Investigating the relationship between the polarity of the first 10 alcohols and their boiling

points

Introduction

The interactions between subatomic particles and their electrostatic attractions has intrigued me

ever since I learnt about the forces between ions in grade 9. Coupled with my personal interest, in a world

where we face an energy crisis due to the lack of non-renewable resources, it is important to determine the

boiling points of compounds to know the minimum amount of energy required to change a unit mass from

liquid to gas(Latent heat of vaporization). However, this process in itself requires a lot of experimentation

and with every new covalent compound discovered, it would be a hassle(both in terms of the energy

wasted experimenting and the time consumed by chemists to experiment) to determine the boiling point

experimentally. Thus, I want to investigate whether there is a correlation between the polarity of a

covalent compound and its boiling point to determine a theoretical method of approximating the boiling

point of every single covalent compound using its dipole moment & a regression model. For this essay, I

will be exploring organic solvents of the same homologous series(Alcohols) as my covalent compounds.

In this investigation, the key terms are dipole moment, boiling, and electronegativity. 1) Polarity

can be quantified using the dipole moment; the mathematical definition of dipole moment is µ = δ𝑟𝑐𝑜𝑠θ

where µ is the magnitude of the polarity, δ is the partial charge on each atom, r is the bond length, and θ is

the bond angle. 2) Boiling is defined as a phase change from liquid to gas such that the intermolecular

forces are extremely weakened to a point where they are negligible. Boiling occurs throughout a liquid at

a specific temperature. 3) Electronegativity is described as the tendency of atoms to attract electrons

towards itself.

It can be established that polar covalent bonds have a net dipole moment(due to there existing an

electronegative difference in the bond) and nonpolar covalent bonds have no net dipole moment. The

1
 27𝑘𝑏𝑇ϵ0
dipole moment will be calculated via the Guggenheim method: µ = 𝑁𝑎(ϵ1+2)(𝑛1+2)
(𝑏ϵ − 𝑏𝑛) where 𝑘𝑏 is

−23 2 −2 −1
the Boltzmann constant(1. 38 × 10 𝑚 𝑘𝑔 𝑠 𝑘 ), T is temperature in kelvin,

23 −1 𝑘
𝑁𝑎(6. 02 × 10 𝑚𝑜𝑙 ) is the Avogadro’s constant, ϵ is the relative permittivity(ϵ = 2 ), and 𝑛1 is the
𝑓

refractive index. The investigation will research the relation of the dipole moment and the boiling point of

the organic solvent.

Hypothesis

Fig 1.00 - Force vector diagram pointing towards oxygen due to oxygen having a high electronegativity

Since the electronegativity of oxygen is way bigger than hydrogen, the force vectors point

towards oxygen. As the linear carbon chain gets bigger, due to the C-C bond having a nonpolar covalent

bond and the C-H bond having an electronegativity difference of 0.35(thus being nonpolar covalent),

every force vector of the C-C and C-H may point towards oxygen, thus increasing the polarity/dipole

moment of oxygen(Sum of every force vector). Hence, as the carbon chain increases for the alcohols,

their polarity may increase, thus the boiling point will increase as well due to the bonds needing a higher

amount of energy to overcome the intermolecular forces.

Materials

- Dipole meter

2
 - Abbe Refractometer

- Thermostat

- Beaker

- Methanol to decanol solvents

- Thermometer

- Plastic cup

Variables

Control variables

Variable Significance How to control?

Temperature of the surrounding
If the temperature varies with
respect to the apparatus, it may
influence the results from the
dipole meter since the
eigenfrequency of the
solvent/solution depends on
1 1
capacitance; 𝑓 = 2π 𝐿𝐶
. C is
capacitance and it varies with
temperature.
Let every apparatus(Abbe
refractometer & dipole meter)
reach a thermal equilibrium that
corresponds with the
surrounding temperature. Use
the thermostat to maintain that
temperature range.

Amount of solvent filled in the The amount of solvent may alter Add a fixed amount(2 drops of
refractometer the refractive index due to it solvent) of solvent to the
altering the angle light enters refractometer prism
through the solution

The purity of the solvent Every solvent must be 100% Buy or find pure versions of the
pure, thus the boiling point of solvent from the lab or online
each solvent will be accurate stores

Thermometer used The thermometer must be the Use the same thermometer
same throughout the boiling throughout the boiling
experiment such that the experiment
systematic uncertainty is
constant(The systematic
uncertainty may change with
respect to the type of
thermometer in question)

Amount of solute added to the If the solute added varies then Add a fixed amount of solute to

3
 organic solvent the weight fraction would
change as well, hence the
gradient of the weight fraction
vs. refractive index will not be
equal to 𝑏𝑛
the alcohols in order to create
the same percentage solution
and maintain a constant change
in weight fraction

Independent variable

The independent variable is the type of solvent because it does not depend on any factor, however,its

quantified identity will be given via its dipole moment. Hence, the dipole moment is the quantity plotted

on the x-axis. The calculation of the dipole moment of each solvent is described above. Obviously, the

dipole moment will depend on the difference in electronegativities of the solvent, thus it changes as the

solvent changes.

Dependent variable

The dependent variable is the boiling point of each solvent as it depends on how strong the intermolecular

forces are(the bigger the force of attraction, the more energy required to reach the boiling point). Thus, the

dependent variable depends on the polarity of the alcohols.

