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COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS

Ciara Maye A. Morales, John Ian V. Nacino, Dean Xavier C. New, Jason A. Ong, Mark Kenneth F. Ong and Leah Kristine C. Reyes Group 7 2B Medical Technology Organic Chemistry Laboratory

ABSTRACT
In order to distinguish different kinds of organic compounds, a series of tests was done by the group based on the certain intrinsic physical properties of the different organic compounds, their behavior towards ignition as well as the infrared spectra of the functional groups present on the compounds. Their physical properties such as the physical state, color and odor at room temperature was observed by the members. The solubility and miscibility properties of the compounds were determined by the use of distilled water, 5% HCl and 5% NaOH as the solvents while the acidity or basicity with the use of litmus paper. The flammability of the compounds was observed on the ignition test with the help of a match and small evaporating dish. Lastly, the infrared spectra were used to classify the organic compounds based on the functional groups present.

INTRODUCTION
Organic Compounds refer to the complex compounds that contain the element Carbon. Since Carbon can share four valence electrons, it can form four strong covalent bonds with other elements as well as another Carbon atom. Because of this, it can form long chains and rings and provide a vast diversity of compounds. Hydrogen, Oxygen and Nitrogen are the most common elements that are attached to Carbon. Because of the immense variety of organic compounds, they are then classified a hydrocarbons and hydrocarbon derivatives in the basis of the replacement of hydrogen by another element or by a functional group (group of different elements). Generally, hydrocarbons are insoluble in water due to their relative nonpolarity. Hydrocarbon derivatives are classified on the basis of the substituent element or the group with the highest priority to the hydrocarbon. Comparative investigation of the organic compounds can be done in order to identify and differentiate them from one another. The physical properties of hydrocarbons like the physical state, color and odor are similar between saturated and unsaturated hydrocarbons. Saturated hydrocarbon refers to organic compounds whose C-C bonds are all single bonds while unsaturated hydrocarbons refer to the compounds whose C-C bonds are either double or triple bonds. The physical state of these compounds at room temperature indicates the interactive forces existing between its molecules. The solubility as well as miscibility of the compounds on certain solvents helps in indicating

the polarity, acidic or basic properties as well as the physical and chemical interactions involved. Reaction with the litmus paper identifies the compound if it is acidic or basic, while the ignition test indicates the flammability of the compounds. Flammability is the measure of the extent at which the compound will support combustion, a chemical change within the sample. The samples are determined by the characteristics of their flame as they burn. Lastly, the Infrared (IR) spectrometry aids in the classification of the functional groups present Condensed Structural Formula of the compounds tested: 1. Cyclohexane (Cycloalkene)

2. DCM (Halogenated Hydrocarbon) CH2Cl2 3. Ethanol (Alcohol) H H HCCOH H H

4. Phenol (Aromatic alcohol)

OH

set, 5% members warming. miscibility

NaOH was introduced. The then noted the color changes, effervescence and solubility or of the mixtures obtained.

5. Benzoic Acid (Carboxylic Acid)

OH

3. Reaction with Litmus Paper From the results obtained on the solubility test, the samples which are soluble or miscible with water were tested with red and blue litmus paper. If the two litmus papers retained their colors, the compound was classified as neutral. If the blue litmus paper retained its color but the red litmus paper turned to blue, the compound was identified as a base. If the blue litmus paper turned to red but the red litmus paper retained its color, then the compound was classified as an acid. 4. Ignition Test 3-5 drops of the liquid sample and a pinch of the solid sample were placed in a small evaporating dish and were lighted with a match. The members observed the flammability of the compounds by noting the color of the flames and classifying them as luminous or non-luminous. 5. Infrared (IR) Analysis With the appendix of the laboratory manual as a guide, the type of the principal bond present in the compound was identified using the observed IR spectra and the wave number range.

6. Ethyl Acetate (Ester)

7. Ethyl Amine (Amine)

EXPERIMENTAL
A. Compounds Tested (or Samples used) Cyclohexane, DCM (dichloromethane), Ethanol, Phenol, Benzoic acid, Ethyl Acetate, Ethyl Amine B. Procedure 1. Physical State, Color and Odor The physical state of the compounds was observed at room temperature as well as the color and odor. The odor was noted with a wafting motion. 2. Solubility Properties 10 drops of the liquid samples and 0.1 g of solid samples were placed on clean and dry test tubes. With a dropper, certain solvents were introduced to the sample. At the first set, 3 mL of distilled water was used. At the second set, 3 mL of 5% HCl as the solvent was used, and at the third

RESULTS AND DISCUSSION


Upon analysis of the tested organic compounds, the following observations were noted and are summarized into tables.

