IB Chemistry on Homologous Series, IUPAC Nomenclature and Structural formula

http://lawrencekok.blogspot.com

Prepared by Lawrence Kok

Tutorial on Organic Chemistry and IUPAC Nomenclature .

http://lawrencekok.blogspot.com/


Homologous Series• same functional group• each member differ from the next by –CH2 - group• similar chemical properties• same chemical formula CnH2n+2

• saturated hydrocarbon• ending with ane

Physical properties • increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C1 – C4 (gas)• C5- C18 (liquid)• C19 – (solid)• Insoluble in water, soluble in organic solvent• Non conductors – simple molecules NOT ions

Hydrocarbon Alkane and Nomenclature

Aliphatic (open chain) Aromatic (benzene structure)

Saturated Carbon – Carbon single bond

UnsaturatedCarbon – Carbon double bond

Alkane Cycloalkane

melting /boiling point increases ↑ as carbon chain increases ↑

Hydrocarbon

CH3CH3 CH3

CH3 CH3

CH3 CH3 CH2 CH2

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

• CH3CH(OH)CH2CH(OH)CH3

Molecular Formula Actual number of atoms/elements present in a moleculeEx : C2H5CI1 – 2 Carbon, 5 Hydrogen, 1 Chlorine

Structural Formula Arrangement of all atoms in a moleculeEx :

H H H │ │ │ H - C – C – C - H │ │ │ H CH3

H

H H H H H │ │ │ │ │ H - C – C – C – C – C - H │ │ │ │ │ H OH H OH H

H H H │ │ │ H - C – C – C - H │ │ │ H CH3

H

Hydrocarbon Alkane and Nomenclature

Nomenclature for Organic Molecules

Name the parent (longest unbranched carbon chain)

7 carbon - heptane

or

7 carbon - heptane

Step 1



Choose the chain which has more alkyl groups attached

7 carbon - heptane

or

or

7 carbon - heptane

Step 1

Step 2

3 alkyl groups 4 alkyl groups



Choose the chain which has more alkyl groups attached

Name alkyl/substituent/attached groups by adding a suffix with ylCH3 – methylC2H5 – ethylC3H7 – propylC4H9 – butyl

7 carbon - heptane

or

or

7 carbon - heptane

Branching groups are• methyl and ethyl

Step 1

Step 2

Step 3

3 alkyl groups 4 alkyl groups

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


If 2 or more identical substituents present, assign prefixes2 identical (Di) – 3 identical (Tri) – 4 identical (Tetra) – 5 identical (Penta)

√ or



Step 5

√3 identical - Trimethyl



2, 4, 5 –trimethylheptane NOT 2, 4, 5 –trimethyl - heptane Use comma, to separate numbersUse hyphen – to separate number and wordWrite prefix and parent as one word

√ or



Step 5

Step 6

√3 identical - Trimethyl



2, 4, 5 –trimethylheptane NOT 2, 4, 5 –trimethyl - heptane Use comma, to separate numbersUse hyphen – to separate number and wordWrite prefix and parent as one word

3 – ethyl – 2, 4, 5- trimethylheptane NOT 2, 4, 5 - trimethyl – 3 – ethylheptane

Arrange the substituents according to alphabetical order

√ or



Step 5

Step 6

Step 7

√ X

√

3 – ethyl – 2, 4, 5 - trimethylheptane

3 identical - Trimethyl

2- methyl- 4- ethylhexane 3- ethyl- 5- methylhexane


X√

2- methyl- 4- ethylhexane 3- ethyl- 5- methylhexane


2, 3 - dimethylpentane 4-ethyl-2 -methylhexane

2, 3, 6 – trimethyl – 4 - ethyloctane 2, 2, 4 - trimethylpentane

X√

Aliphatic (open chain) Aromatic (benzene structure)

Saturated Unsaturated

Hydrocarbon

CH3 CH3

Homologous Series• same functional group (C=C) or (C≡C)• each member differ from the next by –CH2- group• similar chemical properties• chemical formula alkene - CnH2n

• chemical formula alkyne - CnH2n-2

• unsaturated hydrocarbon• alkene ending with ene• alkyne ending with yne

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C2 – C4 (gases)• C5- C10 (liquids)• Insoluble in water, soluble in organic solvent• Non conductors – simple molecules not ions

Hydrocarbon Alkene/Alkyne and Nomenclature

UnsaturatedCarbon – Carbon double bond

UnsaturatedCarbon – Carbon triple bond

CH CHH2C=CH2

Homologous Series• functional group CO bonded to H at the end• contain carbonyl group C=O• each member differ from the next by –CH2- group• similar chemical properties• chemical formula aldehyde - CnH2nO• aldehyde ending with al

