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Johanna Lynne La Rosa, Denise Gianelli Lopez, Anna Reyzell Lundang, Marlon Mallillin III and Jacinto Mari Manual Group 5 2E Pharmacy Organic Chemistry Laboratory

Organic compounds have been subjected to comparative investigation to differentiate the behaviour of one from the other. The physical state at room temperature, odor and color of the samples were noted by simple observation. The samples are classified as to miscible, slightly immiscible or immiscible if it is a liquid and very soluble, soluble, partially soluble or insoluble, depending on its reaction with the solvents. The samples were also tested using litmus paper to classify its acidity, basicity and neutrality. Another test performed was the ignition test which classify the samples to compounds which upon ignition gave non- luminous (blue flame), luminous (yellow flame) with soot or luminous without soot flame. After going through all these tests, it is proven that different organic compounds exhibit different properties.

Organic compounds are defined as compounds that contain carbon. When organic compounds reacts, some existing bonds break and some new bonds form. Bonds form when two atoms share electrons, and bonds break when two atoms no longer share electrons. How readily a bond forms and how easily it breaks depend on the particular electrons that are shared, which, in turn, depend on the atoms to which the electrons belong [2]. There are more than 37 million known organic compounds. Each of these compounds has its own physical properties, such as melting point, and each has its own chemical reactivity. Chemists have learned through years of experience that organic compounds can be classified into families according to their structural features and that the members of a given family often have similar chemical reactivity [1]. Since Carbon atoms are able to create double and triple bonds with other atoms or to itself, it further raises the likelihood for variation in the molecular make-up of organic compounds. All hydrocarbons are insoluble in water because they are non-polar. There are two large classes of hydrocarbon namely: unsaturated and saturated hydrocarbons. Saturated hydrocarbons are the simplest type of organic compounds where all carbon-carbon bonds are single bonds and thus contain the maximum possible number of

hydrogen per carbon. Example of saturated hydrocarbon is an alkane. On the other hand, because of their multiple bond, alkenes and alkynes have fewer hydrogens per carbon than related alkanes and are therefore referred to as unsaturated. Organic compounds may have similar physical properties but differ in chemical properties [8]. Miscibility is the property of liquids to mix in all proportions therefore forming a homogenous solution. Flammability, which is tested through ignition test, measures the extent to which a material or a substance will support combustion. Vapor pressure is an important consideration in determining the ease of ignition of a substance or material. Substances are determined by the characteristics of their flame when they burn. Some compounds exhibits blue flame or yellow, sooty flame due to their high carbon content. Some may burn with flames that are yellow but less sooty [6]. The objective of the experiment is to differentiate the organic compounds in terms of certain intrinsic physical properties and their behavior towards ignition.

A. Compound Tested or Samples Used y Cyclohexane y DCM

y y y y y y y

Ethanol Phenol Benzoic Acid Ethyl Acetate Ethylamine 5% NaOH solution 5% HCl solution

the 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. 3. Reaction with Litmus Paper If the water is soluble in water, the aqueous solution was tested with red and blue litmus paper. The color changes in both litmus paper was noted. 4. Ignition Test 3-5 drops of the liquid sample was placed in a small evaporating dish and then was lighted with a match. If the sample is solid, a pinch amount was used. The sample was observed if it is flammable or not. The color of flame produced was noted.


Figure1. Samples Used in the Experiment A. Observation of Physical State, Odor and Color Table 1. Intrinsic Properties of the Sample
Physical State at RT liquid liquid liquid liquid Color colorless colorless colorless red orange/ colorless white crystals colorless colorless Odor paste-like odor paste-like odor alcohol odor paste-like odor odorless plastic balloon odor ammoniacal odor

B. Procedure 1. Observation of Physical State, Color and Odor The physical state of the sample at room temperature was observed. Then, the color was noted and with a wafting motion, the odor was described. 2. Test for Solubility Properties The sample was introduced into a clean and dry test tube. 4 drops of the sample was used if it is a liquid and 0.1g was used if it is a solid. The solid samples was grinded to increase its surface area. Then, the solvent was added dropwise. The number of drops of solvent added was counted to a total of 3mL. A dry and calibrated dropper was used. The mixture was not heated. The color changes, warming and effervescence was noted. The number of drops of solvent added to completely dissolve the sample was also noted. Based on the amount of solvent added,

Cyclohexane DCM Ethanol Phenol

Benzoic Acid Ethyl Acetate Ethylamine

solid liquid liquid

As show in the table, all of the samples tested are colorless. However, after storing for a long time, many liquid compounds oxidize. Often most of the oxidation products are colored like phenol. Phenol, when not oxidized is colorless, but upon oxidation it became color red orange. All the samples except for benzoic acid crystals are liquid. Cyclohexane, DCM and phenol have the same odor which is paste-like. Ethanol has the

odor of alcohol while benzoic acid is odorless. Ethylamine has the odor of ammonia due to the functional group amine while ethyl acetate is plastic balloon odor.

