IB Chemistry on Functional Group, Homologous series, IUPAC Nomenclature and Structural formula
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IB Chemistry on Functional Group, Homologous series, IUPAC Nomenclature and Structural formula

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IB Chemistry on Functional Group, Homologous Series, IUPAC Nomenclature and Structural Formula

IB Chemistry on Functional Group, Homologous Series, IUPAC Nomenclature and Structural Formula

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  • 1. Hydrocarbon Alkane and NomenclatureHomologous Series Hydrocarbon• same functional group• each member differ from the next by –CH2 - group Aliphatic (open chain) Aromatic (benzene structure)• similar chemical properties• same chemical formula CnH2n+2• saturated hydrocarbon H3C CH3• ending with anePhysical properties Saturated Unsaturated• increase in RMM and molecular size down the series Carbon – Carbon single bond Carbon – Carbon double bond•RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C1 – C4 (gas) H3C CH3 H2C CH2• C5- C18 (liquid)• C19 – (solid)• Insoluble in water, soluble in organic solvent• Non conductors – simple molecules NOT ions Alkane Cycloalkane H3C CH3 CH3
  • 2. Hydrocarbon Alkene/Alkyne and NomenclatureHomologous Series Hydrocarbon• same functional group (C=C) or (C≡C)• each member differ from the next by –CH2- group Aliphatic (open chain) Aromatic (benzene structure)• similar chemical properties• chemical formula alkene - CnH2n H3C CH3• chemical formula alkyne - CnH2n-2•unsaturated hydrocarbon• alkene ending with ene Saturated Unsaturated• alkyne ending with ynePhysical properties –• increase in RMM and molecular size down the series•RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑ Unsaturated Unsaturated• C2 – C4 (gases) Carbon – Carbon double bond Carbon – Carbon triple bond• C5- C10 (liquids)• Insoluble in water, soluble in organic solvent H2C=CH2 HC CH• Non conductors – simple molecules not ions
  • 3. Hydrocarbon Aldehyde and NomenclatureHomologous Series Physical properties – • increase in RMM and molecular size down the series• functional group CO bonded to H at the end •RMM increase ↑ - Van Der Waals forces stronger• contain carbonyl group C=O melting /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 - CH3CH2CH2CHO H H H H H H H H H H │ │ │ │ │ │ │ │ │ │ H- C =O H- C – C = O H- C - C – C =O H- C - C – C – C =O │ │ │ │ │ │ H H H H H H Methanal Ethanal Propanal Butanal Nomenclature for aldehyde H H CH3 H │ │ │ │CH3 – CH –CH – C=O CH3 – CH –CH – C=O CH3 –CH – C=O │ │ │ │ CH3 CH3 CH3 CH3 2 - methylbutanal 2, 3 - dimethylbutanal 2, 2-dimethylpropanal
  • 4. 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=O •RMM 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 - CH3CH2COCH2CH2CH3 H H H H H H H H H H H H H H │ │ │ │ │ │ │ │ │ │ │ │ │ │ H- C - C – C - H H- C - C – C – C -H H- C - C – C – C – C - H H- C - C – C – C – C – C – H │ ║ │ │ │ ║ │ │ │ ║ │ │ │ │ ║ │ │ │ H O H H H O H H H O H H H H O H H H Propanone Butan- 2 - one Pentan- 3-one Hexan-3 - one Nomenclature for ketone CH3 CH3 │ │ CH3 – C –CH – CH3 CH3 – CH – C – CH- CH3 CH3 – C –C – CH3 ║ │ ║ │ ║ │ O CH3 O CH3 O CH33, 3 dimethylbutanone 3- methylbutanone 2, 4 dimethylpentan- 3-one CH3 – C –CH – CH2CH3 ║ │ O CH3 3- methylpentan-2-one
