JEE (MAIN+ADVANCED)

PRACTICAL ORGANIC CHEMISTRY

 CONTENT

S.No Pages

1. Practical Organic Chemistry 01 – 16

2. Exercise-1 (Subjective Questions) 17
3. Exercise-2 (Objective Questions) 18 – 22
4. Exercise-3 (Section-A) 23
5. Exercise-3 (Section-B) 23
6. Exercise-4 24 – 25
7. Answer Key 26
 PRACTICAL ORGANIC CHEMISTRY

PRACTICAL ORGANIC CHEMISTRY

(A) PURIFICATION OF ORGANIC COMPOUNDS

The common technique used for purification are as follows :

(i)Sublimation (ii) Crystallisation
(iii)Distillation (iv) Differential extraction and
(v) Chromatography

Crystallisation
This method is based on the differences in the solubility of the organic compound and its impurities in a
solvent.
(a) Preparation of the solution : Organic substance is powdered and is dissolved in a suitable solvent by
heating. The amount of solvent should be just sufficient to dissolve the whole of the solid on heating.
(b) Filtration of the solution. The hot saturated solution is filtered preferably through a fluted filter paper
placed in a glass funnel. The use of the fluted filter paper makes the filtration rapid. The jacketer of the
hot water funnel is heated from outside and this keeps the solution hot in the glass funnel. This will
prevent the formation of crystals during filtration.

(c) Crystallisation. The hot filtration is allowed to cool slowlyand undisturbed in a beaker or in a crystallising
dish. After some time the crystals of the pure compound are formed.

(d) Separation of the crystals. The crystals formed are separated from the mother liquor by filtration. The
filtration is normallydone by use of Buckner funnel and a suction pump. This enables the filtration under
reduced pressure and is therefore, quite fast.

(e) Drying of crystals. The crystals are dried by pressing between the folds of filter paper and then placed
in a steam of air oven for some time. The crystals are finally dried over sulphuric acid or calcium chloride
in a desiccator.

Sublimation
Certain organic solids directly change from solid to vapour state on heating. This process is called
sublimation. The vapours on cooling change back to the solid form
Heat
Solid Vapours
Cool

The sublimation process is used for the separation of those solids which sublime on heating from non-
volatile solids. The process is generally used for the purification of camphor, naphthalene, anthracene,
benzoic acid, etc. containing non-volatile impurities.

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 PRACTICAL ORGANIC CHEMISTRY

Distillation
This method is used for the purification of liquids which boil without decomposition and contain non-
volatile impurities. The simple distillation involves its boiling point so that it is converted into vapours. On
cooling the vapours, pure liquid is obtained.

Fractional Distillation : This process is used to separate a mixture of two or more miscible liquids
which have boiling points close to each other. The fractionating column is a long tube provided with
obstructions to the passage of the vapours moving upwards and liquid moving downwards. This method
may be used to separate a mixture of acetone (b.p. 330K) and methyl alcohol (b.p. 338. K).

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 PRACTICAL ORGANIC CHEMISTRY

Distillation under Reduced pressure (Vaccum Distillation) : Certain liquids have a tendency to
decompose at a temperature below their boiling points. Such liquids cannot be purified by ordinary
distillation. Therefore vacuum distillation is used for liquids which decompose at a temperature below
their normal boiling points.
Ex. glycerol boils with decomposition at 563K.

Steam distillation : The process of steam distillation is used for the separation and purification of liquid
which is appreciably volatile in steam, from non-volatile components of a mixture. Thus, the process of
steam distillations is used to purifythe substances which
(i) are volatile in steam but are not miscible with water
(ii) possess sufficiently high vapour pressure at the boiling point temperature of water (100ºC)
(iii) contain non-volatile impurities.

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 PRACTICAL ORGANIC CHEMISTRY

DIFFERENTIAL EXTRACTION
When an organic compound is present in an aqueous medium, it is separated by shaking it with an
organic solvent in which it is more soluble than in water. The organic solvent and the aqueous solution
should be immiscible with each other so that they form two distinct layers which can be separated by
separatory funnel. The organic solvent is later removed by distillation or by evaporation to get back the
compound.

CHROMATOGRAPHY
This method is based on the differences in the rates at which the components of a mixture are adsorbed
on a suitable adsorbent. In this method two mutually immiscible phases are brought into contact with
each other wherein one phase is stationary (fixed phase) while the other is mobile (moving phase). The
stationary phase can be either solid or tightly bound liquid on a solid support while mobile phase can be
either liquid or a gas. Different types of chromatographic techniques commonly used are as follows :
(1)When stationaryphase is solid the chromatographyis known as adsorption chromatography.Adsorption
chromatography is further classified into following categories. This classification on the nature of the
mobile phase.
Mobile Phase

Gas Liquid

Gas-Solid Chromatography Liquid-Solid Chromatography

(GSC) (LSC)

Adsorption column Thin-layer

Chromatography Chromatography
(ACC) (ACC)

(2) When stationaryphase is liquid the chromatography is known as partition chromatography. Partition
chromatography is further classified in different categories. This classification depends on the nature of
the mobile phase.

