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COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS Bettina Maria Q. Acuna, Enrico Joseph C. Aguinaldo, Alyanna Patrice L.

Arceo, Jasmine Grace C. Asinas and Sigrid Jessa R. Bello Group 1 2G Pharmacy Organic Chemistry Laboratory ABSTRACT
The experiment was conducted in order to differentiate organic compounds in terms of certain intrinsic physical properties, solubility and miscibility, acidity and basicity and behavior towards ignition test. Physical properties are noted by observing the samples physical state at room temperature, color and odor. Solubility and miscibility were tested using the following reagents: water, 5%NaOH solution, and 5%HCl solution. Acidity and basicity of the compounds were determined by the use of litmus paper. Ignition test was conducted using 3 to 5 drops of the sample in an evaporating dish and lighting it with a match.

Organic compounds are the complex compounds of carbon. Because carbon atoms bond to one another easily, the basis of most organic compounds is comprised of carbon chains that vary in length and shape. Hydrogen, nitrogen, and oxygen atoms are the most common atoms that are generally attached to the carbon atoms. Each carbon atom has 4 as its valence number which increases the complexity of the compounds that are formed. Since carbon atoms are able to create double and triple bonds with other atoms, it further also raises the likelihood for variation in the molecular make-up of organic compounds. Organic compounds can be classified into hydrocarbons and hydrocarbon derivatives, based on the replacement of hydrogen by another element or by a group of different elements (functional group). Specifically, organic compounds are conveniently classified as different classes of hydrocarbon derivatives based on the substituent element or group of highest priority to the hydrocarbon. Functional groups present in an organic compound can be determined by using infrared spectroscopy. Organic compounds have different physical properties, which are intrinsic or (characteristic of the class), such as odor. The physical state of an organic compound at room temperature may indicate the strength of interactive forces that exist between its molecules. The dissolution of organic compounds in certain solvents may involve physical or chemical interaction. Water solubility of these compounds may differ due to their varying polarities. Solubility in acids or bases leads to more specific information about the compound,

i.e., as having either acidic or basic property. Miscibility is the ability of two liquids to mix with each to form a homogeneous solution. Flammability is tested through an ignition test. Ignition of the organic compound brings about a chemical change. Some organic compounds decompose and blacken (charring), while other burst into flames. Condensed structural compounds used: 1. Cyclohexane formula of the

2. DCM CH2Cl2 3. Ethanol

4. Phenol

5. Benzoic acid 3. Reaction with Litmus Paper Drops of the sample tested its aqueous solution with red and blue litmus papers. Color changes with both litmus papers were noted. 4. Ignition Test 3-5 drops of the liquid and pinch amount of solid sample were placed in a small evaporating dish and lighted with a match stick. Any flame produced and observed was noted. The color of the flame and burning time was also noted

6. Ethyl acetate

7. Ethylamine


Most of the hydrocarbons were colorless, but due to oxidation, some compound showed a change in color, such as Phenol giving a red-orange color. The odors of the compounds were quite similar but it has its unique differences. Solubility properties of organic compounds using water, 5%NaOH solution and 5%HCl solution whether the samples are soluble/insoluble or the samples are miscible/immiscible. Based on the results, Cyclohexane is miscible in water, slightly miscible in 5%NaOH and 5%HCl; DCM is immiscible in the 3 solvents; Ethanol, Phenol and Ethylamine were miscible in the 3 solvents; Benzoic acid, miscible in water, slightly miscible in 5%NaOH and 5%HCl; Ethyl acetate is immiscible in water and 5%NaOH, and it is miscible in 5%HCl. Reactions with litmus paper indicates the acidity/basicity of water-soluble samples. If it is from Red to Blue, result will be a base indicator and if it is from Blue to Red, result will be an acid indicator. The Litmus paper that retains its color indicates a neutral compound. Solubility of organic compound also indicates acidity and basicity of the sample. The result of Ignition test indicates the presence of unsaturated or high carbon to hydrogen ratio. The degree of luminosity can be assessed by the presence of yellow flame and soot. The Aromatic compounds burn with sooty flame due to complete combustion which causes the formation of an unburned carbon. In terms of degree of luminosity: aromatic compound> unsaturated hydrocarbon> saturated hydrocarbon.

EXPERIMENTAL A. Compounds tested (or Samples used) Cyclohexane, Dichloromethane, Ethanol, Phenol, Benzoic acid, Ethyl Acetate, Ethylamine B. Procedure
1. Physical State, Color and Odor The physical state of the sample was observed in room temperature. Color and odor was noted. 2. Solubility Properties The samples were introduced into clean and dry test tubes. 4 drops of each sample were introduced if the sample is a liquid; and 0.1g of the sample was introduced if the sample is solid. The solid samples were grinded to increase the surface area. The solvent was added drop wise, counting the number of drops of solvent added to a total of 3mL. Any color changes, warming or effervescence, soluble/insoluble, miscible/immiscible were noted.

Complete combustion is indicated by a blue flame (nonluminous) and there is more heat than light, the carbon is completely oxidized. 2 C10H22 + 31 O2 20 CO2 + 2 H2O Incomplete combustion is indicated by a yellow flame (luminous) and there is much light than heat, the carbon is not completely oxidized.

From the internet xane.htm 9/8/12 m/in-chemistry-what-is-miscibility.htm 9/8/12 9/8/12 From books Bayquen, A.V., Cruz, C.T., De Quia, R.M., Lampa, F.F., Pena, G.T., Sarile, A.S. and Torres P.C. (2009). Laboratory Manual in Organic Chemistry. Quezon City: C and E Publishing, Inc.

Table 1. Comparative Investigation of Organic Compounds

Test Compounds Physical State at RT Color Odor Solubility in H2 O 5% NaOH soln. 5% HCL soln. Reaction with litmus paper Ignition test Cyclohexane Liquid Clear, colorless Mild, sweet odor Miscible Slightly miscible Slightly miscible Neutral Yellow, luminous, flammable DCM Liquid Clear, colorless Acetone-like odor Immiscible Immiscible Immiscible Neutral Non-flammable Ethanol Liquid Clear, colorless Alcohol-like odor Miscible Miscible Miscible Neutral Yellow, luminous, flammable Phenol Liquid Clear, red (oxidized) Paste-like odor Miscible Miscible Miscible Neutral Yellow, luminous, flammable

Table 2. Comparative Investigation of Organic Compounds

Test Compounds Physical State at RT Color Odor Solubility in H2 O 5% NaOH soln. 5% HCL soln. Reaction with paper Ignition test litmus Benzoic acid Solid Clear, colorless Odorless Miscible Slightly miscible Miscible Acidic Non-flammable Ethyl Acetate Liquid Colorless Plastic balloon odor Immiscible Immiscible Miscible Neutral Yellow, flammable luminous, Ethyl Amine Liquid Clear,colorless Fishy Miscible Miscible Miscible neutral Non-flammable