Name: Cheradee V.

Anim Score:
Course & Year Section: Bs Bio/1st Year-28A Date: 04-22-2024

Experiment #9: AROMATIC HYDROCARBONS

Objectives:
 Observe and record the physical properties of the aromatic hydrocarbons
including toluene, phenol, aniline, benzene, and naphthalene
 Observe the reactions of the aromatic hydrocarbons when mixed with different
chemicals

Materials:
Dropper Aniline Naphthalene
Test Tubes Phenol
Match Sticks Toluene
Test Tube Rack Chloroform
Evaporating Dish Potassium Permanganate

Data/Results
Table 9.1 properties of Aromatic HC

Hydrocarbon Physical State Color Solubility in Density

H2O compared to
water

Toluene Liquid Colorless/ Poorly soluble Less dense

transparent than water

Phenol Liquid Red Moderately Denser than

soluble/ slightly water

Aniline Liquid Brown Moderately Denser than

soluble/ slightly water

Benzene Liquid Colorless/ Insoluble Less dense

Transparent than water

Naphthalene Solid White Insoluble Denser than

water
 Table 9.2 Reactions of Aromatic HC

HC CHCl3/AlCl3 Br2-Dark Br2-Light Dilute KMnO4 Combustion

Toluene The powder Mix No The mixture When ignited,

settled at together. significant appeared the flame was
bottom. They Br2 was reaction purple due to yellowish and
don’t combine dissolved in occurred. the presence emitted a
and the colors the toluene, The color of potassium black smoke
stay the resulting in remained permanganate with black
same, a dark- colorless. . ashes as it
transparent. colored dies down.
solution.

Phenol They don’t Do mix The The mixture Not

combine together. bromine color turned combustible
completely Formation water was into lighter but catches
and the color of colorless decolorized shade but the fire eventually
turned dark solution to by phenol. phenol and dies
red pale separates with down
yellowish kmno4 immediately.
color. Yellow flame
and black
smoke.

Aniline Occurs Mix The Formation of Not

formation of together. bromine bubbles on combustible
crystalline-like Formation water was lower portion. but fuels the
substances of a decolorized Color turned to match to
and the color reddish- by aniline. brown. burn. Yellow
changed to brown color. flame and
very pale dark smoke.
yellow as it
reacted with
the mixture

Benzene Benzene and The color of No No significant Burns with a

CHCl3 mix the mixture significant physical sooty flame
with each remains physical reaction and also
other and the unchanged, reaction occurred. carbon
AlCl3 settles as benzene occurred. monoxide gas
at the bottom does not Color can be
of the tube. react with stayed the
 Very pale Br2 same. detected.
brownish
color

Naphthalene Naphthalene Mixed The color of The Creates

and CHCl3 together. the mixture naphthalene yellow flame
combined The color of changed to separated with black
while AlCl3 the mixture a darker from the smoke.
stayed at the changes to reddish- potassium
bottom. The a darker brown. permanganate
color changed hue. and
to golden- submerged at
brown or the bottom.
yellow.

Observation:

In this laboratory activity, we first prepared the needed materials to start the
experiment. Chloroform was used as the solvent in test tubes, and 5 drops of it were
added to each tube. Then, drops of different chemicals (toluene, phenol, aniline, and
naphthalene) were added to separate test tubes. Anhydrous aluminum chloride was
pinched into each mixture, and different reactions occurred. In the toluene mixture,
the colors stayed the same. In phenol mixture, a dark red powder formed, and in the
mixtures with aniline and naphthalene, exhibited a brownish-yellow stain. Potassium
permanganate was then added to the separate set of test tubes containing the same
hydrocarbons. Half of the mixtures formed oil clumps at the top, while the other half
separated from the potassium permanganate, forming a layer on top. Lastly, we
performed the combustion. Upon ignition, only toluene and naphthalene combusted,
emitting black smoke and leaving black ashes. Phenol and aniline did not combust
but still burned eventually.

Questions:
1. What are the formulas of the above HC?
Toluene: C6H5CH3 / C7H8
Phenol: C6H5OH
Aniline: C6H5NH2
Benzene: C6H6
Naphthalene: C10H8
 2. Write the equations for the complete combustion of test compounds.
Toluene: C7H8+9O2→7CO2+4H2O

Phenol: C6H5OH + 7O2 → 6CO2 + 3H2O

Aniline: 2C6H5NH2+17O2→12CO2+10H2O+2NO2

Benzene: C6H6+15O2→6CO2+3H2O

Naphthalene: C10H8+12O2→10CO2+4H2O

Generalization:
With this experiment, I’ve learned new things. By adding these hydrocarbons
to chloroform and mixing them with various chemicals such as anhydrous aluminum
chloride and potassium permanganate, I observed different reactions and physical
changes. These included the formation of transparent solutions, colored powders,
and the separation of layers within the mixtures. These indicate their differences in
their solubility, chemical properties and reactivity. Through observation, I gained a
deeper understanding of how these compounds interact with different chemicals.
This laboratory activity has provided me valuable insights into the physical properties
and reactivity of aromatic hydrocarbons.