Chapter 1

INTRODUCTION

Hydrocarbons are organic compounds that are made of only hydrogen and carbon

atoms. Alkyne is one of the types of unsaturated hydrocarbons. It is identified as organic

chemical compounds that have triple bonds in their chemical structure. Although alkynes, in

general, are highly reactive molecules, certain tests are still needed for the identification of this

hydrocarbon. Some tests for the chemical properties of alkynes include combustion, addition

reactions, oxidation, polymerization and formation of alkynides.

In this experiment, the simplest alkyne, acetylene, will be used and will also be

prepared from calcium carbide and water by means of water displacement. Water displacement

is a method thats suitable for collecting gases which are insoluble or only slightly soluble in

water. For the chemical properties test, flammability, reaction with bromine, Baeyers test for

unsaturation and formation of acetylides will be considered. The test for the reaction with

Bromine involves testing the reactivity of the organic compound with bromine to determine

whether a particular compound have double bonds or triple bonds while the Baeyers test for

unsaturation, as the name implies, is used as a qualitative test for the presence of unsaturation

in hydrocarbons. On the other hand, the test for the formation of acetylides serves as a test to

determine the presence of a triple bond (alkynes).

In this experiment, the researchers intend to know how acetylene is prepared and the

different properties of alkynes in comparison with that of alkenes and alkanes. Having the

knowledge in all of these is important because it will help in identifying what chemical

compound is being used. Acetylene is also an extremely important starting material in

commercial chemical synthesis.

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 Chapter 2

DESIGN AND METHODOLOGY

A. Preparation of Acetylene

A cork carrying a small dropping funnel was

fitted on a dry 100 ml distilling flask and the flask was

clamped on an iron stand. A delivery tube was then

attached to the side arm of the flask then 10 grams of

Figure 1: Set-up for the collection
calcium carbide was added to the flask and 50 ml of of acetylene gas

water to the dropping funnel. After the cork was inserted tightly in the distilling flask, the

water was allowed to flow drop by drop into the calcium carbide. Once the gas collected over

water burned quietly after igniting it, we collected 5 test tubes of acetylene gas. The excess

carbide was then decomposed by adding water to the flask then dilute HCl was added to

dissolve the residue. After which, the material was washed down the sink.

B. Properties of Acetylene

Before anything else, we observed the physical properties of acetylene then we

ignited a test tube of acetylene under a hood to test for flammability. While the gas is

burning, we poured a stream of water into the test tube to keep the gas burning smoothly. For

the test for reaction with Bromine, we added Br2/CCl4 solution drop by drop to a second test

tube of acetylene then the solution was mixed. In Baeyers test for unsaturation, we added a

few ml of dilute solution of potassium permanganate to the third test tube of acetylene.

Lastly, for the test of formation of acetylides, we cautiously added 2 ml of ammoniacal

cuprous chloride solution to a fourth test tube of acetylene and 3 ml of ammoniacal silver

nitrate solution to a fifth test tube of acetylene.

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 Chapter 3

RESULTS AND DISCUSSION

In this experiment, we were able to prepare acetylene using water displacement and we

have observed here that the addition of water and calcium carbide would yield two products, a

grayish material in a form of small lumps in the flask and a colorless and pungent smelling gas

which is slightly soluble in water. When testing for the combustion properties of acetylene,

we noticed that once the acetylene in the test tube was ignited, a popping sound was produced

together with a yellow flame which persisted for seconds after we poured the stream of water

into the test tube. Also, the test for combustion resulted to a formation of soot at the mouth of

the test tube. Test for the reaction with bromine was also conducted and from the results

obtained, the addition of Br2/CCl4 solution to the acetylene gas appeared to have a similar

reaction with that of alkenes but with a much slower pace. This was shown when acetylene

slowly decolorized bromine from deep yellow to a colorless solution. Moreover, when

Baeyers test for unsaturation was conducted by the addition of potassium permanganate, the

purple solution was again decolorized to brown but this time, with the presence of a precipitate

which was also brown in color. The test for the formation of acetylides was also performed but

with the use of two different solutions. The first test was done with the addition of ammoniacal

cuprous chloride which yielded a deep blue solution with the presence of red precipitate which

was not that noticeable at first glance. The second test was performed with the addition of

ammoniacal silver nitrate which resulted to the immediate formation of a white milky

precipitate which later on turned to a grayish stone-like precipitate at the bottom of the test

tube. All these steps were performed cautiously, since some of the chemicals are explosive

when dry especially the cuprous and silver acetylides.

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 Chapter 4

CONCLUSION AND RECOMMENDATIONS

There are different compounds under the hydrocarbons group of alkynes and in this

experiment, acetylene was used. Acetylene belongs to the lower members of alkynes which

are gases. This is the reason why the production of acetylene though water displacement

resulted to an odorous garlic smell that is slightly soluble in water. The solubility and density

of acetylene can be best seen when the evolved gas was being collected. This is because water

displacement would only be possible for gases that are insoluble or slightly soluble in water.

The gas wouldnt also be collected if it has a density greater than water. Moreover, because

the gas is collected over water, it is mixed with vapor from the evaporation of water therefore

it is not pure.

The test tubes used were all completely filled with acetylene gas. Apparently, this factor

had an effect with the combustion of acetylene. This can be clearly observed when the flame

produced was only present at the mouth of the test tube where oxygen is present. In addition,

the resulting yellow flame and the soot produced signifies the incomplete combustion of

acetylene with the carbon (in the acetylene) being released as a soot. These observations,

together with the chemical equation gathered, indicate that oxygen is the limiting reactant and

that acetylene gas will only undergo complete combustion with the proper amount of oxygen.

