Organic Practicals
M.Sc- Semester-II
Prepared By:
Dr. Aniruddhasinh M. Rana
Assistant Professor,
AEPS Institute of Science,
GIDC, Ankleshwar
(Affiliated to VNSGU, Surat)
DR. ANIRUDDHASINH M. RANA 1
1.0 Resacetophenone 03
2.0 Orange-I 05
3.0 m-dinitrobenzene 07
4.0 p-nitro benzoic acid 08
5.0 p- Bromo acetanilide 10
6.0 m-phenylene diamine 12
7.0 Benzoic acid 14
8.0 Estimation: Glycine 16
9.0 Estimation: Acid+Ester 18
10.0 Estimation: Acid+Amide 22
DR. ANIRUDDHASINH M. RANA 2
Preparation of Resacetophenone (Friedel-Craft Acylation)
Resorcinol → Resacetophenone
Equation:
Requirements
Anhydrous ZnCl2, Glacial acetic acid, Resorcinol, 50 % HCl.
Procedure
Take 5.0 gm Anhydrous ZnCl2 in 100 ml beaker and heat it on sand bath to make it
anhydrous. To this add 5 ml Glacial acetic acid and dissolve ZnCl 2. Add more glacial
HAC if required, and then add 5 gm Resorcinol.
Heat this reaction mixture on a sand bath until it just began to boil. Now turn off the
heating and allow the reaction to complete by itself on a sand bath for 30-35 minutes.
After that, add equal amount of 50% HCl with reference to reaction mass drop wise
and shake it well. Resacetophenone slowly separate from the solution in flat orange
yellow needles.
Filter it and wash with water and dry it. Recrystallize it from boiling water.
Calculation:
Theoretical yield:
110 of Resorcinol give 152 gm of Resacetophenone
So, 5.0 gm resorcinol gives= 152 x 5/ 110
DR. ANIRUDDHASINH M. RANA 3
= 6.909
Theoretical yield = 6.909
Practical yield =
%age of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 4
Preparation of Orange– I
Sulphanilic acid → Orange– I
Equation
Requirements
Sulphanilic acid, conc. HCl, α-Naphthol, anhydrous Na 2CO3, NaNO2, 10%NaOH, NaCl, alcohol.
Procedure
Take 3.0 gm of sulphanilic acid in 250 ml beaker, and then add 1.32 gm of anhydrous
Na2CO3, 30 ml of water and warm it until a clear solution is obtained. Cool the solution
under the temperature about 0- 5 0C and then place it in ice bath.
Now, prepare a solution of 1.5 gm of NaNO2 in 5 ml of water in a 100 ml beaker and
place it in an ice bath. Add this NaNO2 solution in reaction mixture with stirring by
maintaining temperature 0 – 5 0C.
After complete addition, pour this resulting solution slowly and with stirring into a
500 ml beaker containing 4 ml of Conc. HCL and 30 gm of crushed ice. Stir this mixture
about 10 minutes and maintain the temperature. Diazobenzene sulphonate will
separate out do not filter it.
DR. ANIRUDDHASINH M. RANA 5
Now, in a 500 ml beaker dissolve 2.6 gm α- naphthol in a 10 ml of cold 10 % NaOH
solution. Place it in an ice bath.
Now, pour the cold solution of diazotized sulphanilic acid into a cold solution of α-
naphthol slowly with constant stirring. Stir well and after 10 minutes, heat the
mixture until all the solid has dissolved.
Add 6.0 gm of NaCl (to decrease the solubility of the product) and warm the solution
for 5 minutes. Allow the solution to cool about 1 hour and then cool it in ice bath until
crystallization is completed.
If ppts are not separate out then dissolve the solution in NaOH and reppts by HCL.
Filter it and wash with cold water and dry it. Recrystallize from alcohol.
Calculation
Theoretical yield:
173.2gmofsulphanilic acidgive350 gm of orange 1
So, 10.0 gm sulphanilic acid gives =350 X 10/173.2
=20.20 (Theoretical yield)
Practical yield =
% of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 6
Preparation of m- dinitrobenzene
Nitro benzene m– dinitrobenzene
Equation
Requirements: conc. H2SO4, conc. HNO3, Nitrobenzene.
