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Title of Practical: The Nitration of Acetanilide Aim: To Observe The Electrophilic Substitution of An Aromatic Compound I.E. Acetanilide

This document outlines an experiment to nitrate acetanilide through electrophilic aromatic substitution. Specifically, it replaces a hydrogen atom with a nitro group on the aromatic ring. The reagents include acetanilide, glacial acetic acid, concentrated sulfuric acid, and nitric acid. The experimental procedure follows the lab manual, with ice water added to lower the temperature and prevent over nitration by slowing the reaction. The balanced reaction and melting point are reported, as well as a discussion of using ice water to control the reaction.

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41 views4 pages

Title of Practical: The Nitration of Acetanilide Aim: To Observe The Electrophilic Substitution of An Aromatic Compound I.E. Acetanilide

This document outlines an experiment to nitrate acetanilide through electrophilic aromatic substitution. Specifically, it replaces a hydrogen atom with a nitro group on the aromatic ring. The reagents include acetanilide, glacial acetic acid, concentrated sulfuric acid, and nitric acid. The experimental procedure follows the lab manual, with ice water added to lower the temperature and prevent over nitration by slowing the reaction. The balanced reaction and melting point are reported, as well as a discussion of using ice water to control the reaction.

Uploaded by

Lonwabo
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Title of Practical: The nitration of acetanilide

Aim: To observe the electrophilic substitution of an aromatic compound i.e. acetanilide


through the mechanisation of the nitration of acetanilide. The specifics of the reaction will
include how a hydrogen is replaced with a nitro group within the aromatic carbon chain.

Reagents and chemicals

 5g of acetanilide
 5ml of glacial acetic acid
 Concentrated sulphuric acid
 Concentrated nitric acid
 Methanol

Modifications to experimental procedure

The procedure for the experiment was followed exactly as the CHEM220 practical manual.
The mixture of acetanilide, glacial acetic acid, concentrated sulphuric and nitric acid could
react at room temperature prior to ice water being added. This iced mixture was filtered,
recrystallised, allowed to cool in ice bucket until solid and re-filtered again. The re-filtered
without ice water as outlined in the practical manual.

Reaction mechanism

Balanced equation:
C8H9NO + HNO3+ 2H2SO4 C8H8N2O3+ H3O++ 2 HSO4-

C8H8N2O3+ H2O C6H6N2O2+ C2H4O2


Melting point of nitroaniline prepared from literature: 214℃ - 216℃ (Ryu & Yoon,
1998)

Melting point of nitroaniline prepared:

Calculation of yield

Limiting reagent
Discussion
In order to prevent the dinitration of acetanilide i.e the replacement of two hydrogens with nitro
groups on the aromatic carbon chain, the temperature was lowered using ice water to slow
down the reaction and avoid over nitration (Ryu & Yoon, 1998). Deviations from the
researched melting point are due to minor products of ortho and meta nitroaniline which are
just the nitroaniline which have different positions of the nitro group on the carbon chain
compared to the major product – the para nitroaniline (Ryu & Yoon, 1998).
REFERENCES
IMAGE SOURCE:http://3.bp.blogspot.com/-
9L2o4n4DAq0/UUm2GqEkcQI/AAAAAAAAADc/uAacAtu_P60/s640/nitration.JPG

Ryu G & Yoon C.S., 1998, Seeded supercooled melt growth and polar morphology of organic
nonlinear optical crystal, metanitroaniline (mNA), Elesevier, 191:1-2, p.190-198.

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