Exercise no.

8a

CLASSIFICATION TESTS FOR FUNCTIONAL GROUPS:

Aromatic Hydrocarbons

Valerie Mae L. Areño October 21, 2019

Monday 7-10AM October 28, 2019

INTRODUCTION

Aromatic hydrocarbons are one of the three classes of compounds found in petroleum. They
are less abundant than the alkanes and cycloalkanes, amounting to only a few percent of the
total, but they are quite important commercially. Most aromatic hydrocarbons contain a
benzene ring.

OBJECTIVES

 Know the different chemical test of aromatic hydrocarbons.

 Show the chemical equations involved in classifying tests.

DISCUSSION

Aromatic compounds such as benzene are example of unsaturated hydro-carbon due

to presence of alternating compounds in the bound. It is a special type of hydrocarbon
compounds it is because it forms cyclic in the structures which means it forms a ring. It
would not behave as to compare with alkenes it is because aromatics are very stable. A
compound may only qualify to aromatics when it obeys the huckel’s rule giving a formula
4n+2 where n is the number of pi bonds present in the structure also it must be integer
in number and would not give in a fraction. Perfect example for this is benzene. In
the first e x p e r i m e n t N i t r a t i o n , B e n z e n e w o u l d r e a c t i o n i n n i t r a t i o n
H e n c e i t reacts with considerable rate, with nitrating mixture to form nitrobenzene.
Reactivity towards electrophilic substitution is influenced by the substituents present on the
ring.
QUESTIONS

1. Does benzene behave in the same manner as the other unsaturated hydrocarbons?
2. What is the role of concentrated sulfuric acid in the nitrification of benzene?
3. Show the mechanism reaction of:
a. Nitrification reaction
b. Le Rosen Reaction

ANSWERS

1. Benzene does behave the same way as the other unsaturated hydrocarbons. Because the
structure of benzene contains 3 alternate single double bonds. However, benzene gives
mostly substitution products because the benzene ring is resonance stabilized. Thus, it
behaves in a different manner as compared to other unsaturated compounds. However,
with strong oxidizing agent like Vanadium Pentoxide gives maleic and anhydride. The
proof of unsaturation in Benzene can be obtained by referring to the structure of the
products obtained on its ozonolysis.

2. The source of the nitronium ion is through the protonation of nitric acid by sulfuric
acid, which causes the loss of a water molecule and formation of a nitronium ion. The
first step in the nitration of benzene is to activate HNO3 with H2SO4 to produce a
stronger electrophile, the nitronium ion. Because the nitronium ion is a good
electrophile, it is attacked by benzene to produce Nitrobenzene.

3. Reaction Mechanism:

A. Nitrification Reaction
 B. Le Rosen Reaction

RESULTS AND OBSERVATION

A. Test for Aromaticity

Structure/ Formula of
Test Reagent Visible Result cpd Responsible of
Visible Result

Hexane White precipitate,

H2SO4 and HNO3 Nitrobenzene
strong odor

Nitration
Have some
Benzene H2SO4 and HNO3
precipitate, odorless

Bubbles formed, has

Benzene 2 layers, and does not
have any visible color.
Le Rosen

It is miscible and does

Hexane
have no visible color.
 B. Ignition Test

Test Sample Observation

Hexane Evaporated after boiling.

Benzene Appeared in a yellow smoke flame and burned.

CONCLUSION

Aromatic hydrocarbon compounds are hydrocarbons containing one or more aromatic rings,
such as the single-ring benzene as well as the multiring systems: naphthalene, anthracene,
and phenanthrene ring systems, which may be linked up with (substituted) naphthene rings
and/or paraffinic side chains. Benzene is the simplest and most stable aromatics and is a single-
ring system that contains conjugated double bonds. Thus, every carbon atom in the ring is
sp2 hybridized, allowing for added stability of the ring system. In this experiment, we clearly
concluded that Benzene is an unsaturated compound, and the source of nitrimuniom ion is from
the protonation of nitric acid by the sulfuric acid.

REFERENCE

 Price, C. "Summary of available production volumes in millions of gallons per year for
selected volatile organic compounds(VOCs) studied by the National Water Quality
Assessment(NAWQA) Program." USGS. March 07, 2005.
water.usgs.gov/nawqa/vocs/national_assessment/aboutvocs/prod_data.xls