Assignment 2 Chem

FACULTY OF EDUCATION
DEPARTMENT OF APPLIED EDUCATION
PART A: STUDENT AND ASSIGNMENT DETAILS

STUDENT NAME : TONDERAI RUSERE
REG NUMBER : R245246A
PROGRAMME : BED DUAL HONOURS SCIENCE AND APPLIED TECHNOLOGIES
LEVEL : 1.1
MODULE CODE : SECH 113
MODULE TITLE : ORGANIC CHEMISTRY
LECTURER : MRS MAMBANGA
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FOR LECTURER USE
PART B : MARKERS COMMENTS
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MARKERS NAME …………………… SIGNATURE …………………………………
DATE :………………………
a) Structure of benzene
As for the stability of benzene has a unique structure. Benzene (C₆H₆) stability comes from the
delocalization of pi electrons across the carbon atoms in the ring. All six carbon-carbon bonds in
benzene are of the same length—139 pm, which is intermediate between typical single (154 pm)
and double (134 pm) bonds. This equal bond length indicates that the electrons are not localized
in double bonds as they would be in alkenes but are shared evenly across all six carbon atoms,
creating a ring of electron density known as aromaticity. It has a hybrid of two equivalent
structures where the double bonds are delocalized around the ring. This delocalization leads to a
lower energy state than any single structure would have, contributing to the molecule’s overall
stability. In benzene, the six p orbitals of the carbon atoms overlap to form a continuous pi
system above and below the plane of the ring. This overlapping allows for the delocalization of
electrons, which stabilizes the molecule. The molecular orbitals formed are degenerate, meaning
they have the same energy level, which is another factor contributing to the stability of benzene.
b). Electrophilic aromatic substitution (EAS) is a fundamental type of reaction that occurs with
benzene and other aromatic compounds. The mechanism involves the following steps:
1. Generation of the Electrophile: The first step in an EAS reaction is the formation of a
strong electrophile, which can be generated in various ways depending on the reaction.
For example, in nitration, the electrophile (nitronium ion, NO₂⁺) is generated from nitric
acid and sulfuric acid1.
2. Formation of the Arenium Ion: The electrophile attacks the electron-rich aromatic ring of
benzene, forming a sigma complex known as an arenium ion. This intermediate is
stabilized by resonance, although it is not aromatic because the delocalization of
electrons is interrupted2.
3. Restoration of Aromaticity: In the final step, a base removes a proton from the carbon
atom that is bonded to the electrophile. This restores the aromatic system, and the
substituent remains attached to the ring, replacing one of the hydrogen atoms2.
An example of an EAS reaction is the nitration of benzene. In this reaction, benzene
reacts with nitric acid (HNO₃) in the presence of sulfuric acid (H₂SO₄) to form
nitrobenzene (C₆H₅NO₂). The sulfuric acid acts as a catalyst, promoting the formation of
the nitronium ion, which is the actual electrophile that attacks the benzene ring2. The
overall reaction can be summarized as follows:
Benzene+HNO3 Nitrobenzene+H2O
d) Acylation of Benzene: Generation of Electrophile: A Lewis acid catalyst, such as AlCl₃, reacts
with an acyl chloride (RCOCl) to form a positively charged acylium ion (RCO⁺).
Attack on Benzene: The benzene ring, acting as a nucleophile, attacks the acylium ion, forming a
resonance-stabilized sigma complex.
Restoration of Aromaticity: A base, usually the AlCl₄⁻ formed during the generation of the
electrophile, abstracts a proton from the sigma complex, restoring aromaticity and yielding the
acylated product1.
Bromination of Benzene: Formation of Electrophile: A Lewis acid, such as FeBr₃, reacts with Br₂
to form the electrophilic bromonium ion (Br⁺).
Formation of Sigma Complex: The benzene ring donates a pair of electrons to the bromonium
ion, forming a resonance-stabilized sigma complex.
Proton Loss: A base, often the FeBr₄⁻ ion, abstracts a proton from the sigma complex,
regenerating the aromatic system and producing bromobenzene2.
Sulphonylation of Benzene:
Generation of Electrophile: Sulfur trioxide (SO₃) or fuming sulfuric acid (oleum) acts as the
electrophile in the reaction.
Attack on Benzene: The benzene ring donates a pair of electrons to the electrophile, forming a
resonance-stabilized sigma complex.
Proton Transfer: The sigma complex loses a proton to a base, such as the bisulfate ion (HSO₄⁻),
restoring aromaticity and yielding benzenesulfonic acid3.

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FACULTY OF EDUCATION

DEPARTMENT OF APPLIED EDUCATION

PART A: STUDENT AND ASSIGNMENT DETAILS

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