Alkanes Prefix None Suffix -ane
In this handout, all of our functional groups are presented as condensed line formulas, 2D and 3D formulas and withnomenclature prefixes and suffixes (if present). Organic names are built on a foundation of alkanes, alkenes and alkynes.Those examples are presented first and you need to know those rules. The strategies can be found in Chapter 4 of ourtextbook (alkanes: pages 93-98, cycloalkanes 102-104, alkenes: pages 104-110, alkynes: pages 112-113 and combinationsof all of them 113-115). After introducing examples of alkanes, alkenes, alkynes and combinations of them, thefunctional groups are presented in order of priority. A few nomenclature examples are provided for each of the functionalgroups. Examples of the various functional groups are presented on pages 115-135 in the textbook. Two overview pagesare on pages 136-137. Some functional groups have a suffix name when they are the highest priority functional groupand a prefix name when they are not the highest priority group, and these are added to the skeletal names with identifyingnumbers and stereochemistry terms (E and Z for alkenes, R and S for chiral centers and cis and trans for rings). Severallow priority functional groups only have a prefix name. A few additional special patterns are shown on pages 98-102.The only way to learn this topic is practice (over and over). The best practice approach is to actually write out the names(on an extra piece of paper or on a white board, and then do it again). The same functional groups are used throughout theentire course. Once you know them, it’s like shuffling a deck of cards. The queen of hearts is always the queen of hearts,and an ester is always an ester. The main variables for a functional group are highest priority (suffix) or lower priority(prefix) and what number identifies it.Alkanesprefix nonesuffix -anealkanes - try to draw 3D structures in a zig-zag shapeH2DHCRRHHCCH H3DHHHCH HHHCHHCCHcondensed line formula5HCH34HHH3-ethyl-2-methylpentaneAdd 2 to "n" to include the end methyl groups (total chain length in parentheses)(CH2)nCH3chain length n 2n 0 ethane (2C)n 1 propane (3C)n 2 butane (4C)n 3 pentane (5C)n 4 hexane (6C)n 5 heptane (7C)n 6 octane (8C)n 7 nonane (9C)n 8 decane (10C)12CHIUPAC: pentaneIUPAC: pentaneCH4 methane (1C)H3CCHprefix: nonealkanesH HCCH3CH2CH2CH2CH3CH Hsuffix: #-aneHbranch names1C methyl2C ethyl3C propyl4C butyl5C pentyl6C hexyl7C heptyl8C octyl9C nonyl10C decyln 9 undecane (11C)n 10 dodecane (12C)n 11 tridecane (13C)n 12 tetradecane (14C)n 13 pentadecane (15C)n 14 hexadecane (16C)n 15 heptadecane (17C)n 16 octadecane (18C)n 17 nonadecane (19C)cycloalkanes(CH2)nring size nn 3 cyclopropanen 4 cyclobutanen 5 cyclopentanen 6 cyclohexanen 7 cycloheptanen 8 cyclooctanen 9 cycononanen 10 cyclodecanen 11 cycloundecanen 12 cyclododecanen 13 cyclotridecanen 14 cyclotetradecanea.2'3'1'structure to namehint109872'1'3'2'121'111'5641'1"2'1"2'321 a branch pointY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
b.structure to namehint657 431'3'897213'3'2'2'3'1'1"1"1"2"c.structure to name1"hint106896'5'1'4'47352'7'3'6'1' 2'11"1' 2'3'5'4'2"1"3'2"4'5'1"23"1"answersa. l)-8-(1-methylpropyl)dodecaneb. t cyclononanec. x nonesuffix -enealkenes (always a suffix on the stem name)Condensed line formulaCH2C(CH3)2RRCR2DCRsuffix: #-eneprefix: noneCH3CHCHCO2H3DHOCHCO34123OH21OHbut-2Z-enoic acidbut-2E-enoic acidHO4OCC2H13HIUPAC: methylprop-2-eneHE high priority opposite sideZ high priority same sidecommon: isobutyleneAlkenesa.2structure to namehint31135422E stereochemistry122b.structure to name1'hint1675124142332'1'3Z stereochemistry2Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
