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Chemistry Coursework

Purpose
Organic chemistry is a topic which is noticeably prevalent in modern day society and is at
the core of much of our world. In Geography, I have learnt about industrialisation and
globalisation to a high level, and this study has prompted questions in my scientific mind.
Fuel is what drives the modern world into a more efficient age, where we have seen
communications and transportation revolutionised, causing what is commonly referred to as
the ‘shrinking world’. Evidence suggests that we are by the day destroying the planet we live
in through our exhaustive consumption of unrenewable fossil fuels. Ethanol is becoming a
highly used form of renewable energy to help relieve the strain on these fossil fuels, and
thus I was intrigued to study how other alcohols compare as viable fuels.

Research Question
How does the length of carbon chain affect the combustion enthalpies of a variety alcohols?
Introduction
The experiment which I carried out is one within the branch of organic chemistry and
thermochemistry, or the study of heat changes in chemical reactions, to deduce which
alcohol is the most energy efficient

Hypothesis
As the chain length of the alcohol increases, the enthalpy of combustion will increase the
temperature of the water by 10oC also increases.
Apparatus
- 150cm3 water
- Spirit Burners containing alcohols:
Methanol; Ethanol; Propan-1-ol; Propan-2-ol; Butan-1-ol; Butan-2-ol; Pentan-1-ol; 2-Methyl
Butanol
- Copper calorimeter
- Clamp stand
- Thermometer (0-100o C) (+/- 0.5oC)
- 200ml Measuring cylinder (+/- 1ml)
- Weighing scales
- Polystyrene lid
- Aluminium foil

Methodology
1. Firstly, the eight different alcohols were poured into eight different spirit burners.
These were then weighed individually and their masses were recorded in the results
table.
2. After this 150ml of water was measure in a 200ml measuring cylinder, and then
poured into the copper calorimeter. The calorimeter was cooled down between
experiments to ensure the heat induced from the previous experiment would not
affect future results
3. With the calorimeter a set distance above the spirit burner, a thermometer was
placed in the water, and the starting temperature was noted. The distance between
the calorimeter and the spirit burner was kept consistent throughout as increasing
the distance between the two would mean more heat would be lost to the
surroundings and thus provide inconsistent results.
4. The wick on the spirit burner was then lit with a match. It was essential to make
sure the alcohols not being used were kept far away from the fame to avoid them
catching alight. I proceeded to wait for there to be a temperature increase of 10o
Celsius. When the water had reached 10o higher than the original temperature, the
lid of the spirit burner was placed on to stop the flame burning further.
5. The spirit burner was then weighed once more, to determine how much alcohol had
been consumed to invoke a temperature increase of 10o. This was noted in my
results table and the change in mass was calculated.
6. I proceeded to repeat the experiment twice more for each alcohol to ensure that
my results were more reliable.
7. Having carried out the experiment, I decided to try and overcome the greatest
factor affecting the validity of my results as I will discuss later was heat loss. To do
this, firstly the calorimeter was covered in aluminium foil, and the experiment was
repeated from steps 2 to 6.
Variables
Independent Variable: Number of Carbon atoms in the alcohol (chain length)
Controlled Variables: Volume of water, 10oC temperature rise, calorimeter, distance from
spirit burner to calorimeter
Dependant Variable: Energy required to heat water by 10oC
Safety Precautions
When experimenting with the alcohols and boiling water, it was important to wear safety
goggles to avoid contact of the chemicals with my eyes as this could cause serious damage.
Equally, it was important to keep the alcohols an any other flammable chemicals away from
the naked flam, to avoid unwanted combustion. As there are sockets and gas taps in the
laboratories it was also important to make sure these were turned off before lighting flames
to avoid electrical fires or gas explosions. Finally I removed my tie and blazer to ensure
these were not at risk of being set alight.