B. Test for Solubility Properties Table 2. Solubility of Sample in Different Solvents

Solubility in: 5% NaOH solution immiscible immiscible miscible miscible insoluble immiscible miscible

H 2O Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethylamine immiscible immiscible miscible immiscible insoluble immiscible miscible

5% HCl solution immiscible immiscible miscible immiscible insoluble immiscible miscible

Reaction with litmus paper indicates the acidity/basicity of the water soluble samples. If the red litmus paper turns to blue or if the blue litmus paper retains its color, it indicates that the solution is basic. But if the blue litmus paper turns to red or if the red litmus paper retains its color, the solution is acidic. If the litmus paper retain its color (blue to blue and red to red), the solution is neutral. Cyclohexane and DCM are not reacted with litmus paper because it is not water soluble. Phenol and benzoic acid are acidic because the litmus paper turn to red to red and blue to red while ethylamine is basic because the litmus paper turn blue to blue and red to blue. Ethanol and ethyl acetate are neutral because the litmus paper retains its color. D. Ignition Test Table 4. Degree of Luminosity of the Samples
Ignition Test luminous (yellow flame); sooty non- flammable non- luminous (blue flame) non- flammable non- flammable Luminous (yellow flame); non sooty luminous (yellow flame); non sooty

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. The principle involved is like dissolves like. Water is a polar solvent so the sample that will is miscible or soluble to it is said to be polar. The solubility in 5% NaOH solution of a water insoluble sample is a strong indication of an acidic functional group. Compounds that behave as bases in aqueous solution are detected by their solubility in 5% HCl solution. Cyclohexane, DCM, and ethyl acetate are immiscible with water, 5% NaOH solution and 5% HCl solution while ethanol and ethylamine are miscible with the said solvents. Phenol is immiscible with water and 5% HCl solution but is miscible with 5% NaOH solution. Benzoic acid is insoluble in water, 5% NaOH solution and 5% HCl solution. C. Reaction with Litmus Paper Table 3. Acidity, Basicity and Neutrality of the Samples
Reaction w/ Litmus Paper Neutral Acidic Acidic Neutral Basic

Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethylamine

Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethylamine

Many liquids burn with a characteristic flame that assists in determining the nature of the compound. Thus, an aromatic hydrocarbon (which has a relatively high carbon content) burns with a yellow but much less sooty. As the oxygen content of the compound increases, the flame becomes more and more clear (blue). The degree of luminosity can be assessed by the presence of yellow flame and soot. The higher the number of Carbon atoms, the higher the degree of luminosity. In addition, the higher the Carbon: Hydrogen Ratio, the higher the degree of luminosity. Complete combustion is indicated by a blue flame (non-luminous) and there is more heat than light, the carbon is complete oxidized. 2 C10H22 + 31 O2 20 CO2 + 22 H2O Incomplete combustion is indicated by a yellow flame (luminous) and there is much light than heat; the carbon is not completely oxidized. 2 C2H2 + 5 O2 4 CO2 + 2H2O + heat

[1] Bruice, P.Y. (2006). Essential Organic Chemistry. USA: Pearson Prentice Hall Inc. [2] Brown, W.H. and Foote, C.S. (2006). Organic Chemistry. 3rd ed. USA: Harcourt College Publishers. [3] Fessenden, R.J., Fessenden, J.J., Feist, P. (2001) Organic Laboratory Techniques. 3rd ed. California, USA: Brooks/ Cole Publishing Company. [4] Landgrebe, J.A. (1993). Theory and Practice in the Organic Laboratory with Microscale and Standard Scale Experiments. 4th ed. California, USA: Brooks/ Cole Publishing Company. [5] Murov, S., Stedjee, B. (1997). Experiments in Basic Chemistry. 4th ed. Canada: John Wiley & Sons Inc. [6] Shriner, R.L., Morill, T.C. (1995). The Systematic Identification of Organic Compounds. 6th ed. Canada: John Wiley & Sons Inc. [7] Singh, M.M., Fike, R.M., Szafran, Z. (1995). Microscale & Selected Macroscale Experiments for General & Advanced General Chemistry. Canada: John Wiley & Sons Inc. [8] Smith, J.G. (2008). Organic Chemistry. New York, USA: McGraw- Hill.