Therese F. Javellana B.S.

in Fisheries III October 6, 2017

(Chem 31.1) Experiment No. 6

Hydrocarbons

I. Introduction
Hydrocarbons are some of the simple organic compounds that contain only hydrogen and
carbon atoms. The functional groups that constitute these hydrocarbons are used to classify them.
Alkanes do not have any functional groups; alkenes have a carbon-carbon double bond; alkynes
have carbon-carbon triple bonds, and; aromatic hydrocarbons have a pi system of electrons in
their structure.
Alkanes are non-polar and have no electronegative atoms which make them useful as
solvents for a wide-range of organic substances. Their non-polar nature also suggests that they
rarely undergo ionic reactions. Alkanes are considered saturated in nature because its single
bonds have high number of hydrogen atoms bonded with them, and it does not have any
functional group present in its structure.
Alkenes (such as cycloalkenes) and aromatic hydrocarbons are alicyclic compounds that
are insoluble in water. Because of the presence of double bonds in their structure, they are
considered unsaturated compounds or those that do not have high amounts of hydrogen atoms
bonded with them (Camarote et al, 2014). Alkynes have triple C-C bonds and overlapping sp
hybridized atoms. They are also unsaturated and are considered chemically active capable of
violent reactions. Alkynes are not naturally-occurring compounds.
Several tests can be conducted to identify and confirm the presence of single, double, and
triple C-C bonds in their structures. These processes are the halogenation of bromine (a
substitution reaction from C-H to C-X), and reactions with Baeyer’s reagent and ammoniacal
silver nitrate (Mendelset, 2011).
In this experiment, the mentioned tests were conducted to confirm the presence of
specific bonds in the structure of hydrocarbons. The different properties of hydrocarbons were
also investigated with the use of these tests.
II. Methodology
Materials and Reagents
Cyclohexane Acetylene Dichloromethane (DCM)
Cyclohexene 10% NaOH Baeyer’s reagent
Benzene conc. H2SO4 Ammoniacal silver nitrate
Toluene 0.05 M Br2/CCl4 Calcium carbide
10 5 mL test tubes Cork/rubber stopper
Vacuum flask Iron stand w/ ring
Separatory funnel Carbon paper

Procedure

A. Investigation of Hydrocarbons
1. The characteristics of the samples were noted down (color, clarity, physical state).
2. Five test tubes were labelled accordingly (alkane - cyclohexane, alkene - cyclohexene,
aromatic hydrocarbons - benzene, toluene, and alkyne - acetylene).

B. Solubility Test
1. One ml of DCM was placed in each of the four test tubes.
2. Ten drops of samples were placed in their respective test tubes. The mixture was swirled.
3. The mixtures were examined for any sign of chemical reaction. Observations were noted
down.
4. Steps 1 to 3 were repeated using water, 10% NaOH, and concentrated sulfuric acid (H2SO4) as
solvents.

C. Reaction w/ Bromine (Halogenation)

1. Eight test tubes were prepared and labelled. Each sample has two test tubes, one of which is
wrapped with carbon paper to prevent exposure to light.
2. Fifteen drops of each sample were placed in their respective test tubes (one covered, one
uncovered).
3. Five drops of 0.05M Br2/CCl4 were added to each test tube. The test tubes were shaken to mix
the substances.
4. The unwrapped test tubes were exposed to light for ten minutes.
5. The carbon paper was removed and the appearances of the mixtures in wrapped and
unwrapped test tubes were compared.

D. Reaction with Baeyer’s Reagent (Oxidation test)

1. Two mL of Baeyer’s reagent were placed in each of the four test tubes. Five drops of each
sample were then added to the test tube and mixed.
2. Color changes, specifically, the disappearance of the characteristic purple color of the KMnO 4
solution, were observed.

E. Reaction with Ammoniacal silver nitrate

1. Ten drops of the silver nitrate reagent were placed in each test tube.
2. Two drops of each sample were added to their respective containers and mixed.
3. The mixture was observed for any signs of chemical reaction.

F. Preparation and Testing of Acetylene Gas

1. About five grams of calcium carbide were placed in an Erlenmeyer flask.
2. The group that served as the experiment’s monitor prepared the set-up for the collection of
acetylene gas.
3. Water was added into the separatory funnel.
4. Water was allowed to fall dropwise on the solid calcium carbide. The acetylene gas emitted
was directed into a rubber tubing.
5. Three test tubes were prepared and added with 0.05 M Br2/CCl4, Baeyer’s reagent and
ammoniacal silver nitrate respectively.
6. Acetylene gas was added separately into the three test tubes containing the solvents for tests C
to E.
7. Observations were noted down.
III. Results and Discussion

The different representative compounds for each classification of hydrocarbons were

subjected to several tests. Observations were noted down and evaluated to summarize the
varying chemical reactions that take place for all the compounds.