Methodology

1. Choose 10 different organic solvents(For this experiment, the first 10 alcohols have been chosen,

thus methanol, ethanol, propanol, butanol,...decanol)

2. Turn on the dipole meter and the thermostat

3. Wait until the thermostat and dipole meter are in a thermal equilibrium

4. Make sure that the refractometer is in the same temperature range as the temperature during the

thermal equilibrium of the thermostat and the dipole meter

5. Prepare 5 solutions of methanol using a solute such that their solution percentage changes

uniformly; for this experiment, the first solution will be 1%, the second will be 2%, the third will

be 3%, and so on.

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 𝑀𝑎𝑠𝑠 𝑜𝑓 𝑡ℎ𝑒 𝑜𝑟𝑔𝑎𝑛𝑖𝑐 𝑠𝑜𝑙𝑣𝑒𝑛𝑡
6. Calculate the weight fraction of each solution(𝑊𝑒𝑖𝑔ℎ𝑡 𝑓𝑟𝑎𝑐𝑡𝑖𝑜𝑛 = 𝑇𝑜𝑡𝑎𝑙 𝑚𝑎𝑠𝑠
)

7. Label the solutions as A1, A2, A3, A4, and A5

8. Fill the dipole meter with 30 mL of the organic solvent using a plastic cup

9. Wait for 10 minutes such that the solvent is in a thermal equilibrium with the apparatus

10. Read the eigenfrequency via the frequency counter

𝑘
11. Using ϵ = 2 , calculate the value of k(Use external sources to get the relative permittivity of
𝑓

methanol). k is the calibration constant.

12. Repeat step 5 to 9 using A1, A2, A3, A4, A5(Label the eigen-frequencies as 𝑓1, 𝑓2, 𝑓3... 𝑓5

respectively)

𝑘
13. Since k has been calculated, find ϵ1, ϵ2, ϵ3... ϵ5 using ϵ𝑛 = 2 for the 5 methanol solutions
𝑓𝑛

14. Record the relative permittivity in a data table

15. Add 2 drops of methanol solvent in the prism of the refractometer

16. Using the eyepiece of the refractometer, read the refractive index of the solvent

17. Repeat step 14 to step 15 for the 10 methanol solutions

18. Plot the graph of the relative permittivity(from ϵ1 to ϵ5) against the weight fraction and calculate

the gradient of the graph(The gradient of the graph will be equal to 𝑏ϵ)

19. Plot the graph for refractive index(from 𝑛1 𝑡𝑜 𝑛5) against the weight fraction and calculate the

gradient of the graph(The gradient of the graph will be equal to 𝑏𝑛)

27𝑘𝑏𝑇ϵ0
20. Using µ = 𝑁𝑎(ϵ1+2)(𝑛1+2)
, calculate the dipole moment of methanol

21. Record the dipole moment of methanol in a data table

22. Place the leftover methanol solvent in a beaker and heat it

23. Using a thermometer, measure the temperature change with respect to time

24. When the temperature becomes constant, mark that as the boiling point of methanol

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 25. Make sure to repeat the boiling experiment 3 times and find its average to get more reliable

results

26. Record the boiling point of methanol in a data table

27. Repeat step 5 to step 24 for ethanol, propanol, butanol,...decanol

(Note that the methodology for the dipole moment calculation is widely based on this practical research paper;

https://www.chem.uzh.ch/dam/jcr:e76290e3-3832-4c4a-b6c8-2c7195c77cd7/Dipole_Moment_HS17.pdf. )

Experimental Precautions

1. Clean the plastic cup and the beaker properly after using it in order to reduce uncertainty when

re-using it for different solvents or solutions

2. Wait until the dipole meter provides a stable frequency rather than it oscillating between high and

low values

3. Make sure that the apparatus are in a thermal equilibrium

4. Do not let air in the capacitor plates(dipole meter prism) as this may alter the results of the

eigenfrequency

Data Tables

Solvent Weight fraction Refractive index

Methanol

Ethanol

Propanol

Butanol

Pentanol

Hexanol

Heptanol

Octanol

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Methanol

Ethanol
Data table for 10 weight fraction values vs. 10 refractive index values to calculate 𝑏𝑛

Solvent Weight fraction Relative

permittivity(Farad/Meter)

Methanol

Ethanol

Propanol

Butanol

Pentanol

Hexanol

Heptanol

Octanol

Methanol

Ethanol
Data table for 10 weight fraction values vs. 10 relative permittivity values to calculate 𝑏ϵ

Solvent Dipole moment(D) Boiling Point(Average)(K)

Methanol

Ethanol

Propanol

Butanol

Pentanol

Hexanol

Heptanol

Octanol

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 Nonanol

Decanol
Data table for the dipole moment vs. boiling point(Main data table)

Bibliography

- PNGEGG - Exclusive Sticker PNG Images. https://www.pngegg.com/.

- Dipole Moment. 2017,

https://www.chem.uzh.ch/dam/jcr:e76290e3-3832-4c4a-b6c8-2c7195c77cd7/Dipole_Moment_H

S17.pdf.

- “UTSC Homepage.” Chemistry Online @ UTSC,

https://www.utsc.utoronto.ca/webapps/chemistryonline/production/refractive.php.

- “Dipole Moment - Definition, Detailed Explanation and Formula.” BYJUS, BYJU'S, 11 May

2022, https://byjus.com/chemistry/dipole-moment/.