Separation Of A Carboxylic Acid Lab Report

The purpose of this experiment is to examine the stoichiometric relationship between reagents and the identity of the products by using three acid/base neutralization reactions of a triprotic acid, phosphoric acid, and varying molar equivalents of sodium hydroxide. The data will be used to determine the formula weight of the products and identify the remaining salt for all three reactions.

14 mL of 9 M H2SO4 was added to the separatory funnel and the mixture was shaken. The layers were given a small amount of time to separate. The remaining n-butyl alcohol was extracted by the H2SO4 solution therefore, there was only one organic top layer. The lower aqueous layer was drained and discarded. 14 mL of H2O was added to the separatory funnel. A stopper was placed on the separatory funnel and it was shaken while being vented occasionally. The layers separated and the lower layer which contained the n-butyl bromide was drained into a smaller beaker. The aqueous layer was then discarded after ensuring that the correct layer had been saved by completing the "water drop test" (adding a drop of water to the drained liquid and if the water dissolves, it confirms that it is an aqueous layer). The alkyl halide was then returned to the separatory funnel. 14 mL of saturated aqeous sodium bicarbonate was added a little at a time while the separatory funnel was being swirled. A stopper was placed on the funnel and it was shaken for 1 minute while being vented frequently to relieve any pressure that was being produced. The lower alkyl halide layer was drained into a dry Erlenmeyer flask and 1.0 g of anhydrous calcium chloride was added to dry the solution. A stopper was placed on the Erlenmeyer flask and the contents were swirled until the liquid was clear. For the distillation

As indicated in Table 1, each of the given substances for this lab were soluble in ethyl acetate. However, the solubility results varied based on the structure of each tested compound. 4-bromoacetanilide and fluorene are both insoluble within solvents of HCl and NaOH. Fluorene will stay soluble within the organic layer since its is a purely made of carbon and hydrogen. 4-bromoacetanilide will act similarly given its nonpolarity from balanced branches and lack of acid/basic characteristics. 4-nitroaniline and 2,5-dichloroaniline travel solubly into the HCl/H2O solvent when added to the separatory funnel, yet form a precipitate after a highly concentrated NaOH is added. Both 4-nitroaniline and 2,5-dichloroaniline are slightly basic organic compounds, and when an acid (HCl) is added a proton will transferred to make them ionic. In their ionic state, both compounds become water-soluble. When NaOH is added to 4-nitroaniline and 2,5-dichloroaniline, it removes the proton causing the compounds to become insoluble in water once again. The same concept can be applied in an opposite fashion to the acid organic compounds of 3-chlorobenzoic acid and resorcinol; both become water-soluble when they lose a proton after mixed with NaOH. They go back to their water insolubility if you add an acid to donate a proton back to 3-chlorobenzoic acid and resorcinol. Therefore, after completing this lab,

12. Write the balanced chemical reaction of the product of the reaction described above (problem 11) with NaOH. Is the product of this reaction soluble in aqueous solution?

Samples of benzophenone, malonic acid, and biphenyl were each tested with water, methyl alcohol, and hexane. Benzophenone was insoluble in water as it is nonpolar while water is highly polar. Benzophenone was soluble in methyl alcohol, dissolving in 15 seconds, because methyl alcohol is intermediately polar as benzophenone is nonpolar. Methyl alcohol is polar but not as much as water. Thus, the nonpolar benzophenone was soluble in methyl alcohol. Benzophenone was partially soluble in hexane because hexane is nonpolar as is benzophenone. Thus, benzophenone was dissolved in hexane. Malonic acid was soluble in water because both malonic acid and water are polar. It took 25 seconds for malonic acid to dissolve in water. Malonic acid was soluble in methyl alcohol because malonic acid is polar and methyl alcohol is intermediately polar, allowing malonic acid to dissolve in the methanol in 15 seconds. Malonic acid was insoluble in hexane because hexane is nonpolar while malonic acid is polar. Biphenyl was insoluble in water as water is highly polar whilst biphenyl is nonpolar. Biphenyl was partially soluble in methanol which is intermediately polar whilst biphenyl is nonpolar, allowing it to dissolve a little. Biphenyl was soluble in hexane because both biphenyl and hexane are nonpolar molecules. Biphenyl dissolved in hexane in 10 seconds.

Sucrose is insoluble in the organic solvent dichloromethane (CH2 Cl2). Aspirin, acetanilide, and phenacetin are soluble in dichloromethane but relatively soluble in water. Aspirin reacts with bases such as sodium bicarbonate to form a salt, sodium acetylsalicylate, which is insoluble in water. Acetanilide and phenacetin are not converted into salts by sodium bicarbonate.

I hypothesize that salicylic acid will react with acetic anhydride to produce acetylsalicylic acid (aspirin) and acetic acid (vinegar).

6. The solubility of the solids were tested using a micro tray, by placing them in water and oil to observe their polarity,

4. NaOH, sodium hydroxide is a strong base. It reacts with HCl and forms NaCl and H2O.

The unknown ionic compound was composed of translucent crystals. It had no odor, was soluble in water, and its electrical conductivity in water was measured at 1.66V, as indicated in Table 1. The compound burned a bright red during the flame test consistent with the flame signature of calcium, as indicated in Table 2, and along with the fact that the compound was soluble in water, this helped us to eliminate the possible presence of the poorly soluble salts (Cooper, 2008). However, tests for these anions were still performed.

A pre-weighed (0.315g) mixture of Carboxylic acid, a phenol, and neutral substance was placed into a reaction tube (tube 1). tert-Butyl methyl ether (2ml) was added to the tube and the solid mixture was dissolved. Next, 1 ml of saturated NaHCO3 solution was added to the tube and the contents were mixed separating the contents into three layers. Once this was completed

After dissolving benzoic acid in 1.0mL CH2Cl2 and 1.0mL 10% NaHCO3 solution, two layers are created, the top layer is 10% NaHCO3 solution and the bottom is CH2Cl2.

The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we

Based on the lab’s results, lipids are soluble in both Acetone and Methanol. However, they are more soluble in the Acetone, and only slightly soluble in the Methanol. Because of the chemical structures, this makes sense, since lipids are insoluble in polar solvents (like methanol), but are very soluble in non-polar organic solvents, such as acetone (Hunt).

Practically insoluble in ethanol, ethanol (95%), ether and water, slightly soluble in benzene and warm ethanol (95%)