Nitration of Benzene: Adia, Sophia Cassandra, A

CHM150L Organic Chemistry 1 Laboratory
1st Quarter SY 2019-2020
Nitration of Benzene
Adia, Sophia Cassandra, A.1
Adia, Sophia Cassandra A., CM150L/B11, School of Chemical, Biological and Material Engineering and Science, Mapua University
ABSTRACT
An alkene bond (C꓿C) is formed by overlapping the p orbitals of the sp2 hybridized carbons. It is the high-energy rotating
layer around the C꓿C which produces the probability of alkene stereoisomers. An alkene system's cis and trans isomers
are either diastereoisomers, or diastereomers. Diastereomers, possesses different physical properties. The objectives of
this experiments are: synthesize an isomer of an alkene, convert maleic acid to fumaric acid and understand the properties
of isomers. Based from the results and discussion of first experiment under this course, maleic acid and fumaric acid have
the same properties yet have a large range between its melting points. Theoretically, these two compounds are isomers.
Maleic acid is categorized as the cis-isomer this is due to the its structure while fumaric acid is a trans isomer. Cis-trans
isomerism deals with the same order of attachment (connectivity) of their atoms, but with a different arrangement of their
atoms in space due to the presence of either a ring or a carbon double bond. Conformation also influences the physical
properties. Due to the crowding of two alkyl groups on the same side of a double bond, cis isomers are typically less stable
than trans isomers. A cis alkene would usually be less stable than its trans alkene stereoisomeric.
Keywords: diastereomers, cis isomers, trans isomers, alkene, steric hindrance
INTRODUCTION
The chemical formula for benzene, C6H6, indicates a high Figure 1.1. Orbital Overlap Model of Benzene (Source:
degree of unsaturation. It has two molecular structures and Introduction to Organic Chemistry 5th Edition, Brown & Poon
formulas: an alkane with six carbons has a molecular 2014)
formula of C6H14, and a cycloalkane with six carbons has a
molecular formula of C6H12. In spite of this characterizations Each Kekulé structure contributes equally to the hybrid;
benzene possess, it is unreactive therefore it does not thus, the C-C bonds are not single or double bonds, but
undergo the addition, oxidation and reduction reactions. something intermediate.
Benzene undergoes chemical reactions, but rather than
addition, the characteristic reaction is substitution. The
benzene carbon skeleton forms a regular hexagon with
120° angles of C-C-C and H-C-C bond. Carbon uses sp2
hybrid orbitals for this form of bonding. Through overlapping
sp2–sp2 hybrid orbitals and one sigma bond to hydrogen by
interfering sp2–1 orbitals, each carbon forms sigma bonds
to two adjoining carbons. Figure 1.2. Resonance Model of Benzene (Source:
Introduction to Organic Chemistry 5th Edition, Brown & Poon
2014)
Resonance energy is the energy difference between a

resonance model and its most stable theoretical
contributing structure. One way to calculate the benzene
resonance energy is to compare the cyclohexene and
benzene hydrogenation heats.
Experiment 12│ Group No. 3│ 10/14/19 1 of 3

Figure 1.3. Resonance Energy of Benzene (Source:

Introduction to Organic Chemistry 5th Edition, Brown & Poon
2014)
MATERIALS AND METHODS
A cold bath is first prepared for the first part of the

experiment. A 12 mL of concentrated nitric acid is
transferred into the round bottom flask. The flask is
immersed into the cold water bath while adding 13.60 mL Figure 3.1. Mechanism of Nitration of Benzene
concentrated sulphuric acid, 1.0 mL at a time while shaking.
Then 14.40 mL is transferred into 14.40 mL of benzene This reaction is carried out via an electrophilic aromatic
using a pipette. After the addition of the reagents, the flask substitution wherein the electrophile is assumed to be a
is placed into the set up of a hot water bath. The mixture nitronium ion (NO2+). A solid electrophile is formed from the
maintained a 55˚C and 60˚C. After 45 minutes of heating, HNO3-H2SO4 acid-base reaction. Nitric acid serves as a
the solution is cooled down before transferring it to a 50 mL basis for accepting a sulfuric acid proton, followed by water
separatory funnel. The acid layer is denser than loss to create a nitronium ion.
nitrobenzene after letting the mixture settle down for a few
minutes. Then the acid layer is carefully withdrawn. For the There is a nitration reaction in which nitrobenzene is formed
nitrobenzene product, it was washed with 15 mL distilled when benzene is treated with a combination of nitric acid
water twice, then a 15 mL of 1 M NaOH then washed again and sulfuric acid. Sulfuric acid is a much stronger acid than
with another 30 mL of water. For the distilled water to be nitric acid, and it will protonate nitric acid when mixed
removed in the solution, a 3.0 g CaCl 2 was added to the together. The resulting nitronium ion then serves as an
crude product. This was shaken for a few minutes. The electrophile in an electrophilic. (Klein, 2017)
liquid was obtained through decantation. The liquid is
weighed and recorded as the crude product. The distillation CONCLUSIONS AND RECOMMENDATIONS
set up is used to purify the product. The boiling point of the
liquid was hypothetically 200˚C to 210˚C. When the The students failed to finish the experiment due to the
distillate was collected, it was weighed and recorded. inadequate time and quality of apparatus used in the
experiment. Thus, they didn’t accomplished the said
2 drops of the distillate was transferred into the micro test objectives.
tube and 0.50 mL of acetone and 2 drops of 1 M NaOH was
added and noted. The students highly recommend the future researchers to
do this experiment in a fast phase. It takes a long time for
RESULTS AND DISCUSSIONS the compound to boil and should be thinking for another
alternative. The students would recommend heating the
No table is used for this chapter of the lab report due to the flask with a Bunsen burner as well to add to the heat of the
lack of data that the students attained during the compound. In this way, it has two main source of heat that
experiment. Only the weigh of the crude product, which is would double up the chances of reaching 200˚C in a short
5.59 g, was useful for this experiment due to the time.
thermometer not reaching 200˚C or the hot plate wasn’t hot
enough. REFERENCES

1. Brown, W.H. & Poon, T. 2014. Introduction to

Organic Chemistry. 5th Edition. John & Wiley SOns
2. Klein, D. 2017. Organic Chemistry. 3rd Edition.
John Wiley and Sons, Inc. ISBN 978-1-119-31615-
2

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CHM150L Organic Chemistry 1 Laboratory

1st Quarter SY 2019-2020

Keywords: diastereomers, cis isomers, trans isomers, alkene, steric hindrance

Resonance energy is the energy difference between a

Experiment 12│ Group No. 3│ 10/14/19 1 of 3

Figure 1.3. Resonance Energy of Benzene (Source:

MATERIALS AND METHODS

A cold bath is first prepared for the first part of the

Experiment 12│ Group No. 3│ 10/14/19 2 of 3

1. Brown, W.H. & Poon, T. 2014. Introduction to

Experiment 12│ Group No. 3│ 10/14/19 3 of 3

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