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Assignment 01

Nitration is a process that introduces a nitro group (NO2) into an organic compound. Nitration of benzene involves treating benzene with a mixture of concentrated nitric acid and sulfuric acid to form nitrobenzene. Sulfuric acid is used because it reacts with nitric acid to form the nitronium ion, NO2+, which acts as the electrophile. Nitration is an electrophilic aromatic substitution reaction. Nitrobenzene is less reactive than benzene towards further substitution due to the electron-withdrawing nitro group decreasing the electron density of the benzene ring.

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95 views8 pages

Assignment 01

Nitration is a process that introduces a nitro group (NO2) into an organic compound. Nitration of benzene involves treating benzene with a mixture of concentrated nitric acid and sulfuric acid to form nitrobenzene. Sulfuric acid is used because it reacts with nitric acid to form the nitronium ion, NO2+, which acts as the electrophile. Nitration is an electrophilic aromatic substitution reaction. Nitrobenzene is less reactive than benzene towards further substitution due to the electron-withdrawing nitro group decreasing the electron density of the benzene ring.

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Ha M Za
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Unit Processes (Ch. E.

-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

Department of Chemical Engineering


Wah Engineering College
University of Wah

Course: Unit Processes (Ch. E.-303) Due Date & Time: 08-10-2019 & 8:10a.m.

Assignment 01 [20 points]

Question No. 01: Answer the following questions: (PLO-01, CLO-01)

1. What is nitration in organic chemistry?


2. What do you understand by nitration explain the mechanism of nitration of benzene?
3. Why is sulfuric acid used in nitration?
4. What conditions are used for nitration?
5. What is the nitration reaction?
6. What type of reaction is nitration of benzene?
7. What reagent is used in the nitration of benzene?
8. Why is the nitration of aromatic rings a useful reaction?
9. Why nitration of toluene is easier than benzene?
10. Why is nitrobenzene less reactive than benzene?
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

Table of Contents
Nitration in organic chemistry ...................................................................................................................... 3
Aromatic Nitration .................................................................................................................................... 3
Mechanism of nitration of benzene ............................................................................................................. 3
Sulfuric acid used in nitration ....................................................................................................................... 4
The electrophilic substitution mechanism ................................................................................................ 4
Conditions are used for nitration .................................................................................................................. 5
Nitration reaction.......................................................................................................................................... 5
Type of reaction is nitration of benzene ....................................................................................................... 5
Sulfonation of Benzene ................................................................................................................................. 6
The mechanism for Sulfonation of benzene ......................................................................................... 6
Nitration of aromatic rings a useful reaction ................................................................................................ 7
Toluene is easier than benzene .................................................................................................................... 7
Explanation: .............................................................................................................................................. 7
Nitrobenzene less reactive than benzene .................................................................................................... 8
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

Answer #01

Nitration in organic chemistry

Nitration is a general class of a chemical process for the introduction of a nitro group into an
organic chemical compound. More loosely the term also is applied incorrectly to the different
process of forming nitrate esters between alcohols and nitric acid, as occurs in the synthesis
of nitroglycerin.
The difference between the resulting structure of nitro compounds and nitrates is that the
nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, typically carbon or
another nitrogen atom, whereas in nitrate esters, also called organic nitrates, the nitrogen is
bonded to an oxygen atom that in turn usually is bonded to a carbon atom (nitrito group).

Aromatic Nitration

Answer #02

Mechanism of nitration of benzene


The electrophonic substitution reaction between benzene and nitric acid.

Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a
temperature not exceeding 50°C. As temperature increases there is a greater chance of getting
more than one nitro group, -NO2, substituted onto the ring.
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

Nitrobenzene is formed.

Or

The concentrated sulphuric acid is acting as a catalyst.

Answer #03

Sulfuric acid used in nitration


The formation of the electrophile.
The electrophile is the "nitronium ion" or the "nitryl cation", NO2+. This is formed by reaction
between the nitric acid and the sulphuric acid.

