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Generic Functional Group Pattern Generic Functional Group Pattern Specific Example Using Suffix Specific Example Using Prefix O O C H C H R O not used in our course carboxylic acid H3C O (it's the highest priority suffix: -oic acid IUPAC: ethanoic acid group that we use) prefix: #-carboxy common: acetic acid O O O O O O O R O R anhydride O O 3 1 OH suffix: -oic -oic anhydride 4 2 (just one -oic anhydride, if symmetrical) IUPAC: ethanooic propanoic anhydride prefix: #-acyloxyalkanecarbonyl 4-acyloxymethanebutanoic acid O alkyl O O O R' R O O O 3 1 OH ester 4 2 suffix: alkyl -oate IUPAC: propyl ethanoate prefix: #-alkoxycarbonyl common: propyl acetate 4-methoxycarbonylbutanoic acid O O O O R Cl Cl acid chloride Cl 3 1 OH 4 2 suffix: -oyl chloride IUPAC: ethanoyl chloride prefix: #-chlorocarbonyl common: acetylchloride 4-chlorocarbonylbutanoic acid O O alkyl O O R1 R N N o o o amides (1 ,2 ,3 ) H2N 3 1 OH R2 alkyl 4 2 suffix: N-alkyl-N-alkyl -amide IUPAC: N-ethyl-N-methylethanamide 4-amidobutanoic acid prefix: #-amido or #-carbamoyl common: N-ethyl-N-methylacetamide 4-carbamoylbutanoic acid N N N C C C O R H C nitrile 3 3 1 4 2 suffix: nitrile IUPAC: ethanenitrile OH prefix: #-cyano common: acetonitrile 3-cyanobutanoic acid O O O H O O R H H aldehyde H 5 3 1 OH suffix: -al 4 2 prefix: #-oxo (if part of longest chain) IUPAC: ethanal #-formyl (if branch off of longest chain) common: acetaldehyde 3-formyl-5-oxopentanoic acid O O O O R1 R2 ketone 3 1 OH 4 2 suffix: -#-one IUPAC: pentan-2-one prefix: #-oxo (older = #-keto) former: 2-pentanone 3-oxobutanoic acid z:\files\classes\314\314 Functional Groups.doc OH OH O O R H alcohol 3 1 OH suffix: -#-ol IUPAC: propan-2-ol 4 2 prefix: #-hydroxy former: isopropyl alcohol 3-hydroxybutanoic acid O O O O R1 R2 ether 3 1 suffix: none 4 2 prefix: #-alkoxy (< 5C) IUPAC: 1-ethoxypropane OH #-alkyloxy (> 5C) former: ethyl propyl ether 3-methoxybutanoic acid S SH SH O R H thiol 3 1 4 2 suffix: -#-thiol OH prefix: #-mercapto IUPAC: propan-2-thiol 3-mercaptobutanoic acid #-sulfanyl common: isopropyl mercaptan 3-sulfanylbutanoic acid S S S O R1 R2 sulfide 3 1 4 2 suffix: none IUPAC: 1-ethylthiopropane OH prefix: #-alkylthio former: ethyl propyl sulfide 3-methylthiobutanoic acid R3 N NH O R R N 1 2 3 1 amines (1o,2o,3o) 4 2 OH suffix: N-alkyl-N-alkyl -#-amine IUPAC: N-ethyl-N-methylpropanamine prefix: #-(N-alkyl-N-alkylamino) former: ethylmethylpropylamine 3-(N-methylamino)butanoic acid X Br F O haloalkane 3 1 OH suffix: none IUPAC: 2-bromopropane 4 2 prefix: #-halo common: isopropyl bromide 3-fluorobutanoic acid X N3 NO2 O X = -NO = nitroso X = NO2 = nitro (X prefix)alkane X = N = azido 3 3 1 OH suffix: none X = N2 = diazo IUPAC: 2-azidopropane 4 2 prefix: #-see list common: isopropyl azide 3-nitrobutanoic acid O O 4 R alkene E = high priority opposite side 3 1 OH 3 1 OH suffix: none Z = high priority same side IUPAC: 2-methylpropene 2 4 2 prefix: #-ene common: