Systematic Nomenclature of Organic Compounds 1. Find the longest continuous carbon chain (parent chain). a. If there is a functional group (double or triple bond, alcohol etc) it must be on or part of the parent chain. b. If there is a ring in the compound either the ring itself or the non-ringed chain will be the parent chain but never both combined. c. If there are two or more chains of equal length, pick the one with the greatest number of substituents. 2. Number the carbons in the parent chain. a. If there is a functional group, assign it the lowest possible position. If the functional group gets the same position from either end then consider the lowest number for the substituents. If there is a functional group on a ring, assign it position 1. Double bonds in a ring are at positions 1 and 2. b. If there is multiple functional groups the priority is carbonyls > alcohols > carboncarbon multiple bonds > amines. If you have a carbon-carbon double bond and a carbon-carbon triple bond, go in the directions that gives the lowest possible positions. If both directions give the same numbers, the double bond will take priority. c. If there are no functional groups, give the substituents the lowest possible numbers. If you get the same numbers from either end assign the alphabetically first substituent the lowest number. 3. Naming your compound. a. If the compound has a specific configuration or geometry (cis/trans, E/Z or R/S) indicate this first. b. The first name is the substituents in alphabetical order. Prefixes that denote a number (di, tri, sec, tert etc.) are not alphabetized. List the position(s) on the parent chain and denote how many with a Greek prefix. If a substituent is on a nitrogen the letter N is used to denote the position in lieu of a number. Hyphens are placed between letters and number whereas commas between two numbers. c. The last name of the compound is the parent chain. The stem of the name indicates the length of the parent chain and the suffix reflects the type of compound. If your parent chain is a ring add the prefix cyclo. If your parent chain had a functional group indicate the position if it’s not obvious. # of C’s 1 2 3 4 5 6 7 8 9 10 Stem meth eth prop but pent hex hept oct non dec 11 12 undec dodec Type of Compound Alkane Alkene Alkyne Alcohol Amine Suffix ane ene, diene, triene yne, diyne, triyne anol, enol, ynol anamine, enamine, ynamine Substituent Names CH3 H3C H3C CH3 methyl butyl ethyl CH3 propyl hexyl CH3 H3C pentyl CH3 H3C CH3 H3C CH3 CH3 isopropyl CH3 CH3 sec-butyl isobutyl CH3 H3C CH3 H3C H3C tert-butyl CH3 benzyl CH2 CH2 vinyl cyclopentyl allyl cyclohexyl phenyl H3C CH3 F Cl Br I fluoro chloro bromo iodo O CH3 methoxy O O O H3C CH3 ethoxy CH3 H3C propoxy isopropoxy