If something is more polar, the mobile phase and stationary phase would stick together. Select one of the two dyes that was present in your unknown dye solution. In Experiment 4B, a chemical reaction occurred to form sodium benzoate. The separatory funnel would provide the most accurate determination of the partition coefficient because there were less separation steps. The product of this reaction contains two stereocenters. Which piece of laboratory glassware did you find to be more efficient for the solvent extraction procedure, and why? Due to this, the conclusion was made that it was Bromocresol Purple, which was not present in the lab room the experiment took place in. Explain the evidence that led to this conclusion. HCl has a pH of about 1, so therefore it is acidic. This change in polarity changes what solvent the products are soluble in. The proper amount is estimated instead. The top spot was propyl bromide and the bottom spot was the 4-methoxyphenol standard. The steam distillate collected in the Hickman still was clear. If substituted for methylene chloride in this partition coefficient experiment, would ethylene chloride form the top or bottom layer? The third distillation had more equal results of hexane and toluene compared to the results of what the redistillation would produce. The reason ethylene chloride would from a layer on the bottom is because it has a higher density than the other two (water and 9-Fluorenone) substances in the solution. In the first error mentioned, we would be conducting calculations using higher mass of 9-Fluorenone than we actually have in the aqueous layer, thus lowering the value of our partition coefficient. Why? This chemical reaction should be included in the Reaction Scheme section (hint: review common types of chemical reactions in aqueous solutions from general chemistry, such as precipitation, acid-base, gas-forming, and oxidation-reduction). Why do the dye compounds have different Rf values? Due to the stereospecificity of the bromination and the symmetry of the product, however, only the meso-diastereomer of stilbene dibromide is produced. Explain your answer in each case, using appropriate supporting data. In the organic product drying step (sodium sulfate) in this experiment, a significant procedural difference was followed compared to previous experiments that involved drying of organic phases (the first three experiments of the semester). The sodium bicarbonate acts as a base in this reaction. In Experiment 4B, a chemical reaction occurred to form sodium benzoate. Polar "In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole or multipole moment. Explain why the solubility properties of the organic starting material change upon conversion to the product. How many possible stereoisomers exist for stilbene dibromide? Consult the IR spectrum of 4-methoxyphenol included below, on page 6. A final source of error is that in our lab section, the heater block did not work. The distillate collected from the steam distillation was cloudy because cinnamaldehyde is not miscible in water. The condenser was used so that the vapors from the reaction would not escape into the room. However, this is due to the product not being compact when being heated. The reaction product that was separated in the aqueous layer during the reaction workup was NaBr. This chemical reaction should be included in the Reaction Scheme section (hint: review common types of chemical reactions in aqueous solutions from general chemistry, such as precipitation, acid-base, gas-forming, and oxidation-reduction). What problem(s) would be associated with using too little or too much sodium sulfate? Write a mechanism for the Williamson ether synthesis of 1-methoxy-4-propoxybenzene from 4-methoxyphenol and propyl bromide. Each of the solvents listed below are commonly used in experiments to extract organic compounds from aqueous solutions. Be sure to comment on the relative peak areas of the two peaks observed for each fraction. The steam distillate was extracted with three portions of methylene chloride because one or two washes would not be as thorough in extracting the cinnamaldehyde from the aqueous layer. Draw the chemical structure of 9-fluorenone and use it to answer the following solubility based questions: What is the purpose of the sodium sulfate? In Unknown 7, the two dyes that were present were Bromocresol Green and Bromocresol Purple. Draw the chemical structure of sodium benzoate and include all charges. The first peak will be higher than the second peak. The product-ether solution 2 should have one spot from the propyl bromide and because the there was no substance with an Rf value similar to the one of 4-methoxyphenol present. Why is it NOT necessary to weigh accurately the sodium sulfate? For the redistillation of Fraction 3, predict how the gas chromatogram of Fraction 3 from the redistillation would have differed from the gas chromatogram of Fraction 3 from the first distillation. One has same looking molecule as the product above, but both chiral centers are R. How are the stereoisomers that you drew in part (b) related to each other? It also required less washes. It may not be complete in terms of showing ALL electron flow(proton transfers, in particular, are often assumed and not drawn out fully). You are responsible for writing complete reaction mechanisms that are inspired by the rules and guidelines set forth in both the lab AND lecture courses. In our sample, there was slightly more 1-methylcyclohexene and less 3-methylcyclohexene.

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