Classification Tests for Hydrocarbons

Authors: C.M. Pineda, D.C. *Quiambao, P.J. Quilinguen, K.B. Reyes, K.R. Reyes Abstract Consisting entirely of hydrogen and carbon atoms is a hydrocarbon. Several tests were performed to differentiate their physical and chemical properties. Physical state, color and odor were first observed. Miscibility of the compound was tested by adding concentrated H2SO4. The degree of luminosity was tested by igniting the compound with a lighted match. Baeyers test and bromine test were tests for the active unsaturation of the hydrocarbon. Aromaticity was determined through nitration. Oxidation was tested by introducing KMnO4 and NaOH to the sample. All of the samples are liquid and colorless solution. Miscibility test shows that all compounds were immiscible and are flammable. Baeyers test and bromine test indicate that hexane, cyclohexane, benzene, and toluene are saturated while cyclohexene is actively saturated. Testing the aromaticity, nitration was used and it shows that only benzene and toluene are aromatic. In the last test, which is basic oxidation, only cyclohexene was oxidized.

Introduction A hydrocarbon is an organic compound consisting entirely of hydrogen and carbon (1). Most hydrocarbons are colorless and odorless. Classifications of hydrocarbons are namely: saturated or unsaturated, cyclic or acyclic, aliphatic or aromatic. Saturated hydrocarbons are the simplest classification because they are mainly composed of single-bonded carbons while unsaturated hydrocarbons are made up of one or more double- or triple-bonded carbons. Hydrocarbons are considered cyclic if a series of atoms forms a loop. Conversely, hydrocarbons are considered acyclic if the atoms form a linear structure. Aliphatic hydrocarbons are acyclic or cyclic and non-aromatic compounds; aromatic hydrocarbons, also known as arenes, are compounds with alternating single and double bonds of carbons and are always cyclic and unsaturated. One of the objectives is to differentiate the hydrocarbons in terms of intrinsic physical properties and

chemical properties in terms of structure and behavior. By means of our senses, we would be able to determine the physical properties of each hydrocarbon. Hexane is an alkane hydrocarbon with the molecular formula of C6H14. It is colorless at room temperature and has a boiling point between 50C to 70C.They are largely unreactive and often used as solvents because they are non-polar (2). Cyclohexane is a cycloalkane with the molecular formula of C6H12. It is used as a non-polar solvent and also as a raw material for industrial production of adipic acid and caprolactam (3). Cyclohexene is a cycloalkene with the molecular formula of C6H10. It is a colorless liquid but with a petroleum gas-like odor. Also, cyclohexene is not stable upon long term storage with exposure to light and air because it forms peroxides (4). Benzene is a cyclic hydrocarbon with a continuous pi bond and has a

molecular formula of C6H6. It is colorless, highly flammable and it smells like a pentel pen (5). Toluene is an aromatic hydrocarbon with the molecular formula of C7H8. It reacts as a normal aromatic hydrocarbon towards electrophilic aromatic substitution. It is colorless, water-insoluble and an odor similar to a pentel pen (6). Another objective is to analyze a hydrocarbon and determine if it is saturated, actively unsaturated, aromatic or an arene. The following tests will determine the classification of each hydrocarbon. Miscibility is the property of substances to mix to form a homogenous solution. Conversely, substances are considered immiscible if it doesnt form a homogenous solution. Concentrated sulfuric acid was used as the solvent. Flammability is the extent on how easily a substance will ignite or undergo combustion. Aromatic hydrocarbons ignite at a yellow flame producing more soot because of the formation of unburned carbon. Aliphatic hydrocarbons ignite with a yellow flame yet producing lesser soot. Baeyers test is a test for the presence of unsaturation. It uses the solution 2% KMnO4. Aromatic compounds do not react on the reagent because of its stability. Baeyers test indicate decolorization of purple solution and a formation of brown precipitate. Alkenes react with potassium permanganate to give a diol and MnO2.