Procedure
Take 7.0 ml of conc. H2SO4 and 7 ml of fuming nitric acid (or 10 ml of Conc. HNO3) in
500 ml round bottom flask along with the few pieces of porcelain.
Add drop wise 4.2 ml nitro benzene with constant stirring. Attach a reflex condenser
and heat the mixture on the water bath for about 1 hour.
Allow the mixture to cool and pour it into ice cold water with constant stirring. Solid
m – dinitro benzene are obtained.
Filter it and wash with cold water and dry it. Recrystallize from alcohol.
Theoretical yield:
123 gm of nitro benzene give 136 gm of m- dinitro benzene
So, 5 gm nitro benzene gives = 136 x 5/ 123
=5.528 gm
Theoretical yield = 5.528
Practical yield =
%age of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 7
Preparation of p–Nitro Benzoic acid
P– Nitro toluene p–Nitro benzoic acid
Equation
Requirements
P-nitro toluene, K2Cr2O7, conc. H2SO4, 5 % H2SO4, 5% NaOH, charcoal, 15% H2SO4, alcohol.
Procedure
Take 5.75 gm of p–nitro toluene, 17 gm of crystallized K 2Cr2O7 and 37.5 ml of water
in R.B.F. Then add 23.2 ml of conc. H2SO4 drop wise during about 30 minutes with
constant stirring.
Attach a reflux condenser to the flask, and heat it for about 2 hour.
Cool the mixture and pour the reaction mixture into 200-250 ml of Cold water.
Filter the crude p- nitro benzoic acid and wash this residue with 100 ml of water.
Transfer the Solid product/Residue to a 500 ml beaker, add about 100 ml of 5 %
H2SO4 and digest on water bath, in order to remove the chromium salts as completely
as possible, allow to cool and filter again.
Transfer the acid into a beaker and add 5 % NaOH solution until the liquid remain
alkaline.
Add 0.625 gm charcoal, warm the mixture about 50 0C with stirring for 5 minutes, and
filter it.
Take 56.5 ml of 15 % H2SO4 in a beaker and add the mother liquid drop wise. Solid p-
nitro benzoic acid are obtained.
Filter it and wash with cold water and dry it. Recrystallize it from alcohol.
DR. ANIRUDDHASINH M. RANA 8
Calculations
Theoretical yield:
137.14 gm of p-nitro toluene give 167.1189gm of p- nitro benzoic acid
So, 5.75 gm p-nitro toluene gives =167.1189 x 5.75/ 137.14
=7.00
Theoretical yield = 7.00
Practical yield =
%age of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 9
Preparation of p–Bromo acetanilide
Acetanilide P - Bromo Acetanilide
Equation
Requirements
Acetanilide, Glacial acetic acid, bromine in glacial acetic acid (20%), alcohol.
Procedure
Dissolve 5.0 gm Acetanilide in 15.0 ml glacial acetic acid in 250 ml conical flask.
Put this mixture in an ice bath. And then Add 12.0 ml bromine in glacial acetic acid
(20%) drop wise with constant stirring.
Allow the reaction mixture to stand at room temperature for 30 minutes with
occasional shaking.
Pour the reaction mixture in ice cold water in 500 ml beaker. Filter it and wash with
cold water and dry it.
Recrystallize the product from alcohol.
Calculation
Theoretical yield
135 gm of Acetanilide give 213.5 gm of P – Bromo Acetanilide
So, 5 gm acetanilide gives = 213.5 x 5/ 135
= 7.907
DR. ANIRUDDHASINH M. RANA 10
Theoretical yield = 7.907
Practical yield =
%age of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 11
Preparation of m–phenylenediamine
m–Dinitro benzene m–phenylenediamine
Equation
Requirements
Fe powder, conc. HCl, m- DNB, Na2CO3, Fe Corning (Or Fe Ore), HCl
Procedure
Take 80 ml water in 500 ml beaker and add 15 to 20 gm Fe powder or Iron corning
then add 20 ml conc. HCl.
Shake it and heat the mixture up to boiling for 5 minutes. And then add 8.4 gm m-
dinitrobenzene in a small portions of not more than 2 gm at a time with continuous
stirring during the time 30 minutes.
After complete addition boil the solution for at least 5 minutes. The boiling solution
is then treated with solid 10.0 gm of anhy. Na2CO3 in small proportion.
