391
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Old 07-12-2012, 12:55 PM   #8
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Np! Thank chad!
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