Bromine test is similar to Baeyers test which tests for the presence of unsaturation. 0.5% Br in CCl4 was used as the reagent. Positive result shows decolorization of an orange solution and involves electrophilic addition reaction because of the reaction of the sample and Br2 and UV. Nitration uses the reagents HNO3 and H2SO4. A positive outcome depicts a yellow oily layer. The mechanism involved is electrophilic substitution wherein H2SO4 acts as a catalyst. Oxidation was tested using 2% KMnO4 and 10% NaOH. A positive result shows the formation of a brown precipitate. It involves the mechanism of redox reaction.

Methodology Physical State, Color, and Odor The physical state of hexane, cyclohexane, cyclohexene, benzene, and toluene are observed at room temperature. The color was noted and the odor was determined by a wafting motion of hand over the opening of the test tube. Solubility in Concentrated H2SO4 One(1) ml of concentrated H2SO4 was added to a drop of sample in the test tube. It is used by a dry and calibrated droppers. Any color change or warming effect was noted. Ignition Test Three(3) to 5 drops of the sample was placed in an evaporating dish, lighted with a match, and observed the

color of the flame and the amount of soot produced. Tests for Active Unsaturation Baeyers Test Two(2) drops of 2% KMnO4 was added to a 5 drops of sample. The solution was shaken vigorously and decolorization was observed. The formation of brown suspension was noted and compared with water as a negative control. The result must be noted immediately for the decolorization occurs within 1 minute. Bromine Test To a 5 drops sample, 10 drops of 0.5% Br in CCl4. The test tube was shaken vigorously and the rate and extent of decolorization was noted. It was compared with water as a negative control. The reaction mixture was exposed to sunlight when the reagent failed to decolorize. Test for Aromaticity: Nitration Two(2) ml of concentrated HNO3 was placed in an Erlenmeyer flask. The flask was immersed in a water bath and gradually added 2 ml of H2SO4. The nitrating mixture was then cooled at room temperature.

Eight(8) drops of nitrating mixture was added to a 5 drops of sample in a dry test tube and shaken to ensure complete mixing. Formation of yellow oily layer or droplet was noted and was diluted with 20 drops of water. If there is no observed reaction within a minute, the test tube was placed in a water bath for 10 minutes. diluted with 20 drops of water, and the results were noted down. Basic Oxidation Eight(8) drops of 2% KMnO4 and 3 drops of 10% NaOH solution was added to 4 drops of sample. The test tube was placed in a water bath for 2 minutes, observed the formation of brown precipitate and noted it.

Figure No. 1 Classification Test of Hydrocarbons

Results
Table No. 1 Classification Test for Hydrocarbons Hexane Cyclohexane A. Physical state Color Odor B. Solubility in conc. H2SO4 Inference C. Ignition Test Inference D. Baeyers Test Bromine Test Liquid Colorless Odorless Liquid Colorless Odorless

Cyclohexene Liquid Colorless Petroleum gaslike odor

Benzene Liquid Colorless Pentel pen-like odor

Toluene Liquid Colorless Pentel pen-like odor

Immiscible

Immiscible

Immiscible

Immiscible

Immiscible

Insoluble Luminous flame No soot No decolorization Became colorless Not actively unsaturated No formation of yellow oily layer Not aromatic No formation of brown ppt Not oxidized

Insoluble Luminous flame No soot No decolorization Color changed to yellow Not actively unsaturated No formation of yellow oily layer Not aromatic No formation of brown ppt Not oxidized

Insoluble Luminous flame No soot Formation of brown ppt Became colorless Actively unsaturated No formation of yellow oily layer Not aromatic Formation of brown ppt Oxidized

Insoluble Luminous flame Produced soot No decolorization Color changed to orange Not actively unsaturated Formation of yellow oily layer Aromatic No formation of brown ppt Not oxidized

