Upload
others
View
6
Download
0
Embed Size (px)
Citation preview
JEE (MAIN+ADVANCED)
PRACTICAL ORGANIC CHEMISTRY
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
CONTENT
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 1
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 solubilityof 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.Thehot filtration isallowed tocool slowlyandundisturbedinabeakeror inacrystallising
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 byfiltration. The
filtration is normallydone byuse ofBuckner 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 finallydried 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
Solid Vapours
Heat
Cool
The sublimation process is used for the separation of those solids which sublime on heating from non-
volatile solids. The process is generallyused for the purification of camphor, naphthalene, anthracene,
benzoic acid, etc. containing non-volatile impurities.
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 2
Distillation
This method is used for the purification of liquids which boil without decomposition and contain non-
volatile impurities.Thesimple distillation involves its boilingpoint so that it is converted intovapours.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 thepassage of the vapours moving upwards and liquid movingdownwards. This method
may be used to separate a mixture of acetone (b.p. 330K) and methyl alcohol (b.p. 338. K).
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 3
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 normalboilingpoints.
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 appreciablyvolatile 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 sufficientlyhigh vapour pressure at the boiling point temperature of water (100ºC)
(iii) containnon-volatile impurities.
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 4
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 bydistillation or byevaporation 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
stationaryphase can be either solid or tightlybound liquid on a solid support while mobile phase can be
either liquid or a gas. Different types of chromatographic techniques commonlyused are as follows :
(1)Whenstationaryphase is solid thechromatographyisknownasadsorptionchromatography.Adsorption
chromatography is further classified into following categories. This classification on the nature of the
mobile phase.
Gas
Gas-Solid Chromatography(GSC)
Liquid
Liquid-Solid Chromatography(LSC)
Adsorption columnChromatography
(ACC)
Thin-layerChromatography
(ACC)
Mobile Phase
(2)When stationaryphase is liquid the chromatographyis known as partition chromatography. Partition
chromatography is further classified in different categories. This classification depends on the nature of
the mobile phase.
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 5
Gas
Gas-Liquid Chromatography(GLC)
Liquid
Liquid- Chromatography(LLC)
Liquid
Partition(TLC)
Reverse Phase PartitionChromatography
(RPPC)
Mobile Phase
Partition ColumnChromatography
(PCC)
PaperChromatography
(PC)
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 chromatographyis 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 stationaryphase (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
Column chromatography. Different stages ofseparation of components of a mixture
ab+c
Glass wool
Adsorbent(stationary phase)
abc
Column chromatographyinvolves separation of a mixture over a column of adsorbent (stationaryphase)
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. Dependingupon the
degree to which thecompounds areadsorbed,complete separation takesplace.Themost readilyadsorbed
substances are retained near the top and others come down to various distances in the column
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 6
(ii) Thin layer chromatography :
Thin layer chromatographychromatogram being developed
base line
jar
adsorbent coatedon glass plate
sample dot
solvent
solventfront
spot
y
base linex
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 :
base line
card board
chromatographypaper
jarspot
solvent
card board
chromatographypaper
jarspot
solvent
base line
Paper chromatography chromatographypaper in two different shapes
Partitionchromatographyisbasedoncontinuousdifferentialpartitioningofcomponentsofmixturebetween
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 dryorganic compound is heated stronglywith drycupric 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)
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 7
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).
CO2C
44 g of CO2 contain C = 12g
m2 g of CO2 contains C =12
44× m2 g
Hence Percentage of carbon = m44
12m2
× 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
m1 g of H2O contains H =2
18× m1 g
Percentage of hydrogen = m18
2m1
× 100
Percentage of C =12
44×
Mass of CO formed
Mass of compound taken2
x 100
Percentage of H =2
18×
Mass of H Oformed
Mass of compound taken2
x 100
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 anatmosphere of carbon dioxide. The carbon and hydrogen are oxidised to carbon dioxide and waterrespectively while nitrogen is set free. If any oxide of nitrogen is produced during this process, it isreduced to nitrogen by passing over a heated copper gauze. The gaseous mixture is collected over anaqueous solution of KOH when all the gases except nitrogen are absorbed. The volume of nitrogenproduced is measured at room temperature and atmospheric pressure. From the volume of N2 produced,percentage of nitrogen in the sample can be calculated.