Results
Qualitative Data:
In carrying out the experiment I noticed that between the alcohols there was little to no
difference in the qualitative data between the alcohols however there is some to note
nevertheless. All the alcohols were colourless liquids both before and after the experiment
and although pungent, all gave off similar odors following the experiment. The flame given
off was similar amongst all the alcohols, but it was difficult to give an objective qualitative
analysis of this factor, and typically there was water vapour given off in all cases, due to the
evaporation of the water due to the heat.
Quantitative Data:
Initial Mass After Mass Average
Alcohol (±0.001) (±0.001) RMM Change Change 2 Change 3 Change
Methanol 156.379 156.094 32.05 0.285 0.255 0.224 0.255
Ethanol 165.196 164.895 46.07 0.301 0.293 0.341 0.312
Propan-1-ol 125.722 125.765 60.1 0.722 0.507 0.432 0.554
Propan-2-ol 170.507 170.007 60.1 0.500 0.401 0.398 0.433
Butan-1-ol 154.921 154.468 74.12 0.453 0.482 0.498 0.478
Butan-2-ol 179.504 179.001 74.12 0.503 0.521 0.492 0.505
Pentan-1-ol 141.025 140.444 88.15 0.581 0.595 0.563 0.580
2-Methyl Butanol 160.807 160.309 88.15 0.498 0.542 0.584 0.541

Graph to show relationship between the average mass change and alcohol chain length:
0.700

0.600
Average Change in Mass (g)

0.500

0.400

0.300

0.200

0.100

0.000
0 10 20 30 40 50 60 70 80 90 100
Relative Molecular Mass (g/mol)

This graph shows that in general there is a noticeable positive correlation between the
average change in mass and the RMM of the alcohol (increased chain length is here
equivalent to the increase in RMM). The circled result is seemingly anomalous, and I will
discuss potential reasons for this further on. This graph however does not tell us the
enthalpy which has been spent on heating the water. The necessary calculations take place
on the next page.
Calculations:
To calculate the enthalpy change during combustion, the following equation must be
employed:

Enthalpy Change During Combustion = Mass of Water x Specific Heat Capacity x Temperature Rise
Q = mcΔT
For this experiment:

m = 150g/0.15kg (as 150cm3 of water has a mass of 150g)


c = 4.18 kJ kg-1 K-1 (as this is the specific heat capacity of water)
ΔT = 10 Kelvin (as an increase of 10oC is equivalent to 10 Kelvin)

These three elements are consistent for every time the experiment was repeated, and
hence the enthalpy change during combustion was also.

Q = 0.15 x 4.18 x 10
Enthalpy Change During Combustion = 6.27 kJ
From this figure we can work out the standard enthalpy of combustion for each of the
alcohols by dividing the figure by the number of moles in each alcohol.

Moles of methanol = Mass 0.255 = 0.00796


RMM 32.05

Repeating this calculation for each alcohol, the results are on the following page:

Alcohol Moles
Methanol 0.00796
Ethanol 0.00678
Propan-1-ol 0.00922
Propan-2-ol 0.00720
Butan-1-ol 0.00645
Butan-2-ol 0.00681
Pentan-1-ol 0.00658
2-Methyl Butanol 0.00614

To work out the ΔH of each alcohol: - ΔH = Q(see above)


Moles

The enthalpy of combustion is given here as positive, although the reaction is endothermic.
This is for ease of representing data in graphs and comparison, however the true values are
the negatives of the figures given.

Alcohol Experimental ΔH of Alcohol (kJ/mol)


Methanol 787.69
Ethanol 924.78
Propan-1-ol 680.04
Propan-2-ol 870.83
Butan-1-ol 972.09
Butan-2-ol 920.26
Pentan-1-ol 952.89
2-Methyl Butanol 1021.17

The graph below compares the standard enthalpy of combustion for the chosen alcohols
and their RMM

Standard Enthalpy of Combustion Experimental Values against


RMM
Standard Enthalpy of Combustion (kJ/mol)

1200

1000

800

600

400

200

0
0 10 20 30 40 50 60 70 80 90 100
RMM (g/mol)

