1.

4
Factors Affecting the
Physical Properties of
Organic Compounds

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1 New Way Chemistry for Hong Kong A-Level Book 3A
1.4 Factors Affecting the Physical Properties of Organic Compounds

Main Factors Affecting the Physical

Properties of Organic Compounds

1. Structure of the functional group

1.1 Dipole moment of the molecule
1.2 Formation of hydrogen bonding
2. Length of carbon chains (London dispersion forces)

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Structure of Functional Group

• Molecules having a polar functional

group have a higher b.p. than others
with a non-polar functional group of
similar molecular masses
! Stronger intermolecular attraction
among molecules

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Structure of Functional Group

Molecule Relative Boiling point
molecular (oC)
mass
Molecules CH3CH2CH2OH 60 97.2
with polar
CH3CH2CH2NH2 59 48.6
functional
groups CH3CH2Cl 64.5 12.5
CH3CH2COOH 60 141
Molecules CH3CH2CH2CH3 58 -0.5
with non-
CH3CH2CH=CH2 56 -6.2
polar
functional CH3CH2CºCH 54 8.1
4
groups
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1.4 Factors Affecting the Physical Properties of Organic Compounds

Dipole Moment of Molecule

• Tetrachloromethane has 4 polar bonds in the
molecule
• M.p. and b.p. are very low
! the molecule is non-polar
è the molecule is tetrahedrally
symmetrical
è the dipole moments of the
C ¾ Cl bond cancel each other
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1.4 Factors Affecting the Physical Properties of Organic Compounds

Examples of Polar Molecules with

Net Dipole Moment

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Examples of Non-polar Molecules

with No Net Dipole Moment

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Solubility of Organic Molecules

• Depends on the polarity of organic
molecules and the solvent
• Non-polar or weakly polar compounds
dissolve readily in non-polar or weakly
polar solvents
• Highly polar compounds dissolve readily
in highly polar solvents
• “Like dissolves like”
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1.4 Factors Affecting the Physical Properties of Organic Compounds

Solubility of Organic Molecules

Hexane in Hexane in water

tetrachloromethane
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1.4 Factors Affecting the Physical Properties of Organic Compounds

Why does Hexane Dissolve Readily in

Tetrachloromethane?

Intermolecular forces among hexane Intermolecular forces

molecules and those among » between hexane and
tetrachloromethane molecules tetrachloromethane
molecules
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1.4 Factors Affecting the Physical Properties of Organic Compounds

Why is Hexane Insoluble in Water?

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 1.4 Factors Affecting the Physical Properties of Organic Compounds

Formation of Hydrogen Bonding

• Molecules having ¾OH or ¾ NH2 groups
are able to form hydrogen bonds
• Hydrogen bonds affect the physical
properties of alcohols and amines with
low molecular masses

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Why does Propan-1-ol have a Higher Boiling Point?

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 1.4 Factors Affecting the Physical Properties of Organic Compounds

Formation of Hydrogen Bonding

• Also affect the solubility of a molecule
• Molecules with ¾OH groups are able
to form hydrogen bonds with
surrounding water molecules
è Soluble in water

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Length of Carbon Chains

• Molecules with higher molecular masses

have higher m.p., b.p. and density
! Higher molecular masses
è Large molecular sizes
è Stronger London dispersion
forces among molecules

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1.4 Factors Affecting the Physical Properties of Organic Compounds

Length of Carbon Chains

• Molecules with branched chains

è b.p. and density lower than its
straight-chain isomer
! Straight-chain isomers have greater
surface area in contact with each other
è Greater attractive force among the
molecules
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1.4 Factors Affecting the Physical Properties of Organic Compounds

Length of Carbon Chains

• Molecules with branched chains
è m.p. higher than its straight-chain
isomer
! Branched-chain isomers are more
spherical
è Packed more efficiently in solid state
è Extra energy is needed to break
down the efficient packing
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1.3 Classification of Organic Compounds
General Functional Example
Family
formula group Formula IUPAC name
Alkane RH (Nil) CH3CH3 Ethane
RCH = CH2
RCH = CHR
Alkene Carbon- CH2 = CH2 Ethene
R2C = CHR
carbon
R2C = CR2 double bond
–CºC–
RC º CH Carbon-
Alkyne HC º CH Ethyne
RC º CR carbon triple
bond

Aromatic
ArH Benzene
hydrocarbon
Phenyl group
18 R = CnH2n+1 –
18 New Way Chemistry for Hong Kong A-Level Book 3A
1.3 Classification of Organic Compounds
General Functional Example
Family
formula group Formula IUPAC name

¾X
Haloalkane RX CH3Cl Chloromethane
halo group

¾ OH
Alcohol ROH CH3OH Methanol
hydroxyl group

¾O¾ CH3 ¾ O ¾
Ether R¾O ¾ R Methoxymethane
oxy group CH3

Aldehyde Methanal

carbonyl group
R = CnH2n+1 –
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1.3 Classification of Organic Compounds
General Functional Example
Family
formula group Formula IUPAC name

Ketone Propanone

carbonyl group

Carboxylic
Ethanoic acid
acid
carboxyl group
RNH2
Amine R2NH CH3NH2 Methylamine
R3 N amino group
¾CºN
Nitrile RCºN CH3CN Ethanenitrile
nitrile group
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20 R = CnH2n+1 –New Way Chemistry for Hong Kong A-Level Book 3A
1.3 Classification of Organic Compounds
General Functional Example
Family
formula group Formula IUPAC name

Methyl
Ester
ethanoate
ester group

Ethanoyl
Acyl halide
chloride
acyl halide
group

Amide Ethanamide

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amide group
New Way Chemistry for Hong Kong A-Level 3A
21 New Way Chemistry for Hong Kong A-Level Book 3A R = CnH2n+1 –
1.3 Classification of Organic Compounds

General Functional Example

Family
formula group Formula IUPAC name

Acid Ethanoic
anhydride anhydride
acid anhydride
group
R = CnH2n+1 –

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 The END

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