Insoluble Luminous flame Produced more soot No decolorization Became colorless Not actively unsaturated Formation of yellow oily layer Aromatic No formation of brown ppt Not oxidized

Inference

E. Nitration

Inference F. Basic Oxidation Inference

Table No. 1 shows that the 6 samples are immiscible in concentrated H2SO4 and flammable producing a luminous flame. Benzene and toluene produced soot because they have

undergone complete combustion. Only cyclohexene act as an actively unsaturated hydrocarbon. Hexane, cyclohexane, and cyclohexene are not aromatic hydrocarbons based on their

structure Benzene aromatic samples, oxidation.

and by the nitration test. and toluene are considered hydrocarbons. Of all the only cyclohexene undergone

Discussion The physical appearance will always be obtained first by merely observing the compounds. The 6 samples were all in the liquid state and is colorless. Hexane and cyclohexane are odorless but cyclohexene, benzene and toluene have different smell. Solubility of hydrocarbons in H2SO4 indicates whether the sample is a very weak base or a neutral compound. This may produce large amounts of heat, change in the color, precipitation formation or combination of these. The hydrocarbon is easily sulfonated because the compound is unsaturated or it possesses a functional group containing oxygen that will dissolve in sulfuric acid. Ignition test determines the degree of luminosity can be seen in the yellow flame and amount of soot produced. Aromatic hydrocarbons produce soot because of the incomplete combustion which causes the formation of unburned carbon. Aromatic compound has the highest degree of luminosity. Next is unsaturated carbon followed saturated carbon. In complete combustion, blue flame (non-luminous) is indicated and there is more heat than light produced. Therefore, the carbon is completely oxidized. Yellow flame (luminous) indicates incomplete combustion. Unlike complete combustion, more light is produced then heat that is why it gives out soot. Thus, the carbon is not completely oxidized.

The test for double bonds or unsaturation is Baeyers test. It involves the mechanism of redox reaction. 2% KMnO4 was the reagent used. Positive result shows the decolorization of a purple solution and the formation of brown precipitate (MnO2). Mn7+ is reduced to Mn4+. Alkenes react with potassium permanganate (KMnO4) that would give the product of an alkene that is oxidized to a diol and MnO2. Aromatic compounds do not react because of their stability. Like Baeyers test, Bromine test is also a test for double bonds. The mechanism involved is electrophilic addition reaction. A positive outcome exhibits decolorization of an orange solution with the addition of 0.5% Br2 in CCl4. Alkenes react to form Br2 to form a trans-dibromoalkane. Similar to Baeyers test, aromatic compounds do not react because of their stability. Yet, aromatic compounds slowly reacts with UV light. The test for aromatic compounds is Nitration. Electrophilic substitution reaction is the mechanism involved. Reagents used were HNO3 and H2SO4 that would give a positive result of yellow oily layer. H2SO4 acts as a catalyst and helps in the formation of nitronium ion (NO2+) which is an electrophile. The nitronium ion substituted one hydrogen atom in the benzene ring. The test for alkylated aromatics or arenes is Basic Oxidation. 2% KMnO4 and 10% NaOH were the reagents used to test for a positive result green solution or brown precipitate. The alkyl group in the aromatic compound is oxidized to a carboxylic acid.

6. http://en.wikipedia.org/wiki/Tolue ne References 1. http://en.wikipedia.org/wiki/Hydro carbon 2. http://en.wikipedia.org/wiki/Hexan e 3. http://en.wikipedia.org/wiki/Cyclo hexane#Structure_and_physical_ properties 4. http://en.wikipedia.org/wiki/Cyclo hexene 5. http://en.wikipedia.org/wiki/Benze ne 7. http://www.scribd.com/doc/37474 567/Classification-test-forhydrocarbons

8. http://www.scribd.com/doc/25377 353/Classification-Tests-forHydrocarbons 9. Bayquen, A.V., Cruz, C.T., et al (2009). Laboratory Manual in Organic Chemistry. Quezon City: C&E Publishing Inc