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BACKGROUND You may or may not be familiar with two of the classifications of organic compounds: alcohols and alkanes. Listed in the table below are the names and formulas of some examples of both. Alcohols methanol CH3OH ethanol CH3CH2OH 1-propanol CH3(CH2)2OH 1-butanol CH3(CH2)3OH t-butanol (CH3)3COH Alkanes pentane CH3(CH2)3CH3 hexane CH3(CH2)4CH3 heptane CH3(CH2)5CH3 octane CH3(CH2)6CH3

You will probably notice several similarities such as the fact that all alkanes are made entirely of carbon and hydrogen atoms and all alcohols have OH in them which, in this case is NOT a hydroxide ion since the oxygen atoms are covalently bonded to the chain of carbon atoms. 2-propanol (or isopropanol) has the same molecular formula but different structure as 1-propanol above and is otherwise known as rubbing alcohol. As you may know, compared to water, isopropanol evaporates easily and when done on your hand, makes your skin feel cold. It also, not surprisingly has a very different molecular structure, molar mass, and polarity than water. In this investigation you will be provided with all of the above compounds and equipment to measure how much cooling is involved in the evaporation process. Come to lab prepared with beginning questions you wish to explore as well as any important preliminary information (i.e. Lewis structures, molar masses, polar vs. non-polar etc) PROCEDURE TIPS As a class you will need to determine the specifics on how to proceed with regard to tests you will perform. However, below is a general explanation of how to measure the cooling effects of evaporation. Measuring cooling 1. Wrap a piece of filter paper around the tip of the temperature probe (so that it's even with the end of the probe) and secure it with a rubber band. 2. Place the wrapped temperature probe in a test tube that contains enough of the test liquid to completely cover the paper. After about 45 seconds, start collecting temperature vs. time data by clicking on the collect button. 3. When the temperature has been stable for about 15 seconds, remove the probe from the liquid and place it on the bench so that the tip extends over the edge of the benchtop, still recording data. Minimize movement near the probe, since that may affect the rate of evaporation. 4. Determine as a class how long you wish to collect data (somewhere between 150-300 seconds should be sufficient) and make sure your experiment is set to collect for that length.

5. Determine the maximum temperature change by clicking on the Analyze menu and selecting Statistics from the pull down menu. 6. When finished collecting data remove the filter paper (is it still wet?) and dispose of it in the trash. 7. Lastly, each trial can be saved by clicking on the Experiment menu and selecting Store Latest Run. WASTE Contaminated filter paper can be placed in the trash. Left over liquids should be kept in their original containers or placed in the appropriate waste containers. Water can be put down the drain. DATA ANALYSIS As you formulate claims to your beginning questions, consider (and answer) the following questions. Some are relevant to the Reading and Reflection component of your lab report. 1. What intermolecular forces are present: a. in the alkanes? b. in the alcohols? 2. How do the T values for the four alkanes compare? a. Are there any trends with molar mass (size of molecule), shape of molecule, polarity? 3. How do the T values for the six alcohols compare (count water as an alcohol in this case). a. Are there any trends with molar mass (size of molecule), shape of molecule, polarity? b. Does water follow these trends? If not, why not? c. How does the T for t-butanol compare to the T for1-butanol? Explain similarities or differences. 4. Explain all these trends/results in terms of the intermolecular forces and what you know about evaporative cooling. 5. Compare 1-butanol with the alkane of the closest molecular weight, and discuss in terms of the strength of intermolecular forces. POST-LAB QUESTIONS 1. Using the evaporative cooling results, predict the order of the vapor pressures of the liquids, from lowest to highest vapor pressure. 2. Predict the order of the boiling points, from lowest to highest boiling point. How do these compare to the values tabulated in the CRC, on-line through MSDS sheets, or in your book?