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Tevin Krishna

Practical Report 1

Practical Report 1:
The Nitration of Acetanilide
Aim: To make an observation on how an Aromatic Electrophilic Substitution reaction
takes place via the nitration of acetanilide.

Reagents and Chemicals:

Acetanilide
Glacial acetic acid
Concentrated sulphuric acid
Concentrated nitric acid
Methanol

Modifications to Experimental Procedure

Procedure was conducted by the giving instructional steps provided CHEM220 2016
practical manual, apart from the recrystallization process as an excess of MeOH was
added the solution did not produce any solids once the MeOH was added and
boiled, the solution was allowed to evaporate in the fume cupboard where it formed
pale yellow crystals that were filtered and allowed to dry.

Reaction Mechanism

Melting Point (literature)

214-216C (Unknown, 2016)

Melting Point (produced substance)

214528375

Tevin Krishna

Practical Report 1

Calculation of Expected Yield

Limiting reactant: Acetanilide
Mass used: 5.01g
Molar Mass: 135.17g/mol
Moles:
n=
=

m
M

5.01g
135.17g/ mol

= 0.03706mol
Therefore, by reaction stoichiometry, the expected amount of product is theoretically
0.03736mol of p-nitroacetanilide.
Molar mass of nitroacetanilide: 180.16g/mol (Unknown, 2016)
Expected mass:
m
n=
m = n M = 0.03706mol 180.16g/mol = 6.6767g
M

Percentage Yield
Mass of actual yield =
% Yield

= (mass of actual yield/mass of theoretical yield) x 100

=(
/6.731g) x 100
=
%

Discussion
It is crucial to add the nitric acid and sulphuric acid mixture drop-wise to the
acetanilide suspension, being careful not to exceed a temperature of 10C. This
ensures a selective reaction and helps isolate the desired products. When doing the
first filtration, do not discard the filtrate doing the filtration once more will allow for
more product. A suggestion to get crystals instead of a powdery substance would be
to allow the solution to reach RT and allow it to evaporate instead of putting into an
ice water slurry.

References
Unknown. (2016). Nitroacetanilide from Druglead:
http://www.druglead.com/cds/nitroacetanilide.html
CHEM220 Practical Manual 2016