Orgo Unit 5.3 Discussion

Orgo Unit 5.3 Discussion - diastereomers and subsequently...

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Topic # 3 Why must enantiomers be converted to diastereomers before separation  processes such as crystallization ? With separation processes such as crystallization, chemists often are taking advantage of the different physical properties of chemicals in order to separate them from one another. The problem with separating enantiomers is that they share essentially the same physical properties (e.g., melting point, freezing point, etc.). Consequently, when using separation techniques, it will be extremely difficult to divide these molecules between one another. According to the McMurry textbook, however, while having the same chemical composition, diastereomers share different physical properties from their complementary compounds. Therefore, it is would only be logical to convert enantiomers into
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Unformatted text preview: diastereomers and subsequently take advantage of their different physical properties in order for separation techniques to be used. Of course, based on what we have discussed in the last topic thread, this method may have some limitations. In order for a molecule to have a diastereomer, there needs to be more than one stereocenter. This method is therefore limited to certain compounds. For example, if we wanted to separate a racemic mixture of ibuprofen molecules, we would not be able to rely on this technique alone. Perhaps this is why manufacturers prefer to produce ibuprofen anti-inflammatory medications in racemic form, because it would otherwise be more difficult to produce a medication containing only the S-ibuprofen enantiomer....
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