The Comparative Investigation of Organic Compounds

Aegan Amican, Karen Ares, Ruvie Ballester, Mark Barcelona, Katherine Calleja, Christelle Capuno Group 1; 2D-Pharmacy, Faculty of Pharmacy, University of Santo Tomas

Abstract
Organic compounds are compounds that contain carbon. They have different chemical and physical characteristics. In this experiment we used cyclohexane, dichloromethane, ethanol, phenol, ethyl acetate and ethyl amine as our organic compounds. We were able to identify some of the differences in the physical characteristics of the different compounds such as they physical state of the substance in room temperature, color and odor of the substance. We were also able to identify some of the differences in the chemical characteristics of the different compounds such as the solubility, its acidity or alkalinity and its flammability. Solubility was tested by the use of different solvents such as purified water, 5%HCl solution and 5% NaOH solution. The substances that were soluble in water were the polar substances, ethanol, phenol and acetyl amine. These samples had been tested with litmus paper to determine if they are acidic or basic. Among samples used, benzoic acid was positive for acidity and ethyl amine was positive for alkalinity. The test for flammability had been used to determine the saturation of the samples. Among the samples, cyclohexane, ethanol and ethyl acetate ignited and produced yellowish flame that is an indicator of the samples unsaturation.

Introduction Organic compounds are compounds that contain carbon and are present in living organisms (Smith,2011). As a group 4 element, carbon atoms can share four valence electrons and form four strong covalent bonds. Furthermore, carbon atoms can bond to one another (McMurry,2011). With this unique ability, carbon can form an immense diversity of compounds. Carbon atoms can also form double or triple bonds with other carbons or other atoms which increases the complexity and variation of the different organic compounds. Organic compounds can be classified as hydrocarbons or hydrocarbon derivatives. Hydrocarbons are organic compounds which contains purely hydrogen and carbon. Hydrocarbons may be further classified to as aliphatic or aromatic compounds. Under aliphatic compounds are saturated hydrocarbons, which are hydrocarbons that posses only single carbon-carbon bonds and contain the maximum number of hydrogen atoms for each atom, and unsaturated hydrocarbons, which are hydrocarbons that contain double or triple bonds with adjacent carbon atoms. Aromatic compounds are any of a large class of unsaturated chemical compounds characterized by one or more planar rings of atoms joint by covalent bonds of two different kinds (Carey,2012). . Hydrogen derivatives are organic compounds that contain hydrogen and carbon along with other atoms. The objective of this experiment are to differentiate the sample organic compounds in

terms of certain intrinsic physical properties such as physical state, color, odor and some chemical properties like solubility, miscibility, acidity or alkalinity and flammability. Solubility is the ability of a substance to dissolve in a particular solvent. Miscibility is the ability of a liquid to mix to a particular solvent to create a homogenous mixture. Acidity is the tendency of a compound to act as an acid(proton donor), alkalinity is the tendency of a compound to act as a base(proton acceptor). Flammability is the measure of the extent a substance will support combustion. Materials For this experiment, the samples had been used were the following : Cyclohexane, Dichloromethane, Ethanol, Phenol, Benzoic Acid, Ethyl Acetate and Ethyl Amine. For the determination of the physical state,color and odor, the samples had been placed inside clean and dry test tubes. With the aid of a calibrated pipette , the solvents that had been used to determine the solubility properties were 5% HCl solution, 5% NaOH and purified water. The application of red and blue litmus paper had been done after the samples were proven positive for solubility in water. For the ignition test, the samples had been placed inside small evaporation disks before the application of a lighted match stick.

Methods Determination of Physical State and Odor The samples were placed inside clean test tubes in room temperature to be able to

describe their physical states and colors. With a wafting motion, the odor of the samples were described and noted. Solubility Properties The samples were introduced into test tubes. 4 drops of the liquid samples were used and 0.1 grams of sample were used for the solid compounds. The solvent was added dropwise to the test tubes containg the samples to make a total of 3mL. Any change or reaction that took place were noted and the extent of solubility or miscibility were described based on the amount of solvent used. Reaction with litmus paper Samples that were dissolved in water were tested with litmus paper to determine their acidity or alkalinity. Ignition Test 3-5 drops of the liquid samples were placed in a small evaporating dish and were lighted with a match stick. For the solid sample, a pinch amount of the sample was placed in the evaporating dish and was lighted with a match stick. The flammability, color of the flame produced and the presence of soot were noted. Results & Discussion In this experiment, the students were able to differentiate organic compounds based on some intrinsic physical properties and behavior towards ignition. Based on research, different organic compounds have different physical properties such as physical state, color and odor, and different chemical properties such as solubility, acidity or alkalinity and flammability.
Cyclohexane State at RT Color Odor Solubility H20 Solubility in 5% NaOH Solubility in 5% HCl Litmus paper Ignition Liquid Clear, colorless Faint ether like Immiscible Miscible Miscible Neutral Flammable, yelloworange flame w/ soot Phenol DCM Liquid Clear, colorless Acetone like Immiscible Miscible Miscible Neutral Nonflammable