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 PRACTICAL ORGANIC CHEMISTRY

Mobile Phase

Gas Liquid

Gas-Liquid Chromatography Liquid-Liquid Chromatography

(GLC) (LLC)

Partition Partition Column Paper Reverse Phase Partition

(TLC) Chromatography Chromatography Chromatography
(PCC) (PC) (RPPC)

Types of chromatography :
Based on the principle involved chromatography is classified into different categories. Two of these
are.
(a) Adsorption chromatography, and (b) Partition chromatography
(a) Adsorption chromatography :
Adsorption chromatography is based on the fact that different compounds are adsorbed on an adsorbent
to different degrees. When a mobile phase is allowed to move over a stationary phase (adsorbent), the
components of the mixture move byvarying distances over the stationaryphase. Following are two main
types of chromatographic techniques based on the principle of differential adsorption.
(i) Column chromatography, and
(ii) Thin layer chromatography.
(i) Column chromatography:

Solvent

a a
b+c b
Adsorbent c
(stationary phase)
Glass wool

Column chromatography. Different stages of

separation of components of a mixture
Column chromatography involves separation of a mixture over a column of adsorbent (stationary phase)
packed in a glass tube. The column is fitted with a stopcock at its lower end. The mixture adsorbed on
adsorbent is placed on the top of the adsorbent column packed in a glass tube.An appropriate eluant
which is a liquid or a mixture of liquids is allowed to flow down the column slowly. Depending upon the
degree to which the compounds are adsorbed, complete separation takes place. The most readilyadsorbed
substances are retained near the top and others come down to various distances in the column

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 PRACTICAL ORGANIC CHEMISTRY

(ii) Thin layer chromatography :

solvent
jar front

adsorbent coated spot

on glass plate
sample dot
base line y
solvent x
base line

Thin layer chromatography

chromatogram being developed
Developed chromatogram

Thin layer chromatography (TLC) is another type of adsorption chromatography, which involves
separation of substances of a mixture over a thin layer of an adsorbent coated on glass plate.
(b) Partition Chromatography :

card board
card board chromatography
paper
chromatography
jar
paper spot
jar base line
base line
spot solvent

solvent
Paper chromatography chromatography
paper in two different shapes

Partition chromatographyis basedon continuous differential partitioningof componentsof mixture between

stationary and mobile phases. Paper chromatography is a type of partition chromatography. In paper
chromatography, a special quality paper known as chromatography paper is used. Chromatography
paper contains water trapped in it, which acts as the stationary phase.

QUANTITATIVE ANALYSIS OF ORGANIC COMPOUNDS

Estimation of Carbon and Hydrogen :
Principle.Aknown weight of the given dry organic compound is heated strongly with dry cupric oxide
in an atmosphere of air or oxygen free from CO2. The carbon and hydrogen of the organic compound
are oxidised to CO2 and water vapour as :
C + 2CuO ––––– CO2 + 2Cu
(from compound)
2H + CuO ––––– H2O + Cu
(from compound)

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 PRACTICAL ORGANIC CHEMISTRY

Procedure :
Let the mass of organic compound taken = m g
Mass of water formed = m1 g
(increase in CaCl2 U-tube)
Mass of carbon dioxide formed = m2 g
increase in potash tubes)
(a) Percentage of Carbon
We know that 1 mole of carbondioxide (44 g) contains 1 gram atom of carbon (12g).
CO2  C
44 g of CO2 contain C = 12 g

12
m2 g of CO2 contains C = × m2 g
44

12m 2
Hence Percentage of carbon = 44  m × 100

(b) Percentage of Hydrogen

We know that one mole of water (18g) contains 2 gram atom of hydrogen (2g)
H2O=2H
18g of H2O contain H = 2g

2
 m1 g of H2O contains H = × m1 g
18

2m 1
Percentage of hydrogen = 18  m × 100

12 Mass of CO 2 formed
Percentage of C = × Mass of compound taken x 100
44

2 Mass of H2 O formed
Percentage of H = × Mass of compound taken x 100
18

Estimation of Nitrogen :
There are two methods for the estimation of nitrogen
(i) Duma’s method (ii) Kjeldahl’s method

Duma’s method :
Principle of the method. Aknown mass of an organic compound is heated with dry cupric oxide in an
atmosphere of carbon dioxide. The carbon and hydrogen are oxidised to carbon dioxide and water
respectively while nitrogen is set free. If any oxide of nitrogen is produced during this process, it is
reduced to nitrogen by passing over a heated copper gauze. The gaseous mixture is collected over an
aqueous solution of KOH when all the gases except nitrogen are absorbed. The volume of nitrogen
produced is measured at room temperature and atmospheric pressure. From the volume of N2 produced,
percentage of nitrogen in the sample can be calculated.

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 PRACTICAL ORGANIC CHEMISTRY

C + 2CuO  CO2 + 2Cu

2H + CuO  H2O + Cu
2N + CuO  N2 + oxides of nitrogen
Oxides of nitrogen + Cu  CuO + N2
Let the mass of organic compound = wg
The volume of nitrogen collected = Vcm3
Atmospheric pressure (from barometer) = P mm of Hg
Room temperature = t0C
Aqueous tension at t0C = a mm of Hg
Pressure of dry nitrogen = (P – a) mm of Hg
Let us first convert the volume of nitrogen to volume at S.T.P.
Experimental conditions S.T.P. conditions
P1 =(P–a) mm Hg P2 =760mm
T1 = (273 + t) K T2 = 273
V1 = V cm3 V2 = ?
P1V1 P2 V2
Applying gas equation = T
T1 2

P1V1T2 (P  a) x V x 273
 V2 = = = x cm3 (say)
P2 T1 760 (273  t)

Now 22400 cm3 of N2 at S.T.P. weight = 28 g

28
x cm3 of N2 at S.T.P. will weigh = ×x g
22400

Mass of nitrogen
 Percentage of nitrogen = x 100
Mass of organic compound

28 x x 100
= 22400 x w

Kjeldahl’s method : This method cannot be used for

(i) Organic compounds containing nitrogen in the ring such as pyridine, quinoline, etc.
(ii) Organic compounds containing nitrogen (-NO2) and diazo (-N = N-) groups.
Principle : A known weight of the organic compound is heated with conc. H2SO4 so that nitrogen is
quantitatively converted into ammonium sulphate. The solution is then heated with excess of sodium
hydroxide. The ammonia gas evolved is passed into a known but excess volume of standard acid (HCl
or H2SO4). The acid left unused is estimated by titrating the solution with standard alkali. From the
amount of acid left unused the amount of acid used for neutralisation of ammonia can be calculated.
From this percentage of nitrogen can be calculated.

