Mesia, Jacquiline R.

July 27, 2019

Experiment 8
Aromatic Hydrocarbons
INTRODUCTION

An aromatic hydrocarbon or arene (or sometimes aryl hydrocarbon) is a hydrocarbon with sigma
bonds and delocalized pi electrons between carbon atoms forming a circle. The term "aromatic" was
assigned before the physical mechanism determining aromaticity was discovered; the term was coined as
such simply because many of the compounds have a sweet or pleasant odor. The configuration of six carbon
atoms in aromatic compounds is known as a benzene ring, after the simplest possible such hydrocarbon,
benzene. It can be divided into mono-cyclic aromatic hydrocarbon, polycyclic aromatic hydrocarbon and
non-benzene aromatic hydrocarbons. For monocyclic aromatic hydrocarbon, its molecule contains only
one benzene ring, such as toluene, xylene, ethylbenzene, styrene, benzene and acetylene. On the other
hand, polycyclic aromatic hydrocarbon contains two or more benzene rings.

According to the interconnected ways of benzene ring, it can be divided into:

1. Polybenzo-aliphatic hydrocarbons including diphenylmethane, triphenylmethane, stilbene, styrene

and so on.
2. Biphenyl and polybenzene, such as biphenyl, terphenyl and tetraphenyl.
3. Polycyclic aromatic hydrocarbons such as naphthalene, anthracene, phenanthrene, indene,
fluorene, acenaphthene, pyrene, coronene and so on.

In this experiment, 3 compounds were used – benzene, toluene, and xylene.

METHODS:

A. Physical State

1. Label three test tubes as Test Tube #1 (Benzene), Test Tube #2 (Toluene) and Test Tube #3
(Xylene) and then add 10gtts of distilled water.

2. Observe the physical state of the entire sample at Room Temperature.

3. Note the color and odor with a waling motion of hand.

B. Ignition Test

A. Combustion
1. In evaporating dish #1-3, add 5 gtts of each sample
2. Ignite and light with a match. Observe the color of the flame and soot.

B. Oxidation
1. In Test Tube #1-3, add 10 gtts of each sample and 10 gtts of KMnO4. Mix.
 2. Heat in water bath for 10 mins. Note the change in color.

C. Bromination
1. In Test Tube #1-3, add 10 gtts of each sample and 10 gtts of Bromine CCl4. Mix.
2. Heat in water bath for 10 mins. Note the change in color.

D. Nitration
1. In TEST TUBE #1-3, add 10 gtts of each sample and 10 gtts of Nitrating mixture. Mix
2. Heat in water bath for 10 mins. Note the change in color.

RESULTS:

Benzene Toluene Xylene

Physical state at RT Liquid Liquid Liquid
Color Colorless Colorless Colorless
Odor Sweet gasoline-like smell Sweet pungent smell Faint sweet smell
Combustion Flammable – Flammable – Non-flammable
Orange flame with black Orange flame with black
soot soot
Oxidation No changes Lightened color brownish
Nitration Yellow top layer – Yellow top layer – Red top layer –
clear bottom layer clear bottom layer orange bottom layer

Ignition test: combustion

Ignition test: oxidation

Nitration

DISCUSSION

Based on the experiment conducted, the benzene and toluene burned and give off an orange
colored sooty flame. This soot is the product of incomplete combustion, notably unreacted carbon
particles, that heat up and glow causing the flame to be yellow and luminous. The chemistry of this
incomplete combustion is very complex and will change depending on the amount of oxygen present.
When benzene undergoes combustion in air, the carbon and hydrogen atoms combine with the molecules
of oxygen present in air to form carbon dioxide and water respectively. Xylene was the only compound that
did not ignite.

Typically, aromatic hydrocarbons are somewhat resistant to chemical oxidation. However, under
biologic conditions aromatic rings may be readily oxidized by cytochrome enzymes to phenol metabolites.
Due to their high ratio of carbon to hydrogen, aromatic compounds are characterized by a sooty yellow
flame. The chemical reaction in which reactant combines with oxygen or loses hydrogen to form the
product is called oxidation reaction.

Nitration happens when one (or more) of the hydrogen atoms on the benzene ring is replaced by
a nitro group, NO2. In the case of nitration of benzene, the reaction is conducted at a warm temperature.
The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-
rich benzene ring: