University of Santo Tomas Faculty of Pharmacy Organic Chemistry Laboratory

Comparative Investigation of Organic Compounds Based on Intrinsic Physical Properties and Behavior towards Ignition
Dela Cruz,K., Estacio,B., Esteban,K., Gerzon,E., Guloy,A. Group 3 -2B Pharmacy – Organic Chemistry Laboratory

The experiment was conducted to differentiate organic compounds in terms of intrinsic properties and behavior towards ignition. Some physical properties were also noted for comparison. The physical state, color and odor were noted by observation. Cyclohexane, DCM, Ethanol, Phenol, Ethyl Acetate and Ethyl Amine were found out to be clear colorless liquids while Benzoic Acid prior to triturating was found out to be a white crystalline sol id. Miscibility was tested by introducing drops of a sample in a solvent. The solvents used for testing the solubility or miscibility were water 5% HCL and 5% NaOH. Cyclohexane DCM ethanol ethylacetate ethylamine was proven to be miscible with water. Benzoic acid was slightly soluble to water. Ethanol phenol ethylamine was miscible with the solvent 5%NaOH. Benzoic acid was soluble to NaOH. The acidity or basicity of water soluble or miscible substances was tested with red and blue litmus paper. Phenol, benzoic acid and ethyl acetate was acidic while ethylamine was found to be basic. Flame tests were performed by placing 3-5 drops of the liquid sample in a small evaporating dish and were lighted with a match. DCM phenol and benzoic acid produced a negative result for flammability test.

Organic compounds can be classified into hydrocarbons and hydrocarbon derivatives (organic halides, ethers, thioethers, alcohols, thiols, etc.). Families of organic compounds were characterized by the presence of distinctiv e functional groups. A functional group is th e structural unit responsible for a given molecule’s chemical reactivity under a particular set of conditions. Organic compounds can be classified based on their different intrinsic physical properties, such as odor. The physical state of an organic compound at room temperature May indicate the strength of the interactive

forces that exist between its molecules. The dissolution of organic compounds in c ertain 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.Ignition of the organic compou nd bringsabout a chemical change. Some organic compounds decompose and blacken or charring, while others burst into flames. The main objective of this experiment is to differentiate organic compounds in terms of their intrinsic physical properties such as color, odour, acidity, basicity and physical state atroom temperature and their reaction to wards ignition.

The organic compounds used were: Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon. Dichloromethane (DCM or methylene chloride) is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents. Ethanol is a straight-chain alcohol, and its molecular formula is C2H5OH. Its empirical formula is C2H6O. An alternative notation is CH3–CH2–OH, which indicates that the carbon of a methyl group (CH3–) is attached to the carbon of a methylene group (–CH2–), which is attached to the oxygen of a hydroxyl group (–OH). It is a constitutional isomer of dimethyl ether. Ethanol is often abbreviated as EtOH, using the common organic chemistry notation of representing the ethyl group (C2H5) with Et. Phenol, also known as carbolic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl (-C6H5), bonded to a hydroxyl (-OH) group. It is produced on a large scale (about 7 billion kg/year) as a precursor to many materials and useful compounds. Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid. The

name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis of many other organic substances. Ethyl acetate (systematically, ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail and cigarettes (see list of additives in cigarettes). Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tons. Ethylamine is an organic compound with the formula CH3CH2NH2. This colorless gas has a strong ammonia-like odor. It immiscible with virtually all solvents and is considered to be a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

For the physical state color and odor we observed the physical state of the sample at room temperature and noted the color. The solubility properties were tested by placing 4 drops of the liquid sample or 0.1g solid of the sample into a dry and clean test tube. Then the solvent was introduced dropwise. The number of drops will be used to describe the sample if it was very soluble, slightly soluble, and insoluble. For the liquid samples we checked if it was miscible, slightly miscible or immiscible. We noted if there is any color change, warming or effervescence.

The water soluble samples were tested with red and blue litmus paper to test for basicity or acidity. An ignition test was performed by placing 3-5 drops of the liquid sample in a small evaporating dish and was lighted with a match. A pinch amount of the benzoic acid was used for the ignition test. The sample is observed if flammable or not. The color of the flame was noted.

