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Vnsgu SF Sem 2 Organic Practical
Vnsgu SF Sem 2 Organic Practical
OH OH
NaHCO3
OH OH
Resorcinol COOH
-Resorcylic Acid
Calculation:-
110 gms Resorcinol gives 154 gms β-Resorcylic Acid
10 gms Resorcinol gives (?) gms β-Resorcylic Acid
Theoretical Yield=14.0gms
Practical Yield = _________ gms
% Yield =
ORGANIC PREPARATION SEM-II
Take 10 gms resorcinol & heat the mixture on a sand bath until it just begins to boil. Now
allow the reaction to complete itself on sand bath without further heating for half hour.
Cool the reaction mixture and dilute it with 50% HCl[about 2 to 3 T.T] keep it for some
times & shake it well Resacetophenone slowly separate from the solution in orange need
filters it & wash water & dry it. Recrystallized it from the boiling water.
M.P.:-144-147 oC
Reaction:-
OH OH
CH3COOH
ZnCl 2
-H2O
OH OH
COCH3
Calculation:-
110 gms Resorcinol gives 152 gms Resacetophenone
10 gms Resorcinol gives (?) gms Resacetophenone
% Yield =
ORGANIC PREPARATION SEM-II
M.P.:-171-172 oC
Reaction:-
NH2 H
N
2 Hrs
H-COOH CH
-2H2O N
NH2
Calculation:-
108 gms O-phenylene diamine gives 118 gms Benzimidazole
10 gms O-phenylene diamine (?) gms Benzimidazole
% Yield =
ORGANIC PREPARATION SEM-II
15 ml Conc. H2SO4 in a wide necked 50 ml flask cool it. Externally till the temp. of the acid
is about 5 oC mean while prepare a solution of Resorcinol [3.7 gms to 4.0 gms] in 4.4 ml of
Ethyl acetoacetate.
Now add the solution of Resorcinol in Ethyl Acetoacetate to Conc H2SO4 slowly. So that the
temp of mixture does not rise about 10 oC continue the stirring for 30 minutes. Pour the
mixture into crushed ice when the solid separates. Filter of the Coumarin at the pump. .
Recrystallized it from Alcohol
M.P.:-188-190 oC
Reaction:-
OH C2 H5 O
O
C HO O O
CH 2
Conc. H2SO4
C
OH H3 C O
CH 3
Resorcinol Ethyl Acetoacetate 4-Methyl-7-Hydroxy Coumarin
Calculation:-
110 gms Resorcinol gives 176 gms 4-Methyl-7-Hydroxy Coumarin
4.0 gms Resorcinol (?) gms 4-Methyl-7-Hydroxy Coumarin
.
= = 10.93 gms 4-Methyl-7-Hydroxy Coumarin
% Yield =
ORGANIC PREPARATION SEM-II
Now heat the contents almost to boiling stage & add 5.0gms of NaCl & again warm it at 80-
90 oC. Until the salt has dissolved completely.
Allow the mixture to cool undisturbed for 15 min & then cool it in ice bath. Filter the
product wash with water & recrystallized it from hot water.
NH2 N=N
N=N N(CH 3) 2
Calculation:-
173 gms Sulphanilic Acid gives 327 gms Methyl Orange
5.0 gms Sulphanilic Acid (?) gms Methyl Orange
.
