-The Wise Man’s Fear by Patrick Rothfuss Nomenclature “Names reflect true understanding of a thing, and when you truly understand a thing you have power of it.” -The Wise Man’s Fear by Patrick Rothfuss

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Simple Names- Linear Alkanes Alkanes have the suffix -ane CH4 methane ethane butane hexane octane decane dodecane tetradecane hexadecane propane pentane heptane nonane undecane tridecane pentadecane # carbons prefix # carbons prefix 1 meth 9 non 2 eth 10 dec 3 prop 11 undec 4 but 12 dodec 5 pent 13 tridec 6 hex 14 tetradec 7 hept 15 pentadec 8 oct 16 hexadec

Simple Names- Haloalkanes First, find the longest linear chain by numbering carbons. This gets the –ane suffix, if you use the halogen prefix. Or, it gets the –yl suffix, if you use the halogen suffix. Cl 1 2 3 4 5 6 7 8 9 10 11 12 13 Halogen prefix suffix F fluoro fluoride chlorotridecane tridecylchloride Cl chloro chloride Br bromo bromide I Iodo iodide

Simple Names- Haloalkanes Next, number the carbons along the chain. The number goes in front of the name separated by a dash. (If the number is 1, then you can ignore it). Cl There are always two directions you can number. You want the scheme that gives you the smallest number. Cl 10-chlorotridecane 10-tridecylchloride 1 2 3 4 5 6 7 8 9 10 11 12 13 4-chlorotridecane 4-tridecylchloride 13 12 11 10 9 8 7 6 5 4 3 2 1

Multiply Substituted Haloalkanes For numbering purposes, the sum should be the lowest possible. Halogen prefixes are generally used. The name should be alphabetical. Separate substituents by dashes. 10-chloro-2-iodopentadecane 2+10=12 I Cl 1 2 3 4 5 6 7 8 9 10 11 12 13 15 14 Halogen prefix F fluoro Cl chloro Br bromo I Iodo 6+14=20 Cl I 13 12 11 10 9 8 7 6 5 4 3 2 1 14 15

Multiply Substituted Haloalkanes When you have the same substituents, add prefixes. The prefixes become part of the substituent’s name. Br 1 2 3 4 5 6 7 8 9 10 Br Br Br I 3-iodo-1,1,4,10-tetrabromodecane Number prefix 2 di 3 tri 4 tetra 5 penta Number prefix 5 penta 6 hexa 7 hepta 8 octa

Simple Names- Branched Alkanes First, find the longest linear chain by numbering carbons, this gets the –ane suffix. hexadecane 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes First, find the longest linear chain by numbering carbons, this gets the –ane suffix. 14<16 tetradecane 1 2 3 4 5 6 8 7 9 10 11 12 13 14 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes First, find the longest linear chain by numbering carbons, this gets the –ane suffix. 11<16 undecane 1 2 3 4 5 6 8 7 9 10 11 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes First, find the longest linear chain by numbering carbons, this gets the –ane suffix. 9<16 nonane 1 2 3 4 6 5 7 8 9 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes First, find the longest linear chain by numbering carbons, this gets the –ane suffix. 12<16 dodecane 1 2 3 4 5 6 7 8 9 10 11 12 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes First, find the longest linear chain by numbering carbons, this gets the –ane suffix. THIS IS THE MAIN BRANCH. hexadecane 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes Number the carbons in the side branch (use lowest number route). The number that main branch attaches to the side branch goes in front of the substituent name. This is then encased in parentheses. (2-pentyl)- hexadecane 1 2 3 4 5 2<4 5 4 3 2 1 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes Number the carbons in the main branch (use lowest number route). The number that side chain attaches to the main branch goes in front of the parentheses. 7- (2-pentyl)- hexadecane 1 2 3 4 5 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 # carbons prefix 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct # carbons prefix

Simple Names- Branched Alkanes 7-(2-pentyl)-hexadecane

Multiply branched alkanes Name this compound: Have you named it? Warning: Next click will bring up the answer 4 1 2 3 14 11 12 13 4 1 2 3 5 6 10 14 1 2 3 4 5 7 8 9 11 12 13 15 16 6 10 14 1 2 3 4 5 7 8 9 11 12 13 15 16 6-butyl-10-(2-pentyl)-hexadecane 10+6<11+7 16>14

Multiply branched alkanes Name this compound: Have you named it? Warning: Next click will bring up the answer 6 10 14 1 2 3 4 5 7 8 9 11 12 13 15 16 17 18 Cl 13 9 5 18 17 16 15 14 12 11 10 8 7 6 4 3 2 1 15 16 9-chloro-5,13-diethyloctadecane 14+10+6=30 18>16 28<30 5+9+13=27

Multiply branched alkanes Name this compound: Have you named it? Warning: Next click will bring up the answer trichloro (2-butyl) (2-propyl) trifluoromethyl Cl F 8 4 13 12 11 10 9 7 6 5 3 2 1 6 10 1 2 3 4 5 7 8 9 11 12 13 4-(2-butyl)-9-(2-propyl)-1,1,1-trichloro-10-trifluromethyltridecane 1+1+1+4+9+10=26 13+13+13+10+5+4=58 4-sec-butyl-9-isopropyl-1,1,1-trichloro-10-trifluromethyltridecane is also ok.

Branched alkanes-special names Some branching patterns are so prevalent that common names are used. IUPAC Name Common name IUPAC Name Common name X X isobutyl (2-propyl) (2-methylpropyl) isopropyl Abbreviation iPr IUPAC Name Common name IUPAC Name Common name X 2-(butyl) sec-butyl 2-(2-methylpropyl) tert-butyl Abbreviation tBu X The prefixes sec and tert are italicized and do not count when alphabetizing. The prefixes iso and neo do. IUPAC Name Common name X (2,2-dimethylpropyl) neopentyl

Exam Level Questions: Draw the following: neopentyliodide isobutylbromide isopropylchoride 1,1-dichloroethane Cl Cl I Br tert-butylfluoride 1,2-dibromopropane 3-iodo-2-methylpentane sec-butylfluoride I F Br F