Veloso, Bettina Alexandra Yap 30B

Experiment No. 2: Distillation of an Unknown Liquid February 22, 2019

Data and Observations

Table A: The Respective Volume, Temperature and Observations of Each Distillate Collection
Volume​ (in milliliters) Temperature​ (in Centigrade) Qualitative Observations

15 ml​ (based on step 1 in the 50 C​ (due to what was ● thin solution

lab manual) instructed by the lab advisor) ● strong, piercing smell
similar to that of
drinking alcohol
● Upon adding 2 drops
to 2 ml of water in a
watch glass, it was
observed that the
unknown liquid is
soluble in water.
● clear (disregarding the
purple dye)

Forerun (an estimated ​1 ml​ or 68 C ● Clear solution

10 drops​) ● Thin
● Same odor

2nd distillate (​5.7 ml​) 70 C ● Clear solution

● Thin
● Same odor

3rd distillate (an estimated ​1 70 C ● Clear solution

ml​ or ​10 drops​) ● Thin
● Same odor

Distilling 2nd batch of ​5.7 ml 72 C Notice​: Distillate was

spilled down the sink.
Prior to this, around
two to three 1 ml
increments were
collected before the
incident and at this
time the temperature
was constant at
around 72 degrees.
● Clear solution
 ● Thin
● Same odor

Discussion
Ethanol (CH3CH2OH) ​is the possible identity of the solution based on the​ matching physical
properties: clear, thin solution with a strong, piercing odor (similar to that of drinking alcohol)
that is soluble in water.​ However, there is also a strong chance that ​the solution could be
isopropyl alcohol​ based on the ​similar physical properties.​ Both are clear, thin solutions with a
strong, piercing odor and are both soluble in water. Although isopropyl alcohol may be easily
ruled out due to the relatively significant gap of its true boiling point (82.5 C) from the boiling
point of the liquid gathered in this experiment (72 C), one must also ​consider that the second part
of this experiment wasn’t fulfilled to completion, leaving a hypothetical possibility for the
temperature to have significantly risen. Moreover, the likely impurities present in the system as
well as the potentially faulty lab equipment such as the thermometer could have caused the
recorded temperature in this experiment to be less than the actual true value of isopropyl alcohol.
Nevertheless, from the accumulated data gathered from this specific experiment, taking into
consideration ​both the physical properties and the boiling point recorded, the unidentified liquid
is most likely ethanol​. The boiling point deduced in the second batch of distillate of ​72 C​.
Amongst the four choices given, the ​true boiling point of ethanol was the closest at 78C​. As
similarly mentioned above, the 5 C difference could be due to the impurities and possible
contaminants present as well as the errors committed by faulty lab equipment such as the
quantitative measuring device for raw data used in the setup: the thermometer. Better equipment
could prevent these types of deviations from occurring as well as ensuring the thorough cleaning
of lab equipment and efficient collection of forerun for the prevention of contaminants and
impurities.

The deviation of these boiling points can be attested to the fact that the solution itself may still
contain impurities​. Despite the collection of forerun prior to the collection of the second batch of
distillate that is supposed to ensure the solution is free from impurities, ​one can never fully
ensure a pure, completely uncontaminated solution in this type of experiment.​ Furthermore,
faulty lab equipment,​ such as the thermometer being ​unable to precisely and accurately
determine the specific temperature at specific times​ may also be a potential cause of error.
Furthermore, another cause of the deviation of boiling points that may lay outside the context of
this experiment are the​ changes in atmospheric pressure​ (less than 1 atm causes lower boiling
point and greater than 1 atm causes higher boiling point) and ​intermolecular forces​ (strong
forces= high boiling points, weak forces= low boiling points).
The temperature during the second fraction of the distillate should not be considered the boiling
point as the​ temperature at this point continues to significantly rise.​ Considering this temperature
as the boiling point would lead to inaccurate and imprecise results. Distilling the 2nd batch into 1
ml increments will allow the performer of the experiment to ​observe a constant temperature of
which is most advisable to be considered the boiling point.

A 100% recovery is not expected of this experiment as ​product is lost to both the forerun and the
third batch of distillate which are not counted as part of the product yield.​ Some vapor and
distillate is also​ lost within the set-up​ due to some uncorrectable faults. ​Evaporation​ from the
collected distillate may also occur but ​this was prevented by the performer of the experiment
beforehand by putting aluminum foil around the mouths of the receiving flasks​. These
conditions plus the points touched in paragraph 1 could be the reason to attest to the 38% percent
product yield of this specific distillation experiment.

In the round bottom flask will be a​ small amount of undistilled liquid as well as impurities
(non-volatile solids) and organic compounds​ that can be explosive at high temperatures which is
the reason as to why one must not distill to dryness. In the receiver flask on the other hand, one
will find the ​distilled liquid with potential lack of impurities.

Based on the qualitatively accumulated data, the ​possible identity of the liquid is ethanol judging
from the physical properties of appearance ( clear, thin looking solution) with a strong, piercing
odor similar to that of drinking alcohol, and its solubility in water.

It is ​not possible to use the simple distillation set-up​ as this can only be used when distilling two
liquids with a ​difference of at least 25C​. ​Fractional distillation​ would be more suitable to distill
n-hexane and isohexane as they have a ​closer difference in boiling points ​of around 8.4 C. This
type of distillation makes use of a fractional column as well as repeated boiling of the distillate to
ensure that the more volatile of the two liquids is evaporated.

In conclusion, although a small percentage product was yielded after the performance of the
experiment, the​ objectives presented before the commencement of said experiment were met.
The identity of the solution was identified as ethanol based on the physical properties as well as
through the comparison of various boiling points of the different organic compounds given as
options. Relevant concepts such as the evaluation of the various organic compounds and
cycloalkanes were steadily applied. Most of all, proper safety and protocol were rigidly followed
by the performer of the experiment at all times whilst inside the laboratory with no accidents to
account for during the performance. This specific experiment warranted a 38% product yield
from the original distillate, however, as mentioned above, these could be due to several
conditions of impurities and potentially inaccurate lab equipment.
Sample Calculations
Calculating the Percent Yield of the Product

The percent yield of this product is calculated through the use of the following formula:
(actual yield/ theoretical yield) x 100 = percent yield of the product
Applying this to the context of the experiment:
5.7 ml→ obtained product from second distillate, possible outcome from distilling second batch
as well, closest value we can work with
15 ml→ the theoretical yield due to it being the original amount of unknown liquid used in the
beginning of the experiment
(5.7ml/15ml) x 100 = 38%

38% ​of the original distillate was recovered.

References
1. Yanza A. Survey of Organic Chemistry Laboratory Manual. 1st ed. Quezon City: Ateneo
de Manila University: 2014.
2. Ethanol [Internet]. Pubchem.ncbi.nlm.nih.gov. 2019 [cited 19 February 2019]. Available
from: ​https://pubchem.ncbi.nlm.nih.gov/compound/ethanol#section=Top
3. Boiling [Internet]. Chem.purdue.edu. [cited 18 February 2019]. Available from:
https://www.chem.purdue.edu/gchelp/liquids/boil.html