Water has a density of 1g/ml while ethylene has a density of 1.26 g/ml. Obviously it's not very soluble at all, but I'm looking to do a salt metathesis that depends on it being very insoluble. I do not know what values to use for the division? caffeine is a polar organic molecule. It will deprotonates the phenolic OH of tannins, rendering these compounds anionic and hence highly soluble in water but with a low solubility in the methylene chloride. The solution 2 only had one spot and it was more faded than the product either solution 1. Place 0.050 g of one of the solids (benzoic acid, succinic acid, or sodium benzoate) in a vial and add 2 mL of methylene chloride and 2 mL of water. Consider the calculated partition coefficents for Experiments 4A and 4B. Note that 44+6, 1+49, and 40+10 all equal 50 which is what you started with. Modifications for Expts 4A and 4B: Partition Coefficient Part B and Solvent Extraction. Is there a correlation between the values of the distribution coefficients and the polarities of the three compounds? Conditioned on the result of an unbiased coin flip, the random variables T1,T2,…,Tn are independent and identically distributed, each drawn from a common normal distribution with mean zero. Our experts can answer your tough homework and study questions. It also has a tertiary carbocation which more stable than the secondary. When you have the Kd for each of them, them make a correlation, if there is one, between the Kd you found and the polarity of the three compounds. All the dyes that I experimented with changed colors after being immersed in HCl. Each compounds move differently on the plate, they have different Rf values. Would it be feasible to simplify the procedure by eliminating the boiling water step and instead extracting the tea leaves directly with methylene chloride? The spot should be the propyl bromide because it wasn't near the 4-methoxyphenol nor did it have a similar Rf value. At the high temp that toluene was extracted, I understood that there would be a small amount of hexane left in the solution. So Kd = 40/10 1 mg of sodium benzoate was recovered from the methylene chloride layer Consequently, toluene was more abundant in the fraction 3 where the temp was higher. Why did you rinse the sodium sulfate with an additional portion of methylene chloride? Why is sodium carbonate used in this procedure? d. Circle and Label (Polar) e. Ion-dipole . It can be produced by reacting sodium hydroxide with benzoic acid. ; John Wiley & Sons, Inc., 2011; pp 141-, 2. The scale that we used for weighing also fluctuated a lot leading us to almost making an inference about the fianl weight. The caffeine would have a lower solubility in the methylene chloride which would lead to an error in our experiment and data. The relative peak areas are consistent with the expected product distribution for the dehydration of 2-methylcyclohexanol. : Full references for the experimental procedure(s) in the following format: 1. The more compounds will interact more with the polar tlc plate and traveled less. Not impossible, but perhaps unlikely. Calculate the distribution coefficient for the solid between methylene chloride and water. Information about your device and internet connection, including your IP address, Browsing and search activity while using Verizon Media websites and apps. The reaction product, NaBr, was separated in the aqueous layer during the reaction workup. Explain why the solubility properties of the organic starting material change upon conversion to the product. Copyright © ScienceForums.Net What was the difference in the drying procedure in this experiment? What property or properties make caffeine an ideal candidate for sublimation? There could have been air bubbles when I was using the volumetric pipet which means that I could have to transfer less than 1 ml. - Definition & Examples, Hydrogen Bonding, Dipole-Dipole & Ion-Dipole Forces: Strong Intermolecular Forces, What is Suspension in Science? It starts as a nonpolar molecule and insoluble in the reactant but ends up polar and soluble in the aqueous phase. This happened because Benzoic Acid is more soluble in methylene chloride because of Benzoic’s Acid ability to hydrogen bond to methylene chloride. Which in water? Why are the compounds soluble in the solvents you chose? If the result of the coin flip is, The random variable W can take on the values of 0, 1, 2, 3, or 4. Why? Check my thinking. toluene would have become more purified due to its high bp. Methylene Chloride: The organic phase will be in the bottom layer because water has a density of 1g/ml while the density of methylene chloride 1.327 g/ml. The Kp value from Experiment A was much larger than it was in experiment 4B. The specific absorbance band frequency values are listed below each band. expt #7: What dye had the largest Rf value? 1/49 will be the smallest number which means the sodium benzoate is the most polar and the least soluble in organic layer (what we thought), 40/10 is the largest number and the most soluble in the organic layer (what we thought for benzoic acid), and succinic acid is the middle one (with a value in the middle). A. Will the organic phase be the upper (top) or lower (bottom) layer when each of these solvents is mixed with water? Why? Obviously it's not very soluble at all, but I'm looking to do a salt metathesis that depends on it being very insoluble. In the redistillation of fraction 3, it would contain much more toluene and even smaller amount of hexane. The pH of 1M HCl is -log(1)=0; however, the pH of the dyes are higher compared to HCl. For one of the specific sources of error that you identified in part (a), indicate the resulting effect (higher or lower) on the calculated partition coefficient value. You have it made, then. Match the peaks to the protons in the molecule using the letter designations. Since we did not use excess NaSO4, it helps us recover and keep more of the products. H-bonds; dipole-dipole; london dispersion forces. 1-methylcyclohexene have the highest peak of 16.65 mm2 because it is a major product and more stable while 3-methylcyclohexene have a peak area of 0.67 because it is a minor product and more unstable. What reaction product (aside from water) was separated in the aqueous layer during the reaction workup? We would obtain a purer results. What effect, if any, did the new drying procedure have on product yield? We did not use excess NaSO4¬ which means we rinsed the solution less. What is the strongest intermolecular force with which sodium benzoate will interact with the solvent water? a. a) Was there a significant difference in the two K, Yes, a pretty big difference in fact. I think it dissolves it to a very, very minor extent. no, it would not be feasible because the caffeine wouldn't mix well in moderately polar substances like methylene chloride. Compared to the elution solvent, they are all acidic and formed acid and conjugate bases. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with, ed. Benzoic acid is more soluble because, when we tested in lan, there were more benzoic acid in water than 9-fluorenone. Tea leaves have tannic acids which are soluble in water like caffeine. It was also separated in the workup. What compound is less polar, 4-methoxyphenol or 1-methoxy-4-propoxybenzene? It is important to put just enough NaSO4 because too much may make it difficult to transfer the methylene chloride and concentrate the solution; too little might leave water molecules in the solution since they were not absorbed. If I substituted ethylene chloride for methylene chloride, it would be the bottom layer. The order of elution is determined by the solutions' boiling points. For product-ether solution 2, briefly describe any differences from product-ether solution 1. 4A’s Partition Coefficient was much larger because Benzoic Acid is more soluble in methylene chloride than in the water layer. NF category: Antimicrobial preservative. BOth are therfore organic compounds... As far i knew..phenyl ring compounds viz., benzene ,benzoates are insoluble in water.. Sodium benzoate is a substance which has the chemical formula C 6 H 5 COONa. The compounds have different Rf values based on polarity. There were some yellow substances in top of the water. There are dipole moments in the C=O bonds. I've looked through the literature (Google Scholar, SciFinder, etc. Note that the assignment of protons e and f is given. For each of the following functional group vibrations, list a specific (do NOT report a general range) absorption band in the IR spectrum. it crystalizes with the water, and by rinsing it with methylene chloride, we could make sure the 9-fluorenone is isolated. All other trademarks and copyrights are the property of their respective owners. tensor9, June 21, 2013 in Organic Chemistry. The NaSO4 reacts with water molecules, so it doesn't affect the final results of the experiment. Since the dielectric constant of... See full answer below.