1. Tutorial on Functional Group, HomologousSeries and IUPAC Nomenclature for HLChemistry . Prepared by Lawrence Kok http://lawrencekok.blogspot.com

2. Hydrocarbon Alkane and NomenclatureHomologous SeriesHydrocarbon same functional group each member differ from the next by CH2 - groupAliphatic (open chain) Aromatic (benzene structure) similar chemical properties same chemical formula CnH2n+2 saturated hydrocarbon H3CCH3 ending with anePhysical properties Saturated Unsaturated increase in RMM and molecular size down the seriesCarbon Carbon single bond Carbon Carbon double bondRMM increase - Van Der Waals forces stronger melting /boiling point increases C1 C4 (gas)H3CCH3 H2C CH2 C5- C18 (liquid) C19 (solid) Insoluble in water, soluble in organic solvent Non conductors simple molecules NOT ions Alkane Cycloalkane H3CCH3CH3 3. Hydrocarbon Alkene/Alkyne and NomenclatureHomologous SeriesHydrocarbon same functional group (C=C) or (CC) each member differ from the next by CH2- groupAliphatic (open chain) Aromatic (benzene structure) similar chemical properties chemical formula alkene - CnH2nH3CCH3 chemical formula alkyne - CnH2n-2unsaturated hydrocarbon alkene ending with ene SaturatedUnsaturated alkyne ending with ynePhysical properties increase in RMM and molecular size down the seriesRMM increase - Van Der Waals forces stronger melting /boiling point increases UnsaturatedUnsaturated C2 C4 (gases)Carbon Carbon double bondCarbon Carbon triple bond C5- C10 (liquids) Insoluble in water, soluble in organic solvent H2C=CH2 HCCH Non conductors simple molecules not ions 4. Hydrocarbon Aldehyde and NomenclatureHomologous Series Physical properties increase in RMM and molecular size down the series functional group CO bonded to H at the endRMM increase - Van Der Waals forces stronger contain carbonyl group C=Omelting /boiling point increases each member differ from the next by CH2- group C1 gas similar chemical properties C2- C10 - liquids chemical formula aldehyde - CnH2nO Methanal CH2O aldehyde ending with al Ethanal - CH3CHO Propanal CH3CH2CHO Butanal - CH3CH2CH2CHOHH H H H HH H H H H- C =OH- C C = O H- C - C C =O H- C - C C C =O HH H H H HMethanal Ethanal Propanal Butanal Nomenclature for aldehydeH HCH3 H CH3 CH CH C=OCH3 CH CH C=OCH3 CH C=O CH3 CH3 CH3CH32 - methylbutanal2, 3 - dimethylbutanal2, 2-dimethylpropanal 5. Hydrocarbon Ketone and NomenclatureHomologous Series Physical properties functional group CO bonded to two hydrocarbon increase in RMM and molecular size down the series contain carbonyl group C=ORMM increase - Van Der Waals forces stronger each member differ from the next by CH2- group melting /boiling point increases similar chemical properties C1 gas chemical formula ketone - CnH2nO C2- C10 - liquids ketone ending with one Propanone CH3COCH3 Butanone- CH3CH2COCH3 Pentan-3-one -CH3CH2COCH2CH3 Hexan-3-one - CH3CH2COCH2CH2CH3H HH H HH H H H H H H H H H- C - C C - H H- C - C C C -HH- C - C C C C - HH- C - C C C C C H H O HH H O HH H O H H H H O H H HPropanoneButan- 2 - one Pentan- 3-one Hexan-3 - one Nomenclature for ketone CH3CH3 CH3 C CH CH3 CH3 CH C CH- CH3 CH3 C C CH3 O CH3O CH3 O CH33, 3 dimethylbutanone3- methylbutanone2, 4 dimethylpentan- 3-oneCH3 C CH CH2CH3 O CH33- methylpentan-2-one 6. Hydrocarbon Carboxylic Acid and NomenclatureHomologous SeriesPhysical properties functional group COOH increase in RMM and molecular size down the series contain carbonyl group C=O RMM increase - Van Der Waals forces stronger each member differ from the next by CH2- groupmelting /boiling point increases similar chemical properties Propanoic acid CH3CH2COOH chemical formula carboxylic acid - CnH2n+1COOH or CnH2nO2 Butanoic acid - CH3CH2CH2COOH acid ending with oic Pentanoic acid - CH3CH2CH2CH2COOH Hexanoic acid - CH3CH2CH2CH2CH2COOHH H OH H H OH H H H O H H H H H O H- C - C C - OHH- C - C C C -OH H- C - C C C C - OH H- C - C C C C C - OH H HH H HH H H H H H H H HPropanoic acid Butanoic acidPentanoic acidHexanoic acidNomenclature for carboxylic acid OCH3 O O CH3 CH CH C -OH CH3 C CH C -OH CH3 CH C -OH CH3 CH3CH3CH3 2, 3 -dimethylbutanoic acid3, 3dimethylbutanoic acid2- methylpropanoic acid 7. Hydrocarbon Alcohol and NomenclatureHomologous Seriessame functional group hydroxyl (OH) each member differ from the next by CH2 - groupsame chemical formula alcohol - CnH2n+1OHending with ol Methanol - CH3OH Ethanol - CH3CH2OH Propanol CH3CH2CH2OH H H HH H H H- C - C C - H H- C - C C - H H H OH H OH H Propan 1-olPropan 2-ol Butanol CH3CH2CH2CH2OH H H H HH H H H H H H H OH H H- C - C C C - HH- C - C C C - H H- C - C C OHH- C - C C H H H H OHH H OH H H CH3 HH CH3 H Butan1-olButan2-ol2- Methylpropan-1-ol 2- Methylpropan-2-ol 8. Hydrocarbon Alcohol and NomenclatureHomologous Seriessame functional group hydroxyl (OH) each member differ from the next by CH2 - groupsame chemical formula alcohol - CnH2n+1OHending with ol Methanol - CH3OH Ethanol - CH3CH2OH Propanol CH3CH2CH2OH H H HH H H H- C - C C - H H- C - C C - H H H OH H OH H Propan 1-olPropan 2-ol Butanol CH3CH2CH2CH2OH H H H HH H H H H H HH OH H H- C - C C C - HH- C - C C C - H H- C - C C OH H- C - C C H H H H OHH H OH H H CH3 H H CH3 H Butan1-olButan2-ol2- Methylpropan-1-ol2- Methylpropan-2-ol Types of alcohol H Primary alcohol 1 0 One alkyl group bonded to C attached to OH group CH3 - C OH Primary alcohol 1 0 H Secondary alcohol 2 o Two alkyl group bonded to C attached to OH groupCH3 Secondary alcohol 2 0 CH3 - C OH H Tertiary alcohol 3 o Three alkyl group bonded to C attached to OH group CH3 CH3 - C OH Tertiary alcohol 3 0 CH3 9. Hydrocarbon Halogenoalkane and NomenclatureHomologous Series Hydrogen atom on alkane replaced by halogen atom chemical formula - CnH2n+1X, X is a halogen, F, CI, Br, IH H each member differ from the next by CH2 - group CH3 - C Br or H - C Br Bromomethane CH3Br Bromoethane - CH3CH2Br H H Bromopropane CH3CH2CH2Br CH3 Types of