  • 5. Hydrocarbon Carboxylic Acid and NomenclatureHomologous Series Physical 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- group melting /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 - CH3CH2CH2CH2CH2COOH H H O H H H O H H H H O H H H H H O │ │ ║ │ │ │ ║ │ │ │ │ ║ │ │ │ │ │ ║ H- C - C – C - OH H- C - C – C – C -OH H- C - C – C – C – C - OH H- C - C – C – C – C – C - OH │ │ │ │ │ │ │ │ │ │ │ │ │ │ H H H H H H H H H H H H H H Propanoic acid Butanoic acid Pentanoic acid Hexanoic acidNomenclature for carboxylic acid O CH3 O O ║ │ ║ ║ CH3 – CH –CH – C -OH CH3 – C –CH – C -OH CH3 –CH – C -OH │ │ │ │ CH3 CH3 CH3 CH3 2, 3 -dimethylbutanoic acid 3, 3–dimethylbutanoic acid 2- methylpropanoic acid
  • 6. Hydrocarbon Alcohol and NomenclatureHomologous Series•same functional group hydroxyl (OH)• each member differ from the next by –CH2 - group•same chemical formula alcohol - CnH2n+1OH•ending with ol• Methanol - CH3OH• Ethanol - CH3CH2OH Propanol – CH3CH2CH2OH H H H H H H │ │ │ │ │ │ H- C - C – C - H H- C - C – C - H │ │ │ │ │ │ H H OH H OH H Propan – 1-ol Propan – 2-ol Butanol – CH3CH2CH2CH2OH H H H H H H H H H H H H OH H │ │ │ │ │ │ │ │ │ │ │ │ │ │ H- C - C – C – C - H H- C - C – C – C - H H- C - C – C – OH H- C - C – C – H │ │ │ │ │ │ │ │ │ │ │ │ │ │ H H H OH H H OH H H CH3 H H CH3 H Butan–1-ol Butan–2-ol 2- Methylpropan-1-ol 2- 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 group CH3 │ 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
  • 7. 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, I H 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 halogenoalkane CH3 - 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 Halogenoalkane │ CH3 H H H H CH3 H H CH3 H │ │ │ │ │ │ │ │ │ H- C - C – C – C - Br CH3 - C – C -Br H- C - C – C – Br Primary halogenoalkane 1 0 │ │ │ │ │ │ │ │ │ H H H H H H H CH3 H 1- bromo- 2 -methylpropane 1- bromo-2, 2 - dimethylpropane 1- Bromobutane CH3 H CH3 H 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 H 2- bromopropane 2- Bromobutane 2 – 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 -methylpropane 2-bromo-2-methylpropane
  • 8. 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 - H CH3 - N – H CH3 - N │ Secondary amine 2 o – Two alkyl group bonded to N CH3 Tertiary amine 3 o – Three alkyl group bonded to N Nomenclature for Amines CH3 │ CH3 -CH – NH2 CH3 -CH – CH2-CH2-CH3 CH3 -C – NH2 CH3 -CH – C- NH2 │ │ │ │ Primary amine 1 0 CH3 NH2 CH3 CH3 propan– 2-amine pentan–2-amine 2- methylpropan–2-amine 2- methylpropan–1-amine CH3 -N -H C2H5 -N -H │ │ Secondary amine 2 0 CH2-CH3 CH2-CH2CH3 N - methylethanamine N - ethylpropanamine CH3 -N –CH3 C3H7 -N –CH3 CH3 │ │ │ Tertiary amine 3 0 C2H5 C2H5 CH3 - NN, N - dimethylethanamine N- ethyl-N- methylpropanamine │ CH3 N, N– dimethylmethanamine
  • 9. 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 Ethanol Methanoic acid Ethanol CH3 - C –O - H H - C -OH ║ + CH3 – CH2 –OH ║ + CH3 – CH2 –OH O O O Ethyl methanoateethanoate O Ethyl ║ ║ CH3 –C –O – CH2 CH3 H –C –O – CH2 CH3 Ethyl ethanoate Ethyl methanoate Ethanoic acid Propanol Ethanoic acid Methanol CH3 - C –O -H CH3 - C –O- H ║ + CH3 -CH2–CH2–OH ║ + CH3 - OH O Oethanoate Methyl O Propyl ethanoate O ║ ║ CH3 –C –O –CH2-CH2 CH3 CH3 –C –O – CH3 Propyl ethanoate Methyl ethanoate
  • 10. Hydrocarbon Amide and NomenclatureHomologous Series•functional 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 acid Ammonia Ethanoic acid Methanamine CH3 - C –O -H H CH3 - C –O - H H ║ + │ ║ + │ O H- N - H O H- N-CH3 O H O H Primary amide 1 0 ║ │ ║ │ CH3 –C –N- CH3 CH3 –C –N- H Ethanamide N-methylethanamide Propanoic acid Ethanamine Propanoic acid N - methylethanamine C2H5 - C –O- H H C2H5 - C –O- H CH3 ║ + │ ║ + │ O H- N-C2H5 O H- N-C2H5 O H O CH3 ║ │ Secondary amide 2 0 ║ │ Tertiary amide 3 0 C2H5 –C –N- C2H5 C2H5 –C –N- C2H5 N-ethylpropanamide N-ethyl- N methylpropanamide
