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Topic: help with Cahn Ingold Prelog naming  (Read 1964 times)

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Offline puzzled

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help with Cahn Ingold Prelog naming
« on: January 22, 2015, 01:37:49 PM »
I'm not a chemist, so I hope you don't mind that I've joined this forum just to get some help with a chemistry puzzle.  I'm a puzzle hobbyist, which often takes me to some strange, unanticipated places.  I've encountered a geocaching puzzle (which will solve the GPS coordinates for a small container holding a log book) that requires determining the Cahn Ingold Prelog naming for the molecules in the image below:



I've tried a bit myself, but my organic chemistry class in college was over 20 years ago, and I'm not quite sure I remember how do to this. 

Once I get the naming, I can figure out the second half of the puzzle (converting the name into GPS coordinates).  There is no prize money or glory for solving this, and asking for help doesn't break any rules.  Thanks in advance for any assistance you might be able to give. 

Offline Babcock_Hall

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Re: help with Cahn Ingold Prelog naming
« Reply #1 on: January 22, 2015, 01:47:03 PM »
According to Forum rules, you must show an attempt before we can help you.

Offline puzzled

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Re: help with Cahn Ingold Prelog naming
« Reply #2 on: January 23, 2015, 01:48:05 AM »
OK, this is embarrassing, but here goes, from left to right and top to bottom:

L 4-amino-5-bromo-3-methyl-2-hydroxy hexane
L 4-amino-2-chloro-5-methoxy-3-methyl hexane
R 2-amino-3-bromo-4-hydroxy-5-cyano hexane
L 2-amino-5-bromo-4-hydroxy-3-thiol hexane
R 5-bromo-2-fluoro-3-methyl-4-phospho hexane
R 5-bromo-3,4-methyl-2-hydroxy hexane
R 2,4-amino-5-methoxy-3-methyl hexane
L 2,5-bromo-5-cyano-3-methyl hexane
L 4-amino-4-bromo-2-hydroxy-3-methyl hexane

It should be fairly obvious from above that I have no idea what I'm doing here.

Offline discodermolide

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Re: help with Cahn Ingold Prelog naming
« Reply #3 on: January 23, 2015, 03:32:38 AM »
As a start the first compound is (2S,3S,4R,5R)-4-amino-5-bromo-3-methylhexan-2-ol.

Then read this page http://en.wikipedia.org/wiki/Cahn–Ingold–Prelog_priority_rules
and this one http://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemistry

Then have another think about the other molecules in your list.
Note the L descriptor has nothing to do with the Cahn-Ingold-Prelog system.
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