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 8
C + 2CuO CO2 + 2Cu
2H + CuO H2O + Cu
2N + CuON2 + oxides of nitrogen
Oxides of nitrogen + CuCuO + 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 = ?
Applyinggas equation1
11
T
VP=
P V
T2 2
2
V2 =P V T
P T1 1 2
2 1=
( )
( )
P a xV x
t
273
760 273= x cm3 (say)
Now 22400 cm3 of N2 at S.T.P. weight = 28 g
x cm3 of N2 at S.T.P. will weigh =28
22400×xg
Percentage of nitrogen =Massof nitrogen
Mass of organic compoundx 100
=28 100
22400
x x
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 : Aknown weight of the organic compound is heated with conc. H2SO4 so that nitrogen isquantitatively converted into ammonium sulphate. The solution is then heated with excess of sodiumhydroxide. The ammonia gas evolved is passed into a known but excess volume of standard acid (HClor H2SO4). The acid left unused is estimated by titrating the solution with standard alkali. From theamount of acid left unused the amount of acid used for neutralisation of ammonia can be calculated.From this percentage of nitrogen can be calculated.
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 9
C, H, S Conc H SO. 2 4 CO2 + H2O + SO2(from organic compound)
N Conc H SO. 2 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 = N1Let vol. of standard alkali used for neutralisation of unused acid = V2 cm3
Normality of standard alkali = N2
{N V
alkali
1 1 =N V
acid
2 2123
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
(V – v) cm3 of N1 NH3 solution contains nitrogen =14
10001( )V v x N
g
Percentage of nitrogen =Massof nitrogen
Mass of organic compoundx 100 =
1000
Nxv)(V14 1×
100
w
=1 4 1. ( )V v x N
w
Estimation of Halogens :
Carius method :
Principle : Aknown mass of the organic substance is heated with fuming HNO3 in a Carius tube. Thesilver halide so obtained is separated, washed, dried and weighed. From the weight of silver halideformed, 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 H2SO4respectively.
C + 2O HNO3 CO2
2H + O HNO3 H2O
S + H2O + 3O HNO3 H2SO4
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 10
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
a g of silver halide will give halogen =X
X( )108 × a g
Percentage of halogen =Mass of ha en
Mass of organic compound
logx 100 =
X x a
X( )108 x
100
w
Here X is the atomic mass of halogen, e.g.
Cl = 35.5 , Br = 80 (79.9 exact),
I = 127 (126.9 exact)
Percentage of halogen =substanceorganicofMasshalogen)ofmassAt.(108
halidesilverofMasshalogenofmassAtomic
× 100
Estimation of Sulphur
Sulphur is estimated byCarius method.
Principle : Aknown mass of the organic compound is heated with fuming HNO3 in a sealed tube whensulphur is quantitatively converted into sulphuric acid. It is then precipitated with barium chloride asbarium sulphate. The precipitate is filtered, washed, dried and weighed. From the weight of BaSO4formed, the percentage of sulphur can be calculated. The main reactions are :
S + H2O + 3O HNO3 H2SO4
H2SO4 + BaCl2 BaSO4ppt.
