Comparative Investigation of Organic Compounds

Tristan Duane G. Lacson, Lara Elize T. Lamigo, Maria Mikaela L. Laysa, Christian Gerard G. Lee and Karen L. Li Group 6 2C Pharmacy Organic Chemistry Laboratory

ABSTRACT
In order to differentiate the organic compounds. The group tested the compounds using the information based on their instinsic physical properties, behavior in ignition,acidity and basicity and their infrared spectra. The physical properties were noted by the reaserchers by the means of their physical state,color and odor.Using the following reagents: H2o, 5% NaOH solution and 5% HCl solution. Solubility and miscibility were tested. Acidity and Basicity of the compounds were determined by the use of litmus paper. Ignition test was conducted using 3 to 5 drops of the sample in a small evaporating dish and light with a match. Lastly, the infrared spectrum was use to classify organic compounds according to their functional groups.

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. Carbon atoms have four valence electrons that make them bond with each other easily. Thus organic compounds are classified according to their 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. Organic compounds can be classified as hydrocarbons and hydrocarbon derivatives on the basis of their hydrogen replacements by other elements or by other group of 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.Unsaturated hydrocarbons contains one or more carbon-carbon multiple bonds like double bonds and triple bonds. Saturated hydrocarbons are the simplest type of organic compounds in which all carboncarbon bonds are single bonds. An

example of a saturated hydrocarbon is an alkane. 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.. 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. Lastly 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. Condensed structural formula of the samples used: 1. Cyclohexane - Cycloalkane

2. DCM Halogenated CH2Cl2 3. Ethanol Alcohol

4. Phenol Phenol

B. Procedure 1. Physical State, Color and Odor The group observed the physical state of the samples at room temperature. The groups noted the color and odor of each compound. 2. Solubility Properties The sample was introduced in a clean and dry test tube. 4 drops of each sample was added if the sample is a liquid; and 0.1 g of sample was added if the sample is 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. 3. Reaction with Litmus Paper

5. Benzoic Acid Carboxylic Acid

Drops of the sample tested its aqueous solution with red and blue litmus papers. Color changes in both litmus papers were noted.
4.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. The color of the flame and the burning time was also noted. 5. Infrared (IR) Analysis The group used the appendix notes as a reference to identify the type of principal bond present in the sample compound that may be observed in the IR spectra and gave its wave number range.

6. Ethyl Acetate Ester

7. Ethylamine Amine

RESULTS AND DISCUSSION Table 1.1

Test Compounds Physical State Color
Cyclohexa ne Liquid, clear Colorless DCM Ethanol Phenol

EXPERIMENTAL
A. Compounds tested (or Samples used) Cyclohexane, DCM, Ethanol, Phenol, Benzoic acid, Ethyl acetate, Ethylamine

Liquid,clear Colorless

Liquid,clear

Liquid clear orange

Colorless

Odor

Rubber like odor

odorless

Astringent odor

Burnt5% like odor

NaOH

Soluble

Miscible

immiscible

soln. 5% soln. HCl

Insoluble miscible miscible

Solubility in: H2O

Immiscible immiscible
miscible

Slightly Reaction misicible

N/A

with litmus paper

Ignition test Nonflammable

Neutral Blue-Blue Red-Red Flammable(33 secs) Luminous flame,sooty

C=O stretch*(s) 1740-1710 C-O stretch(s) 1245-1190

Basic Blue-Blue Red-Blue Flammable Luminous flame

5% NaOH soln. 5% soln. HCl

Immiscible

immiscible

Miscible

miscible

Immiscible

immiscible

Miscible

Observed immiscibl principal IR e peaks(cm-1)

Acidic Blue-Red Red-Red

Reaction with litmus paper

Ignition test

Neutral Blue-Blue Red-Red Flammable (44 sec) Luminous flame, sooty

Neutral Blue-Blue Red-Red Nonflammable

Neutral Blue-Blue Red-Red

table above shows the summary of the results. Most of the hydrocarbons are colorless. The result of the experiment C-H C-H O-H O-H Observed showed that Phenol becomes orange upon stretch(s) Stretch(vs) Stretch(v principal IR stretch(s) *3000-2840 *3000-2840 *3100s) oxidation and white crystals for benzoic peaks(cm ) C-H bend(sC-H bend(s3000 *3100acid. The odors of the compounds are m)* 1475m)* 14750-H 3000 in their own way but are 1350 1350 Bend(m-w) 0-H different C-C C-C 1420-1340 Bend(msomewhat similar to each other. Solubility stretch(vw)* stretch(vw)* C-O w) properties of organic compounds using 1200-800 1200-800 Stretch(s1420m) 1340H 0, 5% NaOH solution and 5% HCL 2 1230-1000 C-O solution indicates whether the sample is Stretch(s -m) soluble or insoluble and if the sample is 1230miscible and immiscible. Based on the 1000 results, Benzoic acid was slightly soluble in H20; insoluble in 5% NaOH solution and Table 1.2 Results with Test Benzoic Ethyl Ethylamine 5% HCL solution because of the fact that Benzoic acid is a solid matter. While compounds acid acetate the rest of the compounds that are liquid Solid Liquid Liquid namely Cyclohexane and DCM were Physical Creptalline Clear Clear state at RT immiscible and immiscible for Phenol when added with 5% HCL soln. As for White crystal colorless Colorless Ethanol, Ethyl Acetate and Ethylamine Color when added with H20,HCL and NaOH it Smoke-like Acetone-like Alcohol odor Odor becomes miscible. Reactions with litmus Odor odor paper indicate the acidity/basicity of the Solubility H20-soluble samples. If the result is from in: Red to Blue it will be a base indicator and if the resulit is from Blue to Red it will be Slightly miscible Miscible H2O an Acid indicator. The Litmus paper that soluble retains its color indicates a neutral
-1

Flammabl e Nonluminous flame Non-sooty

Nonflammabl The e

O-H stretch*(broad s) 3300-2500 C=O stretch*(s) 1730-1680 0-H bend(m) 1440-1390 C-O stretch(s) 1320-1210

N-H stretch*(s) 3500-3300 & 3400-3200 N-H bend*(s) 1640-1560 N-H bend(broad m) 900-650 C-N stretch(s-m) 1330-1030

compound. Solubility of organic compounds in 5% NaOH also reveals the acidity and basicity of the sample. The results of the Ignition test indicates 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 causes the formation of an unburned carbon. Complete combustion is indicated by a blue flame (non-luminous) and there is more heat than light, the carbon is completely oxidized. H2O 2 C10H22 + 31 O2 -> 20 CO2 + 22

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 cm1 ) is used to identify the number and relative positions of groups on a benzene ring. C-H bonds occur in this region.

Incomplete combustion is indicated by a yellow flame (luminous) and there is much light than heat; the carbon is not completely oxidized. heat 2C2H2 + 5O2 = 4CO2 + 2H2O +

Overall, the experiment succeeded in showing the certain intrinsic physical and chemical properties of the compounds, the behavior towards ignition and the infrared spectra of their functional groups.

[4]5http://www.wisegeek.com/whatare-organic-compounds.htm From books [1]Organic Chemistry Laboratory Manual [2]Silverstein, R.M., Webster, F.X.,
Kiemle, D.J. (2005) Spectrometric Identification of Organic Compounds. USA: John Wiley & Sons, Inc

References

From the internet [1]http://www.chemguide.co.uk/orgpr opsmenu.html [2]http://www.britannica.com/EBchec ked/topic/431954/organic-compound [3]http://bcs.whfreeman.com/mohrig 2e/content/cat_010/techniques.pdf