VISAYAS STATE UNIVERSITY

Department of Pure and Applied Physics

0

Chem 120.1: Organic Chemistry

R097 | 10:00 am - 1:00 pm

LABORATORY SCIENTIFIC REPORT

on

Hydrocarbons

Name: Adrianne Marie B. Labaclado

Christal Grace O. Repollo

Student ID #: 24-1-01847

24-1-00264

Course and Year: BSA-1

 CHAPTER 1

INTRODUCTION

Nature and Importance

Hydrocarbons are the primary type of organic molecules. According to the name

itself, hydrocarbons are composed of two elements, namely hydrogen and carbon. In

most cases, hydrocarbons are structured with one or more carbon atoms forming a

central structure surrounded by hydrogen atoms (Donev et al. 2018, as cited in Alvarez,

2021). Hydrocarbons are categorized into four classifications: alkanes, alkenes,

alkynes, and aromatic hydrocarbons or also known as arenes. Furthermore,

hydrocarbons may be classified as either saturated or unsaturated.

Each classification of hydrocarbons possesses unique characteristics and plays

a significant role in various scientific and industrial applications. They are the principal

constituents of petroleum and natural gas. They serve as fuels and lubricants as well as

raw materials for the production of plastics, fibers, rubbers, solvents, explosives, and

industrial chemicals (Carey, 2024). This report aims to explain each classification in

detail, elucidating their respective natures and importance within the broader context of

hydrocarbon chemistry and their purpose through this experiment.

Alkanes or in others terms “paraffins” are often described as saturated

hydrocarbons—saturated because they only have C-C and C-H single bonds and thus
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contain the maximum possible number of hydrogen per carbon. They have the general

formula CnH2n+2, where n is an integer (McMurry, 2011). They exhibit low reactivity

which according to Libretexts (2023) is because of their strong carbon-carbon single

bonds and strong carbon-hydrogen bonds. They are also nonpolar molecules, making

them relatively inert toward polar reagents.

Meanwhile, alkenes and alkynes are unsaturated hydrocarbons since they have

fewer amounts of hydrogen atoms compared to alkanes. Alkenes or olefin has a general

formula CnH2n, which is a chemical compound made of only carbon and hydrogen

atoms containing at least one carbon-to-carbon double bond (McKeen, 2011), meaning

it has both sigma (𝜎) and pi (π) bonds making them more reactive compared to alkane.

Alkynes, on the other hand, are acyclic (either branched or unbranched)

aliphatic hydrocarbons distinguished by the presence of at least one carbon-to-carbon

triple bond, which leads to the general molecular formula CnH2n-n. It is also known as

acetylene, following the established trends, triple bonds are both shorter and stronger

than double bonds; the presence of an additional π bond—resulting in alkynes having

two π bonds—further enhances the reactivity of the triple bond (Stauffer et al., 2008).

Aromatic hydrocarbons, or arenes, are compounds containing benzene rings

with delocalized π-electrons. This contributes to their stability and distinct properties.

They are nonpolar, hydrophobic, and usually insoluble in water but dissolve easily in

organic solvents. Arenes are chemically stable and undergo electrophilic substitution

reactions rather than addition reactions. When burned, they produce sooty flames due

to high carbon content.

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This experiment involved samples like cyclohexane, cyclohexene, benzene,

toluene, and acetylene which highlights the characteristics of hydrocarbons in their

chemical reactivity. The selected samples represent different types of hydrocarbons—

which exhibit varying chemical behaviors. These differences make them ideal for

studying reactivity trends and their potential applications. By exploring the samples,

the experiment demonstrated how the unique properties of hydrocarbons can be

leveraged for practical uses in energy production, manufacturing, and other industries.

Objectives of the Study

The main objectives of the experiment were the following:

● To differentiate types of hydrocarbons.

● To identify the characteristic chemical tests for each of hydrocarbons.

● To understand the chemical properties and reactivities of hydrocarbons through

experimental observation.
 CHAPTER II

MATERIALS AND METHODS

This chapter introduces the materials and methods that were applied to do this

experiment. The use of laboratory equipment and chemical reagents were

systematically applied to conduct tests such as ignition, Bromine, and Potassium

Permanganate and ammoniacal silver nitrate were applied in an orderly manner during

the experiments . Each procedure was designed to examine and compare the behaviors

of various hydrocarbons.

Materials

In this experiment, the laboratory apparatuses that were used are the following:

crucible cover, crucible tong, medicine dropper, tirrill burner, test tube, test tube rack,

wash botte, carbon paper, separatory funnel, filter flask, rubber tubing, blue litmus

paper, and lastly 5 mL pipet. On the other hand, to perform the experiment, the

chemicals/substances that were needed were: Ammoniacal AgNO3, cyclohexane

(C6H12), cyclohexene (C6H10), acetylene (C2H2), 0.1 M Br2 in CCl4, dilute KmnO4,

calcium carbide (CaC2), benzene (C6H6), and toluene (C6H5CH3).