c.2'hintstructure to name3'1'231431523E stereochemistry12621'2'5'3' 4'1"1"2"d.structure to namehint1"32222'1'113'41'1E stereochemistry212181'2'67212'51Z stereochemistry13'e.structure to namehint3'2'1'2341'1'22122'12872312'64Z stereochemistry14'54'12E stereochemistry8'3'12'5'7'2"1"116'5'13'95E stereochemistry2Z stereochemistryanswersa. pent-2E-eneb. 4-ethyl-6-methylhept-3Z-enec. E-ened. E-enee. Z,5E-dieneAlkynesprefix nonesuffix -ynealkynes (always a suffix on the stem name)HC3D2DOHCCRsuffix: #-yneIUPAC: ethyneprefix: nonecommon: ynoic acid321OHbut-3-ynoic acidE/Z is not possible with alkynesY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Alkynesa.structure to namehint2'3'1"3424'11"1'5b.structure to name1'hint5641873921'1'c.structure to namehint1"1893'1'22'4'731"6542"d.structure to namehint57613241"6'5'1'4'2'3'e.structure to namehint78563421910111"6'5'1'4'2'3'answers:a. 4-(4-methylcyclobut-2-enyl)-4-methylpent-1-yneb. 2,2,7-trimethylnon-3-ynec. ned. 4-(6-methylcyclohex-3-enyl)hept-1-en-6-ynee. -triyneY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Combinations of alkenes and alkynesprefix nonealkenes and alkynes (always a suffix on the stem name, -#-en-#-yne)CRCCHH2DCCRsuffix: #-en-#-yneHprefix: noneOH2CC(CH3)CCCH3RCO3DCondensed line formulaRsuffix -#-en-#-yneCCH1CH356OHOH2C4hex-4Z-en-2-ynoic acidIUPAC: 2-methylpent-1-en-3-yneAromatics have many special names, for now we will only use phenyl and benzyl prefixes3D aromaticaromatics nt-3E-en-1-yneHprefix carboxy (we won’t use this one)suffix -oic acidSpecific ExampleUsing Suffix (2D and 3D)when highest priority FGSpecific ExampleUsing Prefix whenlower priority FGcarboxylic acid (3D)IUPAC: ethanoic acidRCO2H or HO2CROCHHRCH(CO2H)Rsuffix: -oic acidFG onthe rightC#-carboxyOOnot used in our course(acids are the highest prioritygroup that we use)HCFG onthe leftFG in themiddleprefix examplecommon: acetic acidH'prefix: #-carboxyHHHHRHCCondensed line formulaHHHC1. carboxylic acid (2D)CHCGeneric Functional Group Patternin ordero of nomenclature priorityin our course.OphenylHHCHC(2D)HHCarboxylic AcidsCHHCHCH3D aromaticCCCCHmany special namesHbenzylHCRHCCHbranchesHcommon: tolueneHCHCRHCHCIUPAC: methylbenzeneHH3CO(2D)carbonyl resonance(C O) is possibleCarboxylic acidsa.structure to nameOO6ClOO457OHClOOhint2389OHOOOH1'1Functional groups1. carboxylic acid2. alcoholOH 3. alkene4. ketone5. ether6. alkyne7. acid chlorideY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
b.structure to nameBrhintOBr8C46OH7CNO2531ONH2Functional groups1. carboxylic acid2. amide3. bromo4. alkene5. amine6. nitrileOHNNH2ONH2NH2c.OOOhintstructure to nameHHNO29HOOHNO28467OH5Functional groups1. carboxylic acid2. ester3. nitro4. aldehyde5. ketone6. alkene7. aldehydeO231OOOHOOOOd.structure to nameOhintO65OH1OH243answers:a. n-8-ynoic acidb. 2-amido-3-bromo-6-amino-7-cyanooct-3Z-enoic acidc. op-1E-enyl)nonanoic acidd. benzoic acid2-methylbenzoic acidAnhydridesprefix too complicated for us2. anhydride (2D)Condensed line formulaIUPAC: ethanoic propanoic anhydrideanhydride (3D)OORCO2COR' or ROCO2CR'suffix -oic -oic anhydrideOH HHCROOHsuffix: -oic -oic anhydride(just one -oic anhydride,if symmetrical)CHCCHH3CHOCH3CH2prefix example(2D)OOHprefix: #-acyloxyalkanecarbonyl(prefix not required for us)CCCROOO4OOcarbonyl resonance(C O) is possible321OH4-acyloxyethanecarbonylbutanoic acid(prefix not required for us - too difficult)Anhydridesa.structure to nameOOhintO2O31OO123Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