halogenoalkaneCH3 - C BrPrimary 1 0 One or NO alkyl group bond to C attach to halogen group HSecondary 2 o Two alkyl group bond to C attach to halogen groupCH3Tertiary 3 o Three alkyl group bond to C attach to halogen group CH3 - C BrNomenclature for Halogenoalkane CH3 H H H HCH3 H H CH3 H H- C - C C C - BrCH3 - C C -BrH- C - C C Br H H H H H H H CH3 H CH3H CH3H H H H C - C C C C- CCH3 - C Br H- C - C C C - H BrH H H Br HCH3 H Br H CH3 - C Br H- C - C C H CH3 H CH3 H 10. Hydrocarbon Halogenoalkane and Nomenclature Homologous Series Hydrogen atom on alkane replaced by halogen atom chemical formula - CnH2n+1X, X is a halogen, F, CI, Br, IH H each member differ from the next by CH2 - group CH3 - C Br or H - C Br Bromomethane CH3Br Bromoethane - CH3CH2Br H H Bromopropane CH3CH2CH2BrCH3 Types of halogenoalkaneCH3 - C Br Primary 1 0 One or NO alkyl group bond to C attach to halogen group H Secondary 2 o Two alkyl group bond to C attach to halogen group CH3 Tertiary 3 o Three alkyl group bond to C attach to halogen group CH3 - C Br Nomenclature for HalogenoalkaneCH3H H H HCH3 H H CH3 H H- C - C C C - BrCH3 - C C -BrH- C - C C Br Primary halogenoalkane 1 0 H H H H H H H CH3 H1- bromo- 2 -methylpropane1- bromo-2, 2 - dimethylpropane1- BromobutaneCH3HCH3H H H H Secondary halogenoalkane 2 0 C - C C C C- C CH3 - C Br H- C - C C C - H Br H H H Br H2- bromopropane2- Bromobutane2 Bromo 4-methylhexane CH3 H Br H Tertiary halogenoalkane 3 0 CH3 - C Br H- C - C C H CH3 H CH3 H2- bromo- 2 -methylpropane2-bromo-2-methylpropane 11. Hydrocarbon Amines and NomenclatureHomologous Seriessame functional - amine or amino group NH2 each member differ from the next by CH2 groupformed when hydrogen atom of NH3 is replaced by alkyl groupssame chemical formula alcohol - CnH2n+1NH2ending with suffix amine Methanamine CH3NH2 Ethanamine - CH3CH2NH2 Propanamine CH3CH2CH2NH2 H CH3CH3Types of amines Primary amine 1 0 One alkyl group bonded to NCH3 N - HCH3 - N H CH3 - N Secondary amine 2 o Two alkyl group bonded to NCH3Tertiary amine 3 o Three alkyl group bonded to NNomenclature for Amines CH3 CH3 -CH NH2 CH3 -CH CH2-CH2-CH3 CH3 -C NH2 CH3 -CH C- NH2 CH3 NH2 CH3CH3CH3 -N -H C2H5 -N -H CH2-CH3 CH2-CH2CH3CH3 -N CH3 C3H7 -N CH3 CH3 C2H5C2H5CH3 - N CH3 12. Hydrocarbon Amines and Nomenclature Homologous Series same functional - amine or amino group NH2 each member differ from the next by CH2 group formed when hydrogen atom of NH3 is replaced by alkyl groups same chemical formula alcohol - CnH2n+1NH2 ending with suffix amine Methanamine CH3NH2 Ethanamine - CH3CH2NH2 Propanamine CH3CH2CH2NH2 H CH3 CH3 Types of amines Primary amine 1 0 One alkyl group bonded to N CH3 N - HCH3 - N HCH3 - N Secondary amine 2 o Two alkyl group bonded to NCH3 Tertiary amine 3 o Three alkyl group bonded to N Nomenclature for AminesCH3CH3 -CH NH2 CH3 -CH CH2-CH2-CH3CH3 -C NH2 CH3 -CH C- NH2 Primary amine 1 0 CH3 NH2CH3CH3 propan 2-amine pentan2-amine 