Calculations :Let the mass of organic compound = w gMass of BaSO4 formed = agBaSO4S137 + 32 + 64 = 32
= 233233 g of BaSO4 contain sulphur = 32 g
a g of BaSO4 will contain sulphur =32
233
x ag
Percentage of sulphur =compoundorganicofMass
sulphurofMass× 100 =
32
233
a×
100
w
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 11
(B)Elementa
lAnalysis
Lass
aigne
meth
od
(Dete
ction
of
elements
)
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–––
Ele
men
tS
od
ium
Ext
ract
(S.E
.)C
on
firm
edT
est
Rea
ctio
n
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–––
Nit
roge
nN
a+
C+
NN
aCN
(S.E
.)S
.E.+
FeS
O4
+N
aOH
,bo
ilan
dco
ol,
FeS
O4
+2
NaO
H
Fe(
OH
) 2+
Na 2
SO
4
(It
iste
sted
ascy
anid
e+
FeC
l 3+
con
c.H
Cl
blu
eo
rgr
een
Fe(
OH
) 2+
6N
aCN
Na 4
[Fe(
CN
) 6]
+2
NaO
H
inN
itro
gen
com
pou
nd)
colo
urN
a 4[F
e(C
N) 6
]+
FeC
l 3F
e 4[F
e(C
N) 6
] 3+
3N
aCl
Pru
ssia
nb
lue
Sul
phur
2N
a+
SN
a 2S
(S.E
.)(i
)S
.E.+
So
diu
mn
itro
pru
ssid
e(A
)(i
)N
a 2S
+N
a 2[F
e(C
N) 5
NO
]
Na 4
[Fe(
CN
) 5N
OS
]
Ad
eep
viol
etco
lou
r.(A
)de
epvi
olet
(ii)
S.E
.+C
H3C
OO
H+
(CH
3CO
OH
) 2Pb
(ii)
Na 2
S+
(CH
3C
OO
) 2P
bP
bS+
2C
H3C
OO
Na
Ab
lack
pp
t.b
lack
pp
t.S
.E.
+H
NO
3+
AgN
O3
Nit
roge
nN
a+
C+
N+
SN
aCN
SA
sin
test
for
nit
roge
n;
inst
ead
of
NaC
NS
+F
eCl 3
[Fe(
CN
S)]
Cl 2
+N
aCl
and
(S.E
.)gr
een
or
blu
eco
lou
r,b
loo
dre
dbl
ood
red
colo
urS
ulph
ur(c
ompo
und
wil
lnot
show
colo
rati
on
con
firm
sp
rese
nce
of
toge
ther
indi
visu
alL
assa
igne
test
inth
isca
se)
Nan
dS
bo
th
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–––
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 12
Ch
lori
ne
:––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
Exp
erim
ent
Ob
serv
atio
ns
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––
1.
Na
+C
lN
aCl
So
diu
mex
trac
tw
ith
con
c.H
2S
O4
give
sN
aCl
+H
2S
O4
HC
l+
NaH
SO
4
(S.E
.)p
un
gen
tsm
elli
ng
gas.
Wh
ich
give
sd
ense
HC
l+
NH
3
NH
4C
l(w
hit
efu
me)
wh
ite
fum
ew
ith
NH
3
2.S
ilve
rnitr
ate
test
Aci
dify
apo
rtio
nof
aque
ous
solu
tion
NaC
l+
AgN
O3
AgC
l+
NaN
O3
(ors
odiu
mca
rbon
ate
extr
act)
wit
hdi
l.W
hite
ppt
HN
O3.
Boi
lfor
som
eti
me,
cool
and
AgC
l+2
NH
4O
H
[Ag(
NH
3) 2
]C
l+2H
2O
add
AgN
O3
solu
tion
.S
olub
leco
mpl
exA
whi
tepp
t.is
form
edw
hich
isso
lubl
ein
amm
onia
hydr
oxid
e.
3.M
anga
nese
diox
ide
test
Hea
tapi
nch
ofth
eS
.E.w
ith
asm
all
2NaC
l+
Mn
O2
+3H
2S
O4
quan
tity
ofM
nO2
and
conc
.H2S
O4.
2N
aHS
O4
+M
nSO
4+
2H2O
+C
l 2
Evo
lutio
nof
gree
nish
yell
owga
sha
ving
aY
ello
wgr
een
pung
enti
rrita
ting
smel
l.It
turn
sm
oist
star
ch-i
odid
epa
perb
lue.