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 PRACTICAL ORGANIC CHEMISTRY

Conc. H2 SO 4
C, H, S    CO2 + H2O + SO2
(from organic compound)
N  Conc

. H2 SO 4
 (NH4)2SO4
(from organic ammonium
compound) sulphate
(NH4)2SO4 + 2NaOH Heat

Na2SO4 + 2NH3 + 2H2O
2NH3 + H2SO4  (NH4)2SO4
NH3 + HCl  NH4Cl

Calculations
Let the mass of organic compound = w g
Volume of standard acid taken = V cm3
Normality of acid = N1
Let vol. of standard alkali used for neutralisation of unused acid = V2 cm3
Normality of standard alkali = N2
N1V1 N2 V2
{
alkali
= 12 3
acid

Let this volume of v cm3

 Vol. of acid used for neutralisation of ammonia
= (V – v) cm3 of N1 normality
Ammonia liberated = (V – v) cm3 of N1 solution
Now, 1000 cm3 of 1N NH3 solution contains nitrogen = 14 g
14 ( V  v) x N1
(V – v) cm3 of N1 NH3 solution contains nitrogen = g
1000
Mass of nitrogen 14 (V  v) x N 1 100
Percentage of nitrogen = Mass of organic compound x 100 = ×
1000 w

1. 4 ( V  v) x N1
=
w
Estimation of Halogens :
Carius method :
Principle : Aknown mass of the organic substance is heated with fuming HNO3 in a Carius tube. The
silver halide so obtained is separated, washed, dried and weighed. From the weight of silver halide
formed, the percentage of halogen can be calculated.
X + AgNO3  AgX
Halogen
Carbon, hydrogen or sulphur present in the compound will be oxidised to CO2, H2O and H2SO4
respectively.
C + 2O HNO
 3
 CO2

2H + O HNO
 3
 H2O

S + H2O + 3O HNO
 3
 H2SO4

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 PRACTICAL ORGANIC CHEMISTRY

Calculations :
Let the mass of organic compound be w g
Mass of silver halide formed = a g
Now, AgX = X
108 + X parts by weight of silver halide contains X parts by weight of halogen (X is its atomic mass)
(108 + X) g of silver halide give halogen = X
X
a g of silver halide will give halogen = ×ag
(108  X)

Mass of ha log en Xxa 100

 Percentage of halogen = x 100 = x
Mass of organic compound (108  X ) w
Here X is the atomic mass of halogen, e.g.
Cl = 35.5 , Br = 80 (79.9 exact),
I = 127 (126.9 exact)
Atomicmassof halogen  Massof silver halide
Percentage of halogen = × 100
(108  At.massof halogen)  Mass of organic substance

Estimation of Sulphur
Sulphur is estimated by Carius method.
Principle : Aknown mass of the organic compound is heated with fuming HNO3 in a sealed tube when
sulphur is quantitatively converted into sulphuric acid. It is then precipitated with barium chloride as
barium sulphate. The precipitate is filtered, washed, dried and weighed. From the weight of BaSO4
formed, the percentage of sulphur can be calculated. The main reactions are :
S + H2O + 3O HNO 3
 H2SO4
H2SO4 + BaCl2  BaSO4
ppt.
Calculations :
Let the mass of organic compound = w g
Mass of BaSO4 formed = a g
BaSO4  S
137 + 32 + 64 = 32
= 233
233 g of BaSO4 contain sulphur = 32 g
32 x a
a g of BaSO4 will contain sulphur = g
233
Mass of sulphur 32 a 100
Percentage of sulphur = × 100 = ×
Mass of organiccompound 233 w

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 (B) Elemental Analysis

Lassaigne method (Detection of elements)

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Element Sodium Extract (S.E.) Confirmed Test Reaction
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Nitrogen Na + C + N NaCN (S.E.) S.E. + FeSO4 + NaOH, boil and cool, FeSO4 + 2NaOH  Fe(OH)2 + Na2SO4
(It is tested as cyanide + FeCl3 + conc. HCl blue or green Fe(OH)2 + 6NaCN  Na4[Fe(CN)6] + 2NaOH
in Nitrogen compound) colour Na4 [Fe(CN)6] + FeCl3 Fe4[Fe(CN)6]3 + 3NaCl
Prussian blue

Sulphur 2Na + S Na2S (S.E.) (i) S.E. + Sodium nitro prusside (A) (i) Na2S + Na2[Fe(CN)5 NO]  Na4[Fe(CN)5 NOS]
A deep violet colour. (A) deep violet
(ii) S.E.+CH3 COOH+(CH3COOH)2Pb (ii) Na2S + (CH3COO)2 Pb PbS + 2CH3COONa
A black ppt. black ppt.
S.E. + HNO3 + AgNO3

Nitrogen Na + C + N + S NaCNS As in test for nitrogen; instead of NaCNS + FeCl3  [Fe(CNS)]Cl2 + NaCl
and (S.E.) green or blue colour, blood red blood red colour
Sulphur (compound will not show coloration confirms presence of
together indivisual Lassaigne test in this case) N and S both

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Page # 11
PRACTICAL ORGANIC CHEMISTRY
 Chlorine :
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Experiment Observations
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1. N a + C l NaCl Sodium extract with conc. H2SO4 gives NaCl + H2SO4  HCl + NaHSO4
(S.E.) pungent smelling gas. Which gives dense HCl + NH3  NH4Cl (white fume)
white fume with NH3

2. Silver nitrate test Acidify a portion of aqueous solution
(or sodium carbonate extract) with dil.
HNO3. Boil for some time, cool and
add AgNO3 solution.
A white ppt. is formed which is soluble in
ammonia hydroxide.
NaCl + AgNO3  AgCl + NaNO3
White ppt
AgCl + 2 NH4OH  [Ag(NH3)2] Cl + 2H2O
Soluble complex

3. Manganese dioxide test Heat a pinch of the S.E. with a small 2NaCl + MnO2 + 3H2SO4
quantity of MnO2 and conc. H2SO4.  2NaHSO4 + MnSO4 + 2H2O + Cl2
Evolution of greenish yellow gas having a Yellow green
pungent irritating smell. It turns moist
starch-iodide paper blue.