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Methods

A. Ignition Test

Each sample was placed in a porcelain crucible, with three (3) drops. The crucible

was then brought to the edge of the burner flame using crucible tongs. Observations

were made regarding the sample's flammability and characteristics, specifically noting

its color and sootiness.

B. Reaction with Bromine

One (1) mL of 0.1M Br2 was placed in CCl4 solution into each of the two (2)

test tubes, ensuring that one (1) tube was wrapped in carbon paper to protect its contents

from light. Then three (3) drops were added of the sample to each test tube, sealed them,

and shook gently to mix the solutions. After approximately ten (10) minutes, any fading

of Br2 was observed in the unwrapped tube and subsequently compared the contents of

both test tubes. Where fading had occurred, the presence of HBr was tested by adding

ten (10) drops of distilled water to the final reaction mixture. The water layer was then

examined using the litmus paper and results were recorded.

C. Reaction with Cold Dilute Permanganate

In a test tube, one (1) mL of dilute KMnO4 was added. Then, five (5) drops of

each sample were added, and the test tube was shaken for 5 minutes to mix the contents.

After this time, the contents of the test tube were examined, and the results were

recorded.
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D. Reaction with Ammoniacal Silver Nitrate Solution

In the clean test tube, the silver reagent was placed in it with ten (10) drops and

then two (2) drops of each sample was added using the medicine dropper. The contents

of the tube were then mixed thoroughly and observed. Any of the precipitate that was

obtained was transferred in a vessel.

Preparation and Testing of Acetylene Gas

Approximately five (5) grams of calcium carbide lumps were introduced into a

dry two hundred fifty (250) mL distilling flask, and the remainder of the apparatus was

assembled for the generation of acetylene gas. About one hundred (100) mL of water

was added to the dropping funnel, and a few drops of water were allowed to fall onto

the solid. The setup was permitted to stand for a couple of minutes to ensure that the air

was displaced from the apparatus. Additional water was added as necessary, and the

gas evolved during this process was subsequently used for tests B, C, and D as

previously described. The generated gas was bubbled through the contents of the test

tube for a full minute whenever the procedure required the addition of hydrocarbons.
 CHAPTER III

RESULTS AND DISCUSSION

This chapter discusses the results acquired from the conducted experiments,

emphasizing the changes reactivity and combustion properties among the hydrocarbons

tested. The data obtained from the chemical tests conducted indicated some properties

of the structure members of hydrocarbons which are saturation, unsaturation and

aromatics. The analysis of these results offers insights into the chemical properties and

practical implementation of hydrocarbons.

Table 1. Ignition test

Samples Chemical Description of Observation during
Formula samples ignition test
Cyclohexane C6H12 Yellow flame No soot formation
Cyclohexene C6H10 Luminous yellow Minimal soot formation
flame
Benzene C6H6 Yellow flame Minimal soot formation
Toluene C6H5CH3 Yellow flame More dark soot formation

In this test, only cyclohexane underwent complete combustion, which is why

there was no soot formation when it was ignited. In contrast, the other samples produced

soot. These results are likely due to their carbon-to-hydrogen ratios. Xuan (2020) stated

the lower the carbon-to-hydrogen ratio, the sootier the flame. In this case, which can be

applied to the results collected.

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Cyclohexane had no soot when burned as it has a carbon-to-hydrogen ratio of

6:12 whereas cyclohexene produced minimal soot due to its slightly lower C:H rate of

6:10 which reduces the hydrogen available for combustion. Benzene also had minimal

soot produced because of their C:H ratio of 12:1, with its aromatic ring structure

contributing to incomplete combustion, but it is also possible that due to experimental

conditions have limited the amount of soot produced. Then again toluene had a darker

soot formation compared to the other samples having a 6:5 carbon-to-hydrogen ratio.

From here, cyclohexane is more stable compared to the other samples.

Table 2. Reaction with bromine in CCl4

Samples Wrapped test Test w/ litmus Unwrapped Test w/ litmus
tube test tube
Cyclohexane No fading Blue to red No fading Blue to red
Cyclohexene Faded Blue to red Faded Blue to red
Benzene No fading Blue to red No fading Blue to red
Toluene No fading Blue to red No fading Blue to red
Acetylene No fading Blue to red No fading Blue to red

This part of this experiment tested the reaction of various hydrocarbons with

bromine in CCl₄ under wrapped and unwrapped conditions, followed by a litmus test.

