Comparative Investigation of the Properties of Organic Compounds through Various Tests

Katrina Marie Taracatac, Camile Vargas, Deric Vengua, Camille Rose Villegas, Howard William Wong Group 9, 2D-Pharmacy, Faculty of Pharmacy, University of Santo Tomas

Abstract
Organic compounds are members of a large class of gaseous, liquid and solid chemical compounds whose molecules contain the element carbon. These exclude carbon monoxide, carbon dioxide, carbonates, cyanides, cyanates, carbides, and thiocyanates, which are still considered inorganic. Organic compounds are classified into two categories, namely hydrocarbons and hydrocarbon derivatives. The objective of this experiment was to differentiate various organic compounds in terms of some of their intrinsic physical properties, solubility and their behaviour towards ignition through the use of some tests. Physical properties such as the state, color, and odor of seven different organic compounds were identified, also their solubility in distilled water, 5% sodium hydroxide and 5% hydrochloric acid. The basicity or acidity of these compounds were also found out through testing their reaction with litmus paper. Lastly, an ignition test was performed to classify the samples as to be inflammable, or flammable. Flammable samples were further more classified as to give off a nonluminous flame, luminous flame, or flames which gave off soot. As a result, the group concluded that different forms of organic compounds exhibit different properties compared to one another.

Introduction Organic chemistry dates back to the late 1700s when it was used to be described as the chemistry of compounds found in living organisms (McMurry, 2010) Little was known during that time about this type of chemistry. This definition was a bit vague, but since then it has evolved through the help of modern technologic research and such. Organic chemistry is chemistry concerned with the structure, properties, and reactions of compounds that contain carbon. Almost all carbon compounds are organic except for a few which are still considered inorganic. These inorganic carbon compounds include the oxides of carbon, the bicarbonates and carbonates of metal ions, the metal cyanides, and a few others. Organic compounds are found all around us. They comprise of the materials that make up our food, the different medicines that treat our illnesses, protect our crops, clean our clothes, and a lot more. Organic compounds may be further be classified into being aliphatic or aromatic, and

hydrocarbons or hydrocarbon derivatives (Bayquen, et. Al., 2009) Aliphatic compounds are compounds wherein the carbon atoms are joined together in linear chains, linear-branched chains and nonaromatic rings. Aromatic compounds are compounds in which the carbon atoms are formed in a ring, which is conjugated so it may be stabilized by resonance. These compounds must also follow the Huckels rule (McMurry, 2010) They are compounds mainly based on benzene rings. Hydrocarbons are the simplest organic compounds. They are compounds which purely contain only hydrogen and carbon atoms which may be linear, branched, or cyclic. Hydrocarbon derivatives, on the other hand, are hydrocarbon compounds in which there is a substitution of one or more of the hydrogen atoms by a specific functional group. Organic compounds under this have conveniently been classified based on the substituent element or group of highest priority to the hydrocarbon.

Organic compounds have different properties, which are characteristics of the class in which they belong in. These include properties such as odor, color, physical state in room temperature, polarity and solubility, acidity or basicity. The main objective of this experiment was to differentiate the sample organic compounds in terms of their intrinsic physical properties, solubility, and their behaviour towards ignition. This report will be tackling the results given off by samples cyclohexane, dichloromethane, ethanol, phenol, benzoic acid, ethyl acetate, and ethyl amine to the various tests performed on them. Materials and Methods Materials This experiment made use of basic laboratory apparatuses such as test tubes, dropper pipettes, evaporating dishes, litmus paper, and matches. Different solvents were also used to perform the solubility tests. These were distilled water (H2O), 5% sodium hydroxide (NaOH), and 5% hydrochloric acid (HCl). Samples of organic compounds, such as cyclohexane, dichloromethane (DCM), ethanol, phenol, benzoic acid, ethyl acetate, and ethyl amine were used to perform the experiment.

