IB Chemistry on Homologous Series, IUPAC Nomenclature and Structural formula

Tutorial on Organic Chemistry and IUPACNomenclature . Prepared by Lawrence Kok http://lawrencekok.blogspot.com

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 melting /boiling point increases ↑ as carbon chain increases ↑

Hydrocarbon Alkane and Nomenclature Molecular Formula Actual number of atoms/elements present in a molecule Ex : C2H5CI1 – 2 Carbon, 5 Hydrogen, 1 Chlorine Structural Formula Arrangement of all atoms in a molecule Ex : H H H │ │ │ H-C– C–C-H │ │ │ H CH3 H Condensed Structural Formula Vs Displayed structural formula• branches in carbon chain are indicated in parentheses all carbon and hydrogen bonds are shown• CH3CH(CH3)CH3 H H H │ │ │ H-C– C–C-H │ │ │ H CH3 H• CH3CH(OH)CH2CH(OH)CH3 H H H H H │ │ │ │ │ H-C– C– C– C– C-H │ │ │ │ │ H OH H OH H

Nomenclature for Organic MoleculesStep 1 Name the parent (longest unbranched carbon chain) or 7 carbon - heptane 7 carbon - heptane

Nomenclature for Organic MoleculesStep 1 Name the parent (longest unbranched carbon chain) or 7 carbon - heptane 7 carbon - heptaneStep 2 Choose the chain which has more alkyl groups attached or 4 alkyl groups 3 alkyl groups

Nomenclature for Organic MoleculesStep 1 Name the parent (longest unbranched carbon chain) or 7 carbon - heptane 7 carbon - heptaneStep 2 Choose the chain which has more alkyl groups attached or 4 alkyl groups 3 alkyl groupsStep 3 Name alkyl/substituent/attached groups by adding a suffix with yl CH3 – methyl C2H5 – ethyl C3H7 – propyl C4H9 – butyl Branching groups are • methyl and ethyl

Nomenclature for Organic MoleculesStep 4 Numbering from end of chain which give substituents the lowest possible numbers √ or Numbering are 2 , 3, 4, 5 Numbering are 3, 4, 5, 6

Nomenclature for Organic MoleculesStep 4 Numbering from end of chain which give substituents the lowest possible numbers √ or Numbering are 2 , 3, 4, 5 Numbering are 3, 4, 5, 6Step 5 If 2 or more identical substituents present, assign prefixes 2 identical (Di) – 3 identical (Tri) – 4 identical (Tetra) – 5 identical (Penta) 3 identical - Trimethyl √

Nomenclature for Organic MoleculesStep 4 Numbering from end of chain which give substituents the lowest possible numbers √ or Numbering are 2 , 3, 4, 5 Numbering are 3, 4, 5, 6Step 5 If 2 or more identical substituents present, assign prefixes 2 identical (Di) – 3 identical (Tri) – 4 identical (Tetra) – 5 identical (Penta) 3 identical - Trimethyl √Step 6 Use comma, to separate numbers Use hyphen – to separate number and word 2, 4, 5 –trimethylheptane NOT 2, 4, 5 –trimethyl - heptane Write prefix and parent as one word

Nomenclature for Organic MoleculesStep 4 Numbering from end of chain which give substituents the lowest possible numbers √ or Numbering are 2 , 3, 4, 5 Numbering are 3, 4, 5, 6Step 5 If 2 or more identical substituents present, assign prefixes 2 identical (Di) – 3 identical (Tri) – 4 identical (Tetra) – 5 identical (Penta) 3 identical - Trimethyl √Step 6 Use comma, to separate numbers Use hyphen – to separate number and word 2, 4, 5 –trimethylheptane NOT 2, 4, 5 –trimethyl - heptane Write prefix and parent as one wordStep 7 Arrange the substituents according to alphabetical order 3 – ethyl – 2, 4, 5- trimethylheptane √ NOT 2, 4, 5 - trimethyl – 3 – ethylheptane X 3 – ethyl – 2, 4, 5 - trimethylheptane

Nomenclature for Organic Molecules √ X 3- ethyl- 5- methylhexane2- methyl- 4- ethylhexane

Nomenclature for Organic Molecules √ X 3- ethyl- 5- methylhexane 2- methyl- 4- ethylhexane 2, 3 - dimethylpentane 4-ethyl-2 -methylhexane2, 3, 6 – trimethyl – 4 - ethyloctane 2, 2, 4 - trimethylpentane