Cyclohexene was the only sample that caused the bromine solution to fade. This

reaction is an example of electrophilic reaction. Bromine is a polarizable molecule, and

the approaching pi bond in cyclohexene polarizes the bromine, forming 1,2-

Dibromocyclohexane. (Libretexts, 2023)

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Figure 1. Chemical formula of cyclohexene in Br2 in CCl4 (Matthew, 2011)

Cyclohexane, as a saturated alkane, and benzene and toluene, as aromatic

compounds, resisted bromine addition, with benzene and toluene requiring specific

conditions (e.g., catalysts) for such reactions. According to Matthew (2011) for

cyclohexane or saturated hydrocarbons to react with bromine you have to add UV light.

So simply adding some bromine to cyclohexane won’t cause a reaction to occur.

Figure 2. Chemical reaction of cyclohexane with Br2 (Codis, 2019)

Acetylene, despite being an alkyne, did not react under these conditions,

possibly due to insufficient reactivity. The litmus test consistently turned red across all

samples, reflecting the acidic nature of the bromine-containing medium. This highlights

bromine's effectiveness in distinguishing between saturated, unsaturated, and aromatic

hydrocarbons.

Table 3. Reaction with potassium permanganate

Samples Observation
Cyclohexane No changes
Cyclohexene Formed a dark brown suspension
Benzene No changes
Toluene No changes
Acetylene Formed a brown suspension

Potassium permanganate is an oxidizing agent that reacts with unsaturated

aliphatic hydrocarbons, but does not react with alkanes or aromatic hydrocarbons. The
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dilute KMnO4 solution has a deep purple color, if there is no reaction you should see

no color change (Cundiff, 2016). This was evident with the result of cyclohexene, an

alkane, and benzene and toluene being aromatic hydrocarbons showed no reactions

when mixed with potassium permanganate. However, when it reacts with unsaturated

aliphatics it produces MnO2, a brown precipitate. This is why acetylene, a usaturated

hydrocarbon, also showed a reaction, which formed a brown precipitate. Because of its

unsaturation, specifically its triple bond. This reaction is useful as a test for the presence

of a multiple bond, if there is no other easily oxidizable group, such as an alcohol or

aldehyde.

Figure 3. Chemical reaction of cyclohexene with KMnO4 (Codis, 2019)

Figure 4. Chemical reaction of acetylene with KMnO4 (Codis, 2019)

Table 4. Reaction with ammoniacal AgNO3

Samples Observation
Cyclohexane Colorless with small gray precipitate
Cyclohexene Colorless, formed two layers with small gray precipitate
Benzene Colorless, with small precipitation
Toluene Colorless
Acetylene Formed white precipitate
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According to Camarote (2015) this test is to determine the presence of a triple

bond, which in this case was shown upon the observations in Acetylene reaction with

AgNO3 , producing silver acetylide, a white precipitate. This means the other samples

have no presence of a triple bond.

Figure 5. Chemical formula of acetylene reacting with ammoniacal AgNO3 (Codis,

2019)

In contrast, the other samples—benzene, toluene, cyclohexane, and

cyclohexene—had minor side reactions or did not react because they lack terminal

triple bonds. Benzene and toluene are aromatic compounds with stable resonance

structures that resist such reactions, cyclohexane is a saturated hydrocarbon without

unsaturation, and cyclohexene, though unsaturated, has a double bond rather than a

terminal triple bond, making it unreactive in this test.

 CHAPTER IV

CONCLUSION

The experiment successfully classified the hydrocarbons—cyclohexane, cyclohexene,

benzene, toluene, and acetylene—through a series of chemical tests that yielded

valuable insights into their structures and reactivity. Each test confirmed the presence

or absence of specific functional groups, facilitating the accurate differentiation among

alkanes, alkenes, alkynes, and aromatic compounds. In the ignition test, cyclohexane

burned cleanly, whereas cyclohexene, benzene, and toluene produced sooty flames,

indicating the presence of unsaturation or aromaticity. The bromine test in CCl₄

revealed that cyclohexene decolorized the solution, confirming its double bond, while

cyclohexane, benzene, toluene, and acetylene showed no reaction. The potassium

permanganate test further supported this, with a brown suspension observed in

acetylene and cyclohexene reacting with a much darker suspension while the other

hydrocarbons remained unchanged. The ammoniacal silver nitrate test reacted

exclusively with acetylene, indicating the presence of a triple bond. The significance of

these tests lies in their ability to illuminate key characteristics such as saturation,

unsaturation, bond types, and aromaticity, all of which are essential for understanding

the behavior and potential applications of these compounds. Overall, the tests produced

reliable results that not only classified the hydrocarbons but also highlighted the
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importance of chemical reactivity in identifying and distinguishing various types of

hydrocarbons.
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