9/19/12 Organic Chemistry Lab #1 Report: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES A. Reflux and Distillation 1.

Was there a stopper on the top of your reflux condenser? Explain your answer in terms of pressure and temperature, relating it to the ideal gas law. PV=nRT No there was not. Inserting a stopper on the top of the reflux condenser would have been hazardous due to the relation between pressure and temperate stated in the ideal gas law. We heated the solution, causing evaporation which in turn resulted in the system reaching over 100C. The ideal gas law states an increase in temperature results in an increase in pressure; this increase in pressure would not only be dangerous, but closing the system would keep heat in and hinder the distillation process. 2. Which way should the water flow in the reflux condenser (from top to bottom or from bottom to top)? Why? The water flow should run from bottom to top as it is more efficient. The purpose of a condenser is to bring vapors back down to liquid phase; cooler water at the site of condensation just makes sense. Bottom to top flow also helps reduce the likelihood of glass breakage due to thermal shock. 3. At what temperature range was your solvent distilling? Is this value close to the boiling point of the distilled component? The solvent reached full reflux and began distilling at 25.1C(measured at joint). Compared to the boiling point of Toluene(111C) it is most obviously lower. However, the temperature quickly rose to around 111C as distillation continued. This initial difference in temperature can be accounted for by taking into consideration the position of the thermometer. It was placed not in the solution but above it, not being heated by the solution but by its vapors.

4. Which solvent did you expect to distill first? Why? Comparison of boiling points lead me to predict Toluene (bp=111C) would distill first, rather than 1-hexanol (bp=155C). 5. According to your data collected, what compound is distilled off first? How did you determine the identity of this compound? A mass to charge ratio of 91 is typical of a compound with a benzyl unit. Toluene does in fact have a benzyl unit while 1-hexanol does not. The distillate GC output indicates a greater %composition for toluene compared to the residual data. Therefore toluene was distilled first. B. Gas Chromatography/Mass Spectrometry 1. Distillate: %comptoluene=9.213*10^6/(9.213*10^6+854583)=91.5% %comp1-hexanol=854583/(9.213*10^6+854583)=8.5% Residual: %comptoluene=2.259*10^7/(2.259*10^7+1.918*10^7)=54.1% %comp1-hexanol=1.918*10^7/(2.259*10^7+1.918*10^7)=45.9%

2. Which compounds are indicated by each peak on the GC spectrum? The peak at 2.963 min represents toluene. The peak at 4.003 min represents 1-hexanol. 3. Is your distillate sample pure? If not, provide an explanation and solution to this problem. No, the distillate sample is not pure. The gas chromatograph indicates there is significantly less 1-hexanol in the distillate, yet it is still present. To enhance purity, it would be a good idea to bring the solution to reflux more slowly. If both compounds are evaporating at the same time, they will condense together and

result in an impure product. 4. Do the mass peaks observed (M+) confirm the identity of both compounds? Explain. Masstoluene=92 Mass1-hexanol=102 Yes. But only because the starting compounds were known. For example, a m/z of 91 is present, indicating toluene(in both distillate and residual). In the residual, a m/z of 84 is seen, hinting that the 1-hexanol lost a water(102-18=84); this value is not as strong in the distillate output. This information gives us a good idea of which compound distilled off first, however, if the starting compounds were not known I could not be said for sure what compounds were present in the distillate/residual.