b.structure to namehintOOOFunctional groups1. anhydride2. phenyl3. alkeneO22413O41O35c.structure to nameOOOhintOOO6425O1O31Functional groups1. anhydride2. ether3. alkene4. aromatic65243answers:a. propanoic anhydride (since it is symmetrical you only have to write the name one time)b. 3-methylbutanoic 3-phenylpent-3Z-enoic anhydridec. benzoic 3-methoxyhex-3Z-enoic anhydrideEstersprefix #-alkoxycarbonyl3. ester (2D)alkyl name (goes in front as separate word)ester (3D)HCCondensed line formulaR'CRCO2R'OOHor R'O2CRCIUPAC: propyl ethanoateCCHCHHcommon: propyl acetateHOHRCH(CO2CH3)R'Hsuffix -oateHHORprefix: “alkyl branch” on oxygenH2CCOH3Cprefix: alkyl suffix: -oate (in longest chain)OCH2CH3prefix exampleOO(2D)prefix: #-alkoxycarbonyl (as a branch)34carbonyl resonance(C O) is possible21OOH4-methoxycarbonylbutanoic acidestersa.structure to nameON2'1O1"1"Ohint4'1'O3'6'5'2N1"Functional groups1. ester2. alkyne3. aromatic4. alkene5. amine3b.structure to ional groups1. ester2. alkene3. nitrile4. ether5. thiol6. alkene7. sulfide8. alcoholNY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
c.structure to 2OFunctional groups1. ester2. cycloalkane3. amide4. ketone5. thiol6'6. aldehyde7. alkeneOH 8. alkyne9. alcoholOd.structure to nameO6O5O24O2NFunctional groups1. ester2. aromatic3. bromo4. nitroO13Branswers:a. 2-benzyl-3-methyl-6-(N,N-dimethylamino)hex-2E-enyl 3-phenylprop-2-ynoateb. 3-methylthio-4-hydroxybut-2Z-enyl 2-cyano-4-methoxy-5-mercaptohex-2E-enoatec. 6-hydroxyhex-2E-en-4-ynyl ated. phenyl benzoatebenzyl 3-bromo-4-nitrobenzoateAcid Chloridesprefix #-chlorocarbonyl4. acid chloride (2D)suffix -oyl chloridecarboxylic acid (3D)CRRCOClClsuffix: -oyl chlorideC'Ocommon: acetylchlorideClHor ClOCRRCH(COCl)Rprefix exampleIUPAC: ethanoyl chlorideCondensed line formulaOCO4ClO321OHHHCOH3Cprefix: #-chlorocarbonyl4-chlorocarbonylbutanoic acidCl(2D)carbonyl resonance (C O) is possible, butweak because of the poor overlap of thechlorine 3p orbital with the carbon 2p orbitalAcid chloridesa.structure to FClFunctional groups1. acid chloride2. fluoro3. alkene4. ether5. sulfide / thioether6. aldehyde7. nitroso8. amine9. ketone10. alcoholY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
b.2'structure to namehintNOOC1'NOOCFunctional groups1. acid chloride2. nitro3. ester4. thiol5. amide6. alkyne7. nitrileOO876SHO45Cl23NO21SHNH2OClNO2NH2c.structure to nameOOClBranswers:a. so-7-amino-8-oxo-9-hydroxynon-2E-enoyl chlorideb. 