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 Unsaturated Unsaturated melting /boiling point increases ↑ Carbon – Carbon double bond Carbon – Carbon triple bond• C2 – C4 (gases)• C5- C10 (liquids) H2C=CH2 HC CH• Insoluble in water, soluble in organic solvent• Non conductors – simple molecules not ions

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

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

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 CH3 CH3 – C –CH – CH2CH3 ║ │ O CH3

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

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 – CH –CH – C -OH CH3 –CH – C -OH │ │ │ │ CH3 CH3 CH3 CH3

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 – CH –CH – C -OH CH3 –CH – C -OH │ │ │ │ CH3 CH3 CH3 CH3 2, 3 -dimethylbutanoic acid 3, 3–dimethylbutanoic acid 2- methylpropanoic acid

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 Primary alcohol 1 0 – Secondary alcohol 2 o – Tertiary alcohol 3 o –

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 │ H Secondary alcohol 2 o – Two alkyl group bonded to C attached to OH group CH3 │ CH3 - C – OH │ H Tertiary alcohol 3 o – Three alkyl group bonded to C attached to OH group CH3 │ CH3 - C – OH │ CH3

Nomenclature for Organic MoleculesC6– C5 – C4 – C3- C2 – C1 C4 – C3 - C2 - C1HO C5 - C4 – C3 - C2 = C1 C5 - C4 – C3 - C2 - C1 │ │ │ │ ║ C2H5 CI CH3 CH3 O C4 – C3 - C2 = C1 C3 - C2 - C1OOH C3 - C2 - C1 - OH CH3 – CH –CHO │ │ │ │ CH3 Br CH3 CH3 CH3 – CH –CH – CH3 CH3 – C = CH2 CH3 – CH –CH2 - OH CH3 – CH –CH2 – CH3 │ │ │ │ │ CH3 OH CH3 CH3 CH2OH CH3 – CH2 – CH - CI OH CH3 – CH –CH2 – CH2OH │ │ │ CH2CH3 C3 - C2 - C1 CH3 │ CH3

Nomenclature for Organic MoleculesC6– C5 – C4 – C3- C2 – C1 C4 – C3 - C2 - C1HO C5 - C4 – C3 - C2 = C1 C5 - C4 – C3 - C2 - C1 │ │ │ │ ║ C2H5 CI CH3 CH3 O 3 ethylhexane 2 – chlorobutanal 3 – methylpent –1-ene 3 methylpentan-2-one C4 – C3 - C2 = C1 C3 - C2 - C1OOH C3 - C2 - C1 - OH CH3 – CH –CHO │ │ │ │ CH3 Br CH3 CH3 2- methylbutene 3 – bromopropanoic acid 2 –methylpropan- 1-ol 2 -methylpropanal CH3 – CH –CH – CH3 CH3 – C = CH2 CH3 – CH –CH2 - OH CH3 – CH –CH2 – CH3 │ │ │ │ │ CH3 OH CH3 CH3 CH2OH 2 - methylpropene 3- methylbutan-2-ol 2- methylpropan-1-ol 2- methylbutan-1-ol CH3 – CH2 – CH - CI OH CH3 – CH –CH2 – CH2OH │ │ │ CH2CH3 C3 - C2 - C1 CH3 │ 3- methylbutan- 1-ol 3 - chloropentane CH3 2 – methylpropan – 2-ol

Nomenclature for Organic MoleculesHO-C(CH3)2 – CH2-CH2-COOH CH3-CH(OH)-CH3 CH3-CH2-CHBr-COOH CH3-C(CH3)2-CH2-CHOCH3-CH(CH3)-CO-CH2-CH3 (CH3 )3C –Br CH3 – CHBr – CH2 –CH2 -OH CH2 -C(CH3)2

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

Nomenclature for Alkene and Alcohol Molecules

Nomenclature for Alkene and Alcohol Molecules6 –chloro–3-ethylhev-1-ene 6 –chloro-2–methylhex-2-ene 3 –methylbut-1-ene 2, 3 –dimethylbut-2-ene 3 –methylpent-1-ene 2 –methylbut-2-ene 4- methylpentan-1-ol 3, 3–dimethylpentan-2-ol 2- methylbutan-2-ol 2 – methylpropan-2 -ol Pent –4-ene –2-ol

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

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IB Chemistry on Homologous Series, IUPAC Nomenclature and Structural formula

by Lawrence Kok on Apr 18, 2012

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