4. Chromyl chloride test Mix a small quantity of the S.E. with a 4NaCl + K2Cr2O7 +3H2SO4  2Na2SO4 + K2SO4
small amount of powdered potassium + 2CrO2Cl2 + 3H2O
dichromate. Take the mixture in a test Chromyl chloride
tube and add conc. H2SO4.

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Heat the tube and pass the red vapours CrO2Cl2 + 4NaOH Na2CrO4 + 2H2O + 2NaCl
evolved into the gas detector containing Sod. chromate
NaOH solution. To the yellow solution Na2CrO4 + (CH3COO)2Pb PbCrO4 + 2CH3COONa
thus obtained, add dil. CH3COOH and Lead chromate
lead acetate solution.A yellow ppt. is formed. (Yellow ppt.)
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PRACTICAL ORGANIC CHEMISTRY
 Bromine
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Experiment Observations
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1. Na + Br NaBr Sodium extract with conc. H2SO4 gives NaBr + MnO2+3H2SO4  2NaHSO4+ MnSO4 + 2H2O+ Br2
(S.E.) Red Brown fumes which intensify on Red Brown
addition of MnO2

2. Silver nitrate test Acidify a portion of aqueous solution (or

sodium carbonate extract) with dil. HNO3.
Boil, cool and addAgNO3 solution.
A light yellow ppt. is obtained which is KBr + AgNO4  KNO3 + AgBr 
partially soluble in NH4OH. (Pale yellow ppt.)
Pale yellow ppt. of silver bromide are
sparinglysoluble in ammonium hydroxide.
3. Chlorine water test
Acidify a portion of aqueous solution (or 2KBr + Cl2  2 KCl + Br2
sodium carbonate extract) with dil. HCl Bromine being soluble in CCl4 imparts an
and add 1-2 ml of carbon disulphide and orange colour to the CCl4 layer.
then chlorine water. Shake vigorously and
allow to stand by this carbon disulphide
layer acquires orange colouration.

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PRACTICAL ORGANIC CHEMISTRY
 Iodine :
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Experiment Observation
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1. Na + I NaI Sodium extract react with conc. H2SO4 2NaI + MnO2+ 3H2SO4 2NaHSO4 + MnSO4 + 2H2O + I2
to give violet fumes.which intensify Violet
on addition of MnO2

2. Silver nitrate test

Acidify a portion of aqueous solution (or KI + AgNO3  KNO3 + AgI
sodium carbonate extract) with dil. HNO3. (Yellow ppt.)
Boil, cool and add AgNO3 solution.
A yellow ppt, is formed which is insoluble
in NH4OH.

3. Chlorine water test Acidify a part of the aqueous solution (or 2KI + Cl2  2KCl + I2
sodium carbonate extract) with dil. HCl, Iodine being soluble in CCl4 imparts a violet
add 1-2 ml of carbon disulphide and then colour to the CCl4 layer.
chlorine water. Shake vigorously and allow
to stand.Carbon disulphide layer acquires a violet
colouration.

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PRACTICAL ORGANIC CHEMISTRY
 PRACTICAL ORGANIC CHEMISTRY

(C) FUNCTIONAL GROUP TEST

1. Unsaturation : Alkenes & alkynes:

(a) Bayers test : Cold dil alk. KMnO4 decolourisation test
Purple colour  Colourless + MnO2 (Brown ppt)
(b) Br2 water decolourisation test
Brown colour of Br2  Colourless
2. Terminal alkynes:
Confirmed by ppt ofAcetylide ion with NaNH2 or AgNO3 or Cu2Cl2NH4OH
3. Alkyl halides:
(a) If they are capable of carbocation formation then they will give ppt withAgNO3.
(b) Beilstein’s test : A green colour is imported to the flame if small amount of organic compound is taken on
copper wire.
4. Alcohol:
(a) Cerric ammonium nitrate  Give red colour
(b) Boil with acetic acid & conc. H2SO4  fruity smell

(c) 2-alkanol & ethanol also give Iodoform test  Yellow ppt. of CH3I on reaction with I2+ OH

5. Aldehyde & Ketones:

2,4- Dinitrophenyl hydrazine (or) Braddy’s reagent give yellow, orange or red color with ald. & Ketones
(2,4-DNP)
6. Aldehydes:
(a) Tollen’s test  Silver mirror
(b) Fehling’s test {except benzaldehyde} Red colour
(c) Benedicts test  Red colour
(d) Schiff’s dye colour regeneration test  Pink colour
(e) Grey ppt with HgCl2 .

7. Ketones:
(a) Methyl Ketones give haloform test
(b) -hydroxy Ketones give Tollen’s & Fehling test’s too.

8. Carboxylic acids:
(a) Brisk effervescence with aq. NaHCO3 solution.
(b) HCOOH alone gives silver mirror test with Tollen’s reagent.
(c) Blue litmus  red
(d) Give fruity smell on reaction with alcohols.

9. Phenols:
(a) Violet colouration with neutral FeCl3
(b) Liebermann test
(c) White ppt with Br2 water
(d) Brisk effervescence with aq. NaHCO3 is observed in case of Nitrophenols.
10. Primary amines:
(a) Carbylamine reaction  Isonitriles have very distinctive foul odour.
(b) Hoffmann mustard oil reaction Oilyliquid with mustard like smell.

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 PRACTICAL ORGANIC CHEMISTRY

11. Aromatic 1° amine  diazo test

12. Amide boil with NaOH  NH3

13. Nitrobenzene  Mullikqn Baker test  Treat it with ZnNH4Cl then boil with Tollen’s reagent  Silver
mirror will appear

14. Proteins:
(a) Biuret test : Also used for urea  Alkaline solution of protein treated with a drop of aq CuSO4 when
bluish violet colour is obtained
(b) Ninhydrin test : Protein treated with a puridine solution of ninhydrin give colour ranging from deep blue
to violet pink.