2-nitro-3-ethyoxycarbonyl-4-sulfanyl-6-carbamoyl-8 –cyanooct-7-ynoyl chloride(sulfanyl mercapto)(carbamoyl amido))c. benzyol chloridebenzyol bromided.Amidesprefix #-amido or #-carbamoylsuffix -amideNitrogen substituents use “N” prefix instead of a number3o amide (3D)H H5. amides (1o,2o,3o) (2D)OCRCondensed line formulaalkylR'R" alkylNHCHCHRCH(CONH2)R'when highest priority functional group1o amides: suffix: -amide2o amides: prefix: N-alkyl suffix: -amide3o amides: prefix: N-alkyl-N-alkyl suffix: -amideHCRCONR2 or R2NOCRNIUPAC: N-ethyl-N-methylethanamidecommon: N-ethyl-N-methylacetamideOHCHCH3CHHHH2CCNprefix exampleOCH3(2D)OCH3H2Ncarbonyl resonance (C O)is possible, it is especiallystrong in amidesprefix when lower priority functional group:1o amides: prefix: #-amido or #-carbamoyl2o amides: prefix: #-(N-alkylamido) or #-(N-alkylcarbamoyl)3o amides: prefix: #-(N-allkyl-N-alkylamido) or #-(N-alkyl-N-alkylcarbamoyl)O43214-amidobutanoic acidor4-carbamoylbutanoic acidOprefix utanoic acidAmidesa.N3structure to nameONhintN3OON624O 2NNH2NH2O2N5O31NH2NH2OHFunctional groups1. amide2. amine3. nitroso4. nitro5. azideY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
b.hintOstructure to nameO2NH7ON5Functional groups1. amide2. nitrile3. alkyl branch4. alkyne5. ketoneNH46C13CONc.Ostructure to namehintNbenzylphenylanswers:a. 2-amino-3-nitroso-5-nitro-6-azidohexanamideb. idec. N-benzyl-N-phenylbenzamided.Nitrilesprefix #-cyano6. nitrile (2D)suffix -nitrile (retain the final “e”)nitrile (3D)prefix exampleNIUPAC: ethanenitrileNCondensed line formulaCRHcommon: acetonitrileCRCN or NCRCCNHsuffix: nitrile(don't drop the final"e" of the stem name)RCH(CN)R'NHprefix: #-cyano4Cnitrile resonance(CºN) is possibleH3C(2D)3O21OH3-cyanobutanoic acidNitrilesa.structure to nameOHhintOHNONFunctional groups1. nitrile2. ether3. alcohol4. nitoso5. alkeneNON3CC1245OO2'61'b.structure to nameOHhintOH2'1'3HCOONH87O5O246C 1Functional groups1. nitrile2. alkene branch3. aldehyde4. alkyne5. ketone6. aldehyde in chainNY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
c.structure to nameOhintO3' 2'4'1'5'NCNCFunctional groups1. nitrile2. cycloalkane3. ketone4. alcoholN2C314OHOH65answers:a. 2-ethoxy-3-hydroxy-4-nitrosohex-4Z-enenitrile (don’t drop the final “e” because nitrile starts with a consonant)b. 2-ethenyl-3-formyl-6,8-dioxooct-4-ynenitrilec. rileAldehydesprefix #-oxo (if at the end of the longest chain)#-formyl (if a side branch on the longest chain)aldehyde (3D)7. aldehyde (2D)Condensed line formulaORCHOorHOOHRCH(CHO)R'prefix examplescommon: acetaldehydeCCRIUPAC: ethanalHOHCRsuffix -alOCHsuffix: -alprefix: #-oxo (if part of longest chain)H3 Ccarbonyl resonance(C O) possible#-formyl (if branch off of longest chain)5CHHOH4H(2D)32O1OH3-formyl-5-oxopentanoic acidAnhydridesa.3'hintstructure to name2'1'O87HOHO65OHOFunctional groups1. aldehyde2. etheer3. ketone4. alkene side chain5. alcoholO4213OHOb.structure to nameSHhintO6'4'7'3'2' 1'HHHS6OOO23OOSH1"5'1H45OOFunctional groups1. aldehyde2. etheer3. thiol4. alkyne5. ketone6. cycloalkadiene7. aldehyde side group8. sulfide / thioetherc.OOhintOstructure to name6N3N3HH54OHH12Functional groups1. aldehyde2. aromatic alcohol (phenol)3. azideOH3answers:a. nalb. ses\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
c. efix #-oxoketone (3D)8. ketone (2D)HCondensed line l resonance(C O) possibleprefix: #-oxo (older #-keto)OOOCHprefix exampleformer: 2-pentanoneHCCsuffix: -#-oneIUPAC: pentan-2-oneCHR1COR2 or R2OCR1CRsuffix -#-one (sounds like cone)H3CCH2(2D)3-oxobutanoic acidCH3Ketonesa.structure to nameClOClhint87O563142OOHFunctional groups1. ketone2. diene3. benzyl4. chloro5. phenyl6. alkyne910b.structure to onal groupsketone1. alcohol2. ketone3. cycloalkadiene4. amine5 alkene6. alkyne7. sulfide / thioetherc.OOstructure to nameanswers:a. neb. ylthionon-4E-en-6-yn-3-onec. acetophenone (1-phenylethan-1-one)benzophenoned.Alcoholsprefix #-hydroxy9. alcohol (2D)ORHsuffix: -#-olprefix: #-hydroxyIUPAC: propan-1-olalcohol (3D)Condensed line formulaRCH2OH or HOH2CRsuffix -#-olHCRCHOHR'HHHHHCCHprefix exampleformer: 1-propanolHcommon: n-propyl alcoholOH2CH3COHCH2OOH4321OH3-hydroxybutanoic acid(2D)Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Alcoholsa.structure to namehint21OHNH43OHO6NH875Functional groups1. alcohol2. 