INTRINSIC PHYSICAL AND CHEMICAL PROPERTIES OF HYDROCARBONS

Alava, P.J., *Alcausin, D.A., Andal M.I., Bagon, N.E., Barretto, D., Bautista, C. 2D-Pharmacy, Faculty of Pharmacy, University of Santo Tomas

Abstract In this experiment entitled classification tests for hydrocarbons, six hydrocarbon compounds were studied. These compounds were hexane, heptane, cyclohexane, cyclohexene, benzene, and toluene. They were subjected to different tests to be able to differentiate their intrinsic physical properties and their chemical properties in terms of structure and behavior. First, by simple observation, the physical state, color, and odor was noted. Then a test in 1 mL of concentrated H2SO4 or sulfuric acid was conducted in order to determine which hydrocarbon compounds were immiscible or not. Color change and/or warming effect was also noted in this solubility test. Ignition test was also conducted to test the flammability of the hydrocarbons. This was achieved by placing 3 5 drops of the liquid sample in an evaporating then lighting it with a match. Tests for active unsaturation was also done by conducting the Baeyers test and Bromine test. In the Baeyers test, 5 drops of the liquid samp le was added with 2 drops of 2% KMnO4.Formation of brown suspension was noted and decolorization of the reagent is immediate if it occurs with 1 minute. On the other hand, in Bromine test, 5 drops of the liquid sample was added with 10 drops of 0.5% Br2 in CCl4 reagent and if the reagent failed to decolorize within 1 minute, exposure to sunlight was done. The second to the last test conducted in this experiment was the Test for Aromaticity: Nitration. This was done by combining 8 drops nitrating mixture composed of concentrated HNO3 and concentrated H2SO4 to 5 drops of the liquid sample. Formation of a yellow oily layer or droplet was noted and if there was no apparent reaction the sample was placed in a water bath for 10 minutes. Lastly, basic test for oxidation was performed. In this test, 4 drops of sample was added with 8 drops of 2% KMnO4 solution and 3 drops of 10% NaOH solution then warmed in a water bath for 2 minutes. Formation of brown precipitate and color change was noted. [1] Introduction In organic chemistry, hydrocarbons are organic compounds containing carbon and hydrogen atoms that are covalently bonded to each other. They are known as the simplest organic compounds. [3] Hydrocarbons are carbon compounds that can be aliphatic or aromatic hydrocarbons. Aliphatic hydrocarbons that contain only sigma bonds are called saturated hydrocarbons and those containing both sigma and pi bonds are called unsaturated hydrocarbons. Aliphatic hydrocarbons are divided into 3 classes: Alkanes, Alkenes, and Alkynes. Alkanes are saturated hydrocarbons with only carbon-carbon single bonds. They can either be straightchain or branched-chain. Alkenes are unsaturated hydrocarbons that contain at least one carbon-carbon double bonds. While alkynes are unsaturated hydrocarbons that contain at least one carbon-carbon triple bonds. [4] Aromatic compounds includes only those with a benzene ring, which is a special six carbon ring compound with three alternating double bonds. [2] Aromatic compounds follow the Huckels Rule and they are cyclic. Resonance stabilizes their structures and they undergo electrophilic substitution and nucleophilic aromatic substitution. [5] The objectives of this experiment was, first, to differentiate hydrocarbons in terms of their intrinsic physical properties and their chemical properties in terms of structure and behavior. Second, is to analyze hydrocarbon and determine if it is

saturated, actively unsaturated, aromatic or an arene. Materials and Methods The sample compounds subjected to different tests in the experiment were hexane, heptane, cyclohexane, cyclohexene, benzene, and toluene. The reagents used were concentrated H2SO4, concentrated HNO3, 2% KMnO4, 0.5% Br2 in CCl4, and 10% NaOH. Physical state, color, and odor The physical state of the hydrocarbons were observed at room temperature. Color of the compounds were observed, and with a wafting motion of the hand over the mouth of the test tube, the odor was sensed. Solubility in Concentrated H2SO4 One milliliter of concentrated H2SO4 was placed on each 6 test tubes. Using a dry and calibrated droppers, a drop of each sample was cautiously added to the test tubes. Color change and/or warming effect was noted. Ignition Test To determine the flammability of the samples, 3 5 drops of each sample was placed in a small evaporating dish and was lighted with a match. The sample was observed whether it was flammable or not. Color of the fame produced was also noted. Optionally, if the sample is flammable, the burning time was observed. Tests for Active Unsaturation: Baeyers Test Two drops of 2% KMnO4 was added to 5 drops of each sample in separate dry test tubes. Shake the test tubes vigorously and the rate and extent at which the reagent is decolorized was observed. Formation of brown suspension and if the decolorization of the reagent occurs within one minute was noted. Bromine Test

