MODULE 3

BENZENE AND ITS DERIVATIVES

………………………………………………………………………………………………………………….
I. INTRODUCTION

This module will explain the physical and chemical properties of alkanes, alkenes, and alkynes.
Alkanes the simplest type of organic compounds. Actually alkanes are members of a large class of
organic compounds called hydrocarbons. A hydrocarbon is a compound composed only of carbon and
hydrogen. Alkanes are saturated hydrocarbons; that is, they contain only carbon – carbon single bonds.
Saturated in this context means that each carbon in the hydrocarbon has the maximum number of
hydrogen bonded to it; an alkane is also often referred to as aliphatic hydrocarbon.
A hydrocarbon that contains one or more carbon – carbon double bonds, triple bonds, and
benzene rings is classified as an unsaturated hydrocarbon. In this module, you will study alkanes
(saturated hydrocarbons); alkenes, alkynes and arenes (the unsaturated hydrocarbons).

II. MODULE CONTENTS:

This module is divided into lesson 1 and lesson 2; Lesson 1 is about Naming Aromatic
Compounds; Lesson 2 is about Characteristics of Benzene and its Derivatives.

III MODULE LEARNING OUTCOMES

In this module, you are expected to:

1. explain the rules in naming Aromatic compounds;

2. determine the characteristic reaction of Benzene and its derivatives; and
3. relate the importance of Benzene and its derivatives in your College of Criminal Justice
Education.

IV Specific Learning Outcomes

In his lesson, the students should be able to:

1. Relate the importance of Benzene in the field of criminology;

2. Explain the differences between the characteristic reaction of Benzene and its derivatives;and
3. solve simple problems on writing, and naming Benzene and its derivatives.

V PRE-ASSESSMENT

Direction: Read each question carefully. Choose the letter of the best answer, and write the letter of
your choice on the space provided for each number
1. Which of the following has a molecular structure of C6H6?
a. alkanes
b. alkenes
c. alkynes
d. benzene
2. Who developed the resonance structure of benzene?
a. Friedrich Kekule
 b. Linus Pauling
c. Isaac Newton
d. James Chadwick
3. What is the term used to described the individual Lewis structure in the resonance structure of
benzene?
a. Resonance Hybrid
b. Contributing structure
c. Kekule Structure
d. Resonance Lewis structure
4. Which of the following locators indicates a consecutive placement of substituents as represented by
1,2- ?
a. meta
b. ortho
c. para
d. giga
5. Halogenation occurs when a halogen reacts with benzene. Which of the following is a halogen?
a. Iron
b. Neon
c. Chlorine
d. Hydrogen
6. What element allows halogens to react rapidly with benzene?
a. Iron
b. Neon
c. Chlorine
d. Hydrogen
7. What characteristic reactions of benzene occurs when a nitro (-NO2) group replaces one of the
hydrogen atoms bonded to the ring?
a. Halogenation
b. Nitration
c. Sulfonation
d. Acidity
8. Which of the following locators indicates a opposite placement of substituents as represented by 1,4-
in benzene?
a. Meta
b. Ortho
c. Para
d. phenyl
9. Which of the following is not a halogen?
a. Fluorine
b. Chlorine
c. Barium
d. Bromine
10. Which of the following locators is represented by 1,4- in benzene?
a. Ortho
b. Meta
c. Para
d. substituent

VI LESSON MAP

Aromatic Compounds

Benzene and its

derivatives

Structure of Benzene Characteristic

and its derivatives Reactions of Benzene
and its derivatives
Naming Benzene and
its derivatives

Kekule’s Structure Halogenation

IUPAC System
Nitration
Resonance Structure

Sulfonation

The map describes the content of the module 4. This module will discuss the structure of
Benzene as well as naming using the IUPAC system and the characteristic reactions of
Benzene and its derivatives

VII CORE CONTENT

a. ENGAGE: LIGHTING A SPARK!

Activity 1: READING ACTIVITY

Instruction. Read the selection below and answer the questions that follow.

