Diana Moreira

Ib Chem Y1

Investigation of the boiling point trend in an

alcohol homologous series
Introduction. It is very important to understand that all physical and chemical properties observed for a
compound are directly related to the compound's molecular structure. Alcohol is a relevant organic
molecule as it plays a significant role in everyday lives, therefore, it is important to understand its physical
properties, specifically boiling points, so that it’s easier to understand how to use it more wisely. Ethanol,
for example, is widely used as a part of hot drinks and beverages so people consume it on a regular basis
which can lead to health problems. Consequently, studying the homologous series of alcohol will provide a
better understanding of how and why alcohol interferes with brain communication pathways, damages our
liver, and weakens the heart muscle. However, besides drinking there are many uses of alcohol in
medicine, industry, research etc. because It has powerful antimicrobial, astringent, and sedative effect
therefore it can be used for sanitation, as a solvent for analysis and even as automobile fuel. Seeing as
alcohol is a world-wide used substance it is critical that it is analyzed in detail regarding its physical and
chemical properties.

Research question
What is the relationship between the number of carbons in an alcohol homologous series
and their respective boiling points?

Background information
Homologous series is defined as a systematic order of organic compounds having same functional group that
can be represented by same general formula. The difference between two consecutive members in the series is
a CH2 group, for example, alcohol: CH3-OH, CH3-CH2-OH, CH3-CH2-CH2-OH. This shows that each alcohol
molecule differs by a CH2 group; a single Carbon atom and two Hydrogen atoms.
Alcohols are organic compounds containing the –OH group which determines the characteristic reactions of the
compound. The general formula of alcohols is CnH2n+1OH and as one moves down the homologous series of
alcohols, the number of Carbon atoms increase and, consequently, so does boiling point.
The OH group in alcohols will cause the boiling temperature to increase because it causes the strongest
intermolecular force, hydrogen bonding, to occur. The factors affecting the boiling points of alcohols are not
only hydrogen bonds, but also van der Waals dispersion forces and dipole-dipole interactions The van der Waals
dispersion forces increase as the length of hydrocarbon chain increases. This is due to the increase in number of
electrons in the molecules, which in turns increases the strength and size of the temporarily induced dipole-
Diana Moreira
Ib Chem Y1
dipole attraction. Therefore, more energy is required to overcome the intermolecular forces, resulting in the
increase in boiling point.

The figures below are the structural formula of Methanol (CH3OH) and Ethanol (C2H5OH):

Figure 1. Methanol Figure 2. Ethanol

ALCOHOL MOLECULAR FORMULA (CnH2n+1OH)

Methanol CH3OH
Ethanol C2H5OH
Propanol C3H7OH
Butanol C4H9OH
Pentanol C5H11OH
Figure 3. General formulas

Variables
Independent: Number of Carbon atoms in the alcohol molecule

Dependent: boiling point

Control variables linear hydrocarbon chain, primary alcohols

Safety and Ethical Issues Discuss your access to the database and any issues here. Who has access? Who pays for it? Who
is responsible for maintaining it?

One of the databases used is called PubChem and it was launched in 2004. PubChem is an open
chemistry database at the National Institutes of Health (NIH) and “open” means that one can put scientific data
in PubChem and that others may use it. This is advantageous in the sense that a lot of data is stored and may
reach the public however if anyone can insert the data into this database, how do they sensor the data and
until what point is it reliable? The database uses processing software to annotate and limit information that is
Diana Moreira
Ib Chem Y1
viewed, and then uses their own software along with additional information from PubChem and other public
databases to perform statistical analysis and relevance-based sampling to identify the most relevant
information and summarize it to a compact form on PubChem. Regarding the NIST database, is The National
Institute of Standards and Technology (NIST) and its maintained by the U.S Department of Commerce and its
reliability is supported by the Standard Reference Data Act. Chemspider builds on the collected sources by
adding additional properties, related information, and links back to original data sources and it integrates and
links compounds from hundreds of sources. It is managed by a small team of full-time curators and its part of
the Royal Society of Chemistry. This demonstrates that the databases appear to be reliable sources of data
collection.

