University of Santo Tomas Faculty of Pharmacy Pharmaceutical Organic Chemistry

Urmaza, Alyssa Mae G.

The Intrinsic Investigation Tests for Hydrocarbons

ABSTRACT:
This experiment attempts to determine the intrinsic physical properties and chemical properties in terms of structure and behavior of selected hydrocarbons - hexane, heptane, cyclohexane, benzene and toluene. Approximately 20 drops of each sample was placed separately in a clean and dry test tube. The physical state, color and odor were observed and noted. A certain volume (5 drops) of each sample was placed separately in seven test tubes. The samples were then tested for solubility by adding a certain volume (1 mL) of concentrated H2SO4 separately in the seven test tubes prepared for each sample. Toluene was soluble. Hexane, heptane, cyclohexane and benzene were immiscble. In the ignition test, benzene and toluene produced yellow flame with soot. Hexane, heptane and cyclohexane with flame produced but without soot. In the Baeyers and Bromine test, samples were then tested by adding a certain volume (2 drops) of 2% KMNO4 and (10 drops) 0.5% Br2 in CCl4 reagent respectively in the seven test tubes prepared for each sample. In the Baeyers test, all of the sample compounds produced no discoloration. In the Bromine test, cyclohexane and benzene produced no change. Hexane, heptane, and toluene were slowly decolorized. Benzene and toluene were unsaturated. Hexane, heptanes and cyclohexane were saturated. In the test for aromatic nitration, benzene produced yellow oily layer. Toluene produced brown oily layer. Hexane, heptane and cyclohexane produced a colorless with oily layer and were not aromatic. Benzene and toluene were aromatic compounds. In the basic oxidation test, all sample compounds produced no precipitate and did not oxidize

INTRODUCTION
Hydrocarbons are compounds that contain only hydrogen and carbon atoms. Hydrocarbons may be divided into two large classes namely: saturated and unsaturated organic hydrocarbons. compounds. Saturated They are

more carbon-carbon multiple bonds like double are bonds, triple bonds, and or both. dienes. Examples of unsaturated hydrocarbons alkenes, alkynes Saturated and unsaturated hydrocarbons have similar physical properties, but their chemical properties are different. Unsaturated hydrocarbons are chemically more reactive than saturated ones. This is because of the presence of of carboncarbon multiple bonds in such compounds and these multiple bonds serve as can locations were chemical reactions

hydrocarbons are the simplest type of hydrocarbons in which all carbon-carbon bonds are single bonds. Examples of saturated hydrocarbons are alkanes and cycloalkanes. Unsaturated hydrocarbons are hydrocarbons that contain one or

occur [1 & 2] .

empty. The criterion for a compound to be There are different techniques on how to identify or classify a sample such as observing its physical properties, its solubility in conc. H2SO4, ignition test, tests for active unsaturation specifically (1) Baeyers Test and (2) Bromine Test, test for aromaticity by means of nitration and its basic oxidation. The physical properties of the sample like physical state, odor and color are the first data to be use in identifying and classifying the compound. The ignition test indicates the presence of unsaturation or high carbon to hydrogen ration. The Baeyers Test is a test for the presence of unsaturation (double bonds). Baeyers test uses a solution called the Baeyers reagent, which is a solution of alkaline potassium permanganate. Reaction with double or triple bonds in an organic material causes the color to fade from purplish-pink to brown. Bromine test is a qualitative test for the presence of unsaturated CC bonds and phenols. The sample is treated with a small amount of bromine. The presence of unsaturation is indicated by the disappearance of the deep brown coloration aromaticity of is bromine. the The test for of special stability aromatic is expressed by the Huckels rule. The basic oxidation was tested using potassium permanganate. Potassium permanganate is an inorganic compound and a very strong oxidizing agent. It is used in the determination of the total oxidizable organic material in an aqueous sample [1-2]. The experiment aims to classify hydrocarbons properties behavior. in in terms of of its certain and intrinsic physical properties and chemical terms structure

