Name: Joses Donna Z.

Calindas Score:

Course/Year: BS BIO 1st Year – 28A Date: 04/19/2024

Experiment # 4: AROMATIC HYDROCARBONS

Objectives:
a. Observe the physical properties of the aromatic compound of toluene, phenol,
aniline, benzene, and naphthalene.
b. Observe the reactions of toluene, phenol, aniline, benzene, and naphthalene
to substance CHCl3/AlCl3, Br2 light and dark, dilute KmnO4.
c. Ignite the toluene, phenol, aniline, benzene, and naphthalene and observe the
character of the flame.

Materials:
Test tubes Phenol
Test tube racks Aniline
Dropper Naphthalene
Spatula Chloroform
Evaporating dish Potassium permanganate
Washing bottle Match sticks
Toluene Anhydrous aluminum chloride

I. Observation
We conducted this experiment last April 18, 2024. We are tasked to observe
the physical properties of the aromatic compound of toluene, phenol, aniline,
benzene, and naphthalene. Second, is to observe the reactions of toluene, phenol,
aniline, benzene, and naphthalene to substance CHCl3/AlCl3, Br2 light and dark,
dilute KMnO4. Lastly, is to perform ignition or combustion reaction with toluene,
phenol, aniline, benzene, and naphthalene, and observe the character of the flame.
But before we conducted our experiment, we fully equipped ourselves with our
personal protective equipment: lab coat, gloves, and mask. Lastly, the part of the
experiment where we needed bromine and benzene are skipped because these
chemicals are unavailable at the moment.
 We meticulously examined the physical properties of the aromatic
compounds. Here is my observation of the different compounds. Toluene appeared
as a colorless liquid with a distinct sweet smell, exhibiting solubility in organic
solvents. Phenol presented as a red liquid with a characteristic medicinal odor, it can
cause chemical burns when in contact with skin or it can burn a hole through gloves
when came in contact, and it is soluble in water. Aniline was observed as a colorless
to pale yellow liquid with a fishy odor, soluble in organic solvents. Benzene is
unavailable so I wasn’t able to see it in real time, however, benzenes appear as a
clear, colorless liquid with a sweet odor, highly volatile and flammable. Lastly,
Naphthalene was noted as white crystalline solid with a strong mothball odor,
sparingly soluble in water but soluble in organic solvents.

Next, we mixed one drop of an aromatic compound with five drops of

chloroform and after mixing we tilted the test tubes and added about 0.5 grams of
anhydrous aluminum chloride at the surface of the liquid and further observe the
reactions. This reaction is called Friedel-Crafts reaction. The resulting solution
exhibited a change in color, with the formation of a colored precipitate. The color
changes and the appearance of the precipitate were recorded for further analysis.
Upon mixing with chloroform and the addition of anhydrous aluminum chloride, the
initially colorless solution of toluene undergoes a transformation, manifesting a
change in color, to a darker hue. This alteration indicates the formation of a complex
between toluene and the aluminum chloride, resulting in the precipitation of a colored
product. Toluene settles at the bottom and there are bubbles that forms like a barrier.
After being mixed they don’t still combine and the color stays the same. When I
introduced phenol to chloroform and anhydrous aluminum chloride, the solution's
color undergoes a discernible shift, becoming tinted or exhibiting a change in hue.
The layer of light color stays at top and the color turned into dark red. They do not
combine completely and the AlCl3 stays at the bottom. The observed alteration in
the solution's appearance serves as evidence of the chemical interaction between
phenol and the reagents, contributing to the understanding of its chemical properties.
Aniline, upon mixing with chloroform and anhydrous aluminum chloride, prompt a
noticeable change in the solution's color, indicating a chemical transformation. In
CHCl3 the two chemicals combined and there is no change in its color. Then, adding
the AlCl3 there is a crystalize-like substance and the crystals or tidbits rocks
changed into yellow brown along with the CHCl3. Lastly, I mixed naphthalene with
chloroform and anhydrous aluminum chloride and it led to changes in the solution's
color, signaling a chemical transformation. Powder totally dissolved and the color
changed from colorless to golden brown/ pinkish and it settles at the bottom and
when shaking the color disappear. The observed alterations in the solution's
appearance and the formation of a precipitate offer insights into the reactivity and
behavior of the aromatic hydrocarbons in the experimental conditions.

Unfortunately, the bromination step could not be conducted due to the

unavailability of bromine. However, this step would typically involve the addition of
bromine to the aromatic hydrocarbons to observe the halogenation reaction.

