University of Santo Tomas Faculty of Pharmacy Organic Chemistry Laboratory

Comparative Investigation of Organic Compounds Manlutac, D.T., Maravillas, M.S., Miranda M.H., Navarro, M.J., Panaligan A.C.

ABSTRACT The goal of this experiment is to differentiate organic compounds in terms of certain intrinsic physical properties, behavior towards ignition, and infrared spectra of their functional groups. This formal report presents the comparative investigation of the different organic compounds and spectrometric analyses. In some cases, certain intrinsic physical property of the different compounds is characterized by physical and chemical properties in terms of structure and behavior. The physical state, color and odor were noted by simple physical observation. Miscibility was tested by introducing drops of a sample whether if it is a liquid or a solid. Flammability was tested by placing 3-5 drops of the liquid sample in a small evaporating dish and lighting it with a match. Note that in the process of ignition testing, flammability of the sample, the color and type of the flame produced, burning time, and the possible production of soot in the process of the ignition test, was also recorded. Reaction to Litmus paper was observed to determine if the compound is basic or acidic, and also to determine its solubility in water. The tests were conducted to find out the presence of certain substances in each compound examined. The effective result of the components is based on differences in the physical properties of the compounds, or of their derivatives. After going all through the tests, the compounds differ in water solubility due to their varying polarities, the solubility in acids or base leads to more specific information about the compound and the different physical and chemical properties and determining by using the infrared spectroscopy analysis. In the infrared spectroscopy analysis, the type of principal bond present in the compound shall be identified. In this experiment, the following samples shall be thoroughly tested. INTRODUCTION Organic compounds are the complex compounds of carbon. Because carbon atoms bond to one another easily, the basis of most organic compounds is comprised of carbon chains that vary in length and shape. Hydrogen, nitrogen, and oxygen are the most common atoms that are generally attached to the carbon atoms. Each carbon atom has 4 as its valence number, which increases the complexity of the compounds that are formed. Since carbon atoms are able to create double and triple bonds with other atoms, it further also raises the likelihood for variation in the molecular make-up of organic compounds. Generally, organic compounds can be classified into hydrocarbons, and hydrocarbon derivatives, based on the replacement of hydrogen by another element or by a group of different elements (functional group). All hydrocarbons are insoluble in water because of their relatively non-polarity and easily distribute. When hydrocarbons burn using oxygen, C02 and H20 are the sole products. There are 2 large classes of Hydrocarbon namely: unsaturated and saturated hydrocarbons. Saturated hydrocarbons are the simplest type of organic compounds in which all carbon-carbon bonds are single bonds. An

example of a saturated hydrocarbon is an alkane. On the other hand, unsaturated hydrocarbons contains one or more carboncarbon multiple bonds like double bonds and triple bonds. These two classes have similar physical properties but differ in chemical properties. Miscibility is the property of liquids to mix in all proportions therefore forming a homogenous solution. Flammability is the measure of the extent to which a material or a substance will support combustion. This is tested through ignition test. Vapor pressure is an important parameter in determining the ease of ignition of a substance or material. Substances are determined by the characteristics of their flame when they burn. Ignition of the compound brings about a chemical change. Some organic compounds decompose and blacken (charring) while others burst into flames. Some compounds produces yellow, sooty flame due to their high carbon content. Some burn with flames that are yellow but produces less soot, while other compounds burn with non-luminous flames. Infrared (IR) spectrometry gives additional information about a compounds structure. It identifies the type of principal bond present in the sample compound that may be observed in the IR spectra and give its wave number range. It also identifies the functional group present in the compound. In this experiment, the compounds shall be differentiated in terms of certain intrinsic physical properties, behavior towards ignition, and the infrared spectra of their functional groups. Condensed structural formula of the samples used: 1. Cyclohexane - Cycloalkane

2. DCM Halogenated CH2Cl2 3. Ethanol Alcohol

4. Phenol Phenol

5. Benzoic Acid Carboxylic Acid

6. Ethyl Acetate Ester

7. Ethylamine Amine

METHODOLOGY A. Compounds Used for Testing: Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Ethyl Amine

B. Procedure Solubility Properties The sample was introduced in a clean and dry test tube. 4 drops of each sample was added if the sample was a liquid; and 0.1 g of sample was added if the sample was a solid. The solid samples were grinded to increase the surface area. The solvent was added drop wise and counted the number of drops of solvent added to a total of 3mL. Any change, warming effects, soluble/insoluble, miscible/immiscible or effervescence was noted. Reaction with Litmus Paper Drops of the sample tested its aqueous solution with red and blue litmus papers. Color changes in both litmus papers were noted. Ignition Test 3-5 drops of the liquid sample and a pinch amount of solid were placed in an evaporating dish and was lighted using a match. Any flame produced and observed was noted. Infrared (IR) Analysis The appendix notes were used to identify the type of principal bond present in the sample compound that may be observed in the IR spectra and its wave number range. RESULTS AND DISCUSSION Most hydrocarbons tested were colorless. However, many liquid compounds oxidized when stored for a long period of time. Often the oxidized products are intensely colored. The result of the experiment showed that Phenol becomes red orange in color upon oxidation and white crystals for benzoic acid. The odors of the compounds are quite similar but still it has different identity. Solubility properties of organic compounds using H20 (water),