DIFFERENTATION TEST

D1. 1°, 2° & 3° alcohols :

(a) Luca’s test : Lucas reagent is conc. HCl + ZnCl2

(b) Victor Meyer’s test (RBC test)

(i) 1° Alcohol  Blood red colour
(ii) 2°Alcohol  Blue
(iii) 3°Alcohol  Colourless

D2. 1°, 2° & 3° amines:

(a) Hinsberg’s reagent

(i) 1°Amine yield a clear solution from which upon acidification an insoluble material separated.
(ii) 2°Amine yield an insoluble compound which is unaffected by acid
(iii) 3°Amine yield insoluble compound

(b) Reaction with HNO2

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 PRACTICAL ORGANIC CHEMISTRY

EXERCISE-1 (Subjective Questions)

Q.1 How will you separate?

(a) Ethane, Ethene & Ethyne (b) 1-Butyne & 2-Butyne
(c) 2-hexyne & 3-hexyne (d) Phenol & Propanol
(e) 2-Propanol & Propanone (f) CH3COOH & HCOOCH3
(g) PhOH & PhCOOH (h) EtOH & EtNH2
(i) EtNH2 & Me2NH (j) EtOH & Et – O – Et

Q.2 On complete combustion, 0.246g of an organic compound gave 0.198g of carbon dioxide and
0.1014g of water. Determine the percentage composition of carbon and hydrogen in the compound.

Q.3 In duma’s method for estimation of nitrogen., 0.3g of an organic compound gave 50mL of nitrogen
collected at 300K temperature and 715 mm pressure. Calculate the percentage composition of
nitrogen in the compound. (Aqueous tension at 300K = 15 mm)

Q.4 During estimation of nitrogen present in an organic compound by Kjeldahl’s method, the ammonia
evolved from 0.5 g of the compound in Kjeldahl’s estimation of nitrogen, neutralized 10 mL of
1 M H2SO4. Find out the percentage of nitrogen in the compound.

Q.5 In Carius method of estimation of halogen, 0.15 g of an organic compound gave 0.12 g of AgBr.
Find out the percentage of bromine in the compound.

Q.6 In sulphur estimation, 0.157 g of an organic compound gave 0.4813 g of barium sulphate. What
is the percentage of sulphur in the compound?

Q.7 0.2475g of an organic compound gave on combustion 0.4950g of carbon dioxide and 0.2025 g
of water. The percentage of carbon and hydrogen are-

Q.8 0.257 g of an organic substance was heated with conc H2SO4 and then distilled with excess of
strong alkali. The ammonia gas evolved was absorbed in 50 ml of N/10 HCl which required 23.2
ml of N/10 NaOH for neutralisation at the end of the process. The percentage of nitrogen in the
compound is-

Q.9 0.395 g of an organic compound by Carius method for the estimiation of sulphur gave 0.582 g of
BaSO4. The percentage of sulphur in the compound is-

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 PRACTICAL ORGANIC CHEMISTRY

EXERCISE-2 (Objective Questions)

[SINGLE CORRECT CHOICE TYPE]
Q.1 Select reagent which is used in laboratory to differentiate 1°, 2° and 3° amines from each other:
(A) NaOH, I2 (B) PhSO2Cl (C) CHCl3 , KOH (D) CS2, HgCl2
Q.2 A mixture contains four solid organic compounds, A, B, C and D. On heating only C changes from
solid to vapour state. C can be separated from the rest in the mixture by-
(A) Distillation (B) Sublimation
(C) Fractional distillation (D) Crystallisation
Q.3 A mixture of acetone and methanol can be separated by-
(A) Vaccum distillation (B) Steam distillation
(C) Fractional distillation (D) None
Q.4 The best method to separate the mixture of ortho and para nitrophenol (1:1) is-
(A) Steam distillation (B) Crystallization (C) Vapourisation (D) Colour spectrum
Q.5 Turpentine oil can be purified by-
(A) Vaccum distillation (B) Fractional distillation
(C) Steam distillation (D) Simple distillation
Q.6 Chromatography is used for the purification of -
(A) Solids (B) Gases (C) Liquids (D) All
Q.7 A bottle containing two immiscible liquids is given to you. These may be separated by-
(A) Fractionating column (B) Separating funnel
(C) Fractional distillation (D) Steam distillation
Q.8 Sublimation is process where a solid-
(A) Melts (B) Changes into liquid form
(C) Boils (D) Changes into vapour form directly
Q.9 The separation of mixture of two compounds by chromatographic technique is based upon-
(A) Differential solubilities (B) Different densities
(C) Different absorption (D) Differential adsorption
Q.10 Which of the following technique is most suitable for purification of cyclohexanone from a mixture
containing benzoic acid , isoamyl alcohol, cyclohexane and cyclohexanone –
(A) Crystallisation (B) IR spectroscopy (C) Sublimation (D) Gas chromatography
Q.11 In Lassaigne test thiourea is converted into-
(A) NaCNS (B) Na2S (C) NaCN (D) Na2SO4
Q.12 In a Lassaignes’s test for sulphur in the organic compound with sodium nitroprusside solution the
purple colour formed is due to-
(A) Na4 [Fe(CN)5 NOS] (B) Na3 [Fe(CN)5 S]
(C) Na2 [Fe(CN)5 NOS] (D) Na3 [Fe(CN)6]
Q.13 The compound that does not give a blue colour in Lassaigne’s test is-
(A) Aniline (B) Glycine (C) Hydrazine (D) Urea

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 PRACTICAL ORGANIC CHEMISTRY