2- methylpropan2-amine2- methylpropan1-amine CH3 -N -H C2H5 -N -HSecondary amine 2 0CH2-CH3 CH2-CH2CH3N - methylethanamine N - ethylpropanamine CH3 -N CH3 C3H7 -N CH3CH3 Tertiary amine 3 0C2H5C2H5 CH3 - NN, N - dimethylethanamineN- ethyl-N- methylpropanamine CH3N, N dimethylmethanamine 13. Hydrocarbon Ester and NomenclatureHomologous Seriesfunctional group COO bonded between acid and alcohol functional group carboxylate COO- chemical formula ester - CnH2nO2 ending with oate Esterification of ester ethyl ethanoate from ethanol and ethanoic acidrequires sulphuric acid as a catalyst (reversible reaction)Ethanoic acid EthanolMethanoic acid EthanolCH3 - C O - H H - C -OH+ CH3 CH2 OH + CH3 CH2 OHOOEthanoic acid PropanolEthanoic acid Methanol CH3 - C O -HCH3 - C O- H +CH3 -CH2CH2OH +CH3 - OH OO 14. Hydrocarbon Ester and NomenclatureHomologous Seriesfunctional group COO bonded between acid and alcohol functional group carboxylate COO- chemical formula ester - CnH2nO2 ending with oate Esterification of ester ethyl ethanoate from ethanol and ethanoic acidrequires sulphuric acid as a catalyst (reversible reaction)Ethanoic acid EthanolMethanoic acid EthanolCH3 - C O - H H - C -OH+ CH3 CH2 OH + CH3 CH2 OHOO OO CH3 C O CH2 CH3H C O CH2 CH3 Ethyl ethanoate Ethyl methanoateEthanoic acid PropanolEthanoic acid Methanol CH3 - C O -HCH3 - C O- H +CH3 -CH2CH2OH + CH3 - OH OO OO CH3 C O CH2-CH2 CH3CH3 C O CH3 Propyl ethanoateMethyl ethanoate 15. Hydrocarbon Ester and Nomenclature Homologous Series functional group COO bonded between acid and alcohol functional group carboxylate COO- chemical formula ester - CnH2nO2 ending with oate Esterification of ester ethyl ethanoate from ethanol and ethanoic acid requires sulphuric acid as a catalyst (reversible reaction) Ethanoic acid EthanolMethanoic acid Ethanol CH3 - C O - H H - C -OH + CH3 CH2 OH + CH3 CH2 OH OOO Ethyl methanoateethanoateO Ethyl CH3 C O CH2 CH3H C O CH2 CH3Ethyl ethanoate Ethyl methanoateEthanoic acidPropanolEthanoic acid MethanolCH3 - C O -HCH3 - C O- H +CH3 -CH2CH2OH + CH3 - OHOOethanoate MethylOPropyl ethanoateOCH3 C O CH2-CH2 CH3 CH3 C O CH3Propyl ethanoateMethyl ethanoate 16. Hydrocarbon Amide and NomenclatureHomologous Seriesfunctional group CONH bonded between carboxylic acid + amine/ammonia functional group amide link C N - O H ending with amide amide link formed by condensation reaction (loss of water molecule)Ethanoic acidAmmonia Ethanoic acidMethanamineCH3 - C O -H HCH3 - C O - H H++ OH- N - HO H- N-CH3 Propanoic acidEthanamine Propanoic acid N - methylethanamineC2H5 - C O- H H C2H5 - C O- H CH3 + + OH- N-C2H5 OH- N-C2H5 17. Hydrocarbon Amide and NomenclatureHomologous Seriesfunctional group CONH bonded between carboxylic acid + amine/ammonia functional group amide link C N - O H ending with amide amide link formed by condensation reaction (loss of water molecule)Ethanoic acidAmmoniaEthanoic acidMethanamineCH3 - C O -H H CH3 - C O - H H+ +OH- N - H O H- N-CH3 O H O H