AUSTRALIAN SCIENCE AND MATHEMATICS SCHOOL

The preparation of
Pentylethanoate
Organic Preparation of an ester
By Jasmin Malhotra
LSG18 Kay Gillett
Stage 2 Chemistry
Marking Teacher: Amanda Watkin
Due: 27th August 2016
SACE Registration: 294924 R

Before completing this practical, a safety hazard risk assessment was completed
to ensure procedures were completed safely, yet efficiently. This can be see
below in table 1.
Table 1: Health and safety risk assessment

Potential Hazard
Burning of skin

Cuts and scrapes

Explosion

Risk management
Keep skin and plastic tube away
from the Bunsen burner flame
Keep liquids sealed when not in
use
Wear gloves when handling
corrosive liquids
Where heat proof gloves when
handling the hot pear-shaped
flask
Wear safety glasses and a lab
coat
Keep glass wear away from edge
of bench top
Do not use a stopper when
completing reflux

Procedure
1. 12ml of Pentanol and Ethanoic acid was measured and recorded.
2. Both the Pentanol and Ethanoic acid that was weighed were placed into a
dry pear-shaped flask from the quickfit apparatus.
3. 1ml (20 drops) of concentrated sulphuric acid was also added to the pearshaped flask.
4. 2 spatulafuls of pumice powder (boiling chips) were also added to the
mixture.
5. As seen below in figure 1, a reflux setup was created and shown to the
teacher before procedure continued.

6. The mixture was heated for 30 minutes whilst the Bunsen burner was
Figure 1: Photograph of reflex setup using the
carefully
controlled
quickfit apparatus
to ensure
the
mixture boiled steadily.
7. The mixture was then allowed to cool until it was comfortable for the pearshaped flask to be handled.
8. The mixture was then poured into a separating funnel and several drops of
distilled water were dropped into the solution. It was observed that the
drops sunk to the bottom through the liquid.
9. 20ml of sodium carbonate solution was added to the mixture and shaken
to mix the layers, and then it was left to settle. The aqueous layer (bottom
most) was discarded leaving the organic product/ester solution.
10.Step 9 was repeated twice more but with distilled water instead of sodium
carbonate solution.
11.The organic product was then poured into a conical flask and 3 spatulafuls
of fused calcium chloride was added to it. 2 spatulafuls of the boiling chips
were added to this solution as well.
12.As seen in figure 2 below, a distillation setup was created and shown to
the teacher before procedure continued.

Figure 2: Photograph of distillation setup

13.The ester
was then
using the quickfit apparatus
collected into a pre-weighed flask. It was noted that the boiling point of
pentylethnoate (the ester) was 149 degrees Celsius.
14.The mixture was held above a Bunsen burner holding a constant safety
flame until the ester reached a temperature of 149 degrees Celsius.

Note: unfortunately in this practical, the yield of an ester was not able to be
distinguished as the mixture was distilled to dryness.

Results
In the table below, observations throughout the practical have been recorded
and can be seen in table 2.
Table 2: Results recorded in the laboratory during procedures

Observations before, during and after Reflux procedure

Before
- Slightly warm
During

Yellow-orange colour
Colour tone changed to a deeper
red and spread through solution

As reflux continued, the entire

solution turned a deep red- black
colour

Boiling
After
Smelt similar to the scent of a
banana
Observations during separation with sodium carbonate
During
- Bubbling of solution
Observations during distillation
During
- The temperature never stayed
consistent in increasing (it was
increasing and decreasing at
times)
-

It was assumed water was a

product

Temperature did not achieve the

required boiling point for the
ester to be formed

Ester was distilled to dryness

Zero yield was given

In this practical, pentanol was reacted with ethanoic acid to produce water and
pentylethanoate. The equation for this reaction can be seen below in semistructural form.
CH3(CH2)4OH + CH3COOH CH3COO(CH2)4 + H2O

As it can be seen, the ratio for the alcohol against the acid is 1:1. Therefore for a
yield to be produced, the initial masses of the alcohol and the acid must be the
same as the number of moles would be affected.
Table 3: Calculated Data used to find percentage yield of the ester produced

Initial Mass (g)