Experimental
In the experiment, all the needed materials were prepared: test tubes and the sample compounds (hexane, heptane, cyclohexane, benzene and toluene). A certain volume (20 drops) of each sample was placed separately in a clean and dry test tube. The physical properties of the samples at room temperature such as physical observed state, and color noted. and The odor were solubility

properties of the samples were also tested by concentrated H2SO4. In testing the solubility of each compound a certain volume (1 mL) of the solvent was added separately the in each The seven samples test tube containing a certain volume (1 drop) of sample. underwent ignition test. A certain volume (3-5 drops) or a pinch amount of the sample were set

planar, cyclic, fully conjugated molecules with 4n + 2 electrons. Such molecules have orbital systems with all bonding molecular orbitals completely filled with all anti bonding and non bonding orbitals

in an evaporating dish and lighted with a match. The flammability of the samples was observed. The results obtained from each test were tabulated. The tests for active unsaturation were tested by two processes. In Baeyers test, a certain volume (5 drops) of samples were added with a certain volume (2 drops) of 2% KMnO4 solution. The test tubes were shaken vigorously and observed. In the Bromine test, also a certain volume (5 drops) of samples were added with a certain volume (10 drops) of 0.5% Br2 in CCl4 reagent. The test tubes were also shaken and observed. In the test for aromatic nitration, the nitrating mixture was first prepared by placing a certain volume (2mL) of conc. that After HNO3 in an Erlenmeyer flask and immersed it in an evaporating of conc. dish contains water, the gradually adding a certain volume (2mL) H2SO4. preparing nitrating mixture, a certain volume (5 drops) of each samples in the test tubes were added a certain amount (8 drops) of nitrating mixture. It was shaken and noted the results. The solutions were diluted with a certain volume (20 drops) of water. In the test for basic oxidation, a certain volume (4 drops) of sample were added with a certain volume (8 drops) of 2% KMnO4 solution and a certain volume (3 drops) of 10% NaOH solution. The solutions were put into water bath for 2 minutes. The color changes and formation

of precipitate were observed. The results obtained from each test were tabulated.

Results & Discussion

To be able to determine if the given organic sample compounds aromatic or aliphatic, a closer look to the definition of or aromatic arene and (aryl double aliphatic should is be a considered first. An aromatic hydrocarbon hydrocarbon) by single and hydrocarbon alternating characterized general bonds

between atoms. The configuration of six carbon atoms in aromatic compounds is known as a benzene ring. Many of these compounds have sweet scent. An aliphatic hydrocarbon is characterized by joined carbon atoms in straight chains, branched chains or non-aromatic rings. They can be joined by single bonds (alkanes), double bonds (alkenes), or triple bonds (alkynes).[3]
Table 1. Structural Formula of the Compounds

Test Compounds:
Hexane Heptane Cyclohexane

Condensed Structural Formula:

CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH3

Benzene

Toluene

Table 2. Physical Compounds

Properties

of

the

Test

compounds does not have bonds with their C atoms with C=O and N=N that makes all of Table formula of 1 the shows the structural them clear and colorless. Odors also provide clues to the identity of a compound. Moreover, the odor is most pronounced in the lower molecular weight members of a class because these are more volatile.[3]
Table 3. Solubility of the Test Compounds in H2SO4

different

compounds.

Hexane is an alkane with six carbon atoms. Heptane is a straight-chain alkane with seven carbon atoms. Cyclohexane is cyclic and has the lowest angle and torsional strain of all the cycloalkanes. Benzene is a cyclic hydrocarbon with a continous pi bond. It is also related to the functional toluene group as arene a which is a generalized structure of benzene. Lastly, reacts normal aromatic hydrocarbon towards electrophilic

Test Compounds
Hexane Heptane Cyclohexane Benzene Toluene

Solubility in H2SO4 immiscible immiscible immiscible immiscible soluble

aromatic substitution. [3] Test Compounds

Hexane Heptane Cyclohexane
Physical State

Color
Clear, colorless Clear, colorless Clear, colorless

Odor
Fruity -like Rubbe r-like Plastic -like or Faint etherlike

chromophoric

groups

with

conjugated

liquid liquid liquid

double bonds or rings are present. They are usually caused by conjugated ring systems with bonds such as C=O and N=N in addition to conjugated C-C bonds. Table 2 shows that all of the sample

Table H2SO4 helps

3 .The

shows

the

solubility consists method

of of of

Benzene Toluene

liquid liquid

Clear, colorless Clear, colorless

Sweet odor Rugby -like

hydrocarbon compounds in concentrated solubility a test taking a small amount of the sample. It provide positive identification of compound.[1]
Table 4. Flammability test of Compounds