Moving on, the aromatic hydrocarbons was subjected to a reaction with dilute
potassium permanganate solution. When toluene is mixed with potassium
permanganate (KMnO4), it undergoes an oxidation reaction. Layer of the toluene
stays at the top and the color turned into a darker color. Toluene is oxidized to
benzoic acid in the presence of KMnO4. The purple color of the potassium
permanganate solution may fade as it reacts with toluene, indicating the
consumption of the oxidizing agent. When phenol was in contact with KMnO4, the
color turned into dark brown and there is powder like solids that formed and it turns
into light brown. Next, I mixed aniline with KMnO4 and observed that the color turned
into a light brown or coffee color and there were bubbles forming at the bottom of the
test tubes. Lastly, when KMnO4 was mixed with naphthalene, the color remains the
same and it doesn't combine thus the powder settles at the bottom. When aromatic
hydrocarbons are mixed with potassium permanganate (KMnO4), they typically
undergo oxidation reactions. The benzene ring in aromatic compounds can be
oxidized by KMnO4 to form carboxylic acids. The reaction results in the cleavage of
the aromatic ring, forming benzoic acids or other carboxylic acids as the primary
products. Additionally, depending on the specific aromatic compound and reaction
conditions, other oxidation products may also be formed. The purple color of the
potassium permanganate solution may fade as it reacts with the aromatic
hydrocarbon, indicating the consumption of the oxidizing agent.
 Lastly, we performed the ignition test with the aromatic hydrocarbons. The
flame produced was noted for its color, intensity, and duration, providing insights into
the combustibility and properties of toluene upon ignition. A small quantity of toluene
was ignited in an evaporating dish, there were black smoke coming out from the fire.
The flame produced was yellow to blue in color, and black soot forms on the surface
of the evaporating dish. The intensity of the flame is relatively bright. The duration of
the flame lasts for several seconds. Next, I ignited phenol in the evaporating dish,
the liquid does not burn or dissolve. Phenol turns into a fuel of the match sticks. the
mechanism is similar to a candle. The flame produced appears yellowish-orange or
even bluish in color. The intensity of the flame is moderate to high, emitting
significant heat. The duration of the flame lasted for several seconds. Aniline, ignited,
the produced flame exhibits a yellow to orange color, with a moderate to high
intensity, emitting significant heat. The duration of the flame was typically short. It
acts as a fuel to the match sticks like what happened to phenol. In the case of
naphthalene, it turned to liquid and the flame produced was bright orange-yellow in
color, with a high intensity, emitting considerable heat. The duration of the flame
lasted for a few seconds before extinguishing. Each ignition left a trace of black
smoke and soot.

Overall, the experiment aimed to delve into the physical and chemical
characteristics of aromatic compounds, shedding light on their behavior in various
reactions and providing a deeper understanding of their properties in organic
chemistry.
 II. Tabulated data / result:
Table 9.1 properties of AROMATIC HC
Hydrocarbon Physical State Color Solubility in H2O Density compound to
water
Toluene Liquid Colorless Poorly soluble in water Toluene is less dense
than water
Phenol Liquid Red Soluble in water Higher density than
water
Aniline Oily Liquid Colorless to Moderately soluble in Denser than water
Brown water.
Benzene Liquid Colorless or Immiscible with water Less dense than water
Light-Yellow
liquid
Naphthalene Solid White Naphthalene dissolves Denser than water
only very slightly in
water and sinks as a
solid.

Table 9.2 Reactions of Aromatic HC

Hydrocarbon CHCl3/AlCl3 Br2 light Br2 dark Dilute KmnO4 Combustion
Toluene Undergoes a This reaction may This reaction It undergoes an There were
transformation, cause the bromine results in a color oxidation black smoke
coming out
manifesting a solution to change change from the reaction. Layer
from the fire.
change in color, color from red- reddish-brown of the toluene The flame
to a darker hue. brown to colorless tint of bromine to stays at the top produced
was yellow to
Toluene settles or a lighter tint as a colorless and the color
blue in color,
at the bottom the bromine is solution. Excess turned into a and black
and there are consumed. bromine may darker color. soot forms
on the
bubbles that Furthermore, the also cause the The purple color
surface of
forms like a presence of a hazy production of a of the potassium the
barrier. After or precipitated white precipitate permanganate evaporating
being mixed they solution could of hydrogen solution may dish. The
intensity of
don’t still indicate the bromide (HBr). fade as it reacts the flame is
combine and the development of the with toluene, relatively
color stays the bromotoluene indicating the bright. The
duration of
same. product. consumption of
the flame
the oxidizing lasts for
agent. several
 seconds.
Phenol The solution's This reaction's Initially, the The color turned The liquid
color undergoes a physical features mixture will turn into dark brown does not burn
or dissolve.
discernible shift, include bromine brown. As the and there is
Phenol turns
becoming tinted or decolorization. reaction develops, powder like solids into a fuel of
exhibiting a The exothermic the brown color that formed and it the match
sticks. the
change in hue. nature of the process fades, suggesting turns into light
mechanism is
The layer of light may also cause a bromine brown. similar to a
color stays at top modest temperature consumption. This candle. The
flame
and the color increase. reaction is often
produced
turned into dark used to detect the appears
red. They do not presence of yellowish-
combine phenol since it is orange or
even bluish in
completely and the selective to phenol color. The
AlCl3 stays at the and other aromatic intensity of the
bottom. chemicals. flame is
moderate to
Additionally, the
high, emitting
phenol will have a significant
unique odor. heat. The
duration of the
flame lasted
for several
seconds.

