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ORGANIC CHEMISTRY I LABORATORY 220L-Tue 1-4pm

Lab #1 Solubility Tests

Kathleen Swanson 9/16/2013

Introduction:

The purpose of the lab, Solubility Tests, is to demonstrate how the molecular structure of compounds has an impact on their properties and therefore their behavior due to intermolecular forces and the polarity of the given compounds. Solubility, the ability of a compound (solute) to be dissolved in a given solvent, is determined by the structure, polarity and temperature of both the solute and the solvent. Integral to the idea of solubility is the ability of solvent with a set of properties, to dissolve other compounds that share similar sets of properties such as polarity and the intermolecular and ionic forces at play. This concept, Like dissolves like, allowed us to formulate working hypothesis with regard to the dissociation of compounds in certain solvent. Predictions of solubility were made for 7 compounds, in each of the three solvents, water, ethanol and ligroin, using knowledge obtained from the lectures, as well as Macroscale and Microscale Organic Experiments (pages 45-48). Predictions were tested in the Laboratory to further exemplify the connections between molecular structure and solubility.

Compounds to be used:

OH

O OH

O Na

Biphenyl OH Benzoic Acid Resorcinol Sodium benzoate

O OH Na 2SO 4 Sodium sulfate

O Benzil

OH Salicylic acid

MW

Density (g/mL) 1.2659 g/mL

Vol. (mL) -

Mass (g) .02 g

mol

Hazard

COMPOUND
(g/mol) Benzoic acid 122.12 g/mole C6H5COOH Resorcinol 110.11 g/mole C6H6O2 Biphenyl 154.21 g/mole (C6H5)2 Sodium Benzoate 144.11 g/mole C7-H5-O2-Na Sodium sulfate 142.06g/mole Na2SO4 Benzil 210.23 g/mole C14-H10-O2 Salicylic acid 138.12 g/mole C7-H6-O3 MW Density (g/mL) 1.0 g/mL Vol. (mL) 1.0 Mass (1g=1mL) 1g 5.55 x Flammable liquid and vapor 46.405 g/mol C2H5OH 0.790 g/mL at 20C 1.0 1g 2.12 x Skin/Eye irritant CNS depressant Extremely Flammable Ligroin 87-114 g/mol unknown 1.0 1g unknown Skin eye irritant Fatal if swallowed mol 1.443 g/mL .02 g 1.45 x .02 g 9.51 x 2.671 g/mL .02 g 1.41 x 4.97(Vapor) .02 g 1.39 x 1.04 g/mL .02 g 1.30 x 1.272 g/mL .02 g 1.82 x 1.64 x Irritant (skin eyes, inhalation, ingestion) Irritant (skin eyes, inhalation, ingestion) Inflammation and irritant (skin, eyes, inhalation) Irritant (skin, eyes, inhalation) Irritant (skin, eyes, inhalation, ingestion) Irritant (skin, eye, inhalation) Irritant (skin, eyes, inhalation, ingestion) Hazard

SOLVENT
Water

(g/mol) 18.02 g/mole

H2O

Ethanol

Figure 1: The above is a compilation of physical properties for each of the 7 compounds and 3 solvents used in the solubility tests.

Experimental:

Necessary equipment was acquired (small test tubes, test tube stand, spatula, beakers, stir rods, ) and a hot water bath started, maintaining a low boil, assumed to be 100C. Each of three small beakers were filled with one of each, water, ligroin, and ethanol (the three solvents). Each of seven test tubes filled with .02 grams of each of seven compounds to be tested. 1.0 mL of solvent was added to each of the seven test tubes and glass stirring rods were used to crush the solute into a form more readily dissolved (if capable of doing so). Observations with respect to solubility at room temperature were recorded (Fig. 2). Any compounds that were insoluble at room temperature were place into a hot water bath, one at a time and to determine solubility at 100C, and recorded (Fig. 2). The above procedure was repeated two additional times, for each of the seven compounds with the the two remaining solvents for a total of three trials.

Discussion:

Compound 25C Benzoic acid Resorcinol Biphenyl Sodium benzoate Sodium sulfate Benzil Salicylic acid No No No Yes Yes No No

Water HOT No Yes No Yes Yes No Yes

Ethanol 25C No Yes No Yes No No Partial HOT Yes Yes Yes Yes No No Yes

Ligroin 25C No No Yes No No Yes No HOT Yes No Yes No No Yes No

Figure 2: Table of results for solubility at room temperature and (assumed) 100C for 7 compounds, in each of 3 solvents.

Water and ethanol are both considered to be polar protic solvents. Protic solvents are distinguished from aprotic solvents because of their O-H and N-H bonds, and thus their ability to form hydrogen bonds and dissolve polar substances. Polar protic solvents can also serve as a source of protons, forming bonds with strong nucleophiles (Master Organic Chemistry, 2013). Water is by far the stronger candidate for a polar protic solvent with a dielectric constant of 80 and dipole moment of 1.85, over ethanols 25 and dipole moment of 1.69. Considered a moderately polar solvent, in addition to it non polar, C-H portions, ethanol still contains polarized OH groups that allow it to dissolve some polar compounds and the capability to form H-bonds, especially with the addition of heat. Ligroin is a nonpolar, hydrocarbon solvent incapable of dissolving any strictly polar compounds, even with addition of heat. Predictions were made solely on the basis of knowledge of polarity and further information concerning protic, aprotic and moderately polar solvents as well as hydrocarbons with polar groups were investigated further upon completion of experimental procedures and results that deviated slightly from original predictions.

