Organic Chemistry Laboratory CH 200L (2012 2013) 2B-Ph Group 5 Experiment 6

Comparative Investigation of Organic Compounds

Divina Mae Y. Jose*, Maria Nicole Juanson, Danica Angela Lamasan, Darwin Bryan Kiong, and Sharmaine Margaret Lee Department of Pharmacy, Faculty of Pharmacy University of Santo Tomas, Espana Street, Manila 1008
Date Submitted: August 14, 2012

Abstract The formal report shows different methods used to satisfy intrinsic and extrinsic investigation of organic compounds, and an additional infrared analysis to determine chemical bonds. Senses were use to identify the extrinsic properties like state, color and odor. Three different solvents were used to determine polarity, and nature or the basicity or acidity of a compound. The use of a litmus paper is another way of determining the compounds nature. Flammability determines indicates an unsaturation of high carbon to hydrogen ratio. A tabular illustration of the results was supplemented and shown in the appendix. A general conclusion is made the all organic compounds are colorless, and oxidation affects their physical and chemical properties. A common characteristic of a strong odor is present among them too.

INTRODUCTION Organic compounds are known as carbon compounds, simply because they contain carbon. There are existing 37 million compounds containing carbon because of the fact that it easily forms bonds, knowing its chemical structure and valence which is four. Carbon can form strong links with four other atoms. It mostly bond to Hydrogen, Nitrogen and Oxygen. It can even bond to itself forming long chains or rings the polymers. Generally, organic compounds can be classified into hydrocarbons made up of hydrogen and carbon, insoluble in water because of their relative non-polarity and easily distribution; another is hydrocarbon derivatives. Hydrocarbons may be unsaturated or saturated. Saturated hydrocarbons are the simplest type of organic compounds in which all carboncarbon bonds are single bonds, while unsaturated hydrocarbons contain one or more carbon-carbon multiple bonds like double bonds and triple bonds. These two classes are similar physically, but not chemically. In comparative investigations of organic compounds experiment, the first observed were physical properties where you have to be very descriptive about color, odor, and phase of the compound). Next, The polarity (attraction to other molecules in a substance which affect its properties) is indicated miscibility (term used when the compounds tested are in liquid-liquid phase) or solubility (term used when compound tested are in solid-liquid phase) to different test compounds mixed were identified. The nature of

compound (whether acidic or basic) was promptly determined. Lastly, flammability (ability to ignite) and Infrared spectrometry (identifies the type of principal bond, wave number range, and the functional group present in the compound). The experiments objectives are: to identify different physical characteristics of some given compounds; its miscibility and solubility in some solvents; its polarity and its flammability; and to be able to compare the given results to one another. MATERIALS AND METHODS A. Compounds tested (or Samples used) The compounds used were Cyclohexane, Dichloromethane, Phenol, Ethanol, Ethyl acetate, Ethylamine (4 drops each liquid), and pure Benzoic acid(0.1g). Solvents used were Distilled water, 5% HCl soln., 5% NaOH soln.

The solid Benzoic acid sample was grinded to increase the surface area. The solvent mentioned above was added drop wise, and the number of drop of solvent added were counted until a total of 3mL is obtained. This procedure was made to test either the miscibility or solubility of the compounds, also changes like warming, or effervescence will be noted. The task is divided among the 2nd, 3rd and 4th members of the group. 3. Reaction with Litmus Paper Afterwards, using litmus papers, the acidity or basicity of compounds were known(blue if basic; red if acidic, no change in the litmus paper color if neutral). This were also done by the 2nd to 4th members. 4.Ignition Test The flammability test; where 3 drops (if a liquid compound) or a pinch amount (if a solid compound) were placed it in a small evaporating dish and lighted with a match. The experiment was done by the 5th member of the group this time. 5. Infrared (IR) Analysis The absorption measurement of different IR frequencies by a sample positioned in the path of an IR beam. This task is also made by the 5th member.