5% NaOH (Sodium Hydroxide) solution and 5% HCL (Hydrochloric Acid) solution indicates whether the sample is soluble or insoluble and if the sample is miscible and immiscible. Based on the results, Benzoic acid was slightly soluble in H20; insoluble in 5% NaOH solution and with 5% HCL solution because of the fact that Benzoic acid is a solid matter. While the rest of the compounds that are liquid namely Cyclohexane and DCM were immiscible and immiscible for Phenol when added with 5% HCL soln. As for Ethanol, Ethyl Acetate and Ethylamine when added with H20,HCL and NaOH it becomes miscible. Reactions with litmus paper indicate the acidity/basicity of the H20-soluble samples. If it is from Red to Blue the result will be a base indicator and if it is Blue to Red the result will be an Acid indicator. The Litmus paper that retains its color indicates a neutral compound. Solubility of organic compounds in 5% NaOH also reveals the acidity and basicity of the sample. 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. The Aromatic compounds burn with sooty flame due to the incomplete combustion, which caused the formation of an unburned carbon. In terms of degree of luminosity: aromatic compounds are greater than unsaturated hydrocarbons, which are greater than saturated hydrocarbons.

Complete combustion is indicated by a blue or non-luminous flame and there is more heat than light, which means that the carbon is completely oxidized. 2 C10H22 + 31 O2 -> 20 CO2 + 22 H2O Incomplete combustion is indicated by a yellow or luminous flame and there is much more light than heat; therefore the carbon is not completely oxidized.

2C2H2 + 5O2 = 4CO2 + 2H2O + heat 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 (16004000 cm-1) is the region in which 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. C-O stretching of alcohols esters are easily assigned. 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. Overall, the experiment succeeded in differentiating the organic compounds tested in terms of certain intrinsic physical and chemical properties, the behavior towards ignition, and the infrared spectra of their functional groups. REFERENCES From Books: Bayquen, A.V., Cruz, C.T., et al (2009). Laboratory Manual in Organic Chemistry. Quezon City: C&E Publishing Inc

Lambert, J., Shurvell,H.,Lightner D., Cooks G. (1987) QD. Introduction to Organic Spectres. New York: John Wiley & Sons, Inc. 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. University of Santo Tomas Department of Chemistry (ed.). (2000). Organic Chemistry Laboratory Experiments Part 1. (unpublished manual based by the Department of Chemistry, College of Science, University of Santo Tomas) From the Internet http://www.chemenv.titech.ac.jp http://www.chemistryabout.com Dee, S. Wise Geek http://www.wisegeek.com/what-areorganic-compounds.htm 08/25/10 http://firstyear.chem.usyd.edu.au/prelab/e 28.shtml http://www.orgchem.colorado.edu http://www.scienceteacherprogram.org/ch emistry/Paul00-2.html

APPENDICES Table.1 Comparative Investigation of Organic Compounds

Test Compounds Physical State at RT Color Odor Test Compounds Solubilty in H20 5% NaOH soln 5% HCL soln Reactions with Litmus Paper Ignition Test Observed Principal -1 IR Peaks (cm )

Cyclohexane Liquid colorless Acid-like Cyclohexane Immiscible Immiscible Immiscible Not Applicable Orange Flame; with soot C-H Stretch 3000-2840 C-H Bond 1475-1350 C-C Stretch 1200-800

DCM Liquid Colorless Acetone-like Odor DCM Immiscible Immiscible Immiscible Not Applicable Non- Flammable C-Cl 580-780

Ethanol Liquid Colorless Strong, pungent odor Ethanol miscible miscible miscible Neutral Yellow Flame; with soot C-O Stretch 1230-1000 C-H Bond 1420-1340 O-H Stretch 3700-3100

Phenol Liquid colorless Paste-like odor Phenol miscible miscible Immiscible Acidic Flammable C-O Stretch 1230-1000 O-H Bond 1420-1340 O-H Stretch 3700-3100

Table 2. Comparative Investigation of Organic Compounds Test Compounds Physical State at RT Color Odor Solubilty in H20 5% NaOH soln 5% HCL soln Reactions with Litmus Paper Ignition Test Observed Principal IR -1 Peaks (cm ) Benzoic Acid Solid White crystals Acid-like odor Slightly soluble Insoluble Insoluble Acidic Non-Flammable O-H stretch 3300-2500 C-O Stretch 1730-1680 O-H Bond 1440-1390 C-O Stretch 1320-1210 Ethyl Acetate Liquid Clear and Colorless Plastic balloon-like Odor Miscible Miscible Miscible Neutral Orange Flame; not sooty C=O Stretch 1740-1210 C-O Stretch 1245-1190 Ethylamine Liquid Clear and Colorless Ammonia-Like Odor Miscible Miscible Miscible Basic Orange Flame; not sooty N-H Stretch 3500-3300 & 3400-3200 N-H Bond 1640-1560 N-H Bond 900-650 C=N Stretch 1330-1030