CH3 C N- CH3CH3 C N- HEthanamideN-methylethanamide Propanoic acidEthanaminePropanoic acidN - methylethanamineC2H5 - C O- H H C2H5 - C O- H CH3 + + OH- N-C2H5 OH- N-C2H5 O HO CH3 C2H5 C N- C2H5 C2H5 C N- C2H5N-ethylpropanamideN-ethyl- N methylpropanamide 18. Hydrocarbon Amide and NomenclatureHomologous Seriesfunctional group CONH bonded between carboxylic acid + amine/ammonia functional group amide link C N - O H ending with amide amide link formed by condensation reaction (loss of water molecule)Ethanoic acidAmmoniaEthanoic acidMethanamineCH3 - C O -H H CH3 - C O - H H+ +OH- N - H O H- N-CH3 O H O HPrimary amide 1 0 CH3 C N- CH3CH3 C N- HEthanamideN-methylethanamide Propanoic acidEthanamine Propanoic acid N - methylethanamineC2H5 - C O- H H C2H5 - C O- H CH3 + + OH- N-C2H5 OH- N-C2H5 O HO CH3 Secondary amide 2 0 Tertiary amide 3 0C2H5 C N- C2H5 C2H5 C N- C2H5N-ethylpropanamideN-ethyl- N methylpropanamide 19. Hydrocarbon Nitrile and NomenclatureHomologous Series same functional group CN or nitrile group each member differ from the next by CH2 - group similar chemical properties same chemical formula CnH2n+1CN ending with nitrileEthanenitrile - CH3-C NPropanenitrile - CH3CH2-C NButanenitrile - CH3CH2CH2-C NHydrocarbon Amide Nomenclature O HO CH3O H O H CH3 C N- HC2H5 C N- C2H5CH3 C N- CH3 C2H5 C N- C2H5O CH3 OO CH3 C2H5 C N- C2H5 CH3 -CH C NH2CH3 C N- CH3CH3 20. Hydrocarbon Nitrile and NomenclatureHomologous Series same functional group CN or nitrile group each member differ from the next by CH2 - group similar chemical properties same chemical formula CnH2n+1CN ending with nitrileEthanenitrile - CH3-C NPropanenitrile - CH3CH2-C NButanenitrile - CH3CH2CH2-C NHydrocarbon Amide Nomenclature O HO CH3O H O H CH3 C N- HC2H5 C N- C2H5CH3 C N- CH3 C2H5 C N- C2H5Ethanamide N-ethyl- N methylpropanamide N-methylethanamide N-ethylpropanamide O CH3O O CH3 C2H5 C N- C2H5CH3 -CH C NH2 CH3 C N- CH3N-ethyl- N methylpropanamideCH3N, N dimethylethanamide 2- methylpropanamide 21. Hydrocarbon Amine NomenclatureC3H7 -N CH3 CH3 -N CH3 C2H5 -N C2H5 C2H5CH3H2N C- C- C- C- C- C - NH2HHydrocarbon Halogenoalkane Nomenclature CH3HCIH CH3 H CH3 CH3 - C C -Br BrBrH- C - C C BrC- C - C CI CH3 - C Br H HCH2 CH2H CH3 H CH3 CIHydrocarbon Ester NomenclatureO O OO H C O CH2 CH3CH3 C O CH3 CH3 O C- CH3H- CO CH3OOCH3 C O CH2 CH2 CH3CH3 CH2 O C- CH2 CH3 22. Hydrocarbon Amine Nomenclature C3H7 -N CH3 CH3 -N CH3C2H5 -N C2H5 C2H5CH3H2N C- C- C- C- C- C - NH2 HN- ethyl-N- methylpropanamine N, N, dimethylmethanamine Hexane 1,6, - diamineN- ethylethanamine Hydrocarbon Halogenoalkane Nomenclature CH3H CIH CH3 H CH3 CH3 - C C -Br BrBr H- C - C C Br C- C - C CI CH3 - C Br H HCH2 CH2 H CH3 H CH3CI1- bromo-2-methylpropane1,1,1-trichloropropane1,2-dibromoethane 1-bromo-2,2-dimethylpropane 2- bromo-2-methylpropane Hydrocarbon Ester NomenclatureOOO O H C O CH2 CH3CH3 C O CH3CH3 O C- CH3 H- CO CH3 Ethyl methanoate Methyl ethanoate Methyl ethanoate