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 Unsaturated

Carbon – Carbon double bond

Alkane Cycloalkane

Hydrocarbon

CH3CH3 CH3

CH3 CH3

CH3 CH3 CH2 CH2

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

Unsaturated

Carbon – Carbon double bond

Unsaturated

Carbon – 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

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

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 – C –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

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

Hydrocarbon Alcohol and Nomenclature

Types of alcohol Primary 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

Butanol – CH3CH2CH2CH2OH

Propanol – CH3CH2CH2OH

Primary alcohol 1 0

Secondary alcohol 2 0

Tertiary alcohol 3 0

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 • each member differ from the next by –CH2 - group • Bromomethane – CH3Br • Bromoethane - CH3CH2Br • Bromopropane – CH3CH2CH2Br

Types of halogenoalkane Primary 1 0 – One or NO alkyl group bond to C attach to halogen group

Secondary 2 o – Two alkyl group bond to C attach to halogen group

Tertiary 3 o – Three alkyl group bond to C attach to halogen group

H │ CH3 - C – Br │ H

H │ H - C – Br │ H

CH3 │ CH3 - C – Br │

H

CH3 │ CH3 - C – Br │ CH3

Nomenclature for Halogenoalkane

H H H H

│ │ │ │ H- C - C – C – C - Br │ │ │ │

H H H H

H H H H

│ │ │ │ H- C - C – C – C - H │ │ │ │

H H Br H

H CH3 H │ │ │ H- C - C – C – Br │ │ │

H CH3 H

H Br H │ │ │

H- C - C – C – H

│ │ │

H CH3 H

CH3

│ CH3 - C – Br │

H

CH3 H

│ │ CH3 - C – C -Br │ │

H H

CH3

│

CH3 - C – Br

│

CH3

CH3 H

│ │ C - C – C – C – C- C │

Br

1- Bromobutane

2- Bromobutane

1- bromo-2, 2 - dimethylpropane 1- bromo- 2 -methylpropane

2 – Bromo – 4-methylhexane

2-bromo-2-methylpropane

2- bromopropane

2- bromo- 2 -methylpropane

or

Primary halogenoalkane 1 0

Secondary halogenoalkane 2 0

Tertiary halogenoalkane 3 0

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

Types of amines Primary amine 1 0 – One alkyl group bonded to N

Secondary amine 2 o – Two alkyl group bonded to N

Tertiary amine 3 o – Three alkyl group bonded to N

H │ CH3 – N - H

CH3 │ CH3 - N – H

CH3 │ CH3 - N │

CH3

Nomenclature for Amines

CH3 -CH – NH2 │

CH3

propan– 2-amine

CH3 -CH – CH2-CH2-CH3

│

NH2

pentan–2-amine

CH3

│ CH3 -C – NH2 │

CH3

2- methylpropan–2-amine

CH3 -CH – C- NH2 │

CH3

2- methylpropan–1-amine

C2H5 -N -H │

CH2-CH2CH3

N - ethylpropanamine

C3H7 -N –CH3

│

C2H5

N- ethyl-N- methylpropanamine

CH3 -N -H │

CH2-CH3

N - methylethanamine

CH3 -N –CH3

│

C2H5

N, N - dimethylethanamine

CH3 │ CH3 - N │

CH3

N, N– dimethylmethanamine

Primary amine 1 0

Secondary amine 2 0

Tertiary amine 3 0

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)

Hydrocarbon Ester and Nomenclature

O ║

CH3 –C –O – CH2 CH3

H - C -OH ║

O

O ║

H –C –O – CH2 CH3

CH3 - OH

O ║

CH3 –C –O – CH3

CH3 -CH2–CH2–OH

O ║

CH3 –C –O –CH2-CH2 CH3

Ethanoic acid

CH3 - C –O - H ║

O

CH3 - C –O- H ║

O

Methanoic acid

CH3 - C –O -H ║

O

Ethanol

CH3 – CH2 –OH

Methanol Propanol

Ethyl ethanoate Ethyl methanoate

Methyl ethanoate Propyl ethanoate

+

Ethanol

+

Ethanoic acid

+ +

Ethanoic acid

Ethyl Ethyl

Propyl Methyl

ethanoate methanoate

ethanoate ethanoate

CH3 – CH2 –OH

Hydrocarbon Amide and Nomenclature

Homologous 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)