4.C
hrom
ylch
lori
dete
stM
ixa
smal
lqua
ntit
yof
the
S.E
.wit
ha
4NaC
l+
K2C
r 2O
7+
3H2S
O4
2Na 2
SO
4+
K2S
O4
smal
lam
ount
ofpo
wde
red
pota
ssiu
m+
2CrO
2C
l 2+
3H2O
dich
rom
ate.
Tak
eth
em
ixtu
rein
ate
stC
hrom
ylch
lori
detu
bean
dad
dco
nc.H
2S
O4.
Hea
tthe
tube
and
pass
the
red
vapo
urs
CrO
2C
l 2+
4NaO
H
Na 2
CrO
4+
2H2O
+2N
aCl
evol
ved
into
the
gas
dete
ctor
cont
aini
ngS
od.c
hrom
ate
NaO
Hso
luti
on.T
oth
eye
llow
solu
tion
Na 2
CrO
4+
(CH
3C
OO
) 2P
bP
bCrO
4
+2C
H3C
OO
Na
thus
obta
ined
,add
dil.
CH
3C
OO
Han
dL
ead
chro
mat
ele
adac
etat
eso
luti
on.A
yell
owpp
t.is
form
ed.
(Yel
low
ppt.)
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 13
Bro
min
e
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–E
xper
imen
tO
bse
rvat
ion
s––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––
1.
Na
+B
rN
aBr
So
diu
mex
trac
tw
ith
con
c.H
2S
O4
give
sN
aBr
+M
nO2+
3H2S
O4
2NaH
SO
4+
MnS
O4
+2H
2O
+B
r 2
(S.E
.)R
edB
row
nfu
mes
wh
ich
inte
nsi
fyo
nR
edB
row
nad
diti
onof
Mn
O2
2.S
ilve
rnitr
ate
test
Aci
dify
apo
rtio
nof
aque
ous
solu
tion
(or
sodi
umca
rbon
ate
extr
act)
wit
hdi
l.H
NO
3.B
oil,
cool
and
add
AgN
O3
solu
tion
.A
ligh
tyel
low
ppt.
isob
tain
edw
hich
isK
Br
+A
gNO
4
KN
O3
+A
gBr
part
iall
yso
lubl
ein
NH
4OH
.(P
ale
yell
owpp
t.)
Pal
eye
llow
ppt.
ofsi
lver
brom
ide
are
spar
ingl
yso
lubl
ein
amm
oniu
mhy
drox
ide.
3.C
hlor
ine
wat
erte
stA
cidi
fya
port
ion
ofaq
ueou
sso
luti
on(o
r2K
Br
+C
l 2
2K
Cl
+B
r 2so
dium
carb
onat
eex
trac
t)w
ith
dil.
HC
lB
rom
ine
bein
gso
lubl
ein
CC
l 4im
part
san
and
add
1-2
mlo
fcar
bon
disu
lphi
dean
dor
ange
colo
urto
the
CC
l 4la
yer.
then
chlo
rine
wat
er.S
hake
vigo
rous
lyan
dal
low
tost
and
byth
isca
rbon
disu
lphi
dela
yera
cqui
res
oran
geco
lour
atio
n.––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–––
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 14
Iod
ine
:––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––E
xper
imen
tO
bse
rvat
ion
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–––
1.N
a+
IN
aIS
odiu
mex
trac
trea
ctw
ith
conc
.H2S
O4
2NaI
+M
nO2+
3H2S
O4
2NaH
SO
4+
MnS
O4
+2H
2O
+I 2
togi
vevi
olet
fum
es.w
hich
inte
nsif
yV
iole
ton
addi
tion
ofM
nO2
2.S
ilve
rnitr
ate
test
Aci
dify
apo
rtio
nof
aque
ous
solu
tion
(or
KI
+A
gNO
3
KN
O3
+A
gIso
dium
carb
onat
eex
trac
t)w
ith
dil.
