Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry.

Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.
Experiment 2:

Distillation of an Unknown Liquid

In this experiment, a certain colorless liquid dyed with a solid dye (methylene blue or food
color) will be distilled. The liquid is a common laboratory solvent that has no more than 6
carbon atoms.

Prelab Questions
1. What type of impurities can be removed using simple distillation?
2. Why shouldn’t the pot mixture exceed two-thirds of the round bottom flask nor be
too little?
3. Why is an air condenser used instead of a water condenser when distilling liquids
with very high boiling points?
4. What intermolecular forces are broken when a liquid boils? Are covalent bonds are
broken when a liquid boils? Explain.
5. What constitutes a forerun? Why is it collected separately from the rest of the
distillate?

Equipment
 aluminum foil
 rubber bands
 boiling chips
 sample vials

Procedures
Obtain about 15 mL of the unknown solution from the stockroom technician.

TIP: Take note of the smell.

Assemble a simple distillation setup. Cover the mouth of the receiving flask with aluminum foil to
minimize the evaporation of the distillate. Punch a hole using the receiver adapter to allow it to pass
through the mouth of the flask. For very volatile compounds, an ice-water bath is used but this is
not necessary for this experiment.

TIP: Use rubber bands to secure the glassware and hold them together.
Record the volume of the unknown liquid. Remove the round bottom flask; pour in the unknown
liquid and add boiling chips. Clamp the flask back into the still head and start distilling.

Take note of the temperature at which the forerun (first ~20 drops) was collected. Quickly replace
the receiving flask and collect another batch of distillate. Take note of the temperature range at
which the change in temperature slowed down or the temperature remained constant. Collect a
new batch of distillate when the temperature starts to rise rapidly. Continue heating until only a
very small amount of liquid remains in the flask but do not distill to dryness.

Measure the total amount of distillate collected but do not mix the liquids together.

Second Edition Draft For use only within the Ateneo de Manila University.
Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.
Boiling Point Determination
Wash the round bottom flask and throw the residue in designated waste containers. Triple-wash
the flask with small amounts of the forerun and distill the second batch of the distillate.

TIP: Use new boiling chips.

If the volume of pot liquid is too little, add some of the forerun or the third batch of distillate. Distill
the liquid. Collect 1-ml fractions with a 10-ml graduated cylinder receiver. Record the temperature
for each fraction and take note of the temperature at which it remained constant. Compare this
with the boiling point of common laboratory solvents and take the other characteristics of the liquid
such as the smell, viscosity, miscibility, etc. into consideration. Submit the vial containing the
distillate.

Postlab Questions
1. Why do liquids boil at temperatures above or below their expected boiling points?
2. Why isn’t the boiling point of the second fraction in the first part of the experiment
used to determine the boiling point of the liquid?
3. Would you expect a 100% recovery in this experiment? Explain.
4. What do you expect to find in the receiving flask after distillation? How about in the
round bottom flask?
5. Is it possible to separate a mixture of n-hexane (bp: 68.7 °C) and isohexane (2-
methylpentane) (bp: 60.3 °C) using the setup used in this experiment? Explain.

References:
Most CF. Experimental Organic Chemistry. USA: Wiley & Sons; 1988.

Palleros DR. Experimental Organic Chemistry. USA: Wiley & Sons; 1988.

Second Edition Draft For use only within the Ateneo de Manila University.