The electrophonic substitution mechanism

Stage one

Stage two
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

Answer #04

Conditions are used for nitration


It acts as a catalyst. It reacts with concentrated nitric acid to form the nitronium ion which acts as
an electrophile in the reaction, and the catalyst is regenerated with the proton that forms as a
product of the reaction.
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.

Answer #05

Nitration reaction
Nitration happens when one (or more) of the hydrogen atoms on the benzene ring is replaced by
a nitro group, NO2. Benzene is treated with a mixture of concentrated nitric acid and
concentrated sulphuric acid at a temperature not exceeding 50°C. The mixture is held at this
temperature for about half an hour.
Nitration of benzene is one of the most common reactions which are used to predict mechanism
of electrophonic substitution reactions of benzene molecule. The product that is nitrobenzene is
commercially use in manufacturing of different chemical compounds like TNT, aniline etc

Answer #06

Type of reaction is nitration of benzene


Organic compounds that contain nitrogen atoms are so important; it stands to reason that
understanding chemical reactions that introduce nitrogen atoms to other substrates are extremely
vital. One of the most important methods of adding a nitrogen atom to an already existing
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

organic substrate is a reaction called nitration. Nitration is the process of adding a nitro group
(NO2) to a benzene ring.

Answer #07

Sulfonation of Benzene
Sulfonation of benzene is a process of heating benzene with fuming sulphuric acid (H2SO4
+SO3) to produce benzenesulfonic acid. The reaction is reversible in nature.

The mechanism for Sulfonation of benzene


Due to higher electronegativity, oxygen present in sulphuric acid pulls an electron towards itself,
generating an electrophile. This attacks the benzene ring, leading to the formation of
benzenesulfonic acid.
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

Typical nitration syntheses apply so-called "mixed acid", a mixture of concentrated nitric
acid and sulfuric acids. This mixture produces the nitronium ion (NO2+), which is the active
species in aromatic nitration.

Answer #08

Nitration of aromatic rings a useful reaction


Benzene is highly prone to electrophonic substitution reactions compared to addition reactions as
it loses its aromaticity during addition reaction. As benzene contains delocalized electrons
spanning over carbon atoms in the ring, it is highly attractive to electrophiles and is also highly
stable to electrophonic substitutions. Generally, the electrophonic is a three-step process
involving:
 Generation of the electrophile.
 Intermediate carbocation formation.
 Removal of proton from carbocation intermediate.

Answer #09

Toluene is easier than benzene


Because it introduces a nitro group or groups onto an aromatic ring; the nitro group can be
further elaborated.

Explanation:

Nitration of the aromatic ring is a fairly easy way to introduce functionality onto a phenyl ring,
even though it uses very harsh electrophonic reagents (HNO3, H2SO4).

Once the nitro group is attached, it can be reduced to amines. Acetaminophen,


paracetamol, p−HO (C6H4) NHC (=O) CH3 is a widely used analgesic (which we have all
used), and nitrobenzene is used as the starting chemical in its industrial synthesis.
Unit Processes (Ch. E.-303)
[UW-17-CH.E-bsc-024] Muhammad Hamza

The CH3 group attached to the benzene ring increases the electron density through + H effect.
The electrophile attacks to the substrate having high electron density. Electrophilic aromatic
substitution reaction is a second order reaction. It depends on the type of substrate as well as
electrophile. The substrate having high electron density can easily undergo EAS reaction.

Answer #10

Nitrobenzene less reactive than benzene


In the Electrophilic Aromatic Substitution reaction between nitrobenzene and an electrophile,
such as the in situ carbocation species formed from acyl chlorides in the presence of AlCl3
catalyst ( Friedel Crafts Acylation), the reactivity is much different. In comparison to benzene,
the presence of the nitro group is highly electron withdrawing, and this then deactivates the ring
as a nucleophile, which actually reduces reactivity.

On the other hand, for Nucleophilic Aromatic Substitution, the reactivity is much different, and
the nitrobenzene is actually more reactive than benzene. This is because the same electron
withdrawing character decreases the LUMO of the benzene ring, and making it more susceptible
to nucleophilic attack.

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