Figure 1. Samples to be tested

Table 1. Observed Physical Properties


Organic Compound Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine Physical State Liquid (Clear) Liquid (Clear) Liquid (Clear) Liquid (Clear) Solid (Crystalline) Liquid (Clear) Liquid (Clear) Color Colorless Colorless Colorless Reddish Brown White Colorless Pale Yellow Odor Odorless Smells like Acetone Smells like Alcohol Smells like paste Smells like Naphthalene Smells like Plastic Balloon Festering Odor

Figure 2. Test Tubes containing results from mixing each compound with H2O, 5% HCl solution and 5% NaOH solution. The Solubility properties of organic compounds using H20, 5% NaOH solution and 5% HCL solution indicates whether the solid sample is soluble or insoluble and if the liquid sample is miscible and immiscible. Based on the given results shown above, Benzoic acid is acidic because it was slightly soluble in acidic solvents like 5% HCL solution but insoluble in basic and polar solvents like 5% NaOH solution and with H20. Cyclohexane and DCM, on the other hand, were immiscible in all the solvents used. Ethanol was miscible with all the solvents used while Phenol is a basic compound because it is only miscible with 5% NaOH solution. Ethyl Acetate is immiscible only with polar solvents like H2O and Ethyl Amine is immiscible with basic solvents like 5% NaOH solution.

The table above shows that the hydrocarbons are generally colorless. However, due to long time storage, they tend to oxidize and gain color, as shown with the reddish brown color of phenol and the white crystals of the benzoic acid. Hydrocarbons tend to have relatively strong interactive forces between its molecules. The odors of these compounds are also relatively similar but each has its own distinct smell. Table 2. Solubility/Miscibility Properties
Organic Compound Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine Solubility in Distilled Water Immiscible Immiscible Miscible Immiscible Insoluble Immiscible Miscible Solubility in 5% HCl solution Immiscible Immiscible Miscible Immiscible Soluble Miscible Miscible Solubility in 5% NaOH soln Immiscible Immiscible Miscible Miscible Insoluble Miscible Immiscible

Figure 3. Obtaining Samples for Litmus Paper Reaction Table 3. Reaction with Litmus Paper
Organic Compound Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine Observed Reaction N/A N/A Blue to Blue Red to Red N/A N/A N/A Red to Blue Blue to Blue

Reactions with the litmus paper indicate the acidity as well as basicity samples which were soluble or miscible with H2O. If the litmus paper retained its color, then the compound was classified as neutral. If the blue litmus paper retained its color but the red litmus paper turned

to blue, then the compound used was a base. On the other hand, if the red litmus paper retained its color but the blue litmus paper turned to red, then the compound was an acid. The only compounds soluble or miscible with H2O are Ethanol and Ethyl Amine. The litmus papers introduced with Ethanol retained their color, indicating that Ethanol is a neutral compound. When Ethyl Amine was introduced, the blue litmus paper retained its color but the red litmus paper turned to blue, indicating that Ethyl Amine is basic due to the presence of Nitrogen in its molecule. Table 4. Results from the Ignition Test
Organic Compound Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine Observed Reaction Flammable (Yellow Flame) Not Flammable Flammable (Blue Flame) Not Flammable Not Flammable Flammable (Blue Flame) Flammable (Blue Flame)

2C10H22+ 31O2

20CO2+ 22H2O

Incomplete combustion is indicated by a luminous yellow flame. There is more light than thermal energy produced because the carbon atoms are not completely oxidized. C6H12+ 8O2 6CO2+ 6H2O + Light

Table 5. Observed Principal IR Peaks


Organic Compound Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine Principal IR Peaks (cm-1) C-H Stretch (Strong) 3000-2840 C-H Stretch (Strong) 3000-2840 O-H Stretch (Very Strong) 3100-3000 O-H Stretch (Very Strong) 3100-3000 O-H Stretch (Broad Strong) 3300-2500 C=O Stretch (Strong) 1740-1710 N-H Stretch (Strong) 3500-3300 & 3400-3200

For IR spectrometry, the position of the band depends upon a number of characteristics of a bond. The higher the bond order, the higher the wave number for the stretching vibration for a bond. The IR spectrum can be broken down into three major regions: 1. The functional group region (1600-4000 cm-1) is the region where functional groups absorb. Most of these absorptions are at least of moderate intensity, and many are quite strong. It is relatively free from overlap or other interferences. 2. The fingerprint region (1000-1600 cm-1) is often quite complex. It is used for band-by-band comparison of the spectrum of a known compound in order to identify the compound. 3. The Aromatic region (675-900 cm-1) is used to identify the number and relative positions of groups on a benzene ring. C-H bonds occur in this region.

Figure 4. Igniting a sample in an evaporating dish with a match for flammability test The results of the ignition test indicate 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. Aromatic compounds burn with sooty flame due to the incomplete combustion which causes the formation of an unburned carbon or carbon in its free state. In terms of degree of luminosity, unsaturated hydrocarbons are more luminous than saturated hydrocarbons but less luminous than aromatic compounds. Complete combustion is indicated by a nonluminous blue flame. There is more thermal energy produced than light because the carbon atom is completely oxidized.

REFERENCES
Bayquen, A.P., Cruz, C.T., De Guia, R.M., Lampa, F.F., Pea, G.T., Sarile, A.S., Torres, P.C. (2009).

Laboratory Manual in Organic Chemistry. Quezon City, Philippines: C & E Publishing, Inc. McMurry, J. (2010). Foundations of Organic Chemistry. Philippine ed. Pasig City, Philippines: Cengage Learning Asia Pte. Ltd. Silverstein, R.M., Webster, F.X., Kiemle, D.J. (2005), Spectrometric Identification of Organic Compounds. USA: John Wiley & Sons, Inc Shriner, R., Hermann, C.K.F., Morrill, Curtin, D.Y. (1998). The Systematic Identification of Organic Compounds. 7th ed. New York: John Wiley & Sons, Inc.