B. Procedure 1. Physical State, Color and Odor The experiment started with the 1st member of the group doing the observations for the physical description of the test compounds each inside their respective test tubes at room temperature. 2. Solubility Properties

RESULTS AND DISCUSSIONS Upon observation, I conclude that mostly, hydrocarbons are colorless. The result of the experiment showed that oxidation changes the physical state of compounds like Phenol becoming orange benzoic acid turning white crystals. All exhibit strong odor.

Miscibility and solubility were tested in addition of three solvents mentioned in methodology. Through that process we can figure out the polarity and the acidity or basicity. Compounds are polar if they are miscible or soluble in water because water is a strong polar substance. The principle that like dissolves like applies into these. Polar among tested compounds are ethanol, ethyl acetate, and ethylamine. Acidity and basicity, can be determined by both the litmus paper test and solubility or miscibility in 5% NaOH and 5% HCl. The 5% NaOH, being a base, react with acid. While 5%HCl, being an acid, react with base. If the substance doesnt react with either solvents, they remain neutral. Acidic compounds are: Phenol and Benzoic acid; neutral compounds are: Cyclohexane, DCM, Ethanol and Ethyl acetate; while the only basic compound is Ethylamine. Acidity and Basicity determination in litmus paper was used to identiy a change in color when a drop or two of the sample is placed in the litmus paper. Red litmus paper has no color change when the solution is acidic; it changes into blue when the solution is basic. A neutral solution is recognized when it is both tested in red and blue litmus but then no noted color change is observed. Ignition test was performed to indicate whether there is an unsaturation of high carbon to hydrogen ratio. Flammable compounds are: Cyclohexane, Ethanol and Ethyl acetate.

To interpret the results tabulated in the data table found in the appendix, we must describe different regions of IR spectrum. IR spectrum can be broken down into three major regions: 1. The functional group region (1600-4000 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. In general, the experiments objectives were attained that the intrinsic analysis of some of the organic compounds physical and chemical characteristics, like their polarity; flammability; acidity, basicity or neutrality; and the functional groups present that were determined through IR analysis. Further study is advised to be made to check whether the study remains true in years or improvements may be applied

REFERENCES From the book [1]Organic Chemistry Laboratory Manual From the internet 1]https://eee.uci.edu/programs/gchem/ D01MANymiscibility.pdf [2]http://www.chm.bris.ac.uk/webproject s2001/may/carboncompounds.htm [3]http://www.prenhall.com/settle/chapte rs/ch15.pdf [4]http://www.wisegeek.com/what-areorganic-compounds.htm

APPENDIX

Table.1 Comparative Investigation of Organic Compounds Test Compounds Physical State at RT Color Odor Test Compounds Solubilty in H20 5% NaOHsoln 5% HCL soln Reactions with Litmus Paper Ignition Test Cyclohexane Liquid colorless Acid-like Cyclohexane DCM Liquid Colorless Acetone-like odor DCM Ethanol Liquid Colorless Strong, pungent odor Ethanol Phenol Liquid colorless Paste-like odor Phenol

Immiscible Immiscible Immiscible Neutral

Immiscible Immiscible Immiscible Neutral

miscible miscible miscible Neutral

miscible miscible Immiscible Acidic

Observed Principal IR Peaks (cm-1)

Orange Flame; with soot C-H Stretch 3000-2840 C-H Bond 1475-1350 C-C Stretch 1200-800

NonFlammable C-Cl 580-780

Yellow Flame; Flammable with soot C-O Stretch 1230-1000 C-H Bond 1420-1340 O-H Stretch 3700-3100 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% NaOHsoln 5% HCL soln Reactions with Litmus Paper Ignition Test Observed Principal IR Peaks (cm-1) 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 balloonlike 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

Table 3. Condensed Structural Formula of Organic Compounds Condensed structural formula Benzoic acid

EthanoL Phenol

CH3CH2OH Cyclohexane

Ethyl acetate Dichloromethane CH2Cl2

Ethylamine

CH3CH2NH2