Survey
* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
1 General Strategy For Naming Simple Organic Compounds (Bare bones summary sheets) 1. Find the highest priority group. These are listed in order of priority in the table of functional groups (next page). 2. Find the longest chain containing the highest priority group. You should know carbon chains of length C1-C19 (listed in the table). 3. Number the longest chain containing the highest priority group to give the highest priority group the lowest number possible in numbering the longest chain. For the first seven functional groups, the functional group carbon will be number 1 (if it is the highest priority group) and the “1” can be omitted, since it is understood that it has to be this way. 4. Usually the highest priority group is named as a suffix at the end of alkane, alk-#-ene or alk-#-yne. The final e is dropped if the suffix begins with a vowel and it is retained if the suffix begins with a consonant (only two for us, “nitrile” and “thiol”). A number will be present in front of the suffix name unless its position is unambiguously clear (e.g. carboxyl groups, aldehydes, nitriles, etc. always = 1, if highest in priority). If there is a C/C pi functional group to identify (alkene or alkyne), the number in front of its part of the name describes its position (see rule 6 below). If both a pi bond and a high priority substituent are present, then two (or more) numbers may be necessary, one for each functionality. 5. Lower priority groups are named with their prefix names and their location numbers based on the numbering of the parent chain (always true for substituents numbered 12 on the next page). The lower priority substituents should be listed in alphabetical order. Some parts of prefix names count in this regard and some don't. We will not emphasize this aspect in this course. 6. Double bonds and triple bonds are named as alk-#-ene or alk-#-yne, respectively. If both are present, name as alk-#en-#-yne. Multiple pi bonds (or other substituents) use the prefixes di, tri, tetra, penta etc. with a number for each occurrence. In such cases, an "a" is added in front of the numerical prefix for better phonetics. (alka-#,#-diene or alka#,#,#-triyne, alka-#,#-dien-#,#-diyne, etc.) The essential functional groups to know (for our course) and their prefixes and suffixes are given in the next page. In this table the term “alkan-#-suffix” is a generic term for any alkane with a functional group suffix, and it must be replaced with the correct parent stem name based on the number of carbons in the longest chain (C1-C19 for us). If there is a double bond, the name will change to “alk-#-en-#-suffix and if there is a triple bond, the name will change to “alk-#-yn-#-suffix. (See #6 above.) 2 Functional Group 1. Carboxylic acid R 2. Anhydride O C R 3. Ester R 4. Acid halide R R 6. Nitrile OH not considered alkanoic acid O C not considered alkanoic anhydride (if symmetrical) #-alkoxycarbonyl alkyl alkanoate (R') (RCO2) Cl #-chlorocarbonyl alkanoyl chloride NH2 #-carbamoyl (or #-amido) alkanamide #-cyano alkanenitrile #-oxo alkanal O C O O C O O C O C 5. Amide prefix suffix R R' R C N 7. Aldehyde 8. Ketone R R O C O C H R' #-oxo (older = #-keto) #-alkanone 9. Alcohol R OH #-hydroxy #-alkanol 10. Thiol R SH #-mercapto (or #-sulfanyl) #-alkanethiol 11. Amine R NH2 #-amino #-alkylamine #-alkanamine 12. Ether R O R' 12. Sulf ide R S R' #-alkoxy (if more than 5C's, then #-alkyloxy) (can also use "#-oxa" pref ix and count as carbon in longest chain) #-alkylthio 12. Halogen R X #-fluoro, #-chloro, #-bromo, #-iodo 12. Azide* R N3 #-azido 12. Diazo* R N2 #-diazo 12. Nitro* R NO2 #-nitro 12. Nitroso R NO #-nitroso 12. Carbon branches R The part of each name specif ic to the f unctional group is in bold and underlined to help you see those f eatures. They are not part of the names. "R" = carbon chains alkane alkyl # chain branch carbons name name 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 methane ethane propane butane pentane hexane heptane octane nonane decane undecane dodecane tridecane tetradecane pentadecane hexadecane heptadecane octadecane nonadecane always pref ixes (no suf f ix names) proper order is alphbetical #-alkyl, #-(alk-#-enyl), #-(alk-#-ynyl) * = f ormal charge is necessary in these Lewis structures and there are two reasonable resonance structures stereoisomerism pref ixes parent stem C/C pi bonds high priority suf f ix R/S and E/Z branches and see box above low priority f unctional groups methyl ethyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl undecyl dodecyl tridecyl tetradecyl pentadecyl hexadecyl heptadecyl octadecyl nonadecyl -ene -yne see list above 3 Practice problems alkanes, alkenes, alkyne, alka-#,#-dienes alka-#,#-diynes, alk-#-en-#-yne Problems a g b h c i d e j f Answers a g octane oct-6E-en-1-yne b oct-1-ene h c 3-methyloct-1-en-7-yne octa-1,5E-diene i d octa-1,6Z-diene 3-methyloct-7-en-1-yne e oct-1-yne f j nona-3E,5Z-dien-1,8-diyne oct-1-en-7-yne 4 Functional group examples (high priority group gets suffix, all others named as prefixes) f unctional group: suf f ix: pref ix: O O O OH name: O name: O 5 f unctional group: amide (1o, 2o, 3o) suf f ix: -amide pref ix: amido or carbamoyl O O NH2 5 4 3 2 1 OH name: butanoyl chloride O O NH2 name: 2-amidopent-4-ynoic acid N name: N-ethyl-N-methylbutanoyl chloride 6 f unctional group: suf f ix: pref ix: O O H OH H name: O O name: H 7 8 9 Miscellaneous nitrogen f unctional groups (all have f ormal charge, all named with pref ixes) O O RNO2 = NO2 N N N = N2 N3 N N N name: R-N3 = RN2 = 10 Complicated structure with most of the functional groups of first year organic chemistry. O O O O O Cl NH2 O O S O H SH C NH2 OH Br O N O H O 6 5 7 4 5 3 6 4 2 1 2 1 1 2 4 2 O 1 O 2 O 5 6 3 4 7 2 O O 1 4 3 3 O 3 5 Cl 8 NH2 O 1 2 1 3 3 8 9 H 14 12 7 6 5 4 2 S 1 O 1 2 10 13 11 O H SH C OH N O NH2 3 5 4 9 7 6 8 O 10 Br This complicated branch (on the ester oxygen) is named first. Not in alphbetical order, named in order encountered along the chains. 1-(4-ethylheptyl)-2-amino-3-amido-4-phenyl-6-oxo-7-(4-chlorocarbonyl-5-methoxycarbnoyl-7-pentylcycloocta-5E,7Z-dienyl)-8-bromo-10-ethylthiodeca-3E,7Z-dienyl 2-benzyl-4-hydroxy-5-(2-methylpropoxy)-6-cyano-7-(3-hexyl-4,4-dimethylcyclobut-2-enyl)-9,14-dioxo-12-f ormyltetradec-5E-en-10-ynoate 11 Problem - Identify each of the substituent patterns below by its common name. Point out an example of a 1 , 2o, 3o and 4o carbon and nitrogen in the side chains. Also, point out an example of a methyl, methylene and methine (methylidene) position. o