2o amine3. alkene4. etherO2'1'1'4'3'1"b.structure to namehintOHOHNO12OBr53'2'1'6'3"4'5'Functional groups1. alcohol2. nitroso3. alkyne4. alkene5. cycloalkene6. bromo7. ether2"1"O34NOBr6c.structure to nameOHOHanswers:a. b. ethylhex-5-en-3-yn-2-olc. benzyl alcoholphenold.Thiolsprefix #-mercapto or #-sulfanyl10. thiol (2D)thiol (3D)Hsuffix: -#-thiol(don't drop the final"e" of the stem name)R1CH2SH or HSH2CR1HHHHCR1CHSHR2prefix exampleIUPAC: propan-1-thiolCondensed line formulaSRsuffix -#-thiolHHSHcommon: propyl mercaptanHCCS4H2CH3CHSHCH2prefix: #-mercapto#-sulfanyl3O21OH3-mercaptobutanoic acid(2D)3-sulfanylbutanoic acidThiolsa.structure to namehintHSHS75432O986O1'2'3'14'Functional groups1. alkyne2. thiol3. alkene4. ether1"b.structure to nameSH1'hintNO25SH1'42N3167NO21'32'4'N3Functional groups1. thiol2. alkyne3. alkene4. alkyl branch5. cycloalkene branch6. azide7. nitro3'Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
c.structure to namehint45SH231SHFunctional groups1. thiol2. benzyl3. phenylanswers:a. 7-(3-methylbutoxy)non-6Z-en-1-ynethiol (retain the “e” because thiol starts with a consonant)b. t-3-ynethiolc. 4-benzyl-5-phenylpentanethiold.Aminesprefix #-aminosuffix -#-amine(if additional alkyl groups are on the nitrogen, use an “N” prefix)11. amines (1o, 2o, 3o) (2D) Condensed line formula3o amine (3D)R'H2NRRNH2R(NR')R"RCH(NH2)R'NRR"when highest priority functional group1o amines: suffix: -amine2o amines: prefix: N-alkyl suffix: -amine3o amines: prefix: N-alkyl-N-alkyl suffix: -amineHH HHCHNCIUPAC: N-ethyl-N-methylpropan-1-amineHCCHHHformer: ethylmethylpropylamineCHHHHprefix exampleCHHprefix when lower priority functional group:1o amines: prefix: #-amino2o amines: prefix: #-(N-alkylamino)3o amines: prefix: D)321OH3-(N-methylamino)butanoic acidAminesa.structure to nameNH21'hintNH23241'15761'2'1"8Functional groups1. amine2. alkyl branches3. alkene4. alkyneb.structure to namehint2'BrHNNO2O2'HN1'1"132O3' 4'5'1'4Br5NO2Functional groups1. amine2. alkyl branch3. alkene4. ether5. cycloalkene branch6. bromo7. nitro1'Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
c.structure to namehint3' 4'2'5'1'2'SS1'NN3N2'11'3'321"ON34OFunctional groups1. amine2. alkyl branches3. alkene4. ether5. cycloalkene branch6. sulfide / thioether7. azide1" 2"51'6answers:a. meb. enyl)-5-nitropent-2Z-enaminec. fix #-alkoxyCondensed line formula12. ether (2D)OR2R1ROR'suffix: noneether (3D)HHHHCRCH(OCH3)R'prefix: #-alkoxy ( 5C)suffix noneH#-alkyloxy ( 5C)H HCHOCprefix exampleCHHIUPAC: 1-ethoxypropaneHO3common: ethyl propyl etherH2CH3CHCO4CH3CH2CH2(2D)O21OH3-methoxybutanoic acidEthersa.structure to namehint43OO21'Functional groups1. ether2. phenyl3. alkyl branches4'2'13'b.structure to namehintOO342511'2'3'64'Functional groups1. ether2. phenyl3. benzylc.structures to nameOOOanswers:a. 1-(2-methylbutoxy)-3-phenylbutane or (2-methylbutyl 3-phenylbutyl ether)b. 1-(1-phenylbutoxy)-4-benzylcyclohex-3-enec. ethoxyethane / diethyl ether / ethyl ether / ethertetrahydrofuran / THFdiphenyl etherd.Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Thioethersprefix #-alkylthio12. sulfide (2D)R1thioether or sulfide (3D)Condensed line formulaSRSR'R2HHprefix: #-alkylthioHHCRCH(SCH3)R'suffix: nonesuffix noneH HHprefix exampleIUPAC: 1-ethylthiopropaneCHS3former: ethyl propyl hiobutanoic acidThioethersa. , b. , c.SSSanswers:a. 1-propylthiocyclohexa-1,3-dieneb. benzyl phenyl sulfidec. 2-ethylthiopent-4-ened.Halogensprefix #-fluoro, chloro, bromo or iodo12. haloalkane (2D)X -F fluoroXX Cl chloroX Br bromoCHX I iodoRbromoalkane (3D)Condensed line formulaHRCH2 Clor ClH2CRRCHClR'suffix: noneHCR'HHHprefix exampleOFBrH(2D)CHCCsuffix noneH3CHBrprefix: #-haloCH3321OHIUPAC: 2-bromopropane4common: isopropyl bromide3-fluorobutanoic a. ocyclohexa-1,3-dieneY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Nitrosoprefix #-nitroso12. nitroso (2D)H3Csuffix:nitroso (3D)Condensed line formulaH2CCH2suffix noneRCH2 NOor ONH2CRIUPAC: 1-nitrosopropaneH HNORCH(NO)R'NCHCH2prefix #-nitroONH2CH3CH HH Hprefix: #-nitrosoOCCnoneNitroprefix exampleO4N(2D)3O21OH3-nitrosobutanoic acidsuffix nonenitroso (3D)12. nitro (2D)H3CCondensed line formulaH2CCH2RCH2 NO2IUPAC: 1-nitropropaneOor O2NCH2RH HNO2RCH(NO2)R'Hsuffix: noneNCOCH2H HH Hprefix exampleH2CH3CCCprefix: utanoic acidOH HCHH3COCCsuffix noneazide (3D)IUPAC: 1-azidopropaneCondensed line formulaRCH2 N3suffix: noneRCHN3R'NCHNNCCH Hprefix: #-azidocommon: propyl azideH Hor N3CH2RNOprefix #-azido12. azides (2D)H2H3CCN3CH2CH2H HCH HNprefix c acidNH2CCH2ON3(2D)H HCNH2CH3CresonanceHOCH2H HH HazidesNH2CNNH Ha.N3structure to nameNONO4'5'6'3'7'2'1'8'12634NO25NO278 Functional groups1. alkyne2. alkene3. nitroso4. nitro5. cycloalkeneanswers:a. 3Z,7-dien-2-yneY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Diazo12. diazo (2D)HH3CCCN2H2prefix #-diazosuffix none (not used in our course)diazo (3D)Condensed line formulaRCH N2IUPAC: 1-diazobutaneor N2CHRRC(N2)R'H H HH HNNCCsuffix: noneprefix: #-diazoCCHCH2H HNH2CH3CNprefix anoic acidH H HHCCH HCCNNNH2CH3CCH2NCHH HNomenclature StrategyPoints to Consider1. What is the highest priority group present?2. What is the longest chain with that group?3. Number that chain (ring) so that the high priority group gets the lowest number.4. Identify branches and other functionality with those numbers. (Usually named as prefixes.)5. Combine everything into one name with proper use of hyphens (between numbers and letters) and commas(between numbers and numbers).6. Identify stereocenters as E/Z for alkenes and R/S for chiral centers. Combine with the number which refers toeach center, with the number written first. (3E, 5Z, 4S, 9R, etc.)Here are a few names that can be written out as structures, opposite to the way we do it.a. 2,4-dimethylhexaneb. 1,3,5,5-tetramethyl-1-cycloheptenec. trans-5-hepten-1-yneor5E-hepten-1-yned. 5-(4-methyl-2-cyclobutenyl)-1-nonenee. trans-3-ethyl-1-isoproplycyclopentanef. cis-1-t-butyl-4-isobutylcyclohexaneg. ,8-diyneh. nyl)-3-(2-propynyl)-6-ethenylcyclodecanei. 1-hepten-6-ynej. -1-(1-methylpropyl)-1-cyclopropenek. enel. decynem. 2,9 ,10-trimethyl-6-butyldodecanen. traeneo. 2,9,10-trimethyl-6-butyldodecanep. trans-(3,3-dimethylbutyl)-3-methylcyclooctaneq. decyner. 1-hepten-6-ynes. cloundecatrienet. s\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