isobutylene but-2Z-enoic acid but-2E-enoic acid O O 1 R 4 2 OH alkene E = high priority opposite side 3 1 OH 3 suffix: none Z = high priority same side IUPAC: ethyne 2 4 prefix: #-ene common: acetylene but-3-ynoic acid but-2-ynoic acid n = 0 = ethane n = 6 = octane CH = methane n = 1 = propane n = 7 = nonane n = 3 = cyclopropane n = 8 = cyclooctane 4 n = 2 = butane n = 4 = cyclobutane n = 9 = cycononane n = 8 = decane (CH ) n = 3 = pentane 2 n n = 5 = cyclopentane n = 10 = cyclodecane H C n = 9 = undecane 3 (CH2)n CH3 n = 4 = hexane n = 10 = dodecane n = 6 = cyclohexane n = 11 = cycloundecane n = 5 = heptane n = 11 = tridecane n = 7 = cycloheptane n = 12 = cyclododecane z:\files\classes\314\314 Functional Groups.doc n-alkanes, n = normal (Straight chain name based on the total number of carbon atoms present.) X X X X n-propyl n-butyl n-pentyl n-hexyl Isoalkanes, iso = 3 carbons with branch off middle carbon. The stem name is based on the total number of carbon atoms present. X X X X isopropyl isobutyl isopentyl isohexyl This is a unique term applied to only secondary substition on a straight 4C chain. sec-butyl X t-alkanes, t = tert = tertiary carbon, having the first pattern and at least 2 methyl groups and a side branch (1C or longer). The stem name is based on the total number of carbon atoms present. X X X X t-butyl t-pentyl t-hexyl t-heptyl Neoalkanes have the 5 carbon pattern shown in the first structure (4o carbon in the middle, with 3 methyl groups and a side branch) using the appropriate stem name based on the total number of carbon atoms present. X X X neopentyl neohexyl neoheptyl Other patterns with special names based on the number of attached carbon atoms (a. to carbon, b. to nitrogen). a. H H R R R C X R C X R C X R C R H R R R 1 carbon atom 2 carbon atoms 3 carbon atoms 4 carbon atoms attached = primary (1o) attached = secondary (2o) attached = tertiary (3o) attached = quaternary (4o) b. H H R R R N R N R N R N R H R R R 1 carbon atom 2 carbon atoms 3 carbon atoms 4 carbon atoms attached = attached = primary amine attached = secondary amine attached = tertiary amine quaternary ammonium ion Other patterns with special names based on the number of attached hydrogen atoms. H H R H2 H3C R R C R R C R R C X R C R H2 H3C X R C X R R R 3 hydrogen atoms 2 hydrogen atoms 1 hydrogen atom 0 hydrogen atoms attached = methyl attached = methylene attached = methine attached = no name Special groups having pi bonds. X X X X X allyl X vinyl X propargyl X benzyl X phenyl X z:\files\classes\314\314 Functional Groups.doc 1 234 O O O O O C H C C C R O R O R C R' R Cl R O 5 678 O O O N C R' C R' C H C R N R N R N R H H R" 9 10 11 O O 12 S O C C R H R H R H R R 13 14 15 16 H R' O S R R H3C CH3 N N R H R H 17 18X 19 R 20 R R' R R N R C C C R C R" R R 21 22 23 24 R O C N N H N R N R O R R O N2 R z:\files\classes\314\314 Functional Groups.doc 1 234 O O O O O C H C C C C R' R O R O R R Cl R O carboxylic acid anhydride acid chloride ester prefix: #-carboxy- prefix: #-acyloxyalkylcarbonyl- prefix: #-chlorocarbonyl- prefix: #-alkylcarbonyl- suffix: -oic acid suffix: -oic anhydride suffix: -oyl chloride suffix: -oate 5 678 O O O N C R' C R' C H C R N R N R N R H H R" o o nitrile 1o amide 2 amide 3 amide prefix: #-amido- prefix: see notes prefix: see notes prefix: #-cyano- suffix: -amide suffix: -amide suffix: -amide suffix: -nitrile 9 10 11 O O 12 S O C C R H R H R H R R aldehyde ketone alcohol thiol prefix: #-oxo- prefix: #-oxo- prefix: #-hydroxy- prefix: #-mercapto- suffix: -al suffix: -#-one suffix: -#-ol suffix: -#-thiol 13 14 15 16 H R' O S R R H3C CH3 N N R H R H ether sulfide / thioether 1o amine 2o amine prefix: #-alkoxy- prefix: #-amino- prefix: #-amino- suffix: none prefix: #-alkylthio- suffix: none suffix: -#-amine suffix: -#-amine 17 18X 19 R 20 R R' R R N X = R C C F #-fluoro C R C R" Cl #-chloro R 3o amine Br #-bromo R alkene alkyne I #-iodo prefix: #-amino- prefix: none prefix: none suffix: -#-amine prefix: #-halo suffix: none suffix: -#-ene suffix: -#-yne 21 22 23 24 R O C N N H N R N R O R R O N2 alkane R nitroalkane nitrosoalkane diazoalkane prefix: #-alkyl- prefix: #-nitro- prefix: #-nitroso- suffix: -ane prefix: #-diazo- suffix: none suffix: none suffix: none z:\files\classes\314\314 Functional Groups.doc Several of the groups below have been paired together because they share some common feature. The only difference is that one has a C=O and one does not. These are easy to confuse, so learn them well. Priority #s are listed with FGs. O O #1 #9 #3 #12 #2 O O H2 C H C H C CH3 H3C CH3 C C H3C O H3C O H C O 3 O H3C O CH3 carboxylic acids alcohols esters ethers anhydrides #6 #7 O #8 O #4O #12 H2 H CCN C 3 C C C H3C Cl H3C H H3C Cl nitriles H3C CH3 aldehydes ketones acid chlorides chloroalkanes O O O H CH3 #5 #11 H2 C H C CH N C H 3 C CH3 H3C N N H C N H C CH H3C N 3 H3C N 3 3 H3C CH3 o H 1 amines 2o amines o o o H o 3 amines 1 amides H 2 amides 3 amides CH3 #9 H 2 #10 #12 O #12 C H H3C S S C H H3C CH3 H3C CH3 H3C O H2 ethers alcohols thiols sulfides / thioethers suffix: -ene > -yne > -ane #12 H2 C H H3C CH3 C H CCC H 3 C H3C Br CH3 H2C H2 alkenes alkynes alkanes bromoalkanes #12 O #12 #12 #12 H3C N C H2C N N H3C N N N H3C N O H2 C O H2 nitrosoalkanes diazoalkanes azidoalkanes nitroalkanes z:\files\classes\314\314 Functional Groups.doc Name ____________________________________ E CH3N(CH3)2 A B O C CH CO CH H3C CH3 CH N CH3CH2CH3 O 3 2 3 D CH2CHCH3 F 3 3 N N CH3COCH3 H3C CH3 H2C CH C C CH 3 H3C N C 3 C H C CH CH3 N H2 3 3 H3C O H G H I J K L O O CH3CH2Br CH CH NO CH CH SH CH3NHCH3 3 2 3 2 CH3NO2 CH3COCl H3C CH3 H3C Br H C O H3C SH N C 3 N C C H C Cl N H3C O H 3 H2 H2 MNCH CH NH O P Q R O 3 2 2 CH3CH2OH CH3OCH3 CH2N2 CH3CN CH3CONH2 H3C NH2 H C OH H3C CH3 3 C H CCN C C 3 H2C N N O H3C NH2 H2 H2 S T V CH SCH U O O W O O CH3CCH 3 3 CH CHO CH3CO2H CH3CO2COCH3 S 3 C C C C H3CCC H H3C CH3 H C O CH H3C H H3C OH 3 3 1.
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