Table.1 Physical state, odor, color analysis

Cyclohexane was mild sweet; DCM was sweet, chloroform-like; Ethanol was alcohol like; Phenol was strong very sweet in odor; Benzoic acid was faint pleasant in odor; Ethyl acetate was pleasant or plastic balloon-like in odor and ethyl amine was amoniacal in odor. Some liquids and solid amines are recognizable by their fishy odors; esters are often pleasantly fragrant. Alcohols, ketones, aromatic hydrocarbons and aliphatic olefins have characteristic odors. On the unpleasant side are thiols, isonitriles and lowmolecular-weight carboxylic acids.
Table.2 Solubility in H2O

Sample Cyclohexane DCM Ethanol Phenol Benzoic acid Ethyl acetate Ethyl Amine

Color Colorless solution Colorless solution Colorless solution Orange solution White crystalline Colorless solution Colorless solution

Odor Mild sweet Sweet chloroform-like Alcohol-like Strong very sweet Faint balsam Ethereal like Plastic balloonlike Strong ammonia-like

Sample Cyclohexane DCM Ethanol Phenol Benzoic acid Ethyl acetate Ethyl Amine

H2O Immiscible Immiscible Miscible Slightly miscible Slightly soluble Miscible Miscible

Table 1 shows the color and odor of cyclohexane, DCM, ethanol, phenol, benzoic acid, ethyl acetate and ethyl amine. Most hydrocarbons are colorless. However, many liquid compounds oxidize when they are stored for a long time. Often the oxidation products are intensely colored. In the case of phenol, it appeared as an orange to brown liquid because of the traces of air oxidation products.

Table 2 shows the solubility of organic compounds in H2O indicates the polarity of the sample and the intermolecular forces of attraction that exists between the sample and H2O. The strength of Intermolecular Forces (IMF) and spend of molecules determines solubility. There are four (4) IMF: ionic, dipole-dipole, hydrogen bonding and London Forces.

Table 3 Solubility in 5% HCl and 5%

Samples Cyclohexane DCM Ethanol Phenol Benzoic acid Ethyl acetate Ethyl amine

5% HCl Immiscible Immiscible Miscible Slightly miscible Slightly soluble Insoluble Soluble

5% NaOH Immiscible Immiscible Miscible Miscible Soluble Insoluble Insoluble

Table 3 shows the solubility of organic compounds in 5% HCl and/or 5%NaOH also reveals the acidity and basicity of the sample. Compounds that are soluble in water may also be soluble in 5% NaOH and 5% HCl solutions because these solutions are largely composed of water.

Although we did not test for the functional group of the samples, figure 1 show the solubility of the sample in different solvents indicates the possible class of organic compounds to where it belongs as shown in figure 1.

Table 4 Reaction with Litmus

Samples Cyclohexane DCM Ethanol Phenol Benzoic acid Ethyl acetate Ethyl amine

Reaction w/ litmus Neutral Neutral Neutral Acidic Acidic Neutral Basic

Table 4 shows Cyclohexane, DCM and Ethanol were neutral in litmus paper test while Phenol, Ethyl Acetate and Benzoic Acid were identified as acidic. Only Ethyl Amine was determined to be basic. Alkanes are neutral in nature, not affected by acids and alkalis at room temperature. Ethanol is a neutral molecule and the pH of a solution of ethanol in water is nearly 7.00. Compounds like ethanol and phenol which contain an -OH group attached to a hydrocarbon are very weak acids. Alcohols are so weakly acidic that, for normal lab purposes, their acidity can be virtually ignored. However, phenol is sufficiently acidic for it to have acidic properties recognized even if it is still a very weak acid.

Table 5 shows data based on the experiment, Cyclohexane, Ethanol, Ethyl acetate and Ethyl amine were found out to be flammable while DCM, Phenol and Benzoic Acid were found out to nonflammable. Flammability means that the compound can react exothermically with oxygen. Because of the high heat of reaction, it means a fire will result from the reaction. Most alcohols and alkanes are prime examples. Their high flammability is the result of their ease of reaction with oxygen, and the large amount of heat given out when they react. Ignition test indicates the presence of unsaturation or high carbon to hydrogen ratio.-higher C/H ratio, higher luminosity, more sooty- Degree of luminosity can be assessed by the presence of yellow flame and soot. The Aromatic compounds should burn with sooty flame due to the incomplete combustion which causes the formation of an unburned carbon. In terms of degree of luminosity: aromatic compound > unsaturated hydrocarbon > saturated hydrocarbon. Unfortunately the aromatic compounds phenol and benzoic acid is non-flammable and did not yield soot.

Table 5 Ignition Test Samples Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl acetate Ethyl amine Flammability Flammable Nonflammable Flammable Nonflammable Nonflammable Flammable Flammable Color of flame Luminous NA Nonluminous NA NA Luminous Luminous

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