Ickes, Wilmes, Reitz 1 Beginning Questions Will molecular structure/Lewis structure of the alkanes and alcohols have an effect

on temperature change of the probe? How does molar mass affect the change in temperature? How do the T values for alcohols compare to the T values of the alkanes? How will the intermolecular forces of the alcohols and alkanes vary and what influence will that have on the rate of cooling? We predicted that weaker intermolecular forces (IMF) would force a faster rate of evaporation and therefore T would be a smaller value. Structures Alcohols Methanol (CH3OH)
H H C H O H
H

Ethanol (C2H5OH)
H C H H C H O H

1-butanol (C4H9OH)

1-propanol (C3H7OH)
H H C H H C H H C O H
H

t-butanol (C4H9OH)
H H C H H O C C H H H C H H

Water (H2O)

Alkanes Pentane (C5H12)

H H C H H C H H C H H C H H C H H H

Hexane (C6H14)
H C H H C H H C H H C H H C H H C H H

Heptane (C7H16)

Octane (C8H18)
H H C H H C H H C H H C H H C H H C H H C H H C H H

Ickes, Wilmes, Reitz 2 Intermolecular Forces (IMF) Present and Molar Masses Substance Pentane Hexane Heptane Octane Methanol Ethanol 1-propanol 1-butanol t-butanol water IMF Present dispersion dispersion dispersion dispersion dispersion, dipole-dipole, hydrogen bonding dispersion, dipole-dipole, hydrogen bonding dispersion, dipole-dipole, hydrogen bonding dispersion, dipole-dipole, hydrogen bonding dispersion, dipole-dipole, hydrogen bonding dispersion, dipole-dipole, hydrogen bonding Molar Mass (g/mol) 72.146 86.172 100.198 114.224 32.041 46.067 60.093 74.119 74.119 18.015

Safety Considerations Safety goggles should be worn at all times in the laboratory. Do not ingest any of these substances. All of these substances (with the exception of water) are flammable, so keep them away from heat or open flame. Do not ingest any of these substances. Dispose of chemicals in the appropriate labeled containers. Always exercise caution around chemicals, as they can be detrimental to good health. Never eat or drink in the laboratory. Procedure and Tests Materials: Temperature probe 10 medium test tubes Chemicals listed above Procedure: To begin, we determined the molar mass of each compound. We then drew out the Lewis structure for each substance and determined which intermolecular forces were present in each. Then we proceeded to obtain 5 ml of the substances, each in separate test tube. After this we set up the data collection program on the computer. We then prepared the temperature probe by rolling the filter paper onto the top of the probe so the tip is flush with the paper. We secured this paper onto the probe with a rubber band. Next, we put the temperature probe into a test tube and let the filter paper absorb the substance for 45 seconds. When we were ready to begin the trial, we Filter paper Pentane Rubber bands

Ickes, Wilmes, Reitz 3 took the probe out and set it on the counter under a fume hood. We collected data until the temperature of the probe began rising again. When this happened we recorded the lowest temperature. When done with the first trial, repeat the experiment until every chemical has been tested four times. Data, Observations, Calculations, and Graphs The difference in temperature from the starting to the ending point was T. Each trial was done four times. We took the average of these values to give our experimental data. This information is listed in the following table. T Trial 1 T Trial 2 T Trial 3 T Trial 4 T Average Substance (C) (C) (C) (C) (C) Pentane -27 -29.9 -28.1 -29.1 -28.5 Hexane -18.3 -17.8 -21.2 -21.7 -19.8 Heptane -13.3 -9.4 -12.4 -12.7 -12.0 Octane -6.2 -4.4 -6.9 -7.6 -6.3 Methanol -23.8 -20.6 -23.3 -28.7 -24.1 Ethanol -14.8 -15.0 -16.8 -17.2 -16.0 1-propanol -9.6 -10.0 -10.8 -8.7 -9.8 1-butanol -4.9 -5.2 -9.3 -9.8 -7.3 t-butanol -21.4 -16.3 -22.2 -15 -18.7 water -11.8 -8.3 -9.7 -12.6 -10.6 Data collection for this experiment was relatively easy. We simply subtracted the initial temperature of the probe from the final temperature to obtain T. A sample calculation is shown below. Sample Calculation, Trial 2Methanol: T = Tf - Ti T = (2.9 C) (23.5 C) T = -20.6 C Claims By measuring the change in temperature and observing the molecular structures, we claim that the alkanes are more efficient at cooling than the alcohols. The alkanes were found to have weaker IMF than the alcohols. Therefore, we also claim that weaker IMF will yield a greater T.