After addition of anhy. Na2CO3, the solution is further boiled for 5 minutes, in order
to decompose completely the soluble iron components.
The liquid should not be filtered until a test on filter paper gives no black stain with
Na2S solution.
The liquid is then filtered and the clear filtrate is treated with sufficient HCl to cause
a slight acid reaction to litmus yielding m–phenylenediamine.
DR. ANIRUDDHASINH M. RANA 12
Calculation
Theoretical yield
168.107gmof m- dinitro benzene give 108.14 gm of m – phenylenediamine
So, 8.4 gm m – dinitro benzene gives = 108.14 x 8.4 / 168.107
= 5.405
Theoretical yield = 5.405
Practical yield =
% age of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 13
Preparation of Benzoic acid
Benzaldehyde Benzoic acid
Equation
Requirements
KOH, Benzaldehyde, petroleum ether, HCl.
Procedure
Take 7.0 gm of KOH dissolved in 30 ml of water in a beaker. Then add 10 ml of
Benzaldehyde drop wise during the time 20 minutes with constant stirring.
Now cool the mixture to 15 0C, if the solution became turbid then add more water.
Clear solution be there.
Now this clear solution is extracted by 45.0 ml petroleum ether. The aqueous layer
should be extracted three times (3 x 15 ml) by ether. So, Finally, One Organic layer
and aqueous layer is collected.
Organic layer contains Benzyl alcohol, while the aqueous layer contains benzoic acid
(Potassium salt of benzoic acid).
To receive benzoic acid, aqueous layer is acidified with 50% aq. HCl to separate crude
benzoic acid.
Filter and dry the product. Recrystallize it from hot water.
DR. ANIRUDDHASINH M. RANA 14
Calculation
Theoretical yield:
106.121 ml of Benzaldehyde give 122.12 gm of Benzoic acid
So, 10 ml Benzaldehyde gives = 122.12x 10 / 106.121
= 11.50
Theoretical yield = 11.50
Practical yield =
%age of yield = Practical yield x 100 / Theoretical yield
DR. ANIRUDDHASINH M. RANA 15
Estimation of Glycine
Aim: to determine the % purity of glycine.
Requirements
Glycine, formaldehyde solution (formalin), 0.1 N NaOH solution, phenolphthalein indicator.
Procedure
Preparation of neutral formaldehyde solution
Take about 50 ml of 40% formaldehyde solution in a conical flask and add about at
least 10 to 12 drops of phenolphthalein indicator.
Now add carefully 0.1 N NaOH solution from burette till just pink color is obtained.
Actual Examination:
Weight out accurately about 2.0 gm of glycine in 250 ml SMF and make up to 250 ml
with D.M water.
Take 25.0 ml of this diluted solution in a conical flask and add 2 to 3 drops of indicator
and add 0.1 N NaOH till just pink color is obtained.
Now add 10.0 ml of neutral formaldehyde solution so the pink color will be
disappeared.
Now add 2 to 3 drop of indicator and titrate it against 0.1 N NaOH (no need to make
B.R=0) pink color appearance is the end point.
Observation and Calculation:
Burette: 0.1 N NaOH
Flask: 25 ml of diluted solution of glycine + 2 to 3 drop of indicator + 0.1 N NaOH (till pink
color) + 10 ml of formaldehyde solution.
Indicator: phenolphthalein
DR. ANIRUDDHASINH M. RANA 16
End point: color less to pink.
No. I. B.R. F.B.R. Diff. Mean
1 0.0 Ml
2 0.0ml X= ml
3 0.0ml
Weight of sample taken = gms. (W)
Now,
1000 ml 1N NaOH = 75 gm of glycine
1 ml 1 N NaOH = 0.075 gm of glycine.
1 ml 0.1 N NaOH = 0.0075 gm of glycine.
X ml 0.1 N NaOH = 0.0075 x X gm of glycine.
Amount of glycine in 25 ml diluted solution = Y gms.
Amount of glycine in given solution = Y x 10
= Z gms.
Now, % purity of glycine = 100 x Z / W
= %
Result:
(1) 25 ml diluted solution of glycine require ______________ ml 0.1 N NaOH.