HN
O3.
(Yel
low
ppt.
)B
oil,
cool
and
add
AgN
O3
solu
tion
.A
yell
owpp
t,is
form
edw
hich
isin
solu
ble
inN
H4O
H.
3.C
hlor
ine
wat
erte
stA
cidi
fya
part
ofth
eaq
ueou
sso
luti
on(o
r2K
I+
Cl 2
2KC
l+
I 2so
dium
carb
onat
eex
trac
t)w
ith
dil.
HC
l,Io
dine
bein
gso
lubl
ein
CC
l 4im
part
sa
viol
etad
d1-
2m
lofc
arbo
ndi
sulp
hide
and
then
colo
urto
the
CC
l 4la
yer.
chlo
rine
wat
er.S
hake
vigo
rous
lyan
dal
low
tost
and.
Car
bon
disu
lphi
dela
yera
cqui
res
avi
olet
colo
urat
ion.
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
––––
–––
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 15
(C) FUNCTIONAL GROUP TEST
1. Unsaturation :Alkenes & alkynes:(a) Bayers test : Cold dil alk. KMnO4 decolourisation test
Purple colourColourless + MnO2 (Brown ppt)(b) Br2 water decolourisation test
Brown colour of Br2Colourless
2. Terminal alkynes:Confirmed by ppt ofAcetylide ion with NaNH2 orAgNO3 or Cu2Cl2NH4OH
3. Alkyl halides:(a) If theyare capable of carbocation formation then they will give ppt withAgNO3.(b) Beilstein’s test : A greencolour is imported to the flame if small amount of organic compound is taken on
copper wire.
4. Alcohol:(a) Cerric ammonium nitrateGive red colour(b) Boil with acetic acid & conc. H2SO4 fruity smell
(c) 2-alkanol & ethanol also give Iodoform testYellow ppt. of CH3I on reaction with I2+ HO
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 testSilver mirror(b) Fehling’s test {except benzaldehyde}Red colour(c) Benedicts testRed colour(d) Schiff’s dye colour regeneration testPink 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 fruitysmellon 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 verydistinctive foul odour.(b) Hoffmann mustard oil reactionOilyliquid with mustard like smell.
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 16
11. Aromatic 1° amine diazo test
12. Amide boil with NaOHNH3
13. NitrobenzeneMullikqn Baker testTreat it with ZnNH4Cl then boil withTollen’s reagentSilvermirror will appear
14. Proteins:(a) Biuret test :Also used for ureaAlkaline solution of protein treated with a drop of aq CuSO4 when
bluish violet colour is obtained(b) Ninhydrin test : Protein treatedwith a puridinesolution of ninhydrin givecolour rangingfromdeep 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°AlcoholBlood red colour(ii) 2°AlcoholBlue(iii) 3°AlcoholColourless
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 byacid(iii) 3°Amineyield insoluble compound
(b) Reaction with HNO2
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 17
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 and0.1014g 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 ammoniaevolved from 0.5 g of the compound in Kjeldahl’s estimation of nitrogen, neutralized 10 mL of1 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. Whatis 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 gof 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 ofBaSO4. The percentage of sulphur in the compound is-
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 18
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 fromsolid 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 mixturecontaining 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 thepurple 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
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 19
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 percentageof 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 theform 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 required20 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%
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 20
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 thepercentage 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 thepercentage 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 withNaNO2 + 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 colourationwith:(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
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 21
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 inthe 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 percentageof 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 formedconverted into MgNH4.PO4 ppt. The ppt. on heating gave 1.332 g of Mg2P2O7. The percentageof 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. Afterfilteration 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 veryclose. 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.
Lassigne solution 4FeSO 3FeCl Prussian blue coloured solution
(A)NH2
(B)
NH2
(C) H2N – NH2 (D)
NH2
[MULTIPLE CORRECT CHOICE TYPE]Q.53 For the crystallisation technique, which of the following statement is correct regardingchoice of solvent.
