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Cahn–Ingold–Prelog priority rules
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=== Examples === The following are examples of application of the nomenclature.<ref name="HartHadad2011">{{cite book|author1=Harold Hart|author2=Christopher M. Hadad|author3=Leslie E. Craine |author4=David J. Hart |title=Organic Chemistry: A Short Course|url=https://books.google.com/books?id=JasIAAAAQBAJ&pg=PA177|date=1 January 2011|publisher=Cengage Learning|isbn=978-1-133-17283-3|pages=177–}}</ref> :{| align="center" class="wikitable skin-invert-image" width=800px |- !colspan="2"|''R''/''S'' assignments for several compounds |- || [[File:R-bromochlorofluoroiodomethane-2D.png|center|600px]] | valign=top| The hypothetical molecule [[bromochlorofluoroiodomethane]] shown in its (''R'')-configuration would be a very simple chiral compound. The priorities are assigned based on [[atomic number]] (''Z''): [[iodine]] (''Z'' = 53) > [[bromine]] (''Z'' = 35) > [[chlorine]] (''Z'' = 17) > [[fluorine]] (''Z'' = 9). Allowing fluorine (lowest priority, number 4) to point away from the viewer the rotation is clockwise hence the ''R'' assignment. |- || [[File:L-serine-skeletal.svg|center|120px]] | valign="top" | In the assignment of [[L-Serine|<small>L</small>-serine]] highest priority (i.e. number 1) is given to the [[nitrogen]] atom (''Z'' = 7) in the [[amino group]] (NH<sub>2</sub>). Both the [[hydroxymethyl]] group (CH<sub>2</sub>OH) and the [[carboxylic acid]] group (COOH) have carbon atoms (''Z'' = 6) but priority is given to the latter because the carbon atom in the COOH group is connected to a second oxygen (''Z'' = 8) whereas in the CH<sub>2</sub>OH group [[carbon]] is connected to a [[hydrogen]] atom (''Z'' = 1). Lowest priority (i.e. number 4) is given to the hydrogen atom and as this atom points away from the viewer, the counterclockwise decrease in priority over the three remaining substituents completes the assignment as ''S''. |- || [[File:(S)-Carvone.svg|center|80px]] | valign=top| The stereocenter in [[Carvone|(''S'')-carvone]] is connected to one hydrogen atom (not shown, priority 4) and three carbon atoms. The isopropenyl group has priority 1 (carbon atoms only), and for the two remaining carbon atoms, priority is decided with the carbon atoms two bonds removed from the stereocenter, one part of the [[ketone|keto]] group (O, O, C, priority number 2) and one part of an alkene (C, C, H, priority number 3). The resulting counterclockwise rotation results in ''S''. |}
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