(2) The % purity of the given sample of glycine is ______________ %
DR. ANIRUDDHASINH M. RANA 17
Estimation of (Acid + Ester)
Aim: Determine the amount of acid and ester in the given solution.
Requirements
0.1 N HCl, 0.1 N NaOH, 1.5 N NaOH, phenolphthalein indicator.
Process
Blank estimation
Take 25.0 ml of 1.5 N NaOH in a 250 ml SMF and diluted it to 250 ml with dist. H 2O.
Take 25 ml of this diluted solution in a conical flasks and titrated it against 0.1 N HCl
solution from burette using phenol phenolphthalein as an indicator.
Disappearance of pink color is the end point.
Estimation of Acid
Take 25.0 ml of given solution (acid + ester) in a conical flask and titrate it against 0.1
N NaOH solution from burette using phenolphthalein as an indicator.
Appearance of pink color as the end point.
Estimation of Ester
Take 25.0 ml of given solution of acid + ester in a 250 ml R.B.F. and add exact 25 ml
of 1.5 N NaOH.
Attach water condenser and reflux it on water bath till hydrolysis is complete, it takes
around 1.30 hour.
After reflux, cool the solution and transfer the refluxed solution in 250 ml SMF and
dilute it to 250 ml with dist H2O.
Take 25.0 ml this diluted solution in a conical flask and titrate it against 0.1 N HCl
from burette using phenolphthalein as an indicator.
DR. ANIRUDDHASINH M. RANA 18
Observation:
Blank Estimation
Burette: 0.1 N HCL
Flask: 25 ml of diluted solution of NaOH
Indicator: phenolphthalein
End point: disappearance of pink color.
No. I. B.R. F.B.R. Diff. Mean
1 0.0Ml
2 0.0ml A= ml
3 0.0ml
25 ml diluted NaOH solution required “A” ml 0.1 N HCl
Normality of given NaOH solution = (A x 0.1 / 25) x 10 = N
Estimation of acid
Burette: 0.1 N NaOH
Flask: 25 ml of diluted solution of (acid + ester)
Indicator: Phenolphthalein
End point: Appearance of pink color.
No. I. B.R. F.B.R. Diff. Mean
1 0.0 ml
2 0.0 ml D= ml
3 0.0 ml
25 ml diluted (acid+ester) solution required “D” ml 0.1 N NaOH
DR. ANIRUDDHASINH M. RANA 19
Calculation:
1000 ml 1 N NaOH = 59 gm succinic acid
= 60 gm CH3COOH
1 ml 0.1 N NaOH = 0.0059 gm succinic acid.
D ml 0.1 N NaOH = 0.0059 x D
= E gm of succinic acid
Amount of succinic acid in 25 ml of diluted solution is E gm
Amount of succinic acid in the given solution E x 10 = X gm.
Estimation of ester
Burette: 0.1 NHCL
Flask: 25 ml of diluted solution of (acid+ester)
Indicator: phenolphthalein
End point: Disappearance of pink color.
No. I. B.R. F.B.R. Diff. Mean
1 0.0 ml
2 0.0 ml B= ml
3 0.0 ml
25 ml diluted acid + ester solution required “B” ml 0.1 N NaOH
Calculation:
Now,
The amount of NaOH solution added in terms of 0.1 N HCl = A= ml
DR. ANIRUDDHASINH M. RANA 20
The amount of NaOH solution unused in terms of 0.1 N HCl= B= ml
The amount of NaOH solution used up for acid ester in terms of 0.1 N HCL = A-B = C= ml
The amount of NaOH solution used up for ester only in terms of 0.1 N HCL =C - D = F= ml
1000 ml 1 N NaOH = 1000 ml 1 N HCL
= 88 gm Ethyl acetate.
1000 ml 1 N NaOH = 88 gm Ethyl acetate.
1 ml 0.1 N NaOH = 88 gm Ethyl acetate.
1 ml 0.1 N HCL = 0.0088 gm Ethyl acetate
F ml 0.1 N HCL = 0.0088 x F gm
= G gm Ethyl acetate
Amount of Ethyl acetate in 25 ml of diluted solution G gm
Amount of Ethyl acetate in the given solution G x 10 = Y gm.
Result:
(1) Normality of given NaOH solution = N
(2) The amount of acid in the given solution = gm
(3) The amount of ester in the given solution = gm
DR. ANIRUDDHASINH M. RANA 21
Estimation of (Acid+Amide)
Aim: Determine the amount of acid and amide in the given solution.