More Complicated Functional Group CombinationsONH2OOOOHHOOOONCNH2SHClBrOOOHPossible answer (each side is a separate word because this is an anhydride 2 x “-oic” )-12S-bromotridec-5Z-enoic anhydrideY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
More Complicated Functional Group le answer (each side is a separate word, the first word is the name of the “alkyl” branch attached to the esteroxygen on the left side and the second part is the name of the branch with the carbonyl group on the right side).113122R3Z1O4HOOCl7S10H3 C98146532NH21134HO655 124 19 2837105431210S2 346844 sses\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
Match each functional group with its name.2D and condensed line ORNRNR'R"20FRRRBrRClRFR'R2425CCRR29RNa. aromaticb. fluoroc. carboxylic acidd. 1o aminee. 2o amidef. nitrileg. thiolh. etheri. bromoj. acid chloridek. ketonel. sulfidem. alkanen. nitroo. 3o amidep. alkeneq. aldehyder. nitrosos. alcoholt. iodou. 2o aminev. alkynew. chlorox. 3o aminey. azidoz. anhydrideaa. 1o amidebb. diazocc. esterdd. 'R'NNRSHRRH14HHROHRCHORCNR16OCR13SROH10CRH(R' R")RCONR'2ONRCONH2OCR"RCONR'R" (R R' files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
12OCOROR'anhydrideprefix: #-acyloxyalkylcarbonyl*2suffix: -oic acidsuffix: -oic anhydride (R R')-oic -oic anhydride (R R')OCCR'NR2o amide89prefix: #-(N-alkylamido)#-(N-alkylcarbamoyl)RRsuffix: -nitrilesuffix: -#-oneH14NRR'prefix: #-oxosuffix: #-alHHthiolalcoholCRprefix: #-oxo- (in chain)or #-formyl (as branch)SHOketoneprefix: #-cyano1312O10RHaldehydenitrileR"prefix: l)suffix: -amideCCsuffix: -amidesuffix: -amidename R' as N-alkyl in front name R',R" as N-alkyl-N-alkyl in front11OR3o amideHHprefix: #-amidoor #-carbamoylprefix: #-alkoxycarbonylNN1o amidesuffix: -oate(R' name as branch at front)NROsuffix: -oyl chlorideR'HResterprefix: #-chlorocarbonylO7Racid chlorideprefix: #-carboxy*16ClCR'CRO5OCOcarboxylic acid4OCCHR3OR"15NRR'3o amineNRR'2o amineH1o amineprefix: #-hydroxyprefix: #-mercaptoor #-sulfanylprefix: #-aminoprefix: #-(N-alkylamino)prefix: #-(N-alkyl-N-alkylamino)-suffix: -#-olsuffix: -#-thiolsuffix: -#-aminesuffix: -#-aminesuffix: 20ClFRRchloroalkanefluoroalkaneprefix: #-alkoxy ( 5C)#-alkyloxy ( 5C)prefix: #-alkylthioprefix: #-bromoprefix: #-chloroprefix: #-fluorosuffix: nonesuffix: nonesuffix: nonesuffix: nonesuffix: none21R22IR23CCsuffix: noneRR26ONnitrosoalkane27Rsuffix: -#-yneNNprefix: #-azidosuffix: nonesuffix: noneCCalkenyneprefix: noneRROnitroalkaneprefix: #-nitro29suffix: none30RHRCalkanediazoalkaneRaromaticprefix: #-diazosuffix: -ane2311CC442prefix: #-alkylmany specialnamessuffix: none*1: not used because we don't use any higher priority group*2: not used because it is too complicated for our level*3: formal charge and resonance is always present.Possible stereochemical features include chiral centers,"R and S" and pi bond configurations, "E and Z".NNazidoalkaneprefix: #-nitroso*3NR*3Rsuffix: -#-en-#-yne28*3NROCalkyneprefix: nonesuffix: -#-ene25CCCalkeneprefix: noneprefix: #-iodoRRRiodoalkaneR24R'1R rectus(clockwise)Numbers (1,2,3,4) indicate priority of groups based on atomic numbers.312CC2CC21S sinister(counter clockwise)2Z zussamen(both "1"s on same side)1E entgegen("1"s on opposite side)Y:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
