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Generic Functional Group Pattern in Ordero of Nomenclature Priority in Our Course. Specific Example Using Suffix (2D and 3D)

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Generic Functional Group Pattern in Ordero of Nomenclature Priority in Our Course. Specific Example Using Suffix (2D and 3D) Generic Functional Group Pattern Specific Example Specific Example in ordero of nomenclature priority Using Suffix (2D and 3D) Using Prefix when in our course. when highest priority FG lower priority FG 1. carboxylic acid (2D) carboxylic acid (3D) O Condensed line formula IUPAC: ethanoic acid O H H prefix example C H common: acetic acid RCO2H or HO2CR C C R O #-carboxy H O RCH(CO H)R' H suffix: -oic acid 2 O not used in our course FG on FG on C H (acids are the highest priority prefix: #-carboxy the right the left H3C O group that we use) FG in the carbonyl resonance (2D) middle (C=O) is possible 2. anhydride (2D) Condensed line formula anhydride (3D) IUPAC: ethanoic propanoic anhydride O O RCO2COR' or ROCO2CR' H H O O H C C C CH C 3 R O R H3C O C H H 2 prefix example H O C H suffix: -oic -oic anhydride (2D) (just one -oic anhydride, O O O C C O if symmetrical) 3 1 H 4 H 2 prefix: #-acyloxyalkanecarbonyl O O OH (prefix not required for us) carbonyl resonance 4-acyloxymethanebutanoic acid (C=O) is possible (prefix not required for us - too difficult) 3. ester (2D) alkyl name (goes in front as separate word) ester (3D) H H H IUPAC: propyl ethanoate O C Condensed line formula C O C common: propyl acetate C R' H H R O RCO2R' or R'O2CR H H C C H O H H2 RCH(CO2CH3)R' prefix: alkyl suffix: -oate H C C CH3 O H C O C prefix example 3 H prefix: #-alkoxycarbonyl 2 O O (2D) 3 1 carbonyl resonance 4 2 (C=O) is possible O OH 4-methoxycarbonylbutanoic acid 4. acid chloride (2D) carboxylic acid (3D) IUPAC: ethanoyl chloride prefix example O Condensed line formula O O Cl common: acetylchloride C RCOCl or ClOCR H 3 1 R Cl 4 2 C C O Cl OH RCH(COCl)R' H suffix: -oyl chloride H O C 4-chlorocarbonylbutanoic acid H C Cl prefix: #-chlorocarbonyl 3 (2D) carbonyl resonance (C=O) is possible, but weak because of the poor overlap of the chlorine 3p orbital with the carbon 2p orbital Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc o o o o 5. amides (1 ,2 ,3 ) (2D) 3 amide (3D) IUPAC: N-ethyl-N-methylethanamide H H O Condensed line formula H H common: N-ethyl-N-methylacetamide alkyl C C O C R' H H RCONR2 or R2NOCR H2 R N H N C C C ' H H3C N CH3 R" alkyl RCH(CONH2)R C C H H CH when highest priority functional group H (2D) 3 prefix example 1o amides: suffix: -amide O O O 2o amides: prefix: N-alkyl suffix: -amide 3o amides: prefix: N-alkyl-N-alkyl suffix: -amide carbonyl resonance (C=O) H N 3 1 OH is possible, it is especially 2 4 2 prefix when lower priority functional group: strong in amides o 1 amides: prefix: #-amido or #-carbamoyl 4-amidobutanoic acid 2o amides: prefix: #-(N-alkylamido) or #-(N-alkylcarbamoyl) or 3o amides: prefix: #-(N-allkyl-N-alkylamido) or #-(N-alkyl-N-alkylcarbamoyl) 4-carbamoylbutanoic acid 6. nitrile (2D) nitrile (3D) IUPAC: ethanenitrile prefix example N Condensed line formula H N C common: acetonitrile R RCN or NCR C C N C O