Benzene and two of its derivatives

Benzene and Worker Cancers: “An American Tragedy”

Bloated and bed-ridden, his skin browned by blood transfusions, John

Thompson succumbed to leukemia on November 11, 2009. A carpenter by trade,
Thompson, then 70, had spent much of his life building infrastructure for the
petrochemical industry in his native Texas — synthetic rubber plants in Port Neches,
chemical facilities in Orange. Throughout the 1960s and early 1970s, he often
encountered benzene, stored on job sites in 55-gallon drums, which he used as a
cleaning solvent. He dipped hammers and cutters into buckets full of the sweet-
smelling liquid; to expunge tar, he soaked gloves and boots in it.
Thompson never figured the chemical could do him harm. Not when it stung
his hands or turned his skin chalky white. Not even when it made him faint. But after
being diagnosed with a rare form of leukemia in 2006, relatives say, he came to
believe his exposure to benzene had amounted to a death sentence. Oil and
chemical companies knew about the hazard, Thompson felt, but said nothing to him
and countless other workers.
Thompson died before a lawsuit filed by his family against benzene suppliers
could play out in court, where science linking the chemical to cancer could be put on
display. Over the past 10 years, however, scores of other lawsuits, most filed by sick
and dying workers like Thompson, have uncovered tens of thousands of pages
of previously secret documents detailing the petrochemical industry’s campaign to
undercut that science.
Although there limitations implemented by the government to reduce and
control exposure to harmful Benzene compounds, a 2004 National Cancer Institute
suggested there’s no safe threshold for people working with the chemical .

Source:https://publicintegrity.org/environment/benzene-and-worker-cancers-an-american-tragedy/

Process Questions:
1. What do you think should be done to limit the workers’ exposure to Benzene?
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2. Cite a similar case in the Philippines, wherein Benzene or other harmful chemicals were involved
in the demise or had cause an injury to an individual.
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3. As a future law enforcer, what laws do you think should be implemented to limit exposure of
factory workers to harmful chemicals aside from Benzene?
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4. Why is it important to study Benzene and its derivatives?

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b. EXPLORE: DISCOVERING BENZENE AND ITS DERIVATIVES

Activity 2: Reading and Analysing Activity

Instruction: Carefully read the texts below. The information you gather here will be used in the latter
sections of this lesson.

A. What is the Structure of Benzene?

Benzene, the simplest aromatic hydrocarbon, was discovered by Michael Faraday in 1825. Its
structure presented an immediate problem to chemists of the day. Benzene has a molecular formula of
C6H6, and a compound with so few hydrogens or its six carbons, chemists argued, should be
unsaturated. But Benzene does not behave like an alkene (the only class of unsaturated hydrocarbons
known at that time). Whereas 1-hexene, for example, reacts instantly with BR2, benzene does not react
at all with this reagent. Nor does benzene react with HBr, H2O/H2SO4,or H2/Pd – all reagents that
normally add to carbon-carbon double bonds.

Kekule’s Structure of Benzene

 The first structure for benzene was proposed by Friedrich August Kekule in 1872 and consisted o
a six-membered ring with alternating single and double bonds, with one hydrogen bonded to each
carbon.

Although Kekule’s proposal was consistent with many of the chemical properties of benzene, it
was contested or years. The major objection was its failure to account for the unusual behaviour of
benzene. If benzene contains double three bonds, Kekule’s critics asked,why doesn’t it undergo
reactions typical of alkenes?

Resonance Structure of Benzene

The concept of resonance, developed by Linus Pauling in the 1930s, provided the first adequate
description of the structure of benzene. According to the theory of resonance, certain molecules and
ions are best described by writing two or more Lewis structures and considering the real molecule or ion
to be a resonance hydrid of these structures. Each individual Lewis structure is called a contributing
structure. Toshow that the real molecule is a resonance hybrid of two Lewis structures, we position a
double headed arrow between them.

Alternating Lewis contributing structures for benzene

B. HOW DOWE NAME AROMATIC COMPOUNDS?
 a) One Substituent
Monosubstituted alkylbenzenes are named as derivatives of benzene – for example,
ethylbenzene. The IUPAC system retains certain common names for several of the simpler
monosubstituted alkylbenzenes, including toluene and tyrene.

The IUPAC system also retains common names for the following compounds;

b) Two Substituent
When two substituents occur on a benzene ring, three isomers are possible. We locate the substituteens
either by numbering the atoms of the ring or by using the locators ortho (o), meta (m), and para (p). The
numbers are 1,2- are equivalent to ortho; 1,3- to meta; and 1,4- for para.