Some colored

compounds because

have of the

are

definitely of

presence

Test Compounds: Hexane Heptane Cyclohexane Benzene Toluene

Ignition test flammable flammable flammable flammable flammable

Inference Blue flame Without soot Blue flame Without soot Blue flame Without soot Yellow flame With soot Yellow flame With soot

Toluene

No discoloration

Slowly decolorized

unsaturated

The Baeyer test for unsaturation is for determining the presence of carboncarbon double bonded compounds, called alkenes or carbon-carbon trible bonded compounds, called alkyne bonds. The reaction is important because it doesnt work on alkanes (compounds with carboncarbon single bonds) or aromatic compounds. Bromine test is a qualitative test for the presence of unsaturated CC bonds and phenols. A positive test for the presence of unsaturation and/or phenol is indicated by the disappearance of the deep brown coloration of bromine, which happens because the bromine has been consumed by reaction with the unknown sample. Table 5 shows that all of the sample compounds produced no discoloration because hexane and heptane are alkenes. Cyclohexane is cycloalkane. Benzene and toluene Regarding are the aromatic Bromine hydrocarbons.

Ignition brings about a chemical change; some higher decompose the and blacken, contents its while of a as others burst into flame. As a rule, the oxygen the bluer compound, flame;

hydrogen increases, the flame becomes more yellow. Table 4 shows that the samples containing oxygen such as hexane, heptane and cyclohexane produce blue flame. Benzene and toluene produced yellow flame with soot. Most aromatic compounds burn with flame.[1-3]
Table 5. Tests for Active Unsaturation

a sooty yellow

test, it clearly shows that hexane, heptane and toluene were unsaturated because it indicates the slow decolorization of the solution[1-4].
unsaturated

Test compounds:

Baeyers test

Bromine test

Inference

Hexane Heptane Cyclohexane Benzene

No discoloration No discoloration No discoloration No discoloration

Slowly decolorized Slowly decolorized No change No change

Table 6. Tests for Aromaticity: Nitration

unsaturated saturated saturated

Test Compounds: Hexane

Test for aromatic nitration

Colorless layer w/ oily

Inference aliphatic

Heptane Cyclohexane Benzene Toluene

Colorless layer Colorless layer

w/ w/

oily oily

aliphatic aliphatic aromatic aromatic

the

compounds

that

are

formed

in

chemical reactions or isolated from natural sources. The tests for the samples are some ways on determining the identity of the compound. Observing its physical properties is the main step in identifying a

yellow oily layer yellow oily layer

Table 6 shows that benzene and toluene are aromatic compounds wherein they produced a yellow oily layer in addition of the nitrating mixture. Hexane, heptane and cyclohexane produced a colorless with oily layer indicates that these hydrocarbon compounds are aliphatic. The test for aromaticity helps determine which compounds are aromatic and aliphatic based on the color and oil layer of the compounds studied.[4]

compound. The other test like solubility test and ignition for test the are use of as a the confirmation identity

compound being analyze [1 &4]. Some of the results do not match with the rules or principles involve in the test. This explains that there are errors in the results acquired. This can be attributed in various factors like the sample may be contaminated, not being able to label the test tubes correctly, using the wrong sample or solvents, recording incorrect information, being careless in doing and

Table 7. Tests for Basic Oxidation

observing the experiment, missing little things which may affect the totality of the experiment and using the wrong sample or solvents [1].

Test Compounds: Hexane Heptane Cyclohexane Benzene Toluene

Test for basic oxidation

No change No change No change No change No change

Inference No oxidation No oxidation No oxidation No oxidation No oxidation

References
[1] Pangan,M., et. al. (1974). Organic chemistry investigation and preparative methods. Manila: University of Santo Tomas. pp.9.212.2.

Table

shows

that

all

hydrocarbon

sample compounds produced no change and no oxidation in the test for basic oxidation. The method or tests performed usually perform by the chemists to identify

[2] Shriner, R.L. & Curtin, D.Y. (1980).Chemical Classification Tests and For Derivatization. 6th ed. New York: John Wiley & Sons, Inc. pp. 3133 & 90-111.

[3] Hart, H., et.al. (2007). Organic Chemistry: A Short Course. 12th ed. New York: Houghton Mifflin Company.

[4] Garcia, C. (ed.). (2006). Laboratory Experiments in Organic Chemistry. (Unpublished manual used by the College of Science, University of Santo Tomas). Pp.31-33.