Our Objective

Our objective is to determine the boiling point of an organic compound.

The Theory

What is the importance of knowing the boiling point of organic compounds?

The boiling point of organic compounds can give important information about their physical properties and structural characteristics.
Boiling point helps identify and characterise a compound. A liquid boils when its vapour pressure is equal to the atmospheric
pressure. Vapour pressure is determined by the kinetic energy of a molecule.

Kinetic energy depends on the temperature, mass and velocity of a molecule. When the temperature increases, the average kinetic
energy of particles also increases. When the temperature reaches the boiling point, the average kinetic energy becomes sufficient to
overcome the force of attraction between the liquid particles. As the force of attraction decreases, the molecules in the liquid state
escape from the surface and turn into gas.

The boiling point of a liquid varies with the surrounding atmospheric pressure. A liquid at a higher pressure has a higher boiling point
than when that liquid is at lower atmospheric pressure.

The normal boiling point of a compound is an indicator of the volatility of that compound. The higher the boiling point, the less
volatile is the compound. Conversely, the lower the boiling point, the more highly volatile is the compound. At a given temperature, if
a compound’s normal boiling point is lower, then that compound will generally exist as a gas at atmospheric pressure. If the boiling
point of the compound is higher, it then exists as a liquid or a solid.

What are the general trends that affect the boiling point?

1. Strength of intermolecular forces

The relative strength of intermolecular forces such as ionic, hydrogen bonding, dipole-dipole interaction and Vander Waals
dispersion force affects the boiling point of a compound. The influence of these forces depends on the functional group present. We
can explain the effect of these forces on the boiling point of compounds with the help of some examples.

Consider butane and its three derivatives such as diethyl ether, n- butanol and sodium n- butoxide. 
n-butane (C4H10) contains no polar functional group. The only attraction between the butane molecules is weak Vander Waals
dispersion forces. The result is that butane boils at a temperature at which water freezes, and is much lower than diethyl ether. In
the case of diethyl ether, the molecules are held together by dipole-dipole interaction which arises due to the polarized C-O bond. Its
boiling point is 35oC.  Compare its boiling point with that of n-butanol. The boiling point of n-butanol is 117 oC. The greatly increased
boiling point is due to the fact that butanol contains hydroxyl group, which is capable of hydrogen bonding. But the boiling point of
sodium butoxide is higher than that of butanol because the attractive force in sodium butoxide is very strong ionic bond.

The intermolecular forces go in the order Ionic > Hydrogen Bonding > Dipole-Dipole > Van der  Waals dispersion force. 

2. Length of carbon-carbon chain

As the number of carbon atoms increases or the length of carbon-carbon chain increases, the boiling point also increases. This is
because the force of attraction between the molecules increases as the molecule gets longer and has more electrons. It takes more
energy to overcome the force of attraction, and so the boiling point rises.
3. Branching decreases the boiling point

As the length of carbon chain increases, the surface area of the compound will also increase. Van der Waals dispersion force is
proportional to the surface area. So the increase of surface area increases the ability of individual molecules to attract each other.
Branching in molecules decreases the surface area thereby decreasing the attractive force between individual molecules. As a
result, the boiling point decreases.

Consider the boiling point of n-pentane and neo-pentane (2,2-dimethyl propane). These are isomers having the same molecular
formula (C5H12), but differ in their structures. 
The boiling point of neopentane is much lower than that of n-pentane. 

4. Polarity

Polarity of the molecule determines the force of attraction between the molecules in the liquid state. In polar compounds, the
positive end of one molecule is attracted by the negative end of another molecule. That means polar molecules are attracted by
opposite charge effect. The polarity of a molecule is determined by its functional group. The greater the polarity, the higher is the
boiling point.

Boiling point of some common organic compounds 

Compound Boiling Point (oC) Compound Boiling Point (oC)

Benzyl Alcohol 205 Ethyl Benzoate 213
Glycerol 290 Methyl Salicylate 223
Ethylene Glycol 197 Nitrobenzene 211
Phenol 182 Aniline 184
o-Cresol 191 o-Toluidine 200
Benzaldehyde 178 Chlorobenzene 132
Acetophenone 202 Bromobenzene 156
 Compound Boiling Point (oC) Compound Boiling Point (oC)
Phenyl Acetate 196 Benzoyl Chloride 197

Materials Required

Observations

Record your observations in the table given below.

Note the temperature when;

Boiling Point of the given
Rapid and continuous evolution The evolution of gas bubbles just stops organic liquid (t1 + t2 / 2 (oC)
of gas bubbles occurs t1(0C) t2 (0C) (after removing from the flame)

207  203  205

292 288 290

199 195 197

184 180 182

180 176 178

205 199 202

214 209 211.5

186 182 184

199 193 196

134 132 130

225 221 223

193 189 191

215 211 213

203 197 200

158 154 156