Hydrocarbon Aldehyde and Nomenclature

H H H │ │ │ H- C - C – C =O │ │ H H

Propanal

H H H H │ │ │ │ H- C - C – C – C =O │ │ │ H H H Butanal

H H │ │ H- C – C = O │ H Ethanal

H │ H- C =O Methanal

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C1 – gas• C2- C10 - liquids• Methanal – CH2O• Ethanal - CH3CHO• Propanal – CH3CH2CHO• Butanal - CH3CH2CH2CHO

H │ CH3 – CH –CH – C=O │ CH3

H │ CH3 – CH –CH – C=O │ │ CH3 CH3

CH3 H │ │ CH3 –CH – C=O │ CH3

Nomenclature for aldehyde

Homologous Series• functional group CO bonded to H at the end• contain carbonyl group C=O• each member differ from the next by –CH2- group• similar chemical properties• chemical formula aldehyde - CnH2nO• aldehyde ending with al

Hydrocarbon Aldehyde and Nomenclature

H H H │ │ │ H- C - C – C =O │ │ H H

Propanal

H H H H │ │ │ │ H- C - C – C – C =O │ │ │ H H H Butanal

H H │ │ H- C – C = O │ H Ethanal

H │ H- C =O Methanal

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C1 – gas• C2- C10 - liquids• Methanal – CH2O• Ethanal - CH3CHO• Propanal – CH3CH2CHO• Butanal - CH3CH2CH2CHO

H │ CH3 – CH –CH – C=O │ CH3

H │ CH3 – CH –CH – C=O │ │ CH3 CH3

CH3 H │ │ CH3 –CH – C=O │ CH3

2 - methylbutanal 2, 3 - dimethylbutanal 2, 2-dimethylpropanal

Nomenclature for aldehyde

Homologous Series• functional group CO bonded to two hydrocarbon• contain carbonyl group C=O• each member differ from the next by –CH2- group• similar chemical properties• chemical formula ketone - CnH2nO• ketone ending with one

Hydrocarbon Ketone and Nomenclature

H H │ │ H- C - C – C - H │ ║ │ H O H

Propanone

H H H │ │ │ H- C - C – C – C -H │ │ ║ │ H H O H Butan- 2 - one

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C1 – gas• C2- C10 - liquids• Propanone – CH3COCH3

• Butanone - CH3CH2COCH3

• Pentan-3-one -CH3CH2COCH2CH3

• Hexan-3-one - CH3CH2COCH2CH2CH3

H H H H H │ │ │ │ │ H- C - C – C – C – C – C – H │ │ ║ │ │ │ H H O H H H Hexan-3 - one

H H H H │ │ │ │ H- C - C – C – C – C - H │ │ ║ │ │ H H O H H Pentan- 3-one

CH3 – C –CH – CH3

║ │ O CH3

CH3 │CH3 – C –C – CH3

║ │ O CH3

CH3 │CH3 – CH – C – CH- CH3

║ │ O CH3

CH3 – C –CH – CH2CH3

║ │ O CH3

Nomenclature for ketone

Homologous Series• functional group CO bonded to two hydrocarbon• contain carbonyl group C=O• each member differ from the next by –CH2- group• similar chemical properties• chemical formula ketone - CnH2nO• ketone ending with one

Hydrocarbon Ketone and Nomenclature

H H │ │ H- C - C – C - H │ ║ │ H O H

Propanone

H H H │ │ │ H- C - C – C – C -H │ │ ║ │ H H O H Butan- 2 - one

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• C1 – gas• C2- C10 - liquids• Propanone – CH3COCH3

• Butanone - CH3CH2COCH3

• Pentan-3-one -CH3CH2COCH2CH3

• Hexan-3-one - CH3CH2COCH2CH2CH3

H H H H H │ │ │ │ │ H- C - C – C – C – C – C – H │ │ ║ │ │ │ H H O H H H Hexan-3 - one