Ickes, Wilmes, Reitz 4 Evidence and Analysis We believe that weaker intermolecular forces yielded a greater T in this experiment because they evaporated more easily. This means that less energy was necessary to cause them to vaporize from the filter paper that was attached to the temperature probe. More molecules were able to evaporate, taking more heat energy with them. Substances with stronger IMF will not evaporate as easily, meaning that even though they take more heat energy with them when they vaporize, this still does not yield a greater T than substances with weaker IMF, because the number of particles evaporating is few. Analysis Both alkanes and alcohols contain dispersion forces. In addition to these, alcohols also contain dipole-dipole, and hydrogen bonding. The T values the alkanes, in order of greatest to least change, are: pentane, hexane, heptane, octane. Pentane, which had a T value of -28.5 C was the smallest of the alkanes, with a molar mass of 72.146 g/mol, and had the weakest IMF. On the other end of the spectrum, T for octane was -6.3 C. Octane was the largest alkane, both in size, and mass, at 114.224 g/mol; The length of the octane molecule yields the strongest dispersion forces out of all the alkanes. The comparison of these two substances and further consultation of the graph shows that in this experiment, the alkanes that yielded the greatest difference in temperature were also those that had the weakest IMF. The biggest, longest molecules allowed stronger dispersion forces, meaning they were less easy to vaporize. Conversely, smaller molecules had weaker IMF, and so are more prone to vaporization. Listed here are the alcohols, in order of IMF from weakest to strongest: IMF Weaker Substance methanol ethanol t-butanol water 1-propanol 1-butanol Average T -24.1 -16 -18.7 -10.6 -9.8 -7.3

Stronger

Ickes, Wilmes, Reitz 5 Again, the trend is for those substances with weaker IMF to yield greater T values and those with stronger IMF, lesser T values. The strengths of the IMF are again attributable to the size of the molecule. Molecules that have shorter structure have less surface area for the influence of intermolecular forces. Therefore, they are held less tightly by neighbor molecules and have the tendency to vaporize more readily. Likewise, the structures that are longer and contain more surface area have the ability to influence stronger intermolecular forces. Therefore, their neighbor molecules hold them more tightly, which makes them difficult to vaporize. The one exception we had to this concerned ethanol and t-butanol. These two were out of order. This could possibly be due to human error. It is also possible that the two are so close in the strength of their IMF that our experiment simply resulted in misrepresentative data. Either way, the difference between the two is not a large value, meaning that the two most likely have similar IMF. Since we are classifying water as an alcohol for the purpose of our experimental analysis, we believe that it does also follow the aforementioned trends. It has significant hydrogen bonding capabilities, but as a small molecule, its dispersion forces are not going to be nearly as strong as those in larger molecules. This makes it a middling substance in terms of intermolecular forces. The T value for t-butanol is -18.7 C, compared with -7.3 C for 1-butanol. These two substances show resonance: similar chemical formulas with different chemical structures. The main difference in their shapes is the length. 1-butanol is a long molecule, allowing dispersion forces to be much greater in it than those present in t-butanol, which is a balled-up molecule. This accounts for the large difference in T between the two. Ultimately for this experiment, our results show the trend that greater IMF will yield smaller T values, and lesser IMF will yield larger T values. As mentioned before, the weaker IMF allowed for a greater number of molecules to evaporate. Vaporization requires heat energy, so the more particles that evaporate, the more heat energy was taken away from the temperature probe. From this experiment, we can come to the conclusion that the number of molecules that vaporize has a far

Ickes, Wilmes, Reitz 6 greater influence on the change in temperature than the individual heat capacity of each substance. The alkane closest to 1-butanol (74.119 g/mol) in molecular weight is pentane, at 72.146 g/mol. The T value for pentane was -24.1 C, compared to -7.3 C for 1-butanol. Comparing the intermolecular forces of the two, it can be seen that hydrogen bonding is present in t-butanol, whereas the strongest IMF in pentane are dispersion forces. This accounts for the large difference in their T values. Reading, Reflection, and Post-Laboratory Questions Sources of error that may have occurred in this experiment could be attributed to a gap between taking the probe out of the vial and start the data collection timer. We could have also encountered air by having an uncontrolled amount of airflow through the testing area. Keeping excess airflow to a minimum is imperative to measuring the actual evaporation rate of the solution. Also, there could have been an unequal amount of vaporizing substance in each test. We can conclude that our error was probably minimal because our averaged results were very similar to that of our classmates. Before the experiment we had no idea what would be the greatest contributing factors in the vaporization of our substances. However, after the tests, we have drawn the conclusion that the greatest contributing factor of vaporization was the structure of the molecule. The strength of the intermolecular forces present also plays an important part of the vaporization. Now that we know that intermolecular forces plays a major role in vaporization, we can think about other structures with various functional groups. We can now think about the ability of a substance to vaporization by its intermolecular forces. A new question we have formulated is which substance has a greater rate of vaporization, if they have the same intermolecular forces? This experiment has demonstrated the importance of intermolecular forces in vaporization. It allowed us to visualize the interactions between similar molecules and predict which would possess the lowest vaporization pressures. This experiment gave us data to back up the information we were taught in lecture.

Ickes, Wilmes, Reitz 7 The phenomenon of vaporization is extremely applicable to the biological function of sweating. When water vaporizes off the skin, it provides a cooling effect to the body. A practical use for this information could be used on a burn victim. To decide what substance to use to treat the burning sensation, you could look into the molecular structures and intermolecular forces. You know that the ones with the lower intermolecular forces are going to be more efficient at cooling. The order of the boiling points, from lowest to highest are: pentane, methanol, t-butanol, hexane, ethanol, heptane, water, 1-propanol, octane, and 1butanol. From this information, we can concluded the order of vaporization pressure from lowest to highest is as follows: 1-butanol, octane, 1-propanol, water, heptane, ethanol, hexane, t-butanol, methanol, and pentane.