Aniline Prompt a The physical Bromine's reddish- The color turned Produced
noticeable change properties noticed brown color may into a light brown flame exhibits
a yellow to
in the solution's during this reaction fade as a result of or coffee color
orange color,
color. In CHCl3 include a color the reaction with and there were with a
the two chemicals change, with aniline. This bubbles forming moderate to
high intensity,
combined and bromine's reddish- reaction produces at the bottom of
emitting
there is no change brown tint a colorless or pale- the test tubes. significant
in its color. Then, disappearing as it yellow solution. heat. The
duration of the
adding the AlCl3 combines with
flame was
there is a aniline. typically short.
crystalize-like It acts as a
substance and the fuel to the
match sticks
crystals or tidbits like what
rocks changed into happened to
yellow-brown phenol.

along with the

CHCl3.
Benzene The mixture of Benzene and The hue of the Potassium Benzene
benzene and bromine are both bromine fades permanganate is burns with a
colorless at first, but gradually as it a dark purple brilliant,
aluminum chloride
then turn reddish combines with crystalline solid, luminous
appears colorless brown. However, as benzene to form whereas benzene flame, usually
to pale yellow the reaction colorless. There is a colorless blue in color,
develops, you will may be a modest liquid. So, when signifying full
liquid or solid. The
notice the brown increase in you mix them, the combustion.
development of color of bromine fade temperature. purple crystals of
the adduct can as it is potassium
consumed. The permanganate will
cause a significant
reaction mixture may be scattered in
increase in become hazy. This the colorless
viscosity when process is benzene. There
compared to pure exothermic, would be no
therefore there may discernible
benzene. be a little increase in difference in the
Furthermore, the temperature. physical
mixture may emit properties of
either substance,
heat when mixed,
such as color,
indicating an odor, or look.
exothermic
reaction.

Naphthalene It led to changes in Bromine's reddish- The intense The color remains It turned to
the solution's brown color reddish-brown the same and it liquid and the
decreases as it is color of bromine doesn't combine flame
color. Powder
consumed, and the fades when it thus the powder produced was
totally dissolved reaction mixture may combines with settles at the bright orange-
and the color turn yellowish-brown naphthalene. The bottom. yellow in color,
due to the creation of development of with a high
changed from
brominated solid products may intensity,
colorless to golden naphthalene cause a decrease emitting
brown/ pinkish and derivatives. in the volume of considerable
Additionally, the odor the reaction heat. The
it settles at the
may alter. mixture. duration of the
bottom and when flame lasted
shaking the color for a few
disappear. seconds
before
extinguishing.
Each ignition
left a trace of
black smoke
and soot.
III. Question:
1. What are the formulas of the above HC’s?
Toluene: C6H5CH3

Phenol: C6H5OH

Aniline: C6H5NH2

Benzene: C6H6

Naphthalene: C10H8

2. Write the equations for the complete combustion of test compounds.

Toluene: C7H8 + 9O2 → 7CO2 + 4H2OC7H8 + 9O2 → 7CO2+4H2O

Phenol: C6H5OH + 7O2 → 6CO2 + 3H2O

Aniline: C6H5NH2 +7.5O2 → 6CO2 + 3H2O + NH3

Benzene: C6H6 + 15O2 → 6CO2 + 3H2O

Naphthalene: C10H8 +12O2→ 10CO2 + 4H2O

Generalization:
In the experiment, the physical properties of the aromatic compounds were
examined, which included their appearance (such as color and state), odor, and
solubility in different solvents. This step helps in identifying and characterizing these
compounds based on their unique physical characteristics.

Next, the chemical reactions of the aromatic compounds with various

substances were investigated. For example, the reaction with CHCl3/AlCl3, known
as the Friedel-Crafts reaction, is a method to introduce alkyl or acyl groups into
aromatic compounds. The reaction with Br2 in light and dark conditions is used to
determine the presence of unsaturation in the compounds, as benzene and other
aromatic compounds undergo substitution reactions rather than addition reactions.
The reaction with dilute KmnO4 is a test for the presence of double or triple bonds in
the compounds, as it oxidizes these functional groups.

Finally, the ignition of each compound was observed to determine the

characteristics of their flames, which can provide information about their combustion
properties and chemical structure. Overall, the experiment aimed to deepen our
understanding of the physical and chemical properties of aromatic compounds,
which are essential in organic chemistry research and applications.