page | of 4 Systematic Nomenclature (IUPAC System) Prefix-Parent-Suffix Parent- number of carbons Prefix- substituents Suffix- functional groups Naming Alkanes General Formula: CaH(2n+2) suffix: -ane Parent Names: lL CHy 2. CH3CH3 3. CH3CHQCH3. 4.” CH3(CH2)2CH3 9. CH3(CH2)3CH3 6. CH3(CH2)4CH3 7. CHB(CH2)sCH3 8 CH3(CH2)6CH3 9. CH3(CH2)7CH3 10: CH3(CH2)gCH3 Alkyl Substituents R= Rest of the molecule 1 BOERMNAUALN Ss CH3-R CH3CH2-R CH3CH2CH2-R CH3(CH2)2CH2-R CH3(CH2)3CH2-R CH3(CH2)4CHp-R CH3(CH2)5CH2-R CH3(CH2)6CH2-R CH3(CH2)7CHD-R CH3(CH2)8CH2-R Methane CH4 Ethane CoHG Propane C3Hg Butane C4H10. Pentane CsHi2 Hexane CoHi4 Heptane Cris Octane CsHig Nonane CoH20 Decane C1oHa2 Methyl Ethyl Propyl Butyl Penty! Hexyl Hepty! Octyl Nonyl Decylpage 2 of 4 Rules for Systematic Nomenclature of Alkanes 1. Find the parent chain 4 Identify the longest continuous carbon chain as the parent chain, CH Gh | 7 carbons= hept- CHy~CH—ch—cH,-cH, Ch.=CH—=cH, 6. Ifmore than one different chains are of equal length (number of carbons), choose the one with the greater number of branch points (substituents) as the parent, it” CHy CHyCH™ CH=CH CH=CH, = CHy—CH—CH=cH~cHy—cH, ch, —cH, cH,—cH, 2 branch pts. 1 branch pt. 2. Numbering the carbons of the parent chain a. Number the carbon atoms of the parent chain so that any branch points have the lowest possible number Vcr, 7 chy 2 CH, 6 CH, CHy-CH=CH—cH.~ cH, CHy-CH=cH—CH,-cH, 34] 5 4] CH= CH=CH, CH CH cHs 5 6 7 32 1 branch pts. at carbons 3 and 4 branch pts. at carbons 4 and 5page 3 of 4 >. If'there is branching equidistant from both ends of the parent chain, number so the second branch point has the lowest number, = 2 ® 8 CHy= CH, HsG CH,—CH, CHy= CH, “| CHy—CHy Chiy CH= CH.—CHy—CH—CH= CH=CH, CHa CH=CH: CH, CH cH=CH,—cHy eee oes 7 6 6 4 32 4 branch pts. at carbons-3, 6, 7 branch pts. at carbons 3,4,7 3. Substituents Identify and number the substituents and list them in alphabetical order ee Parent C-9 = nonane one Hs Cleo, 3 ethyl 4-methyl CHEECH CH HMC —oHs TF meth } 4,7-dimethyl 7 8) 8) 4 3 2) 4 If there are two substituents on the same carbon, assign them the same number. 4. Write out the name a, Write out the name as a single word: hyphens (-) separate prefixes commas (,) separate numbers b. Substituents are listed in alphabetical order If two or more identical substituents are present use the prefixes di- for two tri- for three tetra- for four note: these prefixes (di-, tri-, tetra-, etc.) are not used for alphabetizing purposes. a CH=CH, HsG CHy—CHy CHy—CH—CH,—cH,—CH—CH=cH,—cH, 7 6 5 4 3 2 4 3- ethyl-4,7-dimethylnonanepage 4 of 4 5: Complex Substituents (substituents with branching) Named by applying the four previous rules with some modification Number the complex substituent separately from the parent, Begin numbering at the point of attachment to the parent chain, © Complex substituents are set off by parenthesis cis Che 1 ala 4 5 dt 8 9 ws CH ~CH—Cha GC -CH~ Cy Cy Gry y agaeeaecne 2,6-dimethyl-4-(1-methylpropyl}decane cn, Nonsystematic (trivial) Names: 3-carbons: ~ _ : 7 (chain HC’ opropy- comeryiyn 4-Carbons. Hee, Gly [Parent q choy [Parent = 7 (eran) He jie can | aaa) nuc—cly oe cH, _ __ te-buy. (-methylpropyt) (2-methylpropy!) (,l-dimethylethyl) 5- Carbons Hee hs Hs _ a ee ve CHa-CH>- Chain a. Chain H3C —Chp.- | Chain oh, iy _ on cerepngs oan iEmethytbowy) seopeny @2-dimethylpropyl) (h-dimettylpropy)) Alphabetizing trivial names. 'So- and neo are part of the alky! group name and are used for alphabetizing. see- and tert- are not included in the alphabetical order.