When one of the two substituents on the ring imparts a special name to the compound (for example, -
CH3, -OH, -NH2, or -COOH), we name the compound as a derivative of that parent molecule and
assume that the substitutuent occupies ring position number 1. The IUPAC system retains the common
name xylene for the three Isomeric dimethylbenzenes. Where niether substituent imparts a special
name, we locate the two substituents and list them in the alphabetical order before ending the
“benzene”. The carbon of the Benzene ring with the substituent of lower alphabetical ranking is
numbered C-1.
C) Three or More Subtituents
When three or more subtituents are present on a benzene ring, specify their location by
numbers. If one of the substituents imparts a special name, then name the molecule as a derivative of
parent molecule. If none of the substituents imparts a special name, then locate the substituents,
number them to give the smallest set of numbers, and list them in alphabetical order, before the ending
“benzene”. In the following examples, the first compound derivative of toluene and the second is a
derivative of phenol. Because no substituent in the third compound imparts a special name, list its three
substituents in alphabetical order followed by the word “benzene”.

C. WHAT ARE THE CHARACTERISTIC REACTIONS OF BENZENE AND ITS DERIVATIVES?

The most charactristics reaction of aromatic compounds is substitution at a ring carbon, which
we give the name aromatic substitution.
A. Halogenation
Halogens are the elements that belong to group VIIa of the periodic table. The halogen elements
are fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). Chlorine (Cl)
and Bromine (Br) do note react with benzene under normal circumstances, but when the presence of
iron is used as a catalyst, both halogens react rapidly with benzene. Halogenation occurs when a
halogen reacts with benzene.

B. Nitration
When we heat benzene or one of its derivatives with a mixture of concentrated nitric and sulfuric
acids, a nitro (-NO2) group replaces one of the hydrogen atoms bonded to the ring.
 C. Sulfonation
Heating an aromatic compound with concentrated sulfuric acid results in formation of an
arenesulfuric acid, all of which are strong acids, comparable in strength to sulfuric acids.

c. EXPLAIN

Activity 3: CRITICAL THINKING

Instruction: Answer the questions below.
1. How does the presence of Iron affects Halogenation?
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2. How does the following occur?

a) Halogenation
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b) Sulfonation
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c) Nitration
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Activity 4: Chemical Connections

Instruction: Read the selection below and answer the questions that follow.
 The Nitro Group in Explosives

Treatment of toluene with 3 moles of nitric acid in the presence of sulfuric acid as catalyst
results in nitration of toluene three times to form the explosives 2,4,6-trinitoluene, TNT. The
presence of these three nitro groups confers explosive properties to TNT. Similarly, the presence of
three nitro groups leads to the explosive properties of nitroglycerin.
In recent years, several new explosives have been discovered, all of which contain multiple
nitro groups. Among then are RDX and PETN. It was used in the destruction of Pan Am flight 103
over Lockerbie, Scotland, in December 1988.

PROCESS QUESTIONS:

1. Toluene is one of the derivatives of benzene frequently used in creating explosives. Can you identify
atleast 2 other derivatives of benzene used in similar areas?
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2. Based on the selection above, what characteristic reaction of benzene is used in the process of
creating explosives?
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3. Can you identify similar cases in the Philippines, wherein a benzene or its derivatives is used as a
component in using explosives?
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4. What measures does the government implement to prevent terror attacks from homemade
explosives?
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5. Does the Philippine government implement laws against terror attacks such as the destruction of Pan
Am flight 103? State the law and elaborate.
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d.. EXTEND

Activity 5: CONNECTING TO THE REAL WORLD

Instruction: Identify a Terrorist attack similar to the case of Pan Am flight 103 wherein
explosives/weapons used contains benzene or any of its derivative. Make a Narrative report on
the event highlighting the following:
A. Setting (time and date) - When and Where did the event happened?
B. Casualty (injured and death) - How many were injured? How many died?
C. Weapons used (Explosives, gun, poison, etc.). - What type of weapon/s was used?
D. Indicate the substance (benzene or any of its derivative) used. - What substances were used?
E. How did the authorities of the area respond to the attack?
F. Include pictures if any.
Requirements:
1. Your Paper should follow the following format:
Paper size: Short Bond Paper
Font size: 12
Font Style: Arial
Margin: Normal
2. Submit your paper in PDF format through a google drive link. Allow my personal gmail account -
[email protected] - so that I can view it anytime.
3. Date of submission is on or before May 15, 2021.

e. EVALUATE
f.

Activity 6: Naming Benzene and its derivatives

Instruction: Name the following compounds below.

