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Chemistry 31.

1: Elementary Organic Chemistry Laboratory

Exercise No. 1 Solubility Behavior of Organic Compounds

A laboratory report submitted by: Abbie Glenn M. Estribillo

Laboratory partners: Gem Bryl G. de Paz Maria Victoria O. Pasilan Section: KL-1L

2-BS Food Technology

Abstract Solubility of organic compounds can be used to determine many important information about that certain substance, such as the functional group to which it belongs and specific information about that functional group. Even without experimentation, solubility of a substance can be predicted. The structure of a compound says a lot about its identity. Like dissolves like. This statement means that a substance is soluble in a polar solvent if it is also polar. The experiment Solubility Behavior of Organic Compounds is performed to determine the solubility of some organic compounds in water and different solvents. The solubility of compounds were determine using the following solvents: water, ether, 5% NaOH, 5% NaHCO3, 5% HCl, and concentrated H2SO4. Results of the experiment showed that hexane, ethyl alcohol, ethyl acetate, and acetone are water soluble which are also soluble in ether; benzamide, sucrose, and glycine are also water soluble but are not soluble in ether; aniline is the only test compound that is classified as basic; cellulose, benzyl alcohol, benzaldehyde, and benzoic acid are neutral compounds; dichloromethane and toluene are inert compounds.

III. Introduction Solubility is defined as the extent to which a solute dissolves in a liquid, called the solvent. If the compound used as solute is solid, the term solubility can be directly used. However, if the solute is liquid, the term miscibility is used. In dissolving a compound, the interactions between the molecules or ions of the solute are being broken in order for it to form new interactions between the solute and the solvent (Smith, 2006). In this experiment, different kinds of solvents were used: water, ether, 5% NaOH, 5% NaHCO3, 5% HCl, and concentrated H2SO4. A solute is soluble to a solvent if there intermolecular forces are the same. Water is very polar because of its capacity to form hydrogen bonds with a solute. Solubility can be shown through the miscibility of a solute in a solvent and through chemical reaction. There are factors that affect solubility of a compound. Some of these are temperature, polarity or the nature of the compound, molecular size, and chain branching on the structure of the compound. For the temperature, in an endothermic reaction, solubility increases with increasing temperature; in an exothermic reaction, solubility increases with decreasing temperature. For the nature of the compound, the concept of like dissolves like is applied. Polar solutes are soluble in polar solvents only. The same goes with nonpolar compounds. For the molecular size, an increase in molecular size leads to increased intermolecular forces, which decreases solubility. And lastly, compounds having more chain branches are more soluble than the straight branched compounds. With these factors, the solubility of some compounds can

3 already be predicted. By knowing the structure and the nature of the compounds their solubility in different solvents can be predicted. By determining the solubility of a compound, different information can be obtained. One is the presence of a functional group. Specific information about the functional group can also be obtained. A functional group is an atom or group of atoms with characteristic chemical and physical properties. It is the reactive part of the molecule (Smith, 2006). Solubility of a compound can be seen in a chemical reaction o a simple miscibility. In a chemical reaction, heat may be produced and color change may occur. In a simple miscibility, the resulting solution of solute and solvent is water clear. In case of insolubility some particles of the solute are remained suspended in the solvent. In case both compounds are liquid, immiscibility can be observed if the solute forms a second layer of liquid in the solvent, cloudiness, or liquid droplets in the solvent (Lehman, 1999).

IV. Objectives The experiment Solubility behavior of Organic Compounds generally aims to observe the any physical change that occurs when the test compound is added to the solvent. Specifically, it aims to: 1. determine the solubility of a test compound in water; and 2. further determine the solubility of a compound in other solvent.

V. Method Please refer to Chemistry 31.1 Laboratory Manual for the procedure. The changes made during the experiment are: 1. instead of isopentyl acetate, ethyl acetate was used; and 2. petroleum ether was used instead of ether. The flowchart below was used to identify the classification of the compounds.