2D structures and condensed line formulas12OCOROOcarboxylic acidO7CRNester1o o2 amine19R'RNR'R"oBrR'R"NH18R15HRNH2SR'aldehyde1o aminethiolORCOR'NRSHROHRCHO14RROCRRCN121610OCN3o amide2 amideRacid 3CCHRO3 6H5aromaticRHalkaneY:\files\classes\Organic Chemistry Tool Chest\Nomenclature\0 Functional Groups, nomenclature, 2D, 3D, structures b.doc
and an ester is always an ester. The main variables for a functional group are highest priority (suffix) or lower priority (prefix) and what number identifies it. Alkanes prefix none suffix -ane suffix: #-ane prefix: none IUPAC: pentane 3-ethyl-2-methylpentane 1 2 5 3 alkanes - try to draw 3D structures in a zig-zag shape C R C R HH H H C C C C
Zinc (Zn) 7.09g/cm3 907 419 None None None None Manganese Dioxide (MnO2) 5.026g/cm 3 535 390 None None None None Zinc chloride (ZnCl2) 2.91g/cm 3 732 283 None Slight corrosion None None Ammonium chloride (NH 4Cl) 1.527g/cm 3 520 / None Slight corrosion None None Carbon black / / / None None None None
To Add a Prefix or Suffix: 1. Scan command barcode of " Add Prefix" or" Add Suffix ". 2. Check the prefix or suffix hex value from the ASCII Chart. 3. Scan the 2 digit hex value from the Numeric Bar Codes 4. Repeat Steps 2 and 3 for all the prefix or suffix that you want to add. 5. Scan the output format to enable or disable prefix/suffix output.
Section 12.2 – Alkanes Goal: Write the IUPAC names and draw the condensed or line-angle structural formulas for alkanes and cycloalkanes. Summary: Alkanes: a type of hydrocarbon in which the carbon atoms are connected on by single bonds. To name alkanes “(no substituents), [prefix]ane” The prefix refers to the number of carbons in the chain: .
and other prefix, suffix and root reinforcement games and activities on their own. Prefix/Suffix/Root Literacy Center Set up an area of your classroom that is dedicated to word building and vocabulary development using prefixes, suffixes and roots. Students visiting the center make webs on the Prefix, Suffix or Root Web Reproducibleusing tiles, and
Special IP Addresses THIS computer - all 0's--both prefix and suffix 0.0.0.0 THIS network broadcast - all 1's prefix and suffix 255.255.255.255 remote net broadcast - net prefix all 1's suffix Ex: 137.45.192.255 Networkaddress - net prefix all 0's suffix 137.45.192. loopback - 127.x.x.x but usually 127.0.0.1 Everything else is a HostIP Address .
[1 mark] 02.2 Which statement about alkanes and alkenes is true? Tick one box. Alkanes and alkenes are both part of a homologous series. The general formula for alkanes is C n H 2n and for alkenes is C n H 2n 2 Alkenes are saturated hydrocarbons and alkanes are unsaturated. Alkanes contain a double bond between C atoms
During 1969 the Hi-Power pistol Serial Number code was changed to a two digit year and "C" prefix. Serial Numbers for "T" prefix Hi-Power pistols exceeded T300000 and were shipped into 1970. Year ser. # PreFiX COde 1969 69C prefix before Ser. No. 1970 70C prefix before Ser. No. 1971 196471C prefix before Ser. No. 1972 72C prefix before Ser. No.
Business Bank and the UK Business Angels Association undertook a direct survey of angels across the UK. Our research gathered details of factors such as the background, expertise, portfolio composition and decision-making of over 650 individuals, creating a multi-faceted picture of the UK business angel population. This has enabled us to produce an in-depth analysis of the overall market. It .
