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Synthesis of acetanilide from aniline
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Synthesis of Acetanilide from Aniline l Medicinal Chemistry l Labmonk
BACKGROUND
Principle:
Acetanilide is synthesized from aniline (https://www.amazon.in/gp/product/1356938906
ie=UTF8&tag=satyaranjan0421&creative=24630&linkCode=as2&creativeASIN=1356938906&linkId=8c43e9cadbb095f4fa04e77
acetylating it with acetic anhydride in presence of glacial acetic acid. Aniline or phenylamine is a pri
nature. Acetic anhydride, an anhydride of acetic acid, acts as a source of acyl group here . An
anhydride to form Acetanilide by nucleophilic substitution reaction and the reaction is called acet
aniline acts as the nuclepohile and acyl (CH3CO-) group from acetic anhydride acts as the electrop
atom of –NH2 group is replaced by the acyl group.1
Aim: To prepare acetanilide from aniline.
Reaction:
Mechanism:
Use:
It is an antipyretic agent.
REQUIREMENTS
Chemicals:
Acetic acid/anhydride mixture – 20 ml
Aniline – 10 ml
Apparatus:
Conical flask – 250 ml
Reflux water-condenser set
Buchner funnel
Measuring cylinder
Filter paper
PROCEDURE
Add 20 ml of a mixture of acetic anhydride (https://labmonk.com/synthesis-of-p-bromoacetanilid
glacial acetic acid (equal volumes) to 10 ml (10.3 g) of aniline (https://labmonk.com/to-prepare-and-s
aniline) in a conical flask of 250 ml. Fit a reflux water-condenser to the flask and gently boil the m
pour the hot liquid into 200 ml of cold water with constant stirring. The acetanilide (https://labm
submit-acetanilide-from-aniline) quickly crystallises. Filter yield by a pump and wash the crude ace
Recrystallise from about 60 ml of a mixture of one volume of acetic acid (https://labmonk.com/synt
acid-from-salicylic-acid) and two volumes of water: filter off the colourless crystals at the pump, aga
water, drain and dry.
Note: Alternatively, the crude acetanilide may be recrystallised from boiling water, but in this case
(about 300 ml) of the solvent will be required.
Calculation:
Here limiting reagent is aniline; hence yield should be calculated from its amount taken.
Molecular formula of aniline = C6H7N1
Molecular formula of acetanilide = C8H9O1N1
Molecular weight of aniline = 93 g/mole
Molecular weight of acetanilide = 135 g/mole
Theoretical yield:
1.g aniline forms 135 g acetanilide
Therefore, 10.3 g (10 ml) aniline will form ………? (X) g acetanilide
X =( 135 × 10.3)/93 = 14.95 g
Theoretical yield = 14.95 g
Practical yield = ————- g
% Yield = (Practical Yield)/(Theoretical Yield) × 100
CONCLUSION
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REFERENCES
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