Method Present a step by step numbered procedure to share what you did and what you used.
1. Gather some background research about the homologous series focusing on the trend that is being
analyzed
2. Find a reliable database (s) and collect data on the physical property
3. Process the data into a graph and compare the results to other resources available

Data and Analysis

Raw Data
Table 1. Raw Data measurement of boiling points of alcohols

Compound PubChem Database Chemspider Database NIST chemistry webBook

Boiling Point (ºC) ±1 Boiling Point (ºC) ±1 Boiling Point (ºC) ±1
Methanol 67 65 65
Ethanol 78 78 78
Propanol 97 97 97
Butanol 118 118 118
Pentanol 138 138 138
Diana Moreira
Ib Chem Y1
Processed Data

Variation of Boiling Point of straight chained Alcohols with

Number of Carbons
160 138
140 118
Boiling point (ºC)

120 R² = 0.989
97
100 78
80 67 65/67
60
40
20
0
Methanol Ethanol Propanol Butanol Pentanol
Primary Alchols

Pubchem Chemspider NST WebBook

Linear (Pubchem) Linear (Chemspider)

Figure 4. Graph of boiling point trend in the homologous series

Conclusion
The relationship the data collected shows is that there is a correlation between the number of carbons in an
alcohol homologous series and the respective boiling points. The observation that can be made is that the
boiling point of hydrocarbons increases as the number of carbon atoms in the molecule increases. This is
evidenced in the data because the correlation coefficient between the boiling point and number of carbons in a
chain is 0.989 which shows a very strong linear relationship and that as one variable gets bigger the other also
tends to increase in value. Even though various data sources were used, the evidence generalizes throughout all
the databases and they all portray the same correlation. Therefore, the conclusion that can be reached is that
as more carbons are added to a chain of alcohol in a homologous series, the boiling point of the organic
molecule will increase due to the force of attraction between the molecules increases as the molecule gets
longer and has more electrons. It takes more energy to overcome the force of attraction, and so the boiling
point rises. In this case the strongest force of attraction between particles is the hydrogen bonding provided by
the OH group.
Diana Moreira
Ib Chem Y1
Evaluation
The evidence discussed can be supported by an investigation done by Brown and Ford in which the boiling
points of alkanes and alcohols were analyzed.

Figure 5. Brown and Ford´s processed data of the boiling point trend in regards to the
number of carbons in a chain
The data they collected supports the conclusion that the boiling points of the alcohols increase with increasing
number of carbon atoms seeing as there is a strong linear correlation between the variables portrayed in the
graph above. Also, the values of the boiling points that Brown and Ford collected are the same as the values
that were collected previously from the databases. This enhances the credibility and the reliability of the
databases and of the conclusion that has been reached regarding the relationship between the number of
carbons in an alcohol homologous series and their respective boiling points since the data agrees with
published results. The scientific concept behind these results is that Alcohols contain two types of
intermolecular forces of attraction hydrogen bonding and Van der Waals. The additional forces of attraction
due to hydrogen bonding between the hydroxyl groups in adjacent molecules of an alcohol make their boiling
points higher as the number of carbon atoms increases.
In this case, the uncertainty of ± 1 regarding the value of the boiling points of each molecule in the homologous
series did not affect the results or the outcome of the research because the correlation between the number of
carbons and trend in boiling points can still be observed in the processed data. Therefore, the validity of the
results remains intact regardless of the uncertainty of the values collected.
The methodological procedure did not have errors that significantly impacted the results or their validity. The
databases agreed on all the values of the boiling points except on the value of the boiling point of methanol.
PubChem database said the boiling point was 65ºC while Chemspider and NCST chemistry webbook said the
boiling point value was 67ºC. However, this disagreement in the database values was not relevant.
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Ib Chem Y1
To improve the investigation, more data could be collected, beyond the 5 carbon chain molecule, pentanol, to
give more credibility to the results by showing that the correlation continued along the homologous series. Also
more data could be collected beyond three databases to demonstrate how reliable the results truly are.
Furthermore, the investigation could be extended to know more about the physical property by comparing the
boiling point of, not just primary alcohols, but of secondary and tertiary alcohols and observe how the trend
would be affected. It could also be extended by comparing these results to the molar mass of each molecule of
the homologous to prove whether or not the mass was related to the trend and to show that the size of a
molecule influences its boiling point, again due to increased van der Waals interactions and hydrogen bonding
between molecules.

References MLA citation

Works Cited
The "Data Organization" section in "PubChem Substance and Compound databases", S. Kim et al., Nucleic Acids
Res. 2016; 44(Database issue): D1202–D1213. doi:10.1093/nar/gkv951
C. Brown and M. Ford, Higher Level Chemistry, p 367, Pearson Baccalaureate, 2009
"The Team." ChemSpider, www.chemspider.com/theTeam.aspx.
"NIST Chemistry WebBook." NIST.
"Investigation." sciencesfp.com, www.sciencesfp.com/uploads/2/1/5/9/21597828/ investigation_1_e.pdf.
"Boiling Point." chemlibretexts.org, chem.libretexts.org/Bookshelves/
Organic_Chemistry/ Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)/
chapter_02%3A_Introduction_to_organic_structure_and_bonding_II/ 2.5%3A_Physical_properties_of_organic
_compounds.
"Boiling point." http://amrita.olabs.edu.in, amrita.olabs.edu.in/?brch=7&cnt=1&sim=111&sub=73.