The test for the reaction with Bromine, showed that some behaviors of alkynes are

somewhat the same with that of the alkenes. This is when the acetylene decolorized the

bromine solution from deep yellow to colorless but in a slower pace. Although the reaction of

acetylene with bromine is similar with alkenes, this method can still be used to distinguish

between alkenes and alkynes alkenes decolorize bromine solution very rapidly, but alkynes

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take several minutes. Through Baeyers test for unsaturation, we can say that acetylene is an

unsaturated solution with the presence of a triple bond since the experiment resulted to a

positive test with the disappearance of the purple color of the potassium permanganate and the

appearance of brown precipitate.

Since both alkenes and alkynes decolorize KMnO4, another visual test is necessary to

distinguish them from one another and in this experiment we made use of the test for the

formation of acetylides. When acetylene is passed into a solution of cuprous chloride in

ammonia, cuprous acetylide is produced in the presence of a deep blue solution with a reddish

brown precipitate. Moreover, silver acetylide is formed when acetylene is passed into

an ammoniacal solution of silver nitrate with the appearance of a white milky precipitate.

These substitution reactions which acetylene undergoes to form compounds with metals does

not occur with the alkenes and alkanes.

Concluding, several tests can be done for the confirmations of the presence of acetylene

but the best qualitative test is the test for the formation of acetylides. The qualitative tests done

also verified that alkynes are indeed the most reactive between hydrocarbons.

References

Bettelheim and Landesberg. Laboratory Experiments for General, Organic, and Biochemistry
4th edition. 2010.

Garcia, N. Alkynes: Properties, Uses, Formula & Examples.

http://study.com/academy/lesson/alkynes-properties-uses-formula-examples.html

Gilbert, J.C. & S.F. Martin. Experimental Organic Chemistry: A Miniscale and Microscale
Approach, 6th Ed. 2016.Cengage Learning. Boston, MA.

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 APPENDICES

APPENDIX A

List and Uses of Apparatus

1. A dropping funnel is a type of laboratory glassware used to transfer fluids. They are fitted

with a stopcock which allows the flow to be controlled.

2. A test tube is a thin glass tube closed at one end, used to hold small amounts of material

for laboratory testing or experiments.

3. The iron stand is a raised and usually ventilated metal stand on which a hot flatiron may

be rested when not in use.

4. Wire gauze is placed on the support ring that is attached to the retort stand between

the bunsen burner and the beakers in order to support the beakers or other glassware

or flasks during heating.

5. A graduated cylinder, measuring cylinder or mixing cylinder is a common piece of

laboratory equipment used to measure the volume of a liquid.

6. A water trough is a bowl shaped in the form of a rectangular box. It is used for like

collecting of gas by downward displacement of air.

7. A distilling flask is used to separate two liquids with different boiling points, and is a

common piece of lab distillation apparatus.

APPENDIX B

Definition of Terms

1. Hydrocarbon, any of a class of organic chemical compounds composed only of the

elements carbon (C) and hydrogen (H). The carbon atoms join together to form the

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framework of the compound, and the hydrogen atoms attach to them in many different

configurations.

2. Oxidation is the loss of electrons during a reaction by a molecule, atom or ion. The

opposite process is called reduction, which occurs when there is a gain of electrons or the

oxidation state of an atom, molecule, or ion decreases.

3. Polymerization, any process in which relatively small molecules, called monomers,

combine chemically to produce a very large chainlike or network molecule, called a polymer.

The monomer molecules may be all alike, or they may represent two, three, or more different

compounds.

4. Unsaturated compounds are organic-chemical compounds whose molecular structure

contains one or more carbon-carbon double bonds or triple bonds. These can also

be conjugated.

5. Ammoniacal means containing, using or resembling ammonia.

APPENDIX C

Problems

1. Give the 3 practical uses of acetylene.

Acetylene is used for welding and cutting. The welding process that uses acetylene is
known as oxy-fuel cutting or gas cutting. Among all other gases, acetylene is capable of
producing the hottest flame. For this reason, acetylene serves as an important medium for
heat treating metals and other materials. Acetylene is used in automotive part manufacturing
as well as fabrication of other metal parts where accuracy is crucial.

2. Of the two general types of acetylene derivatives, R-C=C-H and R-C=C-R, which would
be expected to give a positive test with the reagent used in procedure no. 5? What structural
effect or feature is required for the reaction? What is the functions of ammonia in these
reactions?
R-C=C-H would be expected to give a positive test; Ammoniacal solutions are
required for the reactions; ammonia is used to reduce the alkenes.

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3. In what sense is acetylene a protonic acid? Explain why its reactions with ammoniacal
cuprous chloride and silver nitrate are considered as reactions of an acid?
The protons in acetylene (C2H2) are very weakly acidic. With a strong base (eg.
sodium hydride, NaH), they can be abstracted, giving the corresponding metal acetylide
(NaC2H, and Hydrogen, H2).

4. What volume of acetylene measured at standard conditions could be obtained from 10

grams of calcium carbide?
CaC2(s) + 2H2O(l) C2H2(g) + Ca(OH)2(aq)

Molecular weight CaC2 = 64 g/mol

1.00
n CaC2 = 10.0 g x = 0.156 mol
64.0

1 C2H2 : 1 CaC2

C2H2 = 0.156 mol

*At STP: T = 273 K and P = 1 atm

V = nRT / P

(0.156 )(0.08205 )(273.0 )

VC2H2 = 1.0

VC2H2 = 3.494 L