Methyl methanoateO O CH3 C O CH2 CH2 CH3 CH3 CH2 O C- CH2 CH3 Propyl ethanoateEthyl propanoate 23. Hydrocarbon Alcohol NomenclatureCH3 CH CH2 - OHC3 - C2 - C1 - OHCH3 CH CH2 CH3CH3 CH CH2 CH2OH CH3 CH3CH2OHCH3OH CH3 CH CH CH3C3 - C2 - C1 CH3 OH CH3Hydrocarbon Aldehyde/Ketone Nomenclature C4 C3 - C2 - C1HO CH3 CH CHO C5 - C4 C3 - C2 - C1 CICH3 CH3 OHydrocarbon Alkane/alkene NomenclatureC6 C5 C4 C3- C2 C1CH3 C = CH2C4 C3 - C2 = C1 C5 - C4 C3 - C2 = C1 C2H5CH3 CH3 CH3 24. Hydrocarbon Alcohol NomenclatureCH3 CH CH2 - OH C3 - C2 - C1 - OHCH3 CH CH2 CH3 CH3 CH CH2 CH2OH CH3CH3CH2OH CH32- methylpropan-1-ol2 methylpropan-1-ol 2- methylbutan-1-ol 3- methylbutan- 1-ol OHCH3 CH CH CH3 C3 - C2 - C1 CH3 OHCH33- methylbutan-2-ol 2 methylpropan2-olHydrocarbon Aldehyde/Ketone Nomenclature C4 C3 - C2 - C1HOCH3 CH CHOC5 - C4 C3 - C2 - C1 CI CH3CH3 O2 chlorobutanal2 -methylpropanal3 methylpentan-2-one Hydrocarbon Alkane/alkene NomenclatureC6 C5 C4 C3- C2 C1 CH3 C = CH2C4 C3 - C2 = C1C5 - C4 C3 - C2 = C1 C2H5 CH3 CH3CH3 3 ethylhexane2 - methylpropene 2- methylbutene 3 methylpent1-ene 25. Nomenclature for Hydrocarbon with more than 1 functional groupMore complicated NomenclatureIf more than 1 functional group presentPrincipal functional group define the ending and other functional groups and side chains are indicated as prefixesHO C - C -CHOHO C- C - COOH CH3 CH3CH3 CH3 HO C CH2- CH2 COOHHO CH2 CH =CH COOHCH3 C C- C - COOH C C- C CH2OHBrBr 26. Nomenclature for Hydrocarbon with more than 1 functional groupMore complicated NomenclatureIf more than 1 functional group presentPrincipal functional group define the ending and other functional groups and side chains are indicated as prefixes HO C - C -CHOHO C- C - COOH CH3 CH3Side chain Parent chainSide chain Parent chain3-hydroxy- 2-methylpropanal3-hydroxy- 2-methylpropanoic acidCH3CH3 HO C CH2- CH2 COOH HO CH2 CH =CH COOHCH3Parent chainSide chainSide chain Parent chain4-hydroxy- 3-methylbut-2-enoic acid4-hydroxy- 4-methylpentanoic acid C C- C - COOH C C- C CH2OHBrBrSide chain Parent chainSide chain Parent chain2-bromobutanoic acid 2-bromobutan-1-ol 27. Nomenclature for Organic MoleculesHO-C(CH3)2 CH2-CH2-COOHCH3-CH(OH)-CH3 CH3-CH2-CHBr-COOHCH3-C(CH3)2-CH2-CHOCH3-CH(CH3)-CO-CH2-CH3(CH3 )3C BrCH3 CHBr CH2 CH2 -OHCH2 -C(CH3)2 28. Nomenclature for Organic Molecules HO-C(CH3)2 CH2-CH2-COOHCH3-CH(OH)-CH34- hydroxy- 4 methylpentanoic acid propan- 2olCH3-CH2-CHBr-COOHCH3-C(CH3)2-CH2-CHO 2- bromobutanoic acid3, 3 dimethylbutanalCH3-CH(CH3)-CO-CH2-CH3 (CH3 )3C Br2 methylpentan 3-one2- bromo- 2-methylpropaneCH3 CHBr CH2 CH2 -OH CH2 -C(CH3)23- bromo-butan-1-ol 2- methylpropene 29. AcknowledgementsThanks to source of pictures and video used in this presentationThanks to Creative Commons for excellent contribution on licenseshttp://creativecommons.org/licenses/Prepared by Lawrence KokCheck out more video tutorials from my site and hope you enjoy this tutorialhttp://lawrencekok.blogspot.com