Compound Name
Activity 7: Drawing Compounds
Instruction: Draw the following compounds indicated below.
Name Compound

Chlorobenzene

1,3 - Dimethybenzene

1-chloro-4-ethylbenzene

Activity 8: Critical Thinking

Instruction: Answer the questions below.
1. How do we name aromatic compounds with:
a) One Substituents
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b) Two Substituents
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c) Three or more Substituents
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2. Explain the differences between the following characteristic reactions below:
a) Halogenation
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b) Sulfonation
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c) Nitration
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3. Explain the relevance of knowing benzene ad its derivatives to criminology.
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4. How can organic chemistry help law enforcers in solving and investigating crimes?
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VIII TOPIC SUMMARY

In this lesson, you learned that:

• Benzene, the simplest aromatic hydrocarbon, was discovered by Michael Faraday in 1825.
• The first structure for benzene was proposed by Friedrich August Kekule in 1872 and consisted o
a six-membered ring with alternating single and double bonds, with one hydrogen bonded to
each carbon.
 • The concept of resonance, developed by Linus Pauling in the 1930s, provided the first adequate
description of the structure of benzene. According to the theory of resonance, certain molecules
and ions are best described by writing two or more Lewis structures and considering the real
molecule or ion to be a resonance hydrid of these structures.
• The IUPAC system retains certain common names for several of the simpler monosubstituted
alkylbenzenes, including toluene and tyrene.
• When two substituents occur on a benzene ring, three isomers are possible. We locate the
substituteens either by numbering the atoms of the ring or by using the locators ortho (o), meta
(m), and para (p). The numbers are 1,2- are equivalent to ortho; 1,3- to meta; and 1,4- for para.
• Halogenation occurs when a halogen reacts with benzene.
• Nitration occurs when a nitro (-NO2) group replaces one of the hydrogen atoms bonded to the
ring.
• Heating an aromatic compound with concentrated sulfuric acid results in formation of an
arenesulfuric acid, all of which are strong acids, comparable in strength to sulfuric acids.

IX POST-ASSESSMENT

Direction: Read each question carefully. Choose the letter of the best answer, and write the letter of
your choice on the space provided for each number
1. Which of the following has a molecular structure of C6H6?
a. alkanes
b. alkenes
c. alkynes
d. benzene
2. Who developed the resonance structure of benzene?
a. Friedrich Kekule
b. Linus Pauling
c. Isaac Newton
d. James Chadwick
3. What is the term used to described the individual Lewis structure in the resonance structure of
benzene?
a. Resonance Hybrid
b. Contributing structure
c. Kekule Structure
d. Resonance Lewis structure
4. Which of the following locators indicates a consecutive placement of substituents as represented by
1,2- ?
a. meta
b. ortho
c. para
 d. giga
5. Halogenation occurs when a halogen reacts with benzene. Which of the following is a halogen?
a. Iron
b. Neon
c. Chlorine
d. Hydrogen
6. What element allows halogens to react rapidly with benzene?
e. Iron
f. Neon
g. Chlorine
h. Hydrogen
7.What characteristic reactions of benzene occurs when a nitro (-NO 2) group replaces one of the
hydrogen atoms bonded to the ring?
e. Halogenation
f. Nitration
g. Sulfonation
h. Acidity
8. Which of the following locators indicates a opposite placement of substituents as represented by 1,4-
in benzene?
e. Meta
f. Ortho
g. Para
h. phenyl
9. Which of the following is not a halogen?
e. Fluorine
f. Chlorine
g. Barium
h. Bromine
10. Which of the following locators is represented by 1,4- in benzene?
e. Ortho
f. Meta
g. Para
h. substituent

REFERENCES

Books:
Bettelheim, F.A., Brown. W.H., Campbell, M.K., Farrell, S.O., Torres, O.J. (10th edition).
Introduction to General, Organic and Biochemistry. @2014 Cengage Learning Asia Pte Ltd., 1st
Philippine reprint 2014
 Padolina, Ma. Christina D., Simon-Antero, E., Alumaga, Ma. J.B., Estanilla, L.C., Rabago, L.M.
(2004). Conceptual and Functional Chemistry, Modular Approach. Vibal Publishing House, Inc.

Websites:

Anon, (2020). Structures and Names of Alkanes. (2020, September 27). Retrieved March 20,
2021, from https://chem.libretexts.org/@go/page/16064