Ten drops of 0.5% Br2 in CCl4 was added to 5 drops of each sample in separate dry test tubes. The test tubes were shake vigorously and the rate and extent (color change) by which the reagent is decolorized was observed. Optionally, moistened blue litmus paper on a glass rod was placed across the mouth of the test tube and any color change was noted. If the reagent failed to decolorize within 1 minute, the reaction mixture was exposed to sunlight. Test for Aromaticity: Nitration Two milliliters of concentrated HNO3 was placed in an Erlenmeyer flask. The flask was then immersed in an evaporating dish containing water and 2 mL of concentrated H2SO4 was gradually added. The resulting mixture was cooled to room temperature and it served as the nitrating mixture. Eight drops of nitrating mixture was added to 5 drops of each sample in separate dry test tubes. To ensure complete mixing, the test tubes were shake vigorously. Formation of a yellow oily layer or droplet was noted and was then diluted with 20 drops of water. When there was no apparent reaction observed within a minute, the test tube was placed in a water bath for 10 minutes. Then it was diluted again with 20 drops of water. Basic Oxidation Eight drops of 2% KMnO4 and 3 drops of 10% NaOH were added to 4 drops of each sample in separate test tubes. Each test tube was warmed in a water bath for 2 minutes and the color change and the formation of a brown precipitate was noted. Results and Discussion The tests conducted in this experiment were solubility in concentrated H2SO4, ignition test, test for active unsaturation which are Baeyers test and Bromine test, test for aromaticity: nitration, and basic oxidation. These tests are done in order to differentiate and classify the

hydrocarbon compounds. The result of the experiment is shown in Table 1. Table 1. Data gathered after the hydrocarbons were subjected to the different tests

Compounds Studied
Hexane Condensed Structural Formula Heptane Cyclohexane Cyclohexene Benzene Toluene

A. Physical clear liquid state at RT Colorless Color Odor balloon-like B. Solubility in Oily layer concentrated H2SO4 Inference C. Test
Immiscible flame Flammable Plastic

Clear liquid Colorless Chlorinelike Clear light yellow solution with oily layer Immiscible Yellow flame Flammabl e No decoloriza tion Immediate decoloriza tion Saturated

Clear liquid Colorless Alcohol-like Clear yellow orange solution with oily layer

Clear liquid Colorless Gas-like Turbid orange solution

Clear liquid Colorless Gas-like Clear yellow solution with oily layer Immiscible Yellow flame, with soot Flammable No decolorizat ion No decolorizat ion Saturated Yellow oily layer

Clear liquid Colorless Rugby-like Clear layer oily

Immiscible Yellow flame

Immiscible Orange flame with soot Flammable Brown precipitate Immediate decolorization Unsaturated

Immiscible Yellow flame, with soot flammable No decolorizati on No decolorizati on saturated Yellow layer oily

Ignition Yellow

Inference

Flammable No decolorization Immediate decolorization saturated

D. Baeyers No decolorizati Test Bromine Test

on Immediate decolorizati on Saturated

Inference Colorless Colorless with Yellow E. Test for Colorless with oily with oily oily layer solution Aromaticity
layer layer Not aromatic No change Not oxidized Not aromatic No change Not oxidized Not aromatic No change

Inference

without oily layer Not aromatic Brown precipitate Oxidized

Aromatic No change Not oxidized

aromatic Blue-green solution Oxidized

F. Basic Oxidation Not Inference

oxidized

Physical state, color, and odor All the hydrocarbons tested were in liquid state. Also, all of them were colorless but they differ in odor. Hexane smelled like

plastic balloon, while heptane was chlorinelike, and cyclohexane was chlorine-like.