With a few exceptions, most predictions made purely upon the polarity of a given compound were consistent with the experimental findings. These include: biphenyl, benzil, sodium sulfate, and sodium benzonate. Biphenyl, a nonpolar hydrocarbon was predicted to dissolve only in ligroin based upon their shared polarities. Benzil, also a nonpolar compound, held true to the original prediction, only dissolving in ligroin. Both sodium sulfate and sodium benzonate were expected to dissolve in water, and possibly in ethanol due to the polar, ionic portions attributed to the presence of sodium; however only sodium benzonate was able to dissolve in ethanol more than likely due to the fact that sodium sulfate is purely an inorganic salt unlike the organic ethanol and the presence of many C-H bonds found in ethanol.

Resorcinol, benzoic acid, and salicylic acid were all expected to be insoluble in water; however only benzoic acid was completely insoluble in water (at any temperature), while both resorcinol and salicylic acid were soluble in water at 100C. Resorcinol and salicylic acid were completely insoluble in ligroin, and completely soluble in ethanol. Benzoic acid was only able to dissolve in ligroin and ethanol when heat was applied. Further reading was done to better understand the results of these three compounds that all seemed to have non polar hydrocarbon portions with at least 5 carbons, and at least one polarized functional group in stark contrast to its nonpolar portions. The aromatic ring in benzoic acid and its nonpolar presence was far more persuasive than the polarized carboxylic acid group. Also there was nothing favoring the formation of carboxylate over the presence of the carboxylic. This leaning to being more non polar despite its functional group allowed it to be dissolved in the nonpolar solvent, ligroin when heat was applied. Resorcinol (and its carboxylic and alcohol groups) and salicylic acid (with its 2 alcohol groups) were polar enough to overcome the nonpolar hydrocarbon portions (aromatic ring), and when heat was applied to both they were able to dissolve in the very polar solvent, water.

Resources

Macroscale and Microscale Organic Experiments, Williamson, K.L., 2nd Edition. D.C. Health and Company

ChemWiki: The Dynamic Chemistry Textbook, Larsen, Delmar. University of California, Davis, 2010 http://chemwiki.ucdavis.edu/

Master Organic Chemistry, 2013 http://www.masterorganicchemistry.com/

NAME:

Kathi Swanson

DATE:

9/18/13

LAB SECTION:

Tue

POST-LAB QUESTIONS 1. Report your results in tabular form. Show the structures of the solids and the solvents and indicate the solubilitys in cold and hot solvent.

Compound 25C Benzoic acid Resorcinol Biphenyl Sodium benzoate Sodium sulfate Benzil Salicylic acid No No No Yes Yes No No

Water HOT No Yes No Yes Yes No Yes

Ethanol 25C No Yes No Yes No No Partial HOT Yes Yes Yes Yes No No Yes

Ligroin 25C No No Yes No No Yes No HOT Yes No Yes No No Yes No

Coumpounds:
O OH O OH O Na
+

Biphenyl OH Benzoic Acid Resorcinol Sodium benzoate

O OH Na 2SO 4 Sodium sulfate

O Benzil

OH Salicylic acid

Solvents:

Hexane (representative of Ligroin)

Ethanol

Water

2.) Do your results match your predictions from the Pre-Lab assignment

With a few exceptions, most predictions made purely upon the polarity of a given compound were consistent with the experimental findings. These include: biphenyl, benzil, sodium sulfate, and sodium benzonate. Biphenyl, a nonpolar hydrocarbon was predicted to dissolve only in ligroin based upon their shared polarities. Benzil, also a nonpolar compound, held true to the original prediction, only dissolving in ligroin. Both sodium sulfate and sodium benzonate were expected to dissolve in water, and possibly in ethanol due to the polar, ionic portions attributed to the presence of sodium; however only sodium benzonate was able to dissolve in ethanol more than likely due to the fact that sodium sulfate is purely an inorganic salt unlike the organic ethanol and the presence of many C-H bonds found in ethanol.

Resorcinol, benzoic acid, and salicylic acid were all expected to be insoluble in water; however only benzoic acid was completely insoluble in water (at any temperature), while both resorcinol and salicylic acid were soluble in water at 100C. Resorcinol and salicylic acid were completely insoluble in ligroin, and completely soluble in ethanol. Benzoic acid was only able to dissolve in ligroin and ethanol when heat was applied. Further reading was done to better understand the results of these three compounds that all seemed to have non polar hydrocarbon portions with at least 5 carbons, and at least one polarized functional group in stark contrast to its nonpolar portions. The aromatic ring in benzoic acid and its nonpolar presence was far more persuasive than the polarized carboxylic acid group. Also there was nothing favoring the formation of carboxylate over the presence of the carboxylic. This leaning to being more non polar despite its functional group allowed it to be dissolved in the nonpolar solvent, ligroin when heat was applied. Resorcinol (and its carboxylic and alcohol groups) and salicylic acid (with its 2 alcohol groups) were polar enough to overcome the nonpolar hydrocarbon portions (aromatic ring), and when heat was applied to both they were able to dissolve in the very polar solvent, water.