4 VI. Presentation of Results Table 1. Solubility of different test compounds in water and other solvents. Test compound Water Hexane Aniline Benzamide Cellulose dichloromethane benzyl alcohol ethyl alcohol ethyl acetate Acetone Sucrose Toluene Glycine benzaldehyde benzoic acid Evaluation of results: + soluble/miscible insoluble/immiscible + + + + + + + Ether + + + + + + + + + Solvents 5% 5% NaOH NaHCO3 5% HCl Conc. H2SO4

Table 2. Classification of the test compounds based on their solubility to different solvents. Test compound Hexane Aniline Structure Classification Water Soluble (S1) Basic

Benzamide

Water Soluble (S2)

5 Cellulose Neutral

dichloromethane

Inert

benzyl alcohol Neutral ethyl alcohol ethyl acetate Water Soluble (S1) Water Soluble (S1)

Acetone

Water Soluble (S1)

Sucrose

Water Soluble (S2)

Toluene

Inert

Glycine

Water Soluble (S2)

benzaldehyde

Neutral

6 benzoic acid Neutral

VII. Discussion of Results The flowchart in the methodology functions like this: The procedure starts with the solubility test of the test compound in water. If the compound is soluble, the solubility of the compound will be again tested using ether. The compounds soluble in water are called watersoluble compounds. Those soluble in ether are classified under S1, and those insoluble in ether will be under S2. On the other hand, if the compound is insoluble in water, it will be tested using 5% NaOH. Soluble compounds are classified as organic acids. Its strength is determined by its solubility in 5%NaHCO3. Soluble compounds are strong organic acids while the insoluble ones are weak organic acids. If the compound is insoluble in 5% NaOH, it will be tested further using 5% HCl. Soluble compounds are classified as basic compounds. There are cases however where the solubility of the compound is doubtful. In this case, the compound is classified as miscellaneous neutral compounds. Insoluble compounds in 5% HCl proceeds with test using concentrated H2SO4. Soluble compounds in concentrated H2SO4 are classified are neutral compounds while the insoluble ones are inert compounds. Table 1 shows the actual result of the solubility test of the 14 organic compounds namely hexane, aniline, benzamide, cellulose, dichloromethane, benzyl alcohol, ethyl alcohol, ethyl acetate, acetone, sucrose, toluene, glycine, benzaldehyde, and benzoic acid. The experiment results imply that hexane, ethyl alcohol, ethyl acetate, and acetone are water soluble which are also soluble in ether; benzamide, sucrose, and glycine are also water soluble but are not soluble in ether; aniline is the only test compound that is classified as basic; cellulose, benzyl alcohol, benzaldehyde, and benzoic acid are neutral compounds; dichloromethane and toluene are inert compounds, as traced in the flowchart below.

7
Water Insol. Insol. 5% NaOH Sol. 5% NaHCO3 Sol. Conc. H2SO4 Insol. Sol. Insol. Sol. Sol. Ether Insol. Sol.

5% HCl Insol.

Inert compound dichloromethane toluene

Neutral compound Cellucose Benzyl alcohol Benzaldehyde Benzoic acid

Basic compound aniline

Water soluble (S2) benzamide sucrose glycine

Water soluble (S1) hexane ethyl alcohol ethyl acetate acetone

Figure 1. Summary of the classification of test compounds. Table 2 shows the structure of each compound and their classification. The structures were shown as to predict the solubility and classification of each compound and to compare it with the experimental result. Figure 1 below shows the summary of the solubility behavior of the test compounds through a flowchart. Theoretically, hexane, dichloromethane, and toluene are classified as inert compounds. Hexane, with a chemical form of C6H14, is an alkane with six carbon atoms. It has a functional group of hydrocarbon. Dichloromethane (DCM) or methylene chloride, with a chemical formula of CH2Cl2, is also not soluble with water (Rossberg, et al, 2006). Toluene, C7H8, is an aromatic hydrocarbon compound (Smith, 2006). Inert compound, as defined, are saturated carbons, haloalkanes, aryl halides, deactivated aromatic compounds, and diaryl ethers. From this definition, the three mentioned compounds are under this classification Basic compounds, on the other hand, form water-soluble salts with HCl. Therefore they are soluble in 5% HCl. Aniline, is a basic compound, has a chemical form of C6H5NH2. It is an aromatic amine, which is soluble in 5% HCl (McMurry, 2008).

