Analysis of Hydrocarbons Nalus, Shayne Mariz J., Narra, Julie Anne R., Ong, Ivy Camille B.

and Orquia, Patricia Denise Z.* Department of Psychology, University of Santo Tomas, Manila, Philippines

Abstract Four organic compound samples: cyclohexane, cyclohexene, napthalene and toulene were given to serve as reference standards and undergo to three different tests. Nitration, bromine and basic oxidation tests were conducted to classify the different samples from being an aliphatic or aromatic, saturated or unsaturated and alkylated or non-alkylated hydrocarbons. The unknown sample was characterized and differentiated by using the three different tests and found out that it is non-aromatic, saturated and non-alkylated. Introduction This experiment aims to differentiate various types of hydrocarbons, to device a scheme to distiguish hydrocarbons from each type and to characterize an unknown hydrocarbon through parallel chemical tests. There are millions of organic compounds that are already known. One type of which is the most common and the simplest type that is only composed of hydrogen and carbon atom, the hydrocarbons. All hydrocarbons are insoluble in water due to their relatively non-polarity. Instead, they mix with relatively non-polar solvents like dichlromethane or carbon tetrachloride. Hydrocarbons can be characterize on the way in which carbon atoms are connected, the aliphatic and aromatic hydrocarbons. Aliphatic hydrocarbons, from the Greek word aleiphar (fat or oil), are long carbon-chain molecules which are usually found in animal fats and plant oils. In aliphatic hydrocarbons, carbon atoms are joined together in straight chains, branched chains, or non-aromatic rings. Aliphatics undergo free-radical substitution reactions. The aromatic hydrocarbon or arene, are characterized by having molecular structures which are called benzene rings. They are characterized by ionic substitution reactions due to their opposition to addition reactions because of their aromacity, the possession of a closed loop of electrons and a manifestation of cyclic delocalization and low reactivity of resonance.

with the general formula of CnH2n+2. Hydrocarbons react differently in various reagents. Alkenes. Cyclohexane is a cycloalkane with a molecular formula of C 6H12. cyclohexene. benzene. a boiling point of 110. a boiling point of 218 °C and a melting point of 80. where the carbon atoms are joined up in a ring and with the general formula of CnH2n. unsaturated hydrocarbons are highly reactive and undergo addition reactions to their multiple bonds. bromine and basic oxidation tests can be used to determine the type of hydrocarbon of a given sample. The samples that were given to serve as standards are cyclohexane.6°C and a melting point of −93 °C. or ligroin.47°C. are classified as unsaturated hydrocarbons. Saturated hydrocarbons contains only single carbon-carbon bonds and unsaturated hydrocarbons that contains two or more C-C bonds. aromatic. a boiling point of 80. naphthalene and toluene.2°C. It is a monosubstituted benzene derivative that is used extensively as starting material for the manufacture of industrial chemicals .143 g molˉ¹. Saturation refers to the fact that each carbon has its maximum number of bonds to hydrogen.18 g mol ˉ¹. acetone. which have triple bonded C atoms and a general formula of CnH2n-2. Alkylated hydrocarbons undergo alkylation in which there is a transfer of an alkyl group from one molecule to another. and cycloalkanes. and has a molar mass of 84.Another means of classification rely upon the type of bonding that exists between carbons. It is colorless liquid with a sharp smell that is used as an alkylation component and has a molar mass of 82.7°C and a melting point of 6. with double C=C bonds and a general formula of CnH2n.5°C. Cyclohexenes are usually used in industrial processes. It is composed of two fused benzene rings and usually a component of household products like mothballs and diaper pails.98°C and a melting point of -103. white. Cyclohexene is a cycloalkene with a molecular formula of C6H10. ether. It is a colorless and volatile liquid with a slightly pungent odor similar to benzene or chloroform. The three tests: nitration. Hydrocarbons that do not undergo alkylation are called non-alkylated hydrocarbons. a boiling point of 82. the sample must undergo through parallel chemical tests. . solid hydrocarbon with a molecular formula of C10H8. Toluene is a hydrocarbon with a molecular formula of C 7H8. are classified as saturated with a single C-C bond. but can be dissolved in alcohol. and Alkynes. Naphthalene is a crystalline. In characterizing an unknown hydrocarbon. Alkanes. On the other hand. or benzene-like rings. Cyclohexanes are insoluble in water. The presence of a double or triple bond in the molecule opens up many more possibilities for isomerism compared with single bonded molecules. Hydrocarbons can also be grouped if there is an alkyl substitution that has happened to the compound.