CH3 - C –O -H ║

O

Ethanoic acid

H │ H- N - H

Ammonia

+

O H ║ │

CH3 –C –N- H

Ethanamide

CH3 - C –O - H ║

O

Ethanoic acid

H │ H- N-CH3

Methanamine

O H ║ │

CH3 –C –N- CH3

+

N-methylethanamide

C2H5 - C –O- H ║

O

Propanoic acid

H │ H- N-C2H5

Ethanamine

O H ║ │

C2H5 –C –N- C2H5

N-ethylpropanamide

C2H5 - C –O- H ║

O

Propanoic acid N - methylethanamine

CH3

│ H- N-C2H5

O CH3

║ │

C2H5 –C –N- C2H5

N-ethyl- N methylpropanamide

+ +

Primary amide 1 0

Secondary amide 2 0 Tertiary amide 3 0

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

O H ║ │ CH3 –C –N- H

Ethanamide

O ║ CH3 -CH –C –NH2

│ CH3

2- methylpropanamide

O H ║ │ CH3 –C –N- CH3

N-methylethanamide

O H ║ │ C2H5 –C –N- C2H5

N-ethylpropanamide

O CH3

║ │ C2H5 –C –N- C2H5

N-ethyl- N methylpropanamide

O CH3

║ │ C2H5 –C –N- C2H5

N-ethyl- N methylpropanamide

O CH3

║ │ CH3 –C –N- CH3

N, N dimethylethanamide

Hydrocarbon Amide Nomenclature

C3H7 -N –CH3

│

C2H5

C2H5 -N – C2H5

│

H

CH3 -N –CH3

│

CH3 H2N – C- C- C- C- C- C - NH2

1,2-dibromoethane

Br Br │ │

CH2 – CH2

CI │ C- C - C – CI

│

CI

1,1,1-trichloropropane

Hydrocarbon Amine Nomenclature

N- ethyl-N- methylpropanamine N, N, dimethylmethanamine Hexane – 1,6, - diamine N- ethylethanamine

O ║

H –C –O – CH2 CH3

Ethyl methanoate

O ║

CH3 –C –O – CH3

Methyl ethanoate

O ║

CH3 –C –O – CH2 CH2 CH3

Propyl ethanoate Ethyl propanoate

O ║

CH3 –CH2 – O – C- CH2 CH3

Methyl ethanoate

O ║

CH3 –O – C- CH3

O ║

H- C–O – CH3

Methyl methanoate

Hydrocarbon Ester Nomenclature

CH3 H

│ │

CH3 - C – C -Br

│ │

H H

1- bromo-2-methylpropane

H CH3 H │ │ │ H- C - C – C – Br

│ │ │

H CH3 H

1-bromo-2,2-dimethylpropane

CH3

│

CH3 - C – Br

│

CH3

2- bromo-2-methylpropane

Hydrocarbon Halogenoalkane Nomenclature

C6– C5 – C4 – C3- C2 – C1

│

C2H5

C4 – C3 - C2 = C1

│

CH3

C4 – C3 - C2 - C1HO

│

CI

C3 - C2 - C1 - OH

│

CH3

OH │

C3 - C2 - C1

│

CH3

C5 - C4 – C3 - C2 = C1

│

CH3

C5 - C4 – C3 - C2 - C1

│ ║

CH3 O

3 ethylhexane 2- methylbutene

2 – chlorobutanal

2 –methylpropan-1-ol

2 –methylpropan–2-ol

3 –methylpent–1-ene

3 methylpentan-2-one

CH3 – C = CH2

│ CH3

2 - methylpropene

CH3 – CH –CHO │ CH3

2 -methylpropanal

CH3 – CH –CH – CH3

│ │ CH3 OH

3- methylbutan-2-ol

CH3 – CH –CH2 – CH2OH

│ CH3

3- methylbutan- 1-ol

CH3 – CH –CH2 - OH │ CH3

2- methylpropan-1-ol

CH3 – CH –CH2 – CH3

│ CH2OH

2- methylbutan-1-ol

Hydrocarbon Alcohol Nomenclature

Hydrocarbon Aldehyde/Ketone Nomenclature

Hydrocarbon Alkane/alkene Nomenclature

Nomenclature for Hydrocarbon with more than 1 functional group

More complicated Nomenclature

If 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

│

CH3

3-hydroxy- 2-methylpropanal

HO – C- C - COOH

│

CH3

3-hydroxy- 2-methylpropanoic acid

CH3 │ HO – C –CH2- CH2 – COOH │ CH3

4-hydroxy- 4-methylpentanoic acid

CH3 │ HO– CH2 –CH =CH – COOH

4-hydroxy- 3-methylbut-2-enoic acid

C – C- C - COOH

│

Br

2-bromobutanoic acid

C – C- C – CH2OH

│

Br

2-bromobutan-1-ol

Parent chain Side chain Parent chain Side chain

Parent chain

Side chain

Parent chain Side chain

Parent chain Side chain Side chain

Parent chain

Nomenclature for Organic Molecules

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