8 Neutral compounds are compounds that contain oxygen, such as aldehydes, ketones, alcohols, ethers, esters, and anhydrides (McMurry, 2008). These compounds are insoluble in 5%HCl. Cellulose, benzaldehyde, and benzyl alcohol are classified in this category. Water soluble compounds are compounds that have the same characteristics as water. Since the though like dissolves like is being applied, a water soluble compound must also be polar, just like the water (Mayo, Pike, Butcher, and Trumper, 1991). These compounds include ethyl alcohol, ethyl acetate, acetone, sucrose, and glycine. However, there are still classifications with the water soluble compounds. Further solubility behavior is observed with the compounds solubility in ether. Compounds that are soluble in ether are noted as S1. These compounds are polar, contain 5 or less carbon atoms, and have a functional group that is polar and capable of forming hydrogen bonds. Compounds that are not soluble in ether, S2, are ionic and contain two or more polar groups but not more than 4 carbons atoms per functional group (McMurry, 2008). The errors made in the experiment can be attributed to personal errors committed by the person doing the experiment. The following are the possible sources of errors: improper weight/volume of solutes, incorrect interpretation of the chemical reaction, if there is any, volatile compounds may have evaporated. VIII. Conclusion Based on the experiment made, it is concluded that solubility of a compound depend on its structure and the intermolecular forces that occurs in each molecule. The simple solubility or miscibility of a compound can be observed if 0.1 g of solute is totally dissolved in 2mL solvent or if 0.2mL of solute forms a clear solution with 2mL solvent. A chemical reaction can also mean solubility. Insolubility or immiscibility is observed if there are still particles left in the solution or if another liquid layer forms. A compound is soluble to a solvent if they have the same characteristics. A polar compound dissolves in a polar solvent and nonpolar compound dissolves in a nonpolar solvent. Compounds can be classified into groups using the information obtained from its solubility. They can be classified as water soluble (S1 and S2), organic acids (weak and strong), basic compounds, neutral compounds, inert compounds, and miscellaneous neutral compounds. The solvent used in determining the solubility of a compound are water, ether, 5% NaOH, 5% HCl, 5% NaHCO3, and concentrated H2SO4.

IX. Questions and Answers Pre-lab question: Describe the solubility behavior of compounds (a) due to intermolecular forces and (b) due to chemical reaction.

9 (a) Compounds dissolve in solvents having similar kinds of intermolecular forces. The concept of like dissolves like is being applied. Polar compounds dissolve only in polar solvents and nonpolar compounds dissolve in nonpolar solvents. (b) A compound is soluble in a certain solvent if the mixture produced after adding the solute to the solvent is homogeneous. Also, if there are any observable changes in the reaction of the two compounds (such as heat produced), it is also an evidence of solubility. A solute is also soluble in a solvent if the reaction proceeds to an acid-base reaction. The salt produced during the acid-base reaction is usually soluble. Post- lab question: Show through flowchart how the following compounds may be classified into their solubility classes: CH3CO(CH2)4CH3, n-butyl chloride, polystyrene, butanoic acid, and formaldehyde. CH3CO(CH2)4CH3, also known as amyl methyl ketone or 2-heptanone, is grouped under S1 since it is a ketone, a water soluble substance. Also, butanoic acid or butyric acid, a carboxylic acid, is classified under A1. Polystyrene and formaldehyde are grouped under neutral compounds since they are aromatic hydrocarbon and an aldehyde, respectively. Inert compounds like n-Butyl chloride are grouped as such since it is an alkyl halide.

+
Water

+
Ether

S1 S2

CH3CO(CH2)4CH3

+ 5% NaOH

5% NaHCO3

+ +

A1
A2 B

Butanoic acid

+ soluble

5% HCl

M (Miscellaneous neutral compounds) concentrat ed H2SO4

+ -

N I

Polystyrene, Formaldehyde n-Butyl chloride

insoluble

10 X. References Lehman, J. W. 1999. Operational Organic Chemistry: A problem- solving approach to the laboratory course, 3rd edition. USA: Prentice Hall, Inc. Mayo, D. W., Pike, R. M., Butcher, S. S., Trumper, P. K. 1991. Microscale: techniques for the organic laboratory. USA: John Wiley and Sons, Inc. McMurry, J. (2008). Organic Chemistry. USA: Thomson, Brooks and Cole Publishing. Rossberg, M. et al. (2006). Chlorinated Hydrocarbons in Ullmanns Encyclopedia of Industrial Chemistry. Wiley-VCH. Weinheim.doi:10.1002/14356007.a06_233.pu b2 Smith, J. G. (2006). Organic Chemistry. New York: The McGraw-Hill Companies, Inc.