FIGURE 1.0 Samples used for the experiment (Top Bottom; Left Right: Cyclohexane, DCM, Ethanol, Phenol, Benzoic Acid, Ethyl Acetate, and Ethyl Amine)

Method There were four parts to this experiment: First was to identify the physical properties of the given samples. The physical states at room temperature of all the samples were identified. Then the color was noted, and finally with a wafting motion, the odors of the samples were described. Second was to perform a solubility test to all the samples using distilled water, 5% NaOH, and 5% HCl as the solvents. All in all there were twenty four test tubes used. Four drops of each liquid sample, and a pinch amount of the sold sample was placed in these individual test tubes. Using a dry and calibrated dropper pipette, each of the solvents were added drop wise to the samples. The number of drops was taken into account. The maximum amount of the solvent used was only up to 3 mL. Color changes in the samples were also noted. Based on the amount of solvent added, the solid sample was described as very soluble, soluble, slightly soluble, or insoluble. If the sample is liquid, the solubility was described as miscible, slightly miscible, or immiscible.

Third was to identify if the samples were basic, acidic, or neutral by testing them with litmus paper. Blue and red litmus paper were placed on a watch glass. Samples were introduced to them, and then the color changes on the litmus paper were noted. Lastly, an ignition test was performed on all the given samples. A pinch amount of the solid sample, and 3-5 drops of each liquid sample were placed on an evaporating dish. They were lit using a match. The reactions were noted: whether flammable or inflammable; producing luminous or non-luminous flame; producing flames with or without the presence of soot. Results and Discussion The samples used for this experiment represented hydrocarbon and some groups or classes of hydrocarbon derivatives. Cyclohexane represented the hydrocarbons among the samples. Dichloromethane represented the alkyl halides. Ethanol and phenol both come from the class of alcohols. Benzoic acid is from the group of carboxylic acids, while ethyl acetate is an example of an ester. Lastly ethyl amine is from the group of amines.
TABLE 1.0 Intrinsic Properties of the Samples
PHYSICAL STATE Liquid Liquid Liquid Liquid Solid Liquid

Table 1.0 represents the data gathered during the duration of the experiment. Through observation using the senses, the physical state, color, and odor of the samples were all noted. Among all the given samples, benzoic acid was the only one which was solid. The rest were in their respective liquid forms. Being the only solid sample, benzoic acid was the only sample to be identified as a white crystalline powder. Most of the liquid samples were clear and colorless, besides phenol, which was a clear red orange liquid, and ethyl amine, which was clear and yellowish in color. The odors of the samples mostly differed from one another as seen on the table. The physical state or phase of a given compound is important because it relates to the solubility and volatility of a given compound. These factors aid in choosing the proper purification method for the given samples. Liquids are usually purified through the use of distillation or gas chromatography, while solids are purified by recrystallization (Shriner, et. Al., 1998) The color of some compounds is due to impurities. Phenol is one example of this. Pure phenol is a colorless crystalline deliquescent solid, but upon oxidation because of the exposure to air and sunlight, it becomes red orange or pinkish in color. Many liquids and solids are colored due to the presence of chromophoric groups in the molecule. Chromophore is a part of a molecule that is responsible for its color. The color arises when a molecule absorbs certain wavelengths of visible light and transmits or reflects others. Odors of certain compounds cannot be easily and precisely identified, but some basic facts about their odors are well known based on their classes

COMPOUND Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate

COLOR Clear colorless Clear colorless Clear colorless Clear red orange White crystalline Clear colorless Clear yellowish

ODOR Fruity Odorless Alcohollike Paste-like Odorless Plastic balloonlike Ammonialike