H H H H │ │ │ │ H- C - C – C – C – C - H │ │ ║ │ │ H H O H H Pentan- 3-one

CH3 – C –CH – CH3

║ │ O CH3

CH3 │CH3 – C –C – CH3

║ │ O CH3

CH3 │CH3 – CH – C – CH- CH3

║ │ O CH3

3, 3 dimethylbutanone 3- methylbutanone 2, 4 dimethylpentan- 3-one

CH3 – C –CH – CH2CH3

║ │ O CH3

3- methylpentan-2-one

Nomenclature for ketone

Homologous Series• functional group COOH • contain carbonyl group C=O• each member differ from the next by –CH2-

group• similar chemical properties• chemical formula carboxylic acid - CnH2n+1COOH

or CnH2nO2

• acid ending with oic

Hydrocarbon Carboxylic Acid and Nomenclature

H H O │ │ ║ H- C - C – C - OH │ │ H H Propanoic acid

H H H O │ │ │ ║ H- C - C – C – C -OH │ │ │ H H H Butanoic acid

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• Propanoic acid – CH3CH2COOH• Butanoic acid - CH3CH2CH2COOH• Pentanoic acid - CH3CH2CH2CH2COOH• Hexanoic acid - CH3CH2CH2CH2CH2COOH

H H H H H O │ │ │ │ │ ║H- C - C – C – C – C – C - OH │ │ │ │ │ H H H H H Hexanoic acid

H H H H O │ │ │ │ ║ H- C - C – C – C – C - OH │ │ │ │ H H H H Pentanoic acid

O ║ CH3 – CH –CH – C -OH │ │ CH3 CH3

CH3 O │ ║ CH3 – CH –CH – C -OH │ CH3

O ║ CH3 –CH – C -OH │ CH3

Nomenclature for carboxylic acid

Homologous Series• functional group COOH • contain carbonyl group C=O• each member differ from the next by –CH2-

group• similar chemical properties• chemical formula carboxylic acid - CnH2n+1COOH

or CnH2nO2

• acid ending with oic

Hydrocarbon Carboxylic Acid and Nomenclature

H H O │ │ ║ H- C - C – C - OH │ │ H H Propanoic acid

H H H O │ │ │ ║ H- C - C – C – C -OH │ │ │ H H H Butanoic acid

Physical properties –• increase in RMM and molecular size down the series• RMM increase ↑ - Van Der Waals forces stronger melting /boiling point increases ↑• Propanoic acid – CH3CH2COOH• Butanoic acid - CH3CH2CH2COOH• Pentanoic acid - CH3CH2CH2CH2COOH• Hexanoic acid - CH3CH2CH2CH2CH2COOH

H H H H H O │ │ │ │ │ ║H- C - C – C – C – C – C - OH │ │ │ │ │ H H H H H Hexanoic acid

H H H H O │ │ │ │ ║ H- C - C – C – C – C - OH │ │ │ │ H H H H Pentanoic acid

O ║ CH3 – CH –CH – C -OH │ │ CH3 CH3

CH3 O │ ║ CH3 – CH –CH – C -OH │ CH3

O ║ CH3 –CH – C -OH │ CH3

2, 3 -dimethylbutanoic acid 3, 3–dimethylbutanoic acid 2- methylpropanoic acid

Nomenclature for carboxylic acid

Homologous 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

• Butanol – CH3CH2CH2CH2OH

Hydrocarbon Alcohol and Nomenclature

Types of alcoholPrimary alcohol 1 0 –

Secondary alcohol 2 o –

Tertiary alcohol 3 o –

H H H │ │ │ H- C - C – C - H │ │ │ H H OH Propan – 1-ol

H H H │ │ │ H- C - C – C - H │ │ │ H OH H Propan – 2-ol

H H H H │ │ │ │ H- C - C – C – C - H │ │ │ │ H H H OH Butan–1-ol

H H H H │ │ │ │ H- C - C – C – C - H │ │ │ │ H H OH H Butan–2-ol

H H H │ │ │ H- C - C – C – OH │ │ │ H CH3 H 2- Methylpropan-1-ol

H OH H │ │ │ H- C - C – C – H │ │ │ H CH3 H 2- Methylpropan-2-ol

H │ CH3 - C – OH │ H

Homologous 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

• Butanol – CH3CH2CH2CH2OH

Hydrocarbon Alcohol and Nomenclature

Types of alcoholPrimary alcohol 1 0 – One alkyl group bonded to C attached to OH group