Table 1.1 Solubility Test

Observations per solvent
Sample Description
DCM NaOH H2O H2SO4
Upper layer
Clear liquid Precipitate
Cyclohexane Clear liquid Clear cloudy, lower
w/ meniscus bet. Layers
layer is clear
Clear and
immiscible
with
Cloudy to Clear liquid Formation of
Cyclohexene Clear liquid emulsions
clear w/ meniscus orange ppt
forming
between the
layers
Orange ppt
Cloudy upper
Clear, bet 2 layers
layer, clear
Benzene Clear liquid Clear immiscible (lower layer
lower layer
liquid slightly
(w/ meniscus)
orange)
Orange ppt on
Clear,
Clear w/ top (w/ brown
Toluene Clear liquid Clear immiscible
meniscus gel-like ppt
liquid
bet 2 layers)
Gaseous
Not conducted for acetylene gas because of the unavailability of
Acetylene Gas substance w/
the sample during the first part of the experiment
strong odor
 The table above summarizes the results of the solubility tests of hydrocarbons. All
samples were soluble in dichloromethane (CH2Cl2, known as DCM). This is because of the
polarity of the molecules. Solubility is controlled by the balance created by the intermolecular
forces present in the molecules, may it be solute-solute, solvent-solvent, or solute-solvent. The
empirical rule “like dissolves like” summarizes this phenomenon. Most organic compounds are
non-polar, which means that they are highly soluble in organic solvents such as DCM. Polar
solvents, such as water, cannot dissolve organic compounds to high extents. Partial dissolution of
organic molecules is possible in polar solvents if the organic molecules have high ratio of polar
functional groups than the non-polar ones (University of Calgary, n.d.). An example is when they
are treated with an acid or base that could lead to their formation of ionic species with the
molecule (ionic form is generally more polar). These ionic species will not make the organic
molecule totally soluble, hence the formation of precipitate in NaOH and H2SO4 solvents.

Table 1.2 Reaction with Bromine (Halogenation)

Samples Mixture exposed to light Mixture not exposed to light
Cyclohexane Cloudy to colorless Cloudy, yellowish liquid
Cyclohexene Cloudy Cloudy
Benzene Cloudy, yellowish liquid Cloudy, yellowish liquid
Toluene Cloudy Cloudy
Acetylene gas Cloudy to colorless Cloudy, yellowish liquid

The table above shows the final appearance of the mixtures after some of them were
exposed to light or covered with carbon paper. The solvent used for halogenation was Br2/CCl4
which has a brown appearance. The positive reaction between molecules is signified by the
disappearance of the brown color of the bromine reagent. The results show that cyclohexane and
acetylene gas have generated positive results when the mixtures were exposed to light.
Cyclohexene and toluene have reacted positively with or without light (although the
disappearance was cloudy, possibly because of the ratio of organic compound with the solvent).
Benzene remained non-reactive with bromine with or without the presence of light.
 Benzene, an aromatic hydrocarbon, does not react well with electrophiles like bromine.
This is because the pi-bonds of benzene repel Br-Br bonds along the double bonds. This results
to the formation of dipole moments that will make the solvent “polar” (“like dissolves like”
principle). Electrophilic addition is not favoured by aromatic hydrocarbons because the
stabilization of the molecule will be lost (Camarote et al, 2014). Toluene is also an aromatic
hydrocarbon but did not react the same way as benzene. This is possibly caused by
contamination or an error in the ratio of organic molecule to reagent mixture.
CCl4 was used in this part of the experiment to allow reactions to take place. Bromine
alone is polar, and using the “like dissolves like” principle, it will not react with organic
molecules. CCl4 served as the solvent for bromine by lowering the activation energy (Ea) needed
for the reaction to take place.