Ethyl Amine

Liquid

(Shriner, et. Al., 1998) Amines usually have a distinct fishy smell. Thiols and organic sulfides have rotten egg-like odor, while carboxylic acids usually have noxious odors. Esters, on the other hand, have odors identified to be pleasant, and most often characterized as fruity. Hydrocarbons can have very different smells from one another. Benzaldehydes, nitrobenzenes, and benzonitrile compounds have odors which are generally said to be cherrylike. The other classes of compounds have somewhat distinguishable odors, but are far less pronounced.
TABLE 2.0 Solubility/Miscibility of the Samples in H2O, NaOH and HCl
DISTILLED H2O immiscible immiscible miscible miscible insoluble miscible miscible 5% NaOH immiscible immiscible miscible miscible soluble miscible miscible 5% HCl immiscible miscible miscible immiscible insoluble immiscible miscible

Table 3.0 is a summary of the results of the samples when reacted with blue and red litmus papers. Though this we found out which of the test samples were acidic and basic. Ethanol, phenol, and benzoic acid were all found to be acidic, while cyclohexane, DCM, ethyl acetate, and ethyl amine were all basic. The solubility of the samples to the solvent is related to the polarity of the two substances and the intermolecular forces of attraction during the solution process. When a solute dissolves, its molecules or ions become distributed more or less randomly among those of the solvent used. A number of information may be known about an unknown compound by its solubility in certain solvents. First, the presence of a functional group may be indicated (Shriner, et. Al., 1998) An example may be cylohexane, which is a type of hydrocarbon. Hydrocarbons are insoluble or immiscible in water, so a single fact alone that an unknown is partially soluble or miscible in water proves that a polar functional group is present in the unknown substance. Second, the solubility of certain compounds in different solvents often lead to more specific information about the compound's functional group. The solvent 5% NaOH used in the experiment is an example of a basic solvent, while 5% HCl is an example of an acidic solvent. It is important to know these because an increased solubility in either one of these solvents indicate a positive result to know whether an acidic or basic functional group is present in the compound. Besides using the usual test with litmus paper, this may also be done to determine the acidity or basicity of a substance. Lastly, certain deductions on the molecular size and

COMPOUND Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine

Table 2.0 shows the summary of the reactions of the samples when reacted with distilled water, 5% NaOH, and 5% HCl. As seen in the table, the compounds all reacted differently when the solvents were added. Cyclohexane was miscible with all the solvents used, while ethanol and ethyl amine were miscible in all the solvents. The rest differed with each solvent used on them.
TABLE 3.0 Acidity/Basicity of the Samples COMPOUND
Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine

ACIDITY/BASICITY
basic basic acidic acidic acidic basic basic

compositions of the compound may sometimes be made.

TABLE 4.0 Flammability of the Samples COMPOUND
Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine

identify the content and composition of these compounds. References Books: Bayquen, A., Cruz, C., de Guia, R., Lampa, F., Pena, G., Sarile, A. & Torres, P. (2009) Laboratory Manual in Organic Chemistry McMurry, J. (2010) Foundations of Organic Chemistry

NATURE OF FLAME
Yellow (luminous) Inflammable Blue (non-luminous) Inflammable Inflammable Blue (non-luminous) Blue (non-luminous)

The last test conducted in the experiment was the ignition test. Here, all the samples were lit by a match and the nature of their flame was noted, and whether they were flammable or inflammable. Table 4.0 shows the summary of the results obtained from the test. Compounds usually burn with a specific characteristic flame when ignited. These types of flame aid in determining the nature of the compound. Aromatic hydrocarbons, which have a relatively high content of carbon, burn with a yellow sooty flame. Aliphatic hydrocarbons on the other hand, burn with yellow flames but are much less-sooty compared to the fore mentioned one. The flame produced by a compound becomes clearer or blue as the oxygen content in the compound increases (Shriner, et. Al., 1998) In conclusion, organic compounds have different properties respectively. The differences between the organic compounds found all around us are evident, but there are also similarities between them. In order to know that nature of the compound or to know the functional groups present within it, the physical intrinsic properties, solubility, and acidity or basicity must be taken into account. These factors may aid us and make it easier for us to

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