H suffix: nitrile N 3 1 RCH(CN)R' H (don't drop the final C 4 2 "e" of the stem name) nitrile resonance OH H3C (CºN) is possible (2D) prefix: #-cyano 3-cyanobutanoic acid 7. aldehyde (2D) aldehyde (3D) IUPAC: ethanal Condensed line formula H O common: acetaldehyde prefix examples RCHO or OHCR C O C O H H O O O R H RCH(CHO)R' C 5 3 1 suffix: -al H C 4 2 H H3C H H OH prefix: #-oxo (if part of longest chain) carbonyl resonance (2D) (C=O) possible 3-formyl-5-oxopentanoic acid #-formyl (if branch off of longest chain) 8. ketone (2D) ketone (3D) Condensed line formula H H O IUPAC: pentan-2-one C prefix example H R1COR2 or R2OCR1 C H H former: 2-pentanone O O R R' H H C O RCH(COCH )R' 3 C 3 1 C O 4 2 suffix: -#-one C C OH H H2 H H prefix: #-oxo (older = #-keto) H H C C H3C C CH3 3-oxobutanoic acid carbonyl resonance H2 (C=O) possible (2D) 9. alcohol (2D) Condensed line formula alcohol (3D) IUPAC: propan-1-ol prefix example H H former: 1-propanol OH O O RCH2OH or HOH2CR H H R H C H common: n-propyl alcohol 3 1 RCHOHR' C 4 2 suffix: -#-ol C O OH H H2 H C OH prefix: #-hydroxy H 3-hydroxybutanoic acid H3C C H2 (2D) Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 10. thiol (2D) thiol (3D) Condensed line formula IUPAC: propan-1-thiol prefix example S H H SH O R H H H common: propyl mercaptan R CH SH or HSH CR 1 2 2 1 C H 3 1 suffix: -#-thiol C 4 2 (don't drop the final C S H2 OH R1CHSHR2 H C SH "e" of the stem name) H H H C C 3-mercaptobutanoic acid 3 (2D) prefix: #-mercapto H2 #-sulfanyl 3-sulfanylbutanoic acid 11. amines (1o,2o,3o) (2D) Condensed line formula 3o amine (3D) R' RNH H NR H H H 2 2 H H H IUPAC: N-ethyl-N-methylpropan-1-amine N R(NR')R" C C H R R" C former: ethylmethylpropylamine RCH(NH2)R' C N C H when highest priority functional group H o H H H 1 amines: suffix: -amine H prefix example 2o amines: prefix: N-alkyl suffix: -amine C o H H 3 amines: prefix: N-alkyl-N-alkyl suffix: -amine NH O CH3 3 1 prefix when lower priority functional group: H2 4 2 1o amines: prefix: #-amino C N CH3 OH H C C C 2o amines: prefix: #-(N-alkylamino) 3 H2 H2 (2D) 3o amines: prefix: #-(N-allkyl-N-alkylamino) 3-(N-methylamino)butanoic acid 12. ether (2D) Condensed line formula ether (3D) O R OR H H H R1 R2 1 2 H H H C C H C prefix example suffix: none R1CH(OCH3)R2 C O C H IUPAC: 1-ethoxypropane prefix: #-alkoxy (< 5C) H H H H O O common: ethyl propyl ether #-alkyloxy ( 5C) H 3 1 2 4 2 C O CH3 OH H C C C 3 H H (2D) 2 2 3-methoxybutanoic acid 12. sulfide (2D) Condensed line formula ether (3D) S RSR' H H H R1 R2 H H H C C H RCH(SCH )R' C prefix example suffix: none 3 C S C IUPAC: 1-ethylthiopropane H H S O prefix: #-alkylthio H H H former: ethyl propyl sulfide 3 1 H 4 2 2 OH C S CH3 H C C C 3 (2D) 3-methylthiobutanoic acid H2 H2 12. haloalkane (2D) bromoalkane (3D) prefix example X = -F = fluoro Condensed line formula Br X H H X = Cl = chloro H H (2D) F O X = Br = bromo CH CH RCH2 Cl or ClH2CR C X = I = iodo C H3C CH3 R R' C H 3 1 OH H 4 2 suffix: none RCHClR' H IUPAC: 2-bromopropane Br prefix: #-halo common: isopropyl bromide 3-fluorobutanoic acid Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc 12. nitroso (2D) Condensed line formula nitroso (3D) prefix example H 2 IUPAC: 1-nitrosopropane H C