(A) The solvent should dissolve the impurities.(B) The solvent should not react chemicallywith the substance.(C) The organic substance should dissolve in solvent upon heating and get separated on heating.(D) None of these
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 22
Q.54 Distillation techniqueis used for purificationof which liquids:(A) Whichboil without decomposition (B) Which boil with decomposition(C) Whichcontainsvolatile impurities (D) Whichcontains 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 quantityof solvent is required to extract small quantityof 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 purifyplant 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 redcolour 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 andconc. 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) Camphourcontainingnon-volatile impurities (P) Differentialextraction(B) Impure sampleof 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 methodsolid
(B) Molecular mass of a non-volatile (Q) Liebigmethodorganic solid
(C) Estimation of chlorine in carbon (R) Platinichloridemethodtetrachloride
(D) Estimationofnitrogeninaniline (S) Victor Meyer's method(E) Equivalent mass of an organic acid (T) Depression in freezingpoint(F) Equivalent mass of an organic base (U) Carius method(G) Estimation of carbon and hydrogen in an (V) Kjeldahl's method
organic compound
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 23
EXERCISE-3
SECTION-A
(JEE ADVANCED Previous Year's Questions)Q.1 Match the compounds/ion in column Iwith 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 with2,4-dinitrophenylhydrazine
(B) CH3CCH (Q) gives precipitate withAgNO3(C) CN– (R) is a nucleophile(D) I– (S) is involvedin 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 –+ -NH Cl3 (P) sodium fusion extract of the compound gives
Prussian blue colour with FeSO4
(B) HO
NH I3
COOH
+ -
(Q) gives positive FeCl3 test
(C) HO NH Cl3
+ -(R) gives white precipitate withAgNO3
(D) O N2NH – NH Br3
+ -
NO2
(S) reactswithaldehydes to formthecorrespondinghydrazone derivative
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)Simpledistillation [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?
(A)
NO2
(B)N Cl2
–+
(C)N
(D)
NH2
[JEE Main 2018]
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 24
EXERCISE-4 (Rank Booster)
[SINGLE CORRECT CHOICE TYPE]
Q.1 Consider the reaction-
(i) CHCl +NaOH3 P (major) + Q (Minor)(ii) H O3
+
OH
Mixture of P and Q can be best separated by -(A)Steam distillation (B)Vacuumdistillation(C) Fractional distillation (D)Crystallisation
Q.2 Which of the following compound(s) will give blue colour when it is converted into Lassaigne's extractand FeSO4 is added followed by FeCl3.
(I) (II) (III) NH2–OH (IV) 22 NHCNHNH||
O
(A) I and IV (B) IV only (C) I, III & IV (D) I, II, III & IV
[MULTIPLE CORRECT CHOICE TYPE]
Q.3 + AC O2AcONa (P)
CHO
Before isolating (P) unreacted Ph–CHO is removed first. Select the correct statement.(A) P is cinnamaldehyde(B) Removal of PhCHO is done bypassing steam into the mixture(C) Removal is done bysimple 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) Fehlingsolution(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
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 25
Q.5 Match the columnColumn I Column II(Functional group) (Test used or complex formed during confirmatory test)
(A)Aldehydic (P) [(C6H5O)6Fe]–3 (violet)
(B) Phenolic (Q)
CH — C–O–
CH — C–O–
Cu
OO
OO(blue)
(C)Alcohol (R)
RCH(OH)OSONH
RCH(OH)OSONH
C NH
violet red
(D) Glucose (S) (ROH)2Ce(NO3)4 (Red)
(T) Molisch's Test
[SUBJECTIVE]
Q.6 How willyou 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) &
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 26
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 AQ.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 ACDQ.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) QQ.5 (A) Q,P (B) P, (C) S (D) T
PRACTICAL ORGANIC CHEMISTRY
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05 Page # 27
NOTES