Requirement: 0.1 N HCl, 0.1 N NaOH, N NaOH, phenolphthalein indicator.
Process
Blank Estimation
Take 25 ml of 1.5 N NaOH in a 250 ml SMF and diluted it to 250 ml with dist. H 2O.
Take 25 ml of this diluted solution in a conical flasks and titrated it against 0.1 N HCl
solution from burette using phenol phenolphthalein as an indicator.
Disappearance of pink color is the end point.
Estimation of Acid
Take 25 ml diluted solution (acid+amide) in a 250 ml conical flask and titrate it
against 0.1 N NaOH solution from burette using phenolphthalein as an indicator.
Appearance of pink color as the end point.
Estimation of Amide
Take 25.0 ml of given solution of (acid+amide) in a 250 ml R.B.F. and add exact 25 ml
of 1.5 N NaOH.
Attach water condenser and reflux it on water bath till hydrolysis is complete that
take about 1.30 hour.
Cool the refluxed solution and transfer it in 250 ml SMF followed by dilution up to
250 ml with dist H2O.
Take 25 ml this diluted solution in a conical flask and titrate it against 0.1 N HCl from
burette using phenolphthalein as an indicator.
DR. ANIRUDDHASINH M. RANA 22
Observation
Blank Estimation
Burette: 0.1 N HCL
Flask: 25 ml of diluted solution of NaOH
Indicator: phenolphthalein
End point: disappearance of pink color.
No. I. B.R. F.B.R. Diff. Mean
1 0.0 ml
2 0.0 ml A= ml
3 0.0 ml
25 ml diluted NaOH solution required “A” ml 0.1 N HCl
Normality of given NaOH solution = (A x 0.1 / 25) x 10
= N gm
Estimation of acid
Burette: 0.1 N NaOH
Flask: 25 ml of diluted solution of (acid+amide)
Indicator: phenolphthalein
End point: Appearance of pink color.
No. I. B.R. F.B.R. Diff. Mean
1 0.0 ml
2 0.0 ml D= ml
3 0.0 ml
DR. ANIRUDDHASINH M. RANA 23
25 ml diluted acid + ester solution required “D” ml 0.1 N NaOH
Calculation:
1000 ml 1 N NaOH = 59 gm succinic acid.
= 60 gm CH3COOH acid.
1 ml 0.1 N NaOH = 0.0059 gm succinic acid.
D ml 0.1 N NaOH = 0.0059 x D
= E gm of succinic acid
Amount of succinic acid in 25 ml of diluted solution E gm
Amount of succinic acid in the given solution E x 10 = X gm.
Estimation of Amide
Burette: 0.1 N HCl
Flask: 25 ml of diluted solution of (acid+amide)
Indicator: phenolphthalein
End point: Disappearance of pink color.
No. I. B.R. F.B.R. Diff. Mean
1 0.0 ml
2 0.0 ml B= ml
3 0.0 ml
25 ml diluted acid + ester solution required “B” ml 0.1 N NaOH
Calculation:
The amount of NaOH solution added in terms of 0.1 N HCl=A= ml
The amount of NaOH solution unused in terms of 0.1 N HCl = B= ml
DR. ANIRUDDHASINH M. RANA 24
The amount of NaOH solution used up for acid ester in terms of 0.1 N HCl = A-B = C= ml
The amount of NaOH solution used up for ester only in terms of 0.1 N HCl =C - D = F= ml
1000 ml 1 N NaOH = 1000 ml 1 N HCL
= 59 gm Acetamide.
1000 ml 1 N NaOH = 59 gm Acetamide.
1 ml 0.1 N NaOH = 59 gm Acetamide
1 ml 0.1 N HCL = 0.0059 gm Acetamide
F ml 0.1 N HCL = 0.0059 x F gm
= G gm Acetamide
Amount of Ethyl acetate in 25 ml of diluted solution= G gm
Amount of Ethyl acetate in the given solution G x 10= Y gm.
Result:
(1) Normality of given NaOH solution = N
(2) The amount of acid in the given solution = gms.
(3) The amount of amide in the given solution = gms.
DR. ANIRUDDHASINH M. RANA 25