C R1CH2 NO or ONH2CR H H O 3 N O C NO N O H C H2 2 RCH(NO)R' H C H C C O 3 1 C 3 4 2 suffix: none C N OH H H H2 H H prefix: #-nitroso (2D) 3-nitrosobutanoic acid nitroso (3D) 12. nitro (2D) Condensed line formula IUPAC: 1-nitropropane O H2 RCH2 NO2 or O2NCH2R H3C C C NO H H 2 N O H2 prefix example H2 RCH(NO2)R' C H3C C O H C C N suffix: none C H 2 O O H H prefix: #-nitro H H O N O (2D) resonance 3 1 4 2 OH resonance O 3-nitrobutanoic acid H2 H H H3C C O N O C N C H2 H C C O H H H H azide (3D) 12. azides (2D) IUPAC: 1-azidopropane Condensed line formula H2 H C C common: propyl azide 3 H C N RCH2 N3 or N3CH2R H H 3 2 N N N H2 N prefix example C RCHN R' H C H3C C N 3 C C N suffix: none H N3 O H H 2 H H prefix: #-azido 3 1 (2D) 4 2 OH resonance resonance 3-azidobutanoic acid H N H H 2 H3C C N N N N C C N H C H2 C H H H H 12. diazo (2D) diazo (3D) Condensed line formula H IUPAC: 1-diazobutane H3C C RCH N2 or N2CHR C N H H H H 2 2 C N N H2 N RCH(N )R' C 2 H C H3C C N prefix example suffix: none C C C H N O H H 2 2 H H (2D) prefix: #-diazo H 3 1 2 4 OH resonance resonance 3-diazobutanoic acid H N H 2 H H H3C C N C N N C C C H C H2 C H H H H H Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc alkenes (always a suffix on the stem name) O O H 4 R R O H 3 1 OH CC H C C 4 2 3 1 OH IUPAC: 2-methylpropene 2 C C R R O common: isobutylene H but-2Z-enoic acid H but-2E-enoic acid suffix: #-ene H E = high priority opposite side prefix: none Z = high priority same side alkynes (always a suffix on the stem name) H O O C H O H 1 C 4 2 R C C C C 3 OH IUPAC: ethyne 3 1 OH H 2 4 suffix: #-ene but-2-ynoic acid common: acetylene H O prefix: none but-3-ynoic acid E/Z is not possible alkenes and alkynes (always a suffix on the stem name, -#-en-#-yne) O R H O H C CCR 1 OH H C C C C 2 R C 5 3 C C 6 R O 4 H suffix: #-en-#-yne H H hex-4E-en-2-ynoic acid IUPAC: 2-methylpent-1-en-3-yne prefix: none aromatics (2D) 3D aromatic IUPAC: methylbenzene branches H R R H common: toluene H H benzyl C C H C C H C C R C C R C C CH H C C C H H CC H CC H phenyl C C R R H H many special names H H (2D) 3D aromatic H H H H H C C H C C H C C C C C C C C C H H CH H C C C C CC H C C H H H H H H H H 1-phenylpent-3E-en-1-yne alkanes n = 0 = ethane (2C) n = 7 = nonane (9C) cycloalkanes n = 1 = propane (3C) n = 8 = decane (10C) n = 3 = cyclopropane n = 9 = cycononane n = 2 = butane (4C) n = 9 = undecane (11C) n = 4 = cyclobutane n = 10 = cyclodecane CH4 = methane (1C) n = 3 = pentane (5C) n = 10 = dodecane (12C) n = 5 = cyclopentane (CH ) n = 11 = cycloundecane n = 4 = hexane (6C) n = 11 = tridecane (13C) 2 n n = 6 = cyclohexane n = 12 = cyclododecane n = 5 = heptane (7C) n = 12 = tetradecane (14C) n = 7 = cycloheptane H C (CH ) CH n = 13 = cyclotridecane 3 2 n 3 n = 6 = octane (8C) n = 13 = pentadecane (15C) n = 8 = cyclooctane n = 14 = cyclotetradecane Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, Resonance.doc Functional Group Combinations O NH2 O H OH O O O O O N O C NH2 Br Cl O O O H Possible answer (each side is a separate word because this is an anhydride = 2 x “-oic” + anhydride) 1 1 3 2 5Z 3Z 2S 1 3 2 4 1 1 1 O NH2 O H OH O O O O O 12 4 2 2 6 8 10 N 5 3 11O 3 5 7
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