Table 1.3 Reaction with Baeyer’s reagent

Samples Appearance of mixture
Cyclohexane Upper layer – thin, light violet
Lower layer – dark violet
Cyclohexene Upper layer – thin, light yellow to brown
Lower layer – reddish black
Benzene 1st (upper) layer – thin, clear liquid
2nd (middle) layer – pinkish
3rd (lowest) layer – thick, dark violet
Toluene 1st (upper) layer – thin, clear liquid
2nd (middle) layer – pinkish
3rd (lowest) layer – thick, dark violet
Acetylene gas Dark brown substance

Baeyer’s reagent is a cold, alkaline solution of potassium permanganate (KMnO4). The

positive result in this redox test is the formation of dark brown substance or the decolorization of
the purple solution. The results show that acetylene gas and cyclohexene generated positive
results, with acetylene gas exhibiting the expected final appearance more. Alkenes and alkynes
contain double and triple carbon-carbon bonds respectively. They do not have high concentration
of hydrogen bonded to them because of the presence of these double and triple C-C bonds.
Cyclohexane generated the most negative result (the appearance of the solution remained the
same). This is because alkanes are “saturated”, which means that its single bonds have high
amounts of hydrogen bonded to them. Aromatic hydrocarbons (benzene and toluene) are not
considered to be reactive with Baeyer’s reagent because they are inert to oxidation despite of the
unsaturation of hydrogen in their structures (Camarote et al, 2014).

Table 1.4 Reaction with Ammoniacal Silver Nitrate

Samples Final appearance
Cyclohexane Upper layer – thin precipitate
Lower layer – clear, with bubble suspensions
Cyclohexene Upper layer – thin precipitate
Lower layer – clear
Acetylene gas Gray, ash-like precipitate

Reaction with ammoniacal AgNO3 tests the presence of triple bonds in the molecule. The
positive result is signified by the formation of the ash-like precipitate. As seen on the table
above, acetylene gas generated positive results. This is because of the release of the terminal
proton of the alkyne, causing the resulting ion to form insoluble precipitate with Ag+. This
reaction is exclusive alkynes which possess the terminal protons in their triple bonds, hence the
negativity in the reaction of silver nitrate with cyclohexane and cyclohexene (Jones & Fleming,
2014).
In this experiment, acetylene gas was generated by reacting calcium carbide with water.
Water was added in a dropwise manner so as to avoid violent reactions. The reaction is
summarized by the equation:
CaC2(s) + 2H2O(l)  Ca(OH)2(s) + C2H2(g)

Terminal alkynes such as acetylene gas are considered acidic because of its sp
hybridization. Its sp hybridization suggests that its electron pair is near the nucleus, causing it to
lose its hydrogen and form H+ ions (Camarote et al, 2014). The distance of its electron pair to the
nucleus means that its anionic counterpart (conjugate base) is stable, and stable conjugate bases
suggest that the compound is acidic. This also contributes to the unsaturated nature of the
compound that influenced its reactivity with solvents such as Baeyer’s reagent.

IV. Conclusion

Hydrocarbons are non-polar organic compounds and they are soluble in organic solvents
by the “like dissolves like” principle. Other hydrocarbons can be partially soluble in polar
solvents depending on the polarity of the functional groups they possess. Halogenation with
bromine generates positive results when a colorless liquid forms at the end of the reaction. For
Baeyer’s reagent reactions, decolorization of the characteristic purple color indicate positive
results. Alkenes and alkynes have double and triple bonds respectively and show positive results
when reacted with Baeyer’s reagent. Reaction with ammoniacal silver nitrate detects the
presence of triple bonds in the molecule by forming an ash-like precipitate. Only alkynes,
therefore, are reactive in this test.
Several errors can be encountered in this experiment such as the error in the ratio of the
organic compound to the solvent used in the reaction. Another possible cause of errors is the
improper use or incorrect calibration of the equipment required to facilitate such reactions.

V. References
Camarote, BC. Romelo, N. and Valdon, SJ. (2014). Hydrocarbons. University of the Philippines
Visayas Department of Chemisty. Retrieved October 4, 2017 from Academia website,
http://www.academia.edu/12417322/Hydrocarbons
Jones, M. and Fleming, S. (2014). Organic Chemistry 5th ed. Norton & Company. Retrieved
October 4, 2017 from University of Calgary website,
http://www.chem.ucalgary.ca/courses/351/orgnom/functional/func.html
Properties of Hydrocarbons. (2011). Retrieved October 3, 2017 from Mendelset website,
http://www.mendelset.com/articles/689/properties_hydrocarbons
Solubility of Organic Compounds. (n.d.). University of Calgary Chemistry Department.
Retrieved October 3, 2017 from UCalgary website,
http://www.chem.ucalgary.ca/courses/351/laboratory/351expt_01_solubility.pdf