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7 Physical Properties of Organic Compounds

Organic compounds that have the same functional group often have similar physical properties, such as boiling
points, melting points, and solubilities. Physical properties are largely determined by intermolecular forces, the
forces of attraction and repulsion between particles.

 Comparison of Intermolecular and Intramolecular Forces

Intermolecular Forces Intramolecular Forces

o Forces acting between molecules
o Can be formed or broken by physical changes
o Influence physical properties
o Relatively weak (1-15% of a covalent bond’s
strength)
o Forces acting within molecules
o Can be formed or broken by chemical change
o Influence chemical properties
o Relatively strong

Intermolecular Forces
1. Hydrogen bonding: a strong intermolecular attraction between the hydrogen atom from an N-H, O-H, or
F-H group on one molecule, and an N, O, or F atom on another molecule (Polar molecules only)

2. Dipole-dipole interactions: these forces cause polar molecules to cling to each other (Polar molecules
only)

3. London dispersion Forces (or Induced dipole-dipole): weak attractive forces that occur between all
covalent molecules (Both polar and non-polar molecules)

In general, the strength of intermolecular forces can be arranged as:

London forces < dipole-dipole forces < hydrogen bonds < ionic bonds

Let’s think:
How would the strength of intermolecular forces affect melting and boiling points?
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When dealing with functional groups and trying to predict their properties there are 3 questions to work
through:

1. Can the molecules form hydrogen bonds?

- The high electronegativity of nitrogen, oxygen, and fluorine causes an unusually strong dipole-dipole
interaction with H
- If the molecule contains O, N, or F atoms that are not bonded to hydrogen atoms, they cannot form
hydrogen bonds with themselves, however they may form hydrogen bonds with water
o Molecules that can form hydrogen bonds with water are usually soluble in water
o Molecules than can form hydrogen bonds with themselves have a higher boiling point

- Why are H2O, HF and NH3 anomalies in this boiling

point graph?

2. Are the molecules polar?

- The molecules are polar if they have polar bonds that do not cancel each other out due to symmetry
(Recall: VSEPR)
- Dipole-dipole intermolecular force occurs when oppositely charged ends of polar molecules are aligned
causing polar molecules to cling to each other
o Polar molecules usually have a higher boiling point than non-polar
o Polar molecules that can form hydrogen bonds have an even higher boiling point
o Polar molecules with a large non-polar hydrocarbon component are less polar and thus, less
soluble in water

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3. How strong are the dispersion forces?
- Electrons are not uniformly distributed throughout the molecule at every instant. As electrons move
around the nucleus, a momentary non-symmetrical arrangement may occur, resulting in a temporary
dipole. This temporary dipole may induce an instantaneous dipole in a neighboring molecules

**London forces are attractions between an instantaneous dipole and an induced dipole

- Larger atoms have larger electron clouds

which are easier to polarize as they are, on
average, farther from the nuclei and less tightly
held
- Dispersion forces grow in strength as the
hydrocarbon portion grows

Determine the intermolecular forces between each of the following molecules

HBr

HF

CH4

Propan-3-one

Cyclohexanol

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Intermolecular Description Experienced Relative Strength Trends

Force By
London All covalent Number of electrons
Dispersion molecules
Forces (polar and
(weak) non-polar)

Dipole-Dipole Polar Electronegativity

Forces molecules Difference
(relatively
strong)

Hydrogen Molecules Electronegativity

Bonding that contain Difference
(Very strong) O-H, N-H or
F-H bonds
(Polar
molecules
only)

Examples:
1. Which of the following compounds are soluble in water? Which has the highest melting/boiling point?
(a) propane (b) heptane (c) 1-propanol (d) 1-heptanol

2. Does ethanol or methoxymethane have a higher melting/boiling point?

3. Which is more soluble in water? 1-octanol or ethanol?

4. Arrange the following molecules in order of increasing melting/boiling point: propane, 1-propanol,
propanal, propanoic acid
5. Which of the following compounds is considered to be non-polar?
(a) CH3CH2OH (b) CH3CHO (c) CH3COOH (d) CH3CH2NH2 (e) CH3CH2CH3
6. Identify the compound that is likely to have the highest boiling point.
(a) CH4 (b) CH3OH (c) CH3CH3 (d) CH3CH2CH2CH2OH (e) CH3CH2CH2CH2CH3
7. Which of the following compounds is unable to form hydrogen bonds with itself?
(a) CH3CH2CH2CH2OH (b) CH3CH2NH2 (c) CH3COOH (d) CH3CH2CH2COOCH2CH3 (e) CH3CH2CONHCH3

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Organic Compounds listed in order of increasing solubility in water AND melting/boiling points:
1o Amide Because primary amides have two NH bonds, they have even stronger hydrogen
bonds than carboxylic acids.

2o and 3o The CN and NH bonds are polar. Secondary amides also experience hydrogen
Amides bonding.
Their solubility decreases as the non-polar hydrocarbon part of the molecule
increases in size.
Carboxylic The OH and CO bonds make carboxylic acids polar. Hydrogen bonding occurs
Acids between carboxylic acid molecules as well as water molecules. The solubility of
carboxylic acids in water decreases as the number of carbon atoms increases.

Amines CN and NH bonds are polar. The presence of one or more NH bonds allows
hydrogen bonding to take place. The solubility of an amine decreases as the
number of carbon atoms increases. The boiling points of primary and secondary
amines (which contain NH bonds) are higher than the boiling points of tertiary
amines (which do not contain an NH bond).
Alcohols The OH bond is very polar. Alcohols experience hydrogen bonding with other
alcohol molecules and with water. The solubility of an alcohol decreases as the
number of carbon atoms increases.

Alkyl Halides Alkyl halides are similar in structure, polarity, and reactivity to alcohols.

Ester Esters are polar. They contain a CO bond. Therefore, esters can accept
hydrogen bonds from water but not from other ester molecules.

Aldehydes The CO bond is polar, so aldehydes and ketones are polar. They can accept
and Ketones hydrogen bonds from water but not from other aldehyde or ketone molecules.

Ether The CO bond makes ethers polar. Hydrogen bonding cannot occur between
ether molecules but can occur between an ether molecule and water.

Hydrocarbons Hydrocarbons – non polar – the longer they are, the more dispersion forces
they have, and the higher the melting/boiling point. But they are NOT soluble
in water.