Analysis
There is a notable positive correlation between RMM and standard enthalpy of combustion
which is as hypothesised due to the reasons that I will now outline.
The general formula of an alcohol is CnH2n+1OH, and thus an increase to the chain length
increases the number of Carbon atoms within the homologous group. Increasing the length
increases the number of bonds which must be broken, and thus more energy is required to
reach the same end, (in this case increasing the water’s temperature). The breaking of bond
requires a great amount of energy, and thus the more bonds which are needed to break, the
more energy required to break up the hydrocarbon through combustion.
The C-C bond is a strong covalent bond which requires a great deal of energy to break,
along with the subordinate, but still relevant, extra C-H bond. Another reason one can
expect the enthalpy to increase (albeit negatively) with an increase in carbon atoms is due to
London dispersion forces. Although the Hydrogen Bonds and the dipole-dipole forces will
remain relatively similar within the homologous series, London dispersion forces become
more significant as the number of carbon atoms increases. This is because larger molecules
have a greater number of electrons within them, increasing the size of the temporary
dipoles which are formed. Although these forces are less significant than my original
justification, they are another factor which supports my hypothesis.
It is important to note also the difference in enthalpy of combustion amongst the isomers of
the same molecule. Different isomers do not make much of a difference as all of the factors
I have discussed act in the same way on different isomers. However, there is a slight
discrepancy as the structure of the molecule impacts the energy required to break the
intramolecular forces. Straight chain isomers, such as Propan-1-ol, require less energy to
break down than isomers with branching such as Propan-2-ol. This explains why Propan-1-ol
and 2-Methyl-Butan-1-ol have greater ΔH values than their parent molecules. Straight chains
have larger surface area for hydrogen bonding and London dispersion forces meaning more
energy is needed in order to break these bonds. However, Butan-1-ol appears to have a
more significant value than Butan-1-ol. This is most likely due to an error in the experiment
which I will evaluate.
I will also look at findings as per the Average Bond enthalpies of combustion in the IB Data
Booklet on the following page.

Average Bond Enthalpies


C-H = 414 // C-C = 346 // C-O = 358 // O=O = 498 // O-H = 463 // C=O = 804

Ethanol
C2H5OH + 3O2  3H2O + 2CO2

HH
H-C-C-O-H + 3 (O=O)  3 (H-O-H) + 2 (O=C=O)
HH
From the above equation, we can see that 5 C-H, 1 C-O, 1 O-H, 3 O=O, and 1 C-C Bond
must be broken. The total enthalpy of this breaking of bonds can be calculated as follows,
using the average bond enthalpies provided;
(5 x 414) + (1 x 358) + (1 x 463) + (1 x 346) + (3 x 498) = 4731 kJ/mol

Equally, we can see that 6 O-H and 4 C=O bonds must be made;
(6 x 463) + (4 x 804) = 5994 kJ/mol
4731 – 5994 = -1263 kJ/mol

Methanol
2CH3OH + 3O2  2CO2 + 4H2O
Ethanol
C2H5OH + 3O2  2CO2 + 3H2O
Propan-1-ol/Propan-2-ol (Although different structures, both require the same bonds to be broken and
made as contain same bonds)

2C3H7OH + 9O2  6CO2 + 8H2O


Butan-1-ol/Butan-2-ol
C4H9OH + 6O2  4CO2 + 5H2O

Pentan-1-ol/2-Methyl Butanol
2C5H11OH + 15O2  10CO2 + 12H2O

Alcohol Experimental ΔH of Literature Values for ΔH ΔH as per Average Bond


Alcohol (kJ/mol) of Alcohol Enthalpies
Methanol -787.69 726 -1300/2 = -650
Ethanol -924.78 1367 -1263
Propan-1-ol -680.04 2021 -3752/2 = -1876
Propan-2-ol -870.83 2006 -1876
Butan-1-ol -972.09 2675 -2489
Butan-2-ol -920.26 2661 -2489
Pentan-1-ol -952.89 3328 -6204/2 = -3012
2-Methyl Butanol -1021.17 3326 -3012
(n.b. When equations are balanced to include two moles of the alcohol, the result has been divided
by 2 to find the ΔH per mole of the alcohols)
Evaluation
It is important to acknowledge that throughout this process, the apparatus which was used
each has their own uncertainties. These are listed below:

Apparatus Uncertainty Uncertainty %


Uncertainty x 100
Quantity

200ml Measuring Cylinder +/- 1ml 0.667%


Thermometer +/- 0.5o 5%
Measuring Scales BEFORE COMBUSTION: +/-
0.001g
AFTER COMBUSTION: +/-
0.001g
Methanol: 0.784%
Ethanol: 0.641%
Propan-1-ol: 0.361%
Propaan-2-ol: 0.461%
Butan-1-ol: 0.418%
Butan-2-ol: 0.412%
Pentan-1-ol: 0.344%
2-Methyl Butanol: 0.370%

TOTAL UNCERTAINTIES FOR EACH ALCOHOL (0.667 + 5 + Measuring Scales Values)


Methanol 6.541%
Ethanol 6.308%
Propan-1-ol 6.028%
Propan-2-ol 6.128%
Butan-1-ol 6.085%
Butan-2-ol 6.079%
Pentan-1-ol 6.011%
2-Methyl Butanol 6.037%