= = 9.45 gms Methyl Orange
% Yield =
M.P.:- 214 oC
ORGANIC PREPARATION SEM-II
Reaction:-
NHCOCH 3
NHCOCH 3
Cold Mixture
Fuming HNO3 + Conc. H2SO4
Glacial HAc
0 - 10 oC
Acetanilide
NO2
P-Nitro Acetanilide
Calculation:-
135 gms Acetanilide gives 180 gms P-Nitro Acetanilide
10 gms Acetanilide (?) gms P-Nitro Acetanilide
% Yield =
M.P.:- 147 oC
ORGANIC PREPARATION SEM-II
Reaction:-
NHCOCH 3 NH2
Acid Hydrolysis
CH3COOH
NO2 NO2
P-Nitro Acetanilide P-Nitro Aniline
Calculation:-
180 gms P-Nitro Acetanilide gives 138 gms P-Nitro Aniline
10 gms P-Nitro Acetanilide (?) gms P-Nitro Aniline
% Yield =
M.P.:- 167 oC
ORGANIC PREPARATION SEM-II
Reaction:-
NHCOCH 3 NHCOCH 3
Bromination
Acetanilide
Br
P-Bromo Acetanilide
Calculation:-
135 gms Acetanilide gives 214 gms P-Bromo Acetanilide
5 gms Acetanilide (?) gms P-Bromo Acetanilide
% Yield =
M.P.:- 66.6 oC
ORGANIC PREPARATION SEM-II
Reaction:-
NHCOCH 3 NH2
Alkiline Hydrolysis
KOH
Br
Br
P-Bromo Acetanilide P-Bromo Aniline
Calculation:-
214 gms P-Bromo Acetanilide gives 172 gms P-Bromo Aniline
7 gms P-Bromo Acetanilide (?) gms P-Bromo Aniline
% Yield =
Result:-
Mechanism:
Resacetophenone
Reaction:
Mechanism:
OH OH
OH
CH3CO
OH - O H
OCH3C H
O
OH
OH
COCH3
o-Phenylene Diamine
Reaction:
Mechanism:
4-Methyl-7-Hydroxy Coumarin
Reaction:
Mechanism:
Methyl Orange
Reaction:
Mechanism:
H N H H N H H N N O H N N O H
N N N N Cl
+Cl
SO3Na SO3Na
CH3
N N Cl N CH3
CH3
N N N
HCl CH3
SO3Na H
SO3Na
CH3
N N N
CH3
Methyl Orange
SO3Na
P-Nitro Aniline
Step 1:- Acetanilide to P-Nitro Acetanilide [Nitration]
Reaction:
Mechanism:
NHCOCH3 NHCOCH3 NHCOCH3 NHCOCH3
H H NO2
NO2
Reaction:-
NHCOCH3 NH2
Acid Hydrolysis
CH3COOH
NO2 NO2
P-Nitro Acetanilide P-Nitro Aniline
Mechanism:
P-Bromo Aniline
Step 1:- Acetanilide to P-Bromo Acetanilide [Bromination]
Reaction:
Mechanism:
Reaction:
Mechanism:
ORGANIC ESTIMATION SEMESTER-II
Observation:-Blank Estimation:-
Burette:- 0.1N NaOH Soln.
Flask:- 10 ml 10 % Hydroxyl Amine Hydrochloride + 25 ml dist. H2O
Indicator:- Bromo phenol blue Indicator
End point:- yellow to blue colour
Observation:-Actual Estimation:-
Burette:- 0.1N NaOH Soln.
Flask:- weighted formaldehyde soln. + 10 ml 10% Hydroxyl Amine Hydrochloride + 25 ml dist.
H2O
Indicator:- Bromo phenol blue Indicator
End point:- yellow to blue colour
1
ORGANIC ESTIMATION SEMESTER-II
Calculation:-
( )
% of HCHO = .
N=0.104
M=30
Result:-
% purity of Formaldehyde:-___________.
Requirement:- 0.1N HCl (exact), 0.1N NaOH (exact), 1.5N NaOH (approx.), phenolphthalein
indicator
Estimation of Acid:-
Take 25 ml of given mixed soln of acid+amide in a 250 ml S.M.F & dilute it to 250 ml dist. H 2O.
Take 25 ml of this diluted soln.in a conical flask and titrate it against 0.1N NaOH soln. from
burette using phenolphthalein as an indicator. Appearance of pink color is the End point. Take 3
to 4 burette reading. Let the constant burette reading “D” ml.
2
ORGANIC ESTIMATION SEMESTER-II
Estimation of Acid:-
Burette:- 0.1N NaOH Soln.
Flask:- 25 ml dil. Soln. of [Acid + Amide]
Indicator:- phenolphthalein Indicator
End point:- Appearance of pink color
Reaction:-
Calculation:-
Now,
4
ORGANIC ESTIMATION SEMESTER-II
Requirement:- 0.1N HCl (exact), 0.1N NaOH (exact), 1.5N NaOH (approx.), phenolphthalein
indicator
Estimation of Acid:-
Take 25 ml of given mixed soln of acid+Ester in a 250 ml S.M.F & dilute it to 250 ml dist. H 2O.
Take 25 ml of this diluted soln.in a conical flask and titrate it against 0.1N NaOH soln. from
burette using phenolphthalein as an indicator. Appearance of pink color is the End point. Take 3
to 4 burette reading. Let the constant burette reading “D” ml.
5
ORGANIC ESTIMATION SEMESTER-II
Estimation of Acid:-
Burette:- 0.1N NaOH Soln.
Flask:- 25 ml dil. Soln. of [Acid + Ester]
Indicator:- phenolphthalein Indicator
End point:- Appearance of pink color
Reaction:-
Calculation:-
6
ORGANIC ESTIMATION SEMESTER-II
Now,