Liquid

Liquid

Solid

Clear, Colorless Strong alcohol Miscible Miscible Miscible Neutral Flammable, yellow orange flame w/ soot

Clear, Red orange color Paste like Miscible Miscible Immiscible Neutral Nonflammable

White amorphous powder Odorless Insoluble Soluble Insoluble Acidic Nonflammable

Table 1.2 Results for ethanol, phenol and benzoic acid

Ethyl Acetate Liquid Clear, colorless Plastic balloon like Miscible Miscible Miscible Neutral Flammable, orange flame with soot Ethyl Amine Liquid Clear, colorless Corrosive Miscible Immiscible Miscbile Basic Nonflammable

Table 1.3 Results for Ethyl Acetate and Ethyl amine Organic compounds have different physical properties, which are intrinsic such as odor (Bayquen,2009). For the physical properties, the samples had been observed in their physical state at room temperature and were described to be crystalline or amorphous powder for the solid samples and clear, colorless or clear, colored for the liquid samples. The physical state of a substance is a determinant for the strength of the intermolecular forces in a solid compound (Shriner,1980). Based on research, substances that produced odors are mostly unsaturated compounds though the degree of the odor varies with the saturation (Woker,1908). In the results of the experiment, it has been proven that compounds that were saturated produced odors that are quite distinctive to the other compounds. For their chemical properties, the samples had been tested for their solubility or miscibility in different solvents. The different results given to the different samples are caused by the

Table 1.1 Results for Cyclohexane and DCM

Ethanol Benzoic Acid

difference in the molecular composition of the compound, the structure of the atoms and the reactivity of the samples to the given solvent / tests. (Watson, 1937).
Compound Cyclohexane Dichloromethane Condensed Structural Formula

(Mayo,2000). In the experiment, the only substances that were flammable were cyclohexane, ethanol and ethyl acetate. These three compounds exhibited a non-luminous flame and presence of soot that has been used to determine that they were unsaturated compounds. References : Books :

Ethanol Phenol

Bayquen, A.V., et.al. (2009). Laboratory Manual in Organic Chemistry. Quezon City,Philippines: C&E Publishing, inc. Shriner, R., Hermann, C.K.F., et. Al. (1980) Systematic Identification of organic compounds, 6th edition, USA: John Wiley & Sons. McMurry,J. et. Al. (2007) Fundamentals of Organic Chemistry, International Edition, 7th edition, USA: C&E Publising inc. Internet sources :

Benzoic Acid

Ethyl Acetate Ethyl Amine

Table 1.4 Condensed Structural Formula of the compounds Solubility is based on the ability of the substance to dissolve in a solvent and create a homogenous mixture. The main idea behind solubility in solvents is that polar substances dissolve like substances, like dissolves like. Based on research, the solubility of a substance in water, a polar solvent, indicate that a polar group is present (Shriner, 1980). In the experiment, the samples that were soluble in water were ethanol, phenol, ethyl acetate and ethyl amine. This would validate the statement of Shriner that solubility in water is an indicator for presence of polar groups. Solubility in water and in HCl solution(a strong acid) determines the presence of an amine and a basic functional group in the substance. In the experiment, only Ethyl amine was soluble to water and HCl. Insolubility in water and in NaOH solution(a strong base) determines the presence of an acidic functional group in the compound. In the experiment, only benzoic acid was insoluble to water but soluble in the NaOH solution. The ignition test was based on the idea of flammability. Flammability indicates the presence of unsaturation or high carbon to hydrogen ratio of the compound. The general idea is the higher the C/H ratio, the more luminous the flame is, the more sooty it is

1.) http://www.scribd.com/doc/69434439/M odern-Theories-of-Organic-Chemistry1937 2.) http://pubs.acs.org/doi/abs/10.1021/j150 078a003