Q.14 In Lassaigne’s test, the organic compound is fused with sodium metal so as to-
(A) Burn the compound (B) Form a sodium derivative
(C) Convert N, S, or halogen into soluble ionic compound (D) None of these
Q.15 Which of the following compound will give blood red colour while doing the Lassaigne’s test for N.
(A) (NH2)2C=O (B) H2N (C6H4)SO3H
(C) C6H5 SO3H (D) CHCI3
Q.16 In Kjeldahl’s method, CuSO4 acts as-
(A) Oxidising agent (B) Catalytic agent (C) Reducing agent (D) Hydrolysing agent
Q.17 Nitrogen in an organic compound can be estimated by-
(A) Kjeldahl’s method only (B) Duma’s method only
(C) Both method (D) None of these
Q.18 If 0.32 gm of an organic compound containing sulphur produces 0.233g of BaSO4 Then the percentage
of sulphur in it is-
(A) 10 (B) 15 (C) 20 (D) 25
Q.19 Carbon and Hydrogen are estimated by-
(A) Liebig’s method (B) Duma’s method (C) Carius method (D) Kjeldahl’s method
Q.20 Duma’s method involves the determination of content of nitrogen in the organic compound in the
form of -
(A) Gaseous NH3 (B) Gaseous N2 (C) NaCN (D) (NH4)2 SO4
Q.21 In Duma’smethod, the gas which is collected in Nitrometer is-
(A) N2 (B) NO (C) NH3 (D) H2
Q.22 Silica gel is used for keeping away the moisture because it-
(A) Absorbs H2O (B) Adsorbs H2O (C) Reacts with H2O (D) None
Q.23 Which process is suitable for the purification of aniline-
(A) Simple distillation (B) Steam distillation
(C) Fractional distillation (D) Fractional crystallisation
Q.24 Steam distillation is a better method of purification for...........compounds-
(A) Liquids (B) Steam volatile (C) Non-volatile (D) Miscible with water
Q.25 In steam distillation the vapour pressure of the volatile organic compound is-
(A) Equal to atmospheric pressure (B) Less than the atmospheric pressure
(C) More than the atmospheric pressure (D) Just double the atmospheric pressure
Q.26 Ellution is the process for-
(A) Crystallization of compound (B) Separation of compound
(C) Extraction of compound (D) Distillation of compound
Q.27 Boiling point of a liquid can be increased by-
(A) Increasing the pressure (B) Decreasing the pressure
(C) Purifying the liquid (D) Adding water to it
Q.28 0.59 g of an organic substance when treated with caustic soda evolved ammonia, which required
20 c.c. of N/2 sulphuric acid for neutralization. The percentage of nitrogen is-
(A) 40% (B) 53.6% (C) 63.6% (D) 23.73%

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 PRACTICAL ORGANIC CHEMISTRY

Q.29 In organic compounds P is estimated as-

(A) H3PO4 (B) P2O5 (C) Mg3(PO4)2 (D) (NH4)3 PO4 .12MoO3
Q.30 Which statement apply best to vacuum distillation-
(A) Distil liquids quickly with decomposition (B) It is very easy to distill
(C) Distil liquid to avoid decomposition (D) None
Q.31 A mixture of naphthalene and benzoic acid can be separated by-
(A) Extraction with solvent (B) Sublimation
(C) Fractional crystallisation (D) Distillation
Q.32 0.2 g of an organic compounds on complete combustion produces 0.44 g of CO2, then the
percentage of carbon in it is-
(A) 50 (B) 60 (C) 70 (D) 80
Q.33 Which is useful for separating benzoic acid from a mixture of benzoic acid and methyl benzoate-
(A) Aq. NaHCO3 (B) Dil.HCI (C) Dil.H2 SO4 (D) Dil. HNO3
Q.34 The process of differential extraction is based upon -
(A) Differential solubilities (B) Differential molecular masses
(C) Different boiling points (D) Different chemical properties
Q.35 0.2 g of an organic compound on complete combustion produces 0.18 g of water, then the
percentage of hydrogen in it is-
(A) 5 (B) 10 (C) 15 (D) 20
Q.36 In column chromatography the MOVING PHASE is constituted by-
(A) A substance which have to be separated
(B) Eluent
(C) Adsorbent
(D) Mixture of eluent and substances to be separated
Q.37 To detect iodine in presence of bromine, the sodium extract is treated with
NaNO2 + glacial acetic acid + CCl4. Iodine is detected by the appearance of:
(A) yellow colour of CCl4 layer
(B) purple colour of CCl4
(C) brown colour in the organic layer of CCl4
(D) deep blue colour in CCl4
Q.38 In steam distillation the vapour pressure of volatile organic compound is:
(A) equal to atmospheric pressure (B) double the atmospheric pressure
(C) less than atmospheric pressure (D) more than atmospheric pressure
Q.39 The sodium extract prepared from sulphanilic acid, contains SCN–. It gives blood red colouration
with:
(A) a mixture of Na2S and CS2 (B) FeCl3
(C) FeSO4 (D) Na2SO3
Q.40 Before testing halogens the sodium extract is boiled with conc. HNO3 to:
(A) bring common ion effect (B) make solution clear
– –
(C) destroy CN and S ions – (D) make the solution acidic
Q.41 Kjeldahl’s method cannot be used for the estimation of nitrogen in:
(A) Pyridine (B) Nitrocompounds (C) Azo compounds (D) All

