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Acetanilide Preparation From Acetyl Chloride PDF
Acetanilide Preparation From Acetyl Chloride PDF
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PREPARATION OF
ORGANIC COMPOUNDS
EXPERIMENT 10.1
Aim
To prepare acetanilide.
Theory
The replacement of one hydrogen atom of the NH2 group of aniline by CH3CO
group in the presence of glacial acetic acid. Gives acetanilide. In the laboratory,
acetylation is usually carried out with acetic anhydride. Acetyl chloride may
also be used for the purpose of acetylation if acetic anhydride is not available.
Acetylation with CH3COCl is usually carried out in the presence of pyridine.
Material Required
Funnel
Round bottomed flask (100 mL)
Beaker (250 mL)
Air condenser
Sand bath
Clamp and iron stand
Pumice stone
Melting point assembly
no
t
:
:
:
:
:
:
:
:
One
One
One
One
One
One
As per need
One
Aniline
: 5 mL
Acetic anhydride
/Acetyl chloride
: 5 mL
Acetic acid / Pyridine : 5 mL
Procedure
(i)
(iii)
(iv)
(v)
Result
(a)
(b)
Aniline
Acetic
anhydride
Acetyl
chloride
Acetic acid
causes
serious burn
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(ii)
Pyridine
Precautions
(a)
Handle acetic anhydride and acetyl chloride carefully as they cause irritation to
the eyes and acetyl chloride also strongly fumes in air.
(b) Store acetylchloride under dry conditions.
(c) Handle pyridine with extreme caution. Dispense it in an efficient fume cupboard
and wear disposable glasses while using it.
(d) Distil pyridine before use because it absorbs mioisture and the reaction does not
take place under moist conditions.
(e) Wash the solid 2-3 times with cold water till the filtrate is neutral to litmus.
(f) Determine the melting point of perfectly dried and recrystallised sample.
no
t
Material Required
Boiling tube
Water bath
Melting point assembly
Funnel
:
:
:
:
One
One
One
One
Aniline
: 1 mL
Glacial acetic acid : 1 mL
Acetyl chloride
: 1 mL
105
Procedure
(i)
(ii)
(iii)
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(iv)
(v)
(vi)
(vii)
Precautions
(a)
(b)
(c)
(d)
If aniline sample is too much coloured, distill it before carrying out the experiment,
because yield is lowered with impure aniline.
Use perfectly dry apparatus.
Do not inhale the vapours coming out during the addition of acetylchloride.
Determine the melting point of perfectly dried and recrystallized sample.
EXPERIMENT 10.2
Aim
no
t
Theory
106
Material Required
Procedure
(i)
(ii)
(iii)
(iv)
(v)
Result
(a)
(b)
One
One
One
One
Ethanol
NaOH
Benzaldehyde
Acetone
Ice
Ethylacetate
:
:
:
:
:
:
25 mL
3.15 g
3.2 mL
2.3 mL
As per need
As per need
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Ethanol
NaOH
Benzaldehyde
Acetone
Ethyl acetate
Precautions
no
t
(a) Maintain the temperature around 20C while shaking the reaction mixture.
(b) Always use freshly distilled benzaldehyde or the sample from a freshly opened
bottle.
EXPERIMENT 10.3
Aim
To prepare p-nitroacetanilide.
107
Theory
p-Nitroacetanilide is prepared by the nitration of acetanilide by
using a mixture of conc. nitric acid and conc. sulphuric acid as
nitrating reagent. The mixture of the two acids releases nitronium
ion( NO+2 ), which acts as an electrophile in the reaction.
HNO3 + 2H2SO4 NO+2 + H 3O + + 2H SO 4
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Material Required
:
:
:
:
One
One
One
One
Acetanilide
Glacial acetic acid
Conc. H2SO4
Conc. HNO3
Ice
Ethanol/methanol
:
:
:
:
:
:
2g
2 mL
5 mL
1.5 mL
As per requirement
As per requirement
Procedure
Acetic acid
causes severe
burns
Hazard Warning
no
t
108
(vi) Wash the compound with cold water and dry it.
(vii) Recrystallise a small amount of the pale yellow solid from
alcohol. Colourless crystals of p-nitroacetanilide are
obtained. Yellow ortho-nitroacetanilide formed in the small
amount remains dissolved in the mother liquor.
(viii) Record the yield and melting point of the pure compound.
Result
Yield of p-nitroacetanilide is _______ g.
Melting point of p-nitroacetanilide is ______C.
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(a)
(b)
Precautions
Do not allow the temperature of the reaction mixture to exceed 10C during
addition of nitrating mixture.
(b) Add mixture of concentrated nitric acid and sulphuric acid into the solution of
acetanilide slowly and carefully.
(a)
EXPERIMENT 10.4
Aim
Theory
no
t
109
Material required
Beaker (250mL)
:
Conical flask (100mL) :
Glass rod
:
Thermometer (210 C) :
Filter paper
:
Funnel
:
Melting point assembly :
One
One
One
One
As per need
One
One
Aniline
Conc. HCl
Sodium nitrite
-naphthol
Sodium hydroxide
Glacial acetic acid
Ice
Distilled water
:
:
:
:
:
:
:
:
2 mL
6.5 mL
1.6 g
3.2 g
2.0 g
12.0 mL
As per need
As per need
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Procedure
Aniline
HCl
Sodium
nitrite
Sodium
hydroxide
-naphthol
no
t
Acetic acid
causes severe
burns
110
(i)
Result
(a)
(b)
Precautions
(a)
(b)
(c )
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Note : Azo-dye synthesis are mostly so nearly quantitative that one should use amounts of reactants
closely agreeing with equations. Any excess of certain reactants may cause decomposition of
unused material and tar may appear.
EXPERIMENT 10.5
Aim
Theory
no
t
Material Required
:
:
:
:
:
One
One
One
One
One
Diazoaminobenzene
Aniline
Aniline hydrochloride
Glacial acetic acid
Carbon tetrachloride
:
:
:
:
:
3g
7 mL
1.5 g
9 mL
9 mL
111
Procedure
Aniline
Acetic acid
causes
severe burns
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Carbon
tetrachloride
Result
Precautions
no
t
(a)
(b)
(c)
112
Material Required
Funnel
:
Conical flask (100 mL) :
Thermometer
:
Melting point assembly :
Procedure
(i)
(ii)
(iii)
(iv)
(v)
One
One
One
One
Aniline
1.0 M HCl
Carbon tetrachloride
:
:
:
6 mL
4 mL
As per need
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Aniline
Carbon
tetrachloride
HCl
Discussion Questions
(i) Why is acetic anhydride preferred over acetyl chloride for acetylation reaction?
(ii) In the preparation of p-nitroacetanilide another minor product is formed. What is this
compound and how can this be separated from p-nitroacetanilide?
(iii) Is it necessary to recrystallise the compound obtained from the reaction? Explain why.
(iv) How is an organic compound recrystallised?
(vii) Which of the following compounds on diazotisation followed by coupling with naphthol
will form an azo dye?
(b) Benzylamine
(c ) N-Methylaniline.
no
t
(a) p-Toluidine
113