Secondary alcohol 2 o – Two alkyl group bonded to C attached to OH group

Tertiary alcohol 3 o – Three alkyl group bonded to C attached to OH group

CH3 │ CH3 - C – OH │

H CH3

│ CH3 - C – OH │ CH3

H H H │ │ │ H- C - C – C - H │ │ │ H H OH Propan – 1-ol

H H H │ │ │ H- C - C – C - H │ │ │ H OH H Propan – 2-ol

H H H H │ │ │ │ H- C - C – C – C - H │ │ │ │ H H H OH Butan–1-ol

H H H H │ │ │ │ H- C - C – C – C - H │ │ │ │ H H OH H Butan–2-ol

H H H │ │ │ H- C - C – C – OH │ │ │ H CH3 H 2- Methylpropan-1-ol

H OH H │ │ │ H- C - C – C – H │ │ │ H CH3 H 2- Methylpropan-2-ol


C6– C5 – C4 – C3- C2 – C1

│ C2H5

C4 – C3 - C2 = C1

│ CH3

C4 – C3 - C2 - C1HO │ CI

C3 - C2 - C1 - OH │ CH3

C3 - C2 - C1OOH │ Br

OH │ C3 - C2 - C1

│ CH3

C5 - C4 – C3 - C2 = C1

│ CH3

C5 - C4 – C3 - C2 - C1

│ ║ CH3 O

CH3 – C = CH2

│ CH3

CH3 – CH2 – CH - CI │ CH2CH3

CH3 – CH –CHO │ CH3

CH3 – CH –CH – CH3

│ │ CH3 OH

CH3 – CH –CH2 – CH2OH │ CH3

CH3 – CH –CH2 - OH │ CH3

CH3 – CH –CH2 – CH3

│ CH2OH


C6– C5 – C4 – C3- C2 – C1

│ C2H5

C4 – C3 - C2 = C1

│ CH3

C4 – C3 - C2 - C1HO │ CI

C3 - C2 - C1 - OH │ CH3

C3 - C2 - C1OOH │ Br

OH │ C3 - C2 - C1

│ CH3

C5 - C4 – C3 - C2 = C1

│ CH3

C5 - C4 – C3 - C2 - C1

│ ║ CH3 O3 ethylhexane

2- methylbutene

2 – chlorobutanal

2 –methylpropan- 1-ol3 – bromopropanoic acid

2 – methylpropan – 2-ol

3 – methylpent –1-ene 3 methylpentan-2-one

CH3 – C = CH2

│ CH32 - methylpropene

CH3 – CH2 – CH - CI │ CH2CH3

3 - chloropentane

CH3 – CH –CHO │ CH3

2 -methylpropanal

CH3 – CH –CH – CH3

│ │ CH3 OH3- methylbutan-2-ol

CH3 – CH –CH2 – CH2OH │ CH33- methylbutan- 1-ol

CH3 – CH –CH2 - OH │ CH32- methylpropan-1-ol

CH3 – CH –CH2 – CH3

│ CH2OH2- methylbutan-1-ol


HO-C(CH3)2 – CH2-CH2-COOH

CH3-CH(OH)-CH3

CH2 -C(CH3)2

CH3-C(CH3)2-CH2-CHO

CH3-CH(CH3)-CO-CH2-CH3

(CH3 )3C –Br

CH3-CH2-CHBr-COOH

CH3 – CHBr – CH2 –CH2 -OH


HO-C(CH3)2 – CH2-CH2-COOH

4- hydroxy- 4 –methylpentanoic acid

CH3-CH(OH)-CH3

propan- 2–ol

CH2 -C(CH3)2

2- methylpropene

CH3-C(CH3)2-CH2-CHO

3, 3 – dimethylbutanal

CH3-CH(CH3)-CO-CH2-CH3

2 –methylpentan –3-one

(CH3 )3C –Br

2- bromo- 2-methylpropane

CH3-CH2-CHBr-COOH

2- bromobutanoic acid

CH3 – CHBr – CH2 –CH2 -OH

3- bromo-butan-1-ol

Nomenclature for Alkene and Alcohol Molecules

Nomenclature for Alkene and Alcohol Molecules

6 –chloro–3-ethylhev-1-ene

2 –methylbut-2-ene3 –methylpent-1-ene

6 –chloro-2–methylhex-2-ene

2, 3 –dimethylbut-2-ene

3 –methylbut-1-ene

4- methylpentan-1-ol 3, 3–dimethylpentan-2-ol 2- methylbutan-2-ol

2 – methylpropan-2 -ol Pent –4-ene –2-ol

Acknowledgements

Thanks to source of pictures and video used in this presentation

Thanks to Creative Commons for excellent contribution on licenseshttp://creativecommons.org/licenses/

Prepared by Lawrence Kok

Check out more video tutorials from my site and hope you enjoy this tutorialhttp://lawrencekok.blogspot.com

http://creativecommons.org/licenses/


Education

IB Chemistry on Homologous Series, IUPAC Nomenclature and Structural formula