OCHEM questions

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OCHEM questions

Postby MCAT_Retaker » Sun Apr 22, 2018 10:07 pm

Can you explain how if you react enantimomers with chiral object, they become diastereomers? what if the enantiomer only had one chiral center.
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Re: OCHEM questions

Postby NS_Tutor_Andrew » Tue Apr 24, 2018 11:40 am

Hi MCAT_Retaker,

Here's a great overview of the topic. The idea is basically that through acid-base chemistry (more specifically, by using a chiral organic acid) you can put a charge on your molecule of interest while deprotonating the acid -- so you take two neutral compounds and convert them into a (+)-charged compound (the protonated version of your compound of interest) and a (-)-charged compound (the deprotonated version of the acid. A (+)-charged and a (-) charged compound together form a salt, and the resulting salts are diastereomers because they contain two chiral centers (one from the original molecule of interest and one from the chiral acid). These diastereomers can then be separated. Once you understand it, this is a pretty cool technique! It's not the absolute highest of high-yield things, but it can be tested, and is worth knowing :).

Hope this helps!
Andrew D.
Content Manager, Next Step Test Prep.

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