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Q.42 The latest technique used for purification of organic compounds is:
(A) Chromatography (B) Vacuum distillation
(C) Fractional distillation (D) Crystallization
Q.43 If 0.2 gram of an organic compound containing carbon, Hydrogen and oxygen on combustion,
yielded 0.147 gram carbon dioxide and 0.12 gram water. What will be the content of oxygen in
the substance ?
(A) 73.29 % (B) 78.45 % (C) 83.23 % (D) 89.50 %
Q.44 0.765 g of an acid gives 0.535 g of CO2 and 0.138 g of H2O. Then the ratio of the percentage
of carbon and hydrogen is:
(A) 19 : 2 (B) 18 : 11 (C) 20 : 17 (D) 1 : 7
Q.45 2.79 g of an organic compound when heated in Carius tube with conc. HNO3 and H3PO4 formed
converted into MgNH4.PO4 ppt. The ppt. on heating gave 1.332 g of Mg2P2O7. The percentage
of P in the compound is
(A) 23.33 (B) 13.33 (C) 33.33 (D) 26.66
Q.46 Which of the following compounds will give silver mirror test-
(A) CH3COOH (B) HCOOH (C) CH3CO.COOH (D) None
Q.47 If on adding FeCl3 solution to acidified Lassaigne’s solution, a blood red colouration is produced,
it indicates the presence of -
(A) S (B) N (C) N and S (D) S and Cl
Q.48 In carius tube the compound ClCH2 – COOH was heated with fuming HNO3 and AgNO3. After
filteration and washing, a white ppt. was formed. The ppt is-
(A) AgCl (B) AgNO3 (C) Ag2SO4 (D) CH2(ClCOOAg
Q.49 Leibig method is used for the estimation of-
(A) Nitrogen (B) Sulphur
(C) Carbon and hydrogen (D) Halogens
Q.50 During Lassaigne’s test, N and S present in an organic compound changes into-
(A) Na2S and NaCN (B) NaSCN
(C) Na2SO4 and NaCN (D) Na2S and NaCNO
Q.51 Two solids A and B have appreciable different solubilities in water but their melting points are very
close. The mixture of A and B can be separated by-
(A) Sublimation (B) Fractional crystallisation
(C) Distillation (D) Specific method
Q.52 Which compound can not give following test.
 4  FeCl
Lassigne solution FeSO 3  Prussian blue coloured solution
NH2 NH2

(A) (B) (C) H2N – NH2 (D)

NH2

[MULTIPLE CORRECT CHOICE TYPE]

Q.53 For the crystallisation technique, which of the following statement is correct regarding choice of solvent.
(A) The solvent should dissolve the impurities.
(B) The solvent should not react chemically with the substance.
(C) The organic substance should dissolve in solvent upon heating and get separated on heating.
(D) None of these
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 PRACTICAL ORGANIC CHEMISTRY

Q.54 Distillation technique is used for purification of which liquids:

(A) Which boil without decomposition (B) Which boil with decomposition
(C) Which contains volatile impurities (D) Which contains non-volatile impurities
Q.55 Correct statement regarding differential extraction:
(A) Organic compound should be in aqueous medium
(B) Organic solvent is used which is immisible in water
(C) Organic compound is more soluble in organic solvent than water.
(D) Very large quantity of solvent is required to extract small quantity of compound.
Q.56 Correct statement about chromatography :
(A) It can be used to separate ortho and para nitro-anilines.
(B) It is used to separate blue and red dyes.
(C) It is used to purify plant pigments.
(D) It is used to separate compounds having dissimilar boiling points.
Q.57 Which of the following element is confirmed when soda-extract is treated with FeCl3 and blood red
colour appears in the Lassaigne test.
(A) Nitrogen (B) Sulphur (C) Iodine (D) Bromine
Q.58 Which of the following element is identified when red brown fumes are produced bysodium extract and
conc. H2SO4?
(A) Iodine (B) Nitrogen (C) Bromine (D) Chlorine
Q.59 The incorrect statement for Lassaigne's test regarding sodium extract :
(A) It is used to form sodium derivative which are non-soluble.
(B) It is used to convert elements into soluble ionic compound
(C) It is used to make element flammable.
(D) It is used as an oxidising agent.
[MATRIX TYPE]
Q.60 Match the compound in group I to the best technique of separation listed in group II.
Group I Group II
(A) Camphour containingnon-volatile impurities (P) Differential extraction
(B) Impure sample of aniline (Q) Sublimation
(C) Ortho and para nitro- anilines (R) Distillation
(D) Ether from ethyl alcohol. (S) Chromatography
Q.61 Column I Column II
(Property to be determined) (Method used for determination)
(A) Molecular mass of a volatile organic (P) Silver salt method
solid
(B) Molecular mass of a non-volatile (Q) Liebig method
organic solid
(C) Estimation of chlorine in carbon (R) Platinichloride method
tetrachloride
(D) Estimation ofnitrogen in aniline (S) Victor Meyer's method
(E) Equivalent mass of an organic acid (T) Depression in freezing point
(F) Equivalent mass of an organic base (U) Carius method
(G) Estimation of carbon and hydrogen in an (V) Kjeldahl's method
organic compound

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 PRACTICAL ORGANIC CHEMISTRY

EXERCISE-3
SECTION-A
(JEE ADVANCED Previous Year's Questions)
Q.1 Match the compounds/ion in column I with their properties/ reaction in Column II. Indicate your answer
by darkening the appropriate bubbles of the 4 × 4 matrix given in the OMR. [JEE 2007]
Column I Column II
(A) C6H5CHO (P) gives precipitate with
2,4-dinitrophenylhydrazine
(B) CH3CCH (Q) gives precipitate withAgNO3
(C) CN – (R) is a nucleophile
(D) I– (S) is involved in cyanohydrin formation
Q.2 Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II.
Indicate your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the OMR.
Column I Column II [JEE 2008]
+ -
(A) H2N – NH3Cl (P) sodium fusion extract of the compound gives
Prussian blue colour with FeSO4
+ -
NH3I
(B) HO (Q) gives positive FeCl3 test
COOH
+ -
(C) HO NH3Cl (R) gives white precipitate withAgNO3