Cyclohexene and benzene both smelled like gas, while toluene was rugby-like. Solubility in Concentrated H2SO4 In hydrocarbon solubility, the rule is like dissolves like. Hydrocarbons are nonpolar compound, on the other hand, concentrated sulfuric acid is a highly polar reagent. And because of this, most hydrocarbons are insoluble in concentrated H2SO4. This test indicates whether a compound is a weak base or a neutral compound. Dissolution of the compounds in the reagent caused warming and also change in color of the solution and/or precipitate. In the experiment, it was observed that all hydrocarbons were immiscible with concentrated H2SO4. Most hydrocarbons have solutions with clear oily layers. Cyclohexene was the only one that has a turbid orange solution with an oily layer. Ignition Test Flammability is a test that determines different properties of compounds. Almost all organic compounds are readily flammable. In the ignition test that was done, presence of unsaturation or high carbon to hydrogen ration was indicated. Degree of luminosity was assessed by the presence of yellow flame and soot. Aromatic compounds burn with sooty flame due to incomplete combustion. All the hydrocarbon compounds ignited produced yellow flame, except cyclohexene which produced an orange flame. Only cyclohexene, benzene, and toluene produced soot. Tests for Active Unsaturation: Baeyers Test Baeyers test for unsaturation is used to determine the presence of carboncarbon double bonded compound, known as alkenes, or carbon-carbon triple bonded compounds, known as alkynes. The reagent used as an oxidizing agent was 2% KMnO4. A positive result for Baeyers test is the immediate decolorization of purple solution

and the formation of brown precipitate. Aromatic compounds did not show any reaction to this test because of their stability. The only hydrocarbon that produced brown precipitate was cyclohexene. It can be concluded that cyclohexene is an active unsaturated compound. Bromine Test Just like in Baeyers test, bromine test is conducted in order to determine whether a compound has a carbon-carbon double bonds. Aromatic compounds also shown no reaction in this test because of their stability. Since alkane only conatin carbon-carbon single bonds, bromine did not react with it. Alkanes merely dilute the red-brown bromine color to an orange or yellow color in the absence of a strong catalyst. On the other hand, alkenes react readily with bromine due to their carboncarbon double bonds. When bromine was reacted with the alkene, the red-brown color of bromine was immediately lost. Hexane, heptane, cyclohexane, and cyclohexene undergone immediate decolorization, while benzene and toluene did not show any reaction. Test for Aromaticity: Nitration Test for aromaticity was determined through nitration. Nitrating mixture, which was a combination of concentrated H2SO4 and concentrated HNO3, was used as the reagent. Aromatic compounds are extremely stable and will not react without a catalyst so they act as alkanes but are still unsaturated compounds. In the test, NO2+ ion was produced from the nitrating mixure, thus it can be attacked by an aromatic ring. However, alkenes in the presence of acid do not react. Hexane, heptane, and cyclohexane produced clear oily layer. Cyclohexene did not react, while benzene and toluene produce yellow oily layer which was a positive result of the test. Basic Oxidation The inorganic chemical compound used in the test was 2% KMnO4, which is a strong oxidizing agent. Sodium hydroxide was also added to produce a precipate.

Cyclohexene formed a brown precipitate which was a positive result of the test. Also, toluene produced a blue-green solution which was also a positive result of the test. So it can be concluded that cyclohexene and toluene are the only hydrocarbon compounds tested that were oxidized.

References [1] Bayquen, A.V. et al (2009). Laboratory Manual in Organic Chemistry. C & E Publishing, Inc. pp. 81 93 [2] Classification of Hydrocarbons (2003) Retrieved on September 11, 2013 from http://www.elmhurst.edu/~chm/vchembook/ 500hydrocarbons.html [3] Hydrocarbons. Retrieved on September 11, 2013 from http://hyperphysics.phyastr.gsu.edu/hbase/organic/hydrocarbon.ht ml#c1 [4] Alkanes, Alkenes, and Alkynes. Retrieved on September 11, 2013 from http://organicchemstudysite.tripod.com/alka nes.html [5] Brown, W. Poon, T. (2011). Introduction to Organic Chemistry. John Wiley & Sons (Asia) Pte Ltd. [6]Properties of Hydrocarbons. (2011) Retrieved on September 12, 2013 from http://www.mendelset.com/articles/689/prop erties_hydrocarbons