Preparing Esters

Purpose:
The purpose of this experiment is to investigate and observe what physical properties the
esters produced from ethanol with ethanoic acid and propan-1-ol with ethanoic acid have, and to
draw a conclusion about what kind of impact the synthesizing of esters has on the environment.

Hypothesis:
I predict that the ester formed from ethanol with ethanoic acid will smell like nail polish remover
and the ester formed from propan-1-ol with ethanoic acid will smell like pear, because ethyl
acetate (ethanol + ethanoic acid) has the distinctive odour of nail polish remover, while propyl
acetate (propan-1-ol + ethanoic acid) has the distinctive odour of pear.

Materials/Apparatus:
Materials Apparatus
- distilled water
- ice cubes
- ethanol
- propan-1-ol
- ethanoic acid
- sulfuric acid
- 2 pipettes
- 250 ml beakers (2)
- 50 ml beakers (2)
- hot plate
- retort stand
- 2 clamps
- thermometer
- cap (half of the bulb cut off from a pipette)
- watch glass

Data/Observations:
Table 1: Odours
Chemical Odour
Ethanol Hand Sanitizer
Propan-1-ol Rubbing Alcohol
Ethanoic Acid Vinegar
Ethanol + Ethanoic Acid Nail Polish Remover
Propan-1-ol + Ethanoic Acid Paint Thinner

Sample Calculations:
N/A

Discussion:
1. How do you know that a new product was formed in each reaction? Explain.
I know that a new product was formed in each reaction because when the reactants were
combined, they produced a different odour, which means that they underwent chemical changes
and that a new product was formed.

2. Describe the odour of the ester produced in each reaction and compare this to the initial odour
of the reactants.
The odour of the ester produced from ethanol and ethanoic acid smelled like nail polish
remover, while the initial odour of its reactants smelled like hand sanitizer and vinegar. The
odour of the ester produced from propan-1-ol and ethanoic acid smelled like paint thinner, while
the initial odour of its reactants smelled like rubbing alcohol and vinegar.

3. Explain why the synthesized ester does not always match the odour of the fragrance found in
nature.
The synthesized ester does not always match the odour of the fragrance found in nature
because natural esters are more complex than synthesized esters. Also, there might have been
errors in the synthesizing of the ester, like not all of the reactants reacted or maybe another
product was produced as well that might have affected the odour.

4. Describe the physical properties of each product that was formed.
The physical properties that I observed of ethyl acetate and propyl acetate were that they
were both clear and colourless. Also, the states of matter that they were in were liquids.

5. What were the possible sources of error that occurred if a strong odour was not observed in
each of your reactions? How could you improve your procedure to result in a better product?
The possible sources of error that may have occurred are: that the amount of each
chemical that we poured into a beaker might not have been the exact amount listed in the
procedure, and that we might not have heated or cooled the mixtures the exact amounts of time
listed in the procedure. Also, the temperature of the hot-water bath wasnt a constant temperature
and we had to keep adjusting it during the experiment. I could improve my procedure to result in
a better product by finding a way to measure the reactants more precisely, and by finding a way
to keep the temperature of the hot-water bath constant. Also, maybe I could use a more precise
thermometer.

6. Review the safety precautions necessary for this investigation and conclude whether the
manufacture of esters is safe for the environment.
I do not think the manufacture of esters is safe for the environment, because the safety
precautions necessary for this investigation include: to make sure that there is no open flame in
the laboratory because the compounds are very flammable, to use a fume hood for all steps
involving acids because the procedures need to be carried out in a well-ventilated area, and to
treat the acids with extreme care because if you spill any on yourself, it might harm you.

Sources of Error:
(Described in detail in question #5 of Discussion)

Conclusion:
In my hypothesis, I stated that I thought ethyl acetate would smell like nail polish
remover and the results proved this to be correct, but I also stated that I thought propyl acetate
would smell like pears and the results proved this to be incorrect. The part of my hypothesis that
didnt agree with the results may have been because there were many possible sources of error,
and synthesized esters do not always match the odour of the fragrance found in nature.