+ -
(D) O2N NH – NH 3Br (S) reacts with aldehydes to form the corresponding
hydrazone derivative
NO2 SECTION-B
(JEE Main Previous Year's Questions)
Q.1 Match the catalysts to the correct processes: [JEE Main 2015]
Catalyst Process
(A) TiCl3 (i) Wacker process
(B) PdCl2 . (ii) Ziegler -Natta Polymerization
(C) CuCl2 (iii) Contact process
(D)V2O5 (iv) Deacon’s process
(A) (A) -{ii), (B) -(iii), (C) -(iv), (D) -(i) (B) (A) -(iii), (B) -(i), (C) -(ii), (D) -(iv)
(C) (A) -(iii), (B) -(ii), (C) -(iv), (D) -(i) (D) (A) -(ii), (B) -(i), (C) -(iv), (D) -(iii)
Q.2 The distillation technique most suited for separating glycerol from spent-lye in the soap industry is :
(A) Distillation under reduced pressure (B) Simple distillation [JEE Main 2016]
(C) Fractional distillation (D) Steam distillation
Q.3 Which of the following compounds will be suitable for Kjeldahl's method for nitrogen estimation?
+ –
NO2 N2Cl NH2
(A) (B) (C) (D)
N
[JEE Main 2018]
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 PRACTICAL ORGANIC CHEMISTRY

EXERCISE-4 (Rank Booster)

[SINGLE CORRECT CHOICE TYPE]

Q.1 Consider the reaction-
OH
(i) CHCl3+NaOH
+
P (major) + Q (Minor)
(ii) H3O
Mixture of P and Q can be best separated by -
(A) Steam distillation (B)Vacuum distillation
(C) Fractional distillation (D) Crystallisation

Q.2 Which of the following compound(s) will give blue colour when it is converted into Lassaigne's extract
and FeSO4 is added followed by FeCl3.

O
||
(I) (II) (III) NH2–OH (IV) NH 2  NH  C  NH 2

(A) I and IV (B) IV only (C) I, III & IV (D) I, II, III & IV

[MULTIPLE CORRECT CHOICE TYPE]

CHO
Q.3 AcONa (P)
+ AC2O

Before isolating (P) unreacted Ph–CHO is removed first. Select the correct statement.
(A) P is cinnamaldehyde
(B) Removal of PhCHO is done by passing steam into the mixture
(C) Removal is done by simple distillation
(D) P is cinnamic acid.

[MATRIX TYPE]
Q.4 Match the column
Column I Column II
(component of mixture) (Reagent)
(A) Crystalline Na2CO3 + Sodium citrate + CuSO4(aq. sol.) (P) Fehling solution
(B) CuSO4 + Rochelle Salt + NaOH(aq. sol.) (Q) Nesseler's Reagent
(C) 10%  - naphthol in alcohol (R) Benedict's solution
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch's Reagent

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 PRACTICAL ORGANIC CHEMISTRY

Q.5 Match the column

Column I Column II
(Functional group) (Test used or complex formed during confirmatory test)

(A)Aldehydic (P) [(C6H5O)6Fe]–3 (violet)

–
CH — C–O
O O
Cu
(B) Phenolic (Q) O (blue)
O
–
CH — C–O

RCH(OH)OSONH
(C)Alcohol (R) C NH
RCH(OH)OSONH violet red

(D) Glucose (S) (ROH)2Ce(NO3)4 (Red)

(T) Molisch's Test

[SUBJECTIVE]

Q.6 How will you differentiate?

(a) Propane & Propene (b) 1-Butyne & 2 - Butyne
(c) 2-Hexyne & 3-hexyne (d) 1,1-Dichloroethane & 1,2-Dichloroethane
(e) Chloroethane & Chloroethene (f) Pure & Oxidized CHCl3
(g) p-chlorotoluene & benzylchloride (h) n-propylchloride & isopropylchloride
(i) Methanol & ethanol (j) Isobutanol & tert-butanol
(k) 2-Pentanol & 3-pentanol (l) O-cresol & benzylalcohol
(m) Ethanol & Propanol (n) Propanone & Ethanol
(o) HCHO & PhCHO (p) Glucose & Fructose
(q) HCOOH & CH3COOH (r) HCOOH & HCHO

(s) MeNH2 & Me2NH (t) &

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 PRACTICAL ORGANIC CHEMISTRY

ANSWER KEY
EXERCISE-1

Q.2 21.95 %, 4.58 % Q.3 17.46% Q.4 56.0 %

Q.5 34.04 % Q.6 42.10 % Q.7 54.54, 9.09
Q.8 14.6 Q.9 20.24

EXERCISE-2

Q.1 B Q.2 B Q.3 C Q.4 A Q.5 C Q.6 D Q.7 B

Q.8 D Q.9 D Q.10 D Q.11 A Q.12 A Q.13 C Q.14 C
Q.15 B Q.16 B Q.17 C Q.18 A Q.19 A Q.20 B Q.21 A
Q.22 B Q.23 B Q.24 B Q.25 B Q.26 B Q.27 A Q.28 D
Q.29 D Q.30 C Q.31 A Q.32 B Q.33 D Q.34 A Q.35 B
Q.36 D Q.37 B Q.38 D Q.39 B Q.40 C Q.41 D Q.42 A
Q.43 A Q.44 A Q.45 B Q.46 B Q.47 C Q.48 A Q.49 C
Q.50 A Q.51 B Q.52 C Q.53 BC Q.54 AD Q.55 ABCD
Q.56 ABC Q.57 AB Q.58 C Q.59 ACD
Q.60 (A) Q (B) R (C) RS (D) R Q.61 (A) S (B) T (C) U (D) V (E) P (F) T (G) Q

EXERCISE-3

SECTION-A

Q.1 (A) P, S; (B) Q; (C) Q, R, S; (D) Q,R Q.2 (A) R,S (B) P,Q (C) P,Q,R (D) P,S

SECTION-B
Q.1 D Q.2 A Q.3 D

EXERCISE-4
Q.1 C Q.2 B Q.3 BD Q.4 (A)R (B) P (C) S (D) Q
Q.5 (A) Q,P (B) P, (C) S (D) T

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NOTES

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