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Practical Report 1
Nitration of Acetanilide
Aim: To observe how an Aromatic Electrophilic Substitution reaction takes place through the nitration of
acetanilide, as in, how a hydrogen on a carbon chain is replaced with a nitro group.
Reagents and Chemicals:
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Acetanilide
Glacial acetic acid
Concentrated sulfuric acid
Concentrated nitric acid
Methanol
Modification to experimental procedure: Procedure was conducted exactly as the instructions in our
CHEM220 practical manual book. After recrystallization had taken place, the solution was cooled to
room temperature. It was then filtered. The solution and resulting crystals were not ice cold before
filtration as instructed in the practical manual book. The filtration process was carried out more than
once to remove all crystals from the solution. This was done to increase levels of accuracy.
Reaction Mechanism
Balanced equation:
C8H8N2O3+ H3O++ 2 HSO4-
C8H9NO + HNO3+ 2H2SO4
C8H8N2O3+ H2O
C6H6N2O2+ C2H4O2
Melting point (literature):
214-216 °C (Unknown, 2009)
Melting point:
150-152 °C
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Expected yield:
72% (Unknown, 2009)
Calculation of expected mass:
Limiting reactant: Acetanilide
Moles limiting reagent: mass / molar mass
: 4.81g/135.17g/mol
: 0.0356mol
Moles product: stoichiometric factor x moles
: 0.0356mol x1
: 0.0356mol
Mass product expected: moles x molar mass
: 0.0356mol x180.16g/mol
: 6.41g
%yield: (mass product obtained / mass product expected) x100
: (1.03g/6.41g) x100
: 16.07%
Short discussion:
Concentrated sulfuric and nitric acids, in combination, form a very hazardous and corrosive mixture.
These acids should be poured together carefully, and this procedure should be carried out in a hood,
since noxious vapors are produced. You will begin with the sample of acetanilide you isolated and
purified in the first two experiments. Avoid contact of all chemicals with skin, eyes, and clothing. Wash
all contact areas with large quantities of water.
References:
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homepages.wmich.edu/~jkiddle/.../REAC%20716%20Nitration.pdf
Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the elements (2nd edition),
Oxford;Butterworth-Heinemann
http://www.scribd.com/doc/138384661/Nitration-of-Acetanilide
Practical One
ANMchunu
214513535