Alcohol
Acid

9.272
10.685

Percentage yield ( )=

Perentage Yield=

Molar Mass (gmol1

)
88.15
60.05

Number of Moles
(mol-1)
0.105
0.178

Actual yield
100
Theoretical Yield

0
100=0
0.105

Discussion
Reflux is the process of heating a solution of reactants for an extended period of
time with minimum loss of the reactants and products by evaporation. This
practical was prepared by reacting under reflux condition; pentanol and ethanoic
acid with sulphuric acid acting as a catalyst (esterification) with water resulting
as a second product (Evans, McCann and Morton, 2016).
An ester is formed whenever a carboxylic acid reacts with an alcohol.
The equation for the reaction between an acid RCOOH and an alcohol R'OH
(where R and R' can be the same or different) is:

(Chemguide.co.uk, 2016)
In this reaction, the alcohol that was used was pentanol and the carboxylic acid
used what ethanoic acid. A small amount of concentrated sulphuric acid, H 2SO4
was also used as a catalyst. H2SO4 is a dehydrating agent and removes water
from the products. The alcohol loses OH and the carboxylic acid lost H. Prior to
reacting the solutions, an equation was written for the reaction and
pentylethanoate was predicted as being the ester that would be formed. This
equation can be seen below.
CH3(CH2)4OH + CH3COOH CH3COO(CH2)4 + H2O
In the structure of the compounds at the atomic level, the hydrogen is replaced
by the pentyl group. This can be represented as below in the structural formula
of the same equation.

The circled OH from the alcohol and H from the acid show that in the ester, the H
from OH is replaced with the pentyl group.
After the heating procedures, the solution was then put into a separating funnel
to undergo a washing procedure with water. This washing with water was done to
remove most of the water soluble species including any excess alcohol,
carboxylic acid and sulfuric acid. The ester is not very soluble and therefore it will
separate into a different layer. The ester is also less dense compared to water;
therefore it will float above the aqueous solution. This separation can be seen in
figure 3.
The washing was also completed with sodium carbonate, Na 2CO3. This was done
to remove remaining traces of acid left in the organic solution. An aqueous
solution of Na2CO3 was used to neutralise any remaining acid. This process can
be seen in the equation below.
CO32-(aq) + 2H+(aq) CO2(g) +

H2O(l)

The addition of Na2CO3 caused

dioxide bubbles to form. Once
neutralised, bubbles
(Ausetute.com.au, 2016).

the formation of carbon

the acid completely
discontinued forming
Figure 3: Before
separation of the
aqueous solution
(white/middle)
from the organin
solution
(yellow/top most)

The trouble with heating a

mixture
of an organic acid, alcohol and
a small
amount of acid catalyst is that
it also
causes a reverse reaction as
well as
a forward reaction. Unless
there is a way to drive the
reaction towards the right, it
will cause a small yield. An
equilibrium equation suggests
that if there are more
reactants used, the
equilibrium will want to
increase the products to create a balance. To improve this, according to Le
Chatelier Principle; an excess of the alcohol in the reaction could be used in
order to drive the forward reaction towards the products.
A random error that could have affected why a yield was not able to be identified
was the amount of time that the solution was refluxed for. The solution was
refluxed for 30 minutes. This could have been increased so that more of the
reactants could have been converted into products. This short time limit would
definitely affect the accuracy of the yield to the true value. A larger time limit is
required to achieve the most ester out of the reactants.
After the washing procedures, it was required for the waste solution to be
discarded from beneath the ester. Some of the ester solution could have come

out along with the waste solution toward the end of the removal process. This
was a random error that could have affected the amount of yield of ester that
was created.
A systematic error could have been related to the thermometer that was used.
The thermometer was not initially calibrated to confirm it was working correctly.
As the boiling point of ethyl acetate is 149 degrees celcius, this temperature
should have been reached to confirm that pentylethanoate has been formed.
However the temperature did not reach this before the solution had dried in the
flask.
Even though 0% yield was the result of this practical, and ester was still created.
A smell of a banana scent throughout the practical and the separation of the
aqueous and organic layer in the separating funnel can confirm that an ester was
created, however not enough was created for a yield to be identified.

References
Evans, C., McCann, M. and Morton, B. (2016). Chemistry workbook sace stage 2.
7th ed. Adelaide: Greg Eather in association with Adelaide Tuition Centre, pp.268269.
Chemguide.co.uk. (2016). esterification - alcohols and carboxylic acids. [online]
Available at:
http://www.chemguide.co.uk/organicprops/alcohols/esterification.html [Accessed
23 Aug. 2016].
Ausetute.com.au. (2016). Chemistry Tutorial : Esters and Esterification. [online]
Available at: http://www.ausetute.com.au/esters.html [Accessed 27 Aug. 2016].