  • 11. Hydrocarbon Nitrile and Nomenclature Homologous Series • same functional group C≡N or nitrile group • each member differ from the next by –CH2 - group • similar chemical properties • same chemical formula CnH2n+1CN • ending with nitrile Ethanenitrile - CH3-C ≡ N Propanenitrile - CH3CH2-C ≡ N Butanenitrile - CH3CH2CH2-C ≡ N Hydrocarbon Amide Nomenclature O H O CH3 O H O H ║ │ ║ │ ║ │ ║ │ CH3 –C –N- H C2H5 –C –N- C2H5 CH3 –C –N- CH3 C2H5 –C –N- C2H5 Ethanamide N-ethyl- N methylpropanamide N-methylethanamide N-ethylpropanamide O CH3 O O CH3 ║ │ ║ ║ │ C2H5 –C –N- C2H5 CH3 -CH –C –NH2 CH3 –C –N- CH3 │N-ethyl- N methylpropanamide CH3 N, N dimethylethanamide 2- methylpropanamide
  • 12. Hydrocarbon Amine Nomenclature C3H7 -N –CH3 CH3 -N –CH3 C2H5 -N – C2H5 │ │ │ C2H5 CH3 H2N – C- C- C- C- C- C - NH2 HN- ethyl-N- methylpropanamine N, N, dimethylmethanamine Hexane – 1,6, - diamine N- ethylethanamine Hydrocarbon Halogenoalkane Nomenclature CH3 H CI H CH3 H CH3 │ │ │ │ │ │ │ CH3 - C – C -Br Br Br H- C - C – C – Br C- C - C – CI CH3 - C – Br │ │ │ │ │ │ │ │ │ H H CH2 – CH2 H CH3 H CH3 CI1- bromo-2-methylpropane 1,1,1-trichloropropane 1,2-dibromoethane 1-bromo-2,2-dimethylpropane 2- bromo-2-methylpropane Hydrocarbon Ester Nomenclature O O O O ║ ║ ║ ║ H –C –O – CH2 CH3 CH3 –C –O – CH3 CH3 –O – C- CH3 H- C–O – CH3 Ethyl methanoate Methyl ethanoate Methyl ethanoate Methyl methanoate O O ║ ║ CH3 –C –O – CH2 CH2 CH3 CH3 –CH2 – O – C- CH2 CH3 Propyl ethanoate Ethyl propanoate
  • 13. Hydrocarbon Alcohol NomenclatureCH3 – CH –CH2 - OH C3 - C2 - C1 - OH CH3 – CH –CH2 – CH3 CH3 – CH –CH2 – CH2OH │ │ │ │ CH3 CH3 CH2OH CH32- methylpropan-1-ol 2 –methylpropan-1-ol 2- methylbutan-1-ol 3- methylbutan- 1-ol OH │ CH3 – CH –CH – CH3 C3 - C2 - C1 │ │ │ CH3 OH CH33- methylbutan-2-ol 2 –methylpropan–2-ol Hydrocarbon Aldehyde/Ketone Nomenclature C4 – C3 - C2 - C1HO CH3 – CH –CHO C5 - C4 – C3 - C2 - C1 │ │ │ ║ CI CH3 CH3 O 2 – chlorobutanal 2 -methylpropanal 3 methylpentan-2-one Hydrocarbon Alkane/alkene NomenclatureC 6– C 5 – C 4 – C 3- C 2 – C 1 CH3 – C = CH2 C4 – C3 - C2 = C 1 C5 - C4 – C3 - C2 = C1 │ │ │ │ C2H5 CH3 CH3 CH3 3 ethylhexane 2 - methylpropene 2- methylbutene 3 –methylpent–1-ene
  • 14. Nomenclature for Hydrocarbon with more than 1 functional groupMore complicated NomenclatureIf more than 1 functional group present•Principal functional group define the ending and other functional groups and side chains are indicated as prefixes HO – C - C -CHO HO – C- C - COOH │ │ CH3 CH3 Side chain Parent chain Side chain Parent chain 3-hydroxy- 2-methylpropanal 3-hydroxy- 2-methylpropanoic acid CH3 CH3 │ │ HO – C –CH2- CH2 – COOH HO– CH2 –CH =CH – COOH │ CH3 Parent chain Side chain Side chain Parent chain 4-hydroxy- 3-methylbut-2-enoic acid 4-hydroxy- 4-methylpentanoic acid C – C- C - COOH C – C- C – CH2OH │ │ Br Br Side chain Parent chain Side chain Parent chain 2-bromobutanoic acid 2-bromobutan-1-ol
  • 15. Nomenclature for Organic Molecules HO-C(CH3)2 – CH2-CH2-COOH CH3-CH(OH)-CH34- hydroxy- 4 –methylpentanoic acid propan- 2–ol CH3-CH2-CHBr-COOH CH3-C(CH3)2-CH2-CHO 2- bromobutanoic acid 3, 3 – dimethylbutanal CH3-CH(CH3)-CO-CH2-CH3 (CH3 )3C –Br 2 –methylpentan –3-one 2- bromo- 2-methylpropane CH3 – CHBr – CH2 –CH2 -OH CH2 -C(CH3)2 3- bromo-butan-1-ol 2- methylpropene