Percentage uncertainties to actual uncertainties: Experimental ΔH Values x % Uncertainty

Alcohol ΔH of Alcohol Literature Values Adjusted Literature Values % Error


(kJ/mol) (with uncertainty) (does uncertainty explain
results)
Methanol 787.69 726 +/- 51.5 777.5 -NO 1.31
Ethanol 924.78 1367 +/- 58.3 1308.7 – NO 29.3
Propan-1-ol 680.04 2021 +/- 41.0 1980 - NO 65.7
Propan-2-ol 870.83 2006 +/- 53.4 1952.6 – NO 55.4
Butan-1-ol 972.09 2675 +/- 59.2 2615.8 - NO 62.8
Butan-2-ol 958.72 2661 +/- 58.3 2602.7 - NO 63.2
Pentan-1-ol 952.89 3328 +/- 57.3 3270.7 – NO 70.9
2-Methyl Butan1ol 1021.17 3326 +/- 64.5 3261.5 - NO 68.7

The % Error was calculated by the following calculation:

% Error = Adjusted Literature Value - Experimental Value x 100


Adjusted Literature Value
The fact that my results are still not equal to the literature values including uncertainties
proves that the error is not down to the equipment but is a systematic error.
Systematic Errors

1. Heat loss to the surroundings is the main source of error in this experiment. As most of
the heat from the Bunsen burner did not reach the calirometer, nor remain inside the
calorimeter once it reached, much more alcohol was needed to increase the temperature of
the water by 10o. To see the extent of this factor, I tried to reduce the heat lost to
surroundings by covering the calorimeter in aluminium foil and then add a lid also. The
results of this change are below using Propan-1-ol.

The aluminium conducts the heat ensuring it is not lost to the surroundings and keeps the
heat in the system, and adding a lid also ensures heat does not leave the system. If I carried
out the experiment with aluminium foil and a lid for every experiment I would have yielded
results much more representative of the true literature values.
2. The specific heat capacity of the calorimeter was not considered when producing the
results (and equally the aluminium in my altered experiment). The calorimeter absorbed
some of the heat from the spirit burner also, yet this is not considered in the results which
were produced
3. There is also the situation in that the alcohols underwent incomplete combustion. In
incomplete combustion, carbon monoxide and carbon are formed instead of carbon dioxide.
This process was visible as there was soot on the bottom of the calorimeter, showing that
carbon had been formed. In situations of incomplete combustion, the enthalpies of
combustion are not accurate as the reaction is not complete.
4. The spirit lamps continued to burn for a short period of time after the experiment had
been completed as the lid was put on afterwards to put out the flame. This means that the
mass of the alcohols decreased by a greater degree than they should have.
The method of the experiment could have been altered to help reduce these systematic
errors. One way it could have been aided is by carrying the experiment out in a place of
constant temperature, such as a fume cupboard, to ensure the temperature values were
consistent and the increase was truly 10o C. Also, the water could have been stirred to
evenly distribute the water throughout the system. A magnetic stirrer would make for a
more consistent stirring. The experiment also ought to have been carried out in a place
with an excess of oxygen, so that only complete combustion occurred. Finally, the
experiment could have been repeated for each alcohol to yield more representative results.

Conclusion
From my experiment, I have discovered that as the number of carbon atoms in the
homologous series of alcohols increases, the enthalpy of combustion of the alcohols
increases. The results of my experiment show a positive correlation between these two
factors, and upon further analysis of the literature values for enthalpy of combustion, I can
support my conclusion. With an increase in carbon atoms, there are more strong covalent
bonds which must be broken between the atoms, and these bonds require a large amount
of energy to break and thus an increase in the number of bonds means an increase in the
energy needed to break them. Ethanol has become such a popular fuel due to its relatively
low ΔH meaning one can use little fuel to carry out the same task (eg. heat water by 10oC as
in this experiment). This efficiency is why ethanol is preferable to other alcohols.

Methanol, given it has the lowest ΔH, would seem like the most viable fuel but there are
many reasons why this is not the case, thus giving ethanol the title. Methanol is highly toxic
and can cause blindness if consumed. Of course, one would not expect to drink fuel, but
given biofuels’ prevalence in low-income countries, crops are likely to contaminate each
other. Also, methanol is a carcinogenic and thus not appropriate for use, where the reward
is certainly not worth the risk.

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