Otherwise. The basis for determining the type of hydrocarbon is the differences in their reactions.Results and Discussion Hydrocarbons react differently due to their distinctness in properties. The reagents for nitration are nitric acid. It determines the aromacity of a compound. The sulfuric acid (H2SO4) functions as a catalyst and facilitates the formation of nitronium ions (NO2+) which is an electrophile. the hydrocarbon is considered to be aliphatic. bromine and Basic Oxidation tests can be used to identify the type of hydrocarbon of a given compound. HNO3 and sulfuric acid. Simple aromatic hydrocarbon will react with the H2SO4 to produce a sulfonic acid which will dissolve and precipitate when =NO2 is reacted. Results of Standard Samples Nitration Test Results – Standard Samples Nitration is the reaction between a nitrating agent and an organic compound that results in one or more nitro groups. . Nitration test involves electrophilic substitution reaction in which an electrophile displaces a group in a compound . Standards Tests Nitration Test Cyclohexane colorless solution (-) aliphatic light brown translucent solution (-) saturated violet solution (-) non-alkylated Cyclohexene colorless solution (-) aliphatic colorless solution (+) unsaturated green mixture with brown precipitate (+) alkylated Naphthalene Toluene translucent mixture translucent mixture with yellow globule with yellow globule (+) aromatic (+) aromatic yellowish yellowish translucent solution translucent solution (+) unsaturated (+) unsaturated violet solution (-) non-alkylated green mixture with brown precipitate (+) alkylated Bromine Test Basic Oxidation Test Table 1. A hydrocarbon is aromatic if there are yellow globule present. H2SO4. Nitration.

aromatic compounds do not react because of their stability. If there is a decolorization of an orange solution. It involves electrophilic addition reaction in which a pi bond is broken and two new bonds are formed. that is why when bromine is added to an alkene or alkyne. Bromine is a reddish-brown color. The triple bond of an alkyne also undergoes an addition becoming a single bond. Since alkanes only have single C-C bonds.Bromine Test Results . The double bond of an alkene transforms to a single bond and one bromine atom becomes bonded to each of the carbons that had shared the double bond. A 0. they will react slowly upon using FeBr3 or through the action of ultraviolet light. but in this case. the red-brown color depletes quickly.5% Br2 in tetrachloromethane (CCl4) is used as the reagent for bromine tests. Alkenes contain pi bond and react with Br2 to form a trans-dibromoalkane. All of the other substances in these reactions are colorless. On the other hand. However. bromine will not be added to it. each of the carbons that had been joined by the triple bond will now hold two bromine atoms. the hydrocarbon is characterized as unsaturated. Basic Oxidation Test Results– Standard Samples .Standard Samples Bromine test is used to determine if there are double bonds in a compound or the unsaturation of a compound .

Otherwise. The Mn7+ is reduced to Mn6+ or Mn4+ depending on the extent of the reaction. Tests Nitration Test Bromine Test Basic Oxidation Test Unknown Sample colorless solution (-) aliphatic brown translucent solution (-) saturated violet solution (-) non-alkylated Table 2. bromine and basic oxidation tests were used to characterized the unknown sample given. A 2 % potassium permanganate (KmnO4) and a 10% sodium hydroxide (NaOH) are used as reagents for this test. According to the results indicated in Table 2. the hydrocarbon is constitute a non-alkylated one. This test involves redox reactions in which the oxidation state of atoms are changed. In comparison to Table 1. Unknown Sample Testing Nitration. it can be concluded that the unknown sample is a cyclohexane based on the reactions that had happened. the unknown sample is found to be non-aromatic.The alkyl group of the aromatic hydrocarbon is oxidized and becomes a carboxylic acid.The basic oxidation test is used to recognize alkylated aromatics. The NaOH provides a basic environment for the reaction. Experimental Section Experiment Set-up . saturated and non-alkylated. Alkylated aromatics produce green solution of MnO4 and brown precipitate of MnO2.

F. “Organic Chemistry II for Dummies”. naphthalene and toluene samples were provided to serve as standards for the experiment. For the nitration test. & Landerberg.In the experiment.. M.scribd. J. In determing the unknown sample. Organic and Biochemistry” (7th ed). 4 clean test tubes were prepared and labeled for each test. The observations were gathered. Cyclohexane. Inc: . Observations were noted for each test tubes on the three tests. [2] Bettelheim. California. 8 drops of the nitrating agent (1:1 conc HNO3 / conc H2SO4) were added to each of the 4 test tubes. Indiana. bromine and basic oxidation tests. For the bromine test. California. The results were compared to the positive and negative references and on the data that were convened about the standard samples. W. Brooks/Cole Cengage Learning: Belmont.. S. (2010). Brown. and Farrell. For the basic oxidation test. The 3 unknown test tubes underwent nitration. [3] Moore. Each test tube was filled with 5 drops of each of the samples given using droppers. 3 test tubes were prepared and was filled with 5 drops of the unknown sample. Campbell. 3 drops of 1% KMnO4 and 2 drops of 10% NaOH were added to the test tubes. 2 test tubes for positive and negative references for each test were prepared. J. F. Wiley Publishing. Retrieved from http://www. cyclohexene. Brooks/Cole Cengage Learning: Belmont. 5 drops of Br2 solution were added to each test tubes. References [1] Buttelheim. “Laboratory Experiments for Introduction to General. R. (2010). [4] Comparative Investigation of Organic Compounds. and Langley. (2010). “Introduction to Organic and Biochemistry” (7th ed).