Qualitative and Quantitative

Analysis
3
Method of Purification of organic compound
(i) Sublimation (ii) Crystallisation (iii) Distillation (iv) Differential extraction
(v) Chromatography

(1) Sublimation
 On heating, some solid substance change from solid to vapour state without passing through liquid state
 It is used to separate sublimable compound from non sublimable impurities
Example :- Iodine, Naphthalene, Ammonium chloride etc

(2) Crystallisation
 It is used for the purification of solid organic compound
 It is based on the difference in the solubililties of the compound and the impurities in a suitable solvent

(3) Distillation (Very Very Important)

 Distillation Techniques
Types Condition Examples
(A) Simple Distillation (i) When volatile liquid has non- (i) Mixture of chloroform (B.P.
volatile impurities 334K) and aniline (B.P. 457 K)
(ii) When boiling point difference is (ii) Mixture of ether (B.P. 308K)
suffient (80° K or more) and toluene (384K)
(B) Fractional Distillation When difference in boiling point of two (i) Crude oil in petroleum
liquid is very low (10K) industry
(ii) Acetone (329k) and methyl
alcohol (338k)
(iii) Hexane and pentane
(C) Distillation under When liquids having very high boiling (i) Recovery of Glycerol from
reduced pressure point and those, which decompose at or spent lye in soap industry
below their boiling point (ii) Concentration of sugar juice
(iii) Glycerol

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 Qualitative and Quantitative Analysis
(D) Steam Distillation When the substance is steam volatile (i) Aniline is separated from
and immiscible with water water
In steam distillation, the liquid boils (ii) Ortho nitro phenol (steam
when the sum of vapour pressure due to volatile) is separated from para
the organic liquid (P1) and that due to nitro phenol.
water (P2) become equal to the
atmospheric pressure (P)
i.e. (P=P1 + P2)

(4) Differential extraction

When an organic compound 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 aqueous solution should be immiscible with each other so that they form two
distinct layers which can be separated by separatory funnel
Example :- Organic compound separated from water

(5) Chromatography
In this technique, mixture of substance are applied on stationary phase which may be solid or liquid. A
pure solvent, mixture of solvent or a gas is allowed to move slowly over stationary phase. The moving phase
is called mobile phase. The component of the mixture get gradually separated from one another
According to principle involved, chromatography is classified into category. Two of these are

(i) Adsorption chromatography:-

Principle Adsorption
Adsorbate Substance which are being purified
Adsorbent Silica gel and alumina

(ii) Partition Chromatography:-

Principle :- Continuous differential partioning of componeuts of a mixture between stationary and mobile
phase
Adsorption Chromatography Partition
chromatography
(a) Column chromatography (b) Thin layer (b) Paper chromatography
chromatography
Stationary phase Silica gel and alumina Silica gel and alumina Chromatography paper
contain water trapped in it
which act as the stationary
phase
Mobile phase liquid or mixture of liquid Liquid or mixture of Liquid or mixture of liquid
liquid
Process Mobile phase flow from top to Mobile phase flow from Mobile phase flow from
bottom in a column having bottom to top over a thin bottom to top over
stationary phase layer of an adsorbent chromatography paper
coated on glass plate

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1 | Qualitative and Quantitative Analysis

Exercise - 1 Objective Problems | NEET

1. Lassaigne's Test for the detection of nitrogen 7. When 0.01 mol of an organic compound
will fail in the case of- containing 60% carbon was burnt completely.
(1) NH2CONH2 4.4g of CO2 was produced. The molar mass of
(2) NH2—CO—NH—NH2.HCl comp. is ______ g mol–1.
(3) NH2—NH2.HCl (1) 300 (2) 250
(4) C6H5NH—NH2. 2HCl (3) 200 (4) 150

2. In kjeldahl's method nitrogen present is 8. A sample of 0.125 g of an organic compound

estimated as: when analysed by duma's method yields 22.78
(1) N2 (2) NO2
ml of nitrogen gas collected over KOH solution
(3) NH4SO4 (4) NH3
at 280K and 759 mm Hg. The % of nitrogen in
the given organic compound is__? (Consider
3. The Prussian blue color obtained during the test
aquous tension zero)
of nitrogen by lassaigne's test is due to the
(1) 36 (2) 22
formation of-
(3) 12 (4) 48
(1) Fe4[Fe(CN)6]3 (2) Na3[Fe(CN)6]
(3) Fe(CN)3 (4) Na4[Fe(CN)5NOS]
9. The transformation occurring in duma's method
4. In lassaigne's extract of an organic compound is given below:-
both nitrogen and sulphur are present, which  y
C2H7N +  2x   CuO 
given blood red color with Fe3+ due to the  2 
formation of- y z  y
xCO2 + H2O + N 2   2x   Cu
(1) NaSCN 2 2  2
(2) [Fe(CN)5 NOS]4– The value of 'y' is__
(3) [Fe(SCN)]2+
(4) Fe4[Fe(CN)6]3.H2O (1) 14 (2) 7
(3) 7/2 (4) None of these
5. Nitric acid added to sodium extract before
adding silver nitrate for testing halogen because 10. Nitrogen can be estimated by kjeldahl's method
(1) Nitric acid reduces sulphide
for which of the following compound?
(2) Nitric acid decomposes "NaCN" and "Na2S"
(3) Nitric acid oxidises the organic compound (1) (2)
(4) Nitric acid acts as a dehydrating agent

NNCl CH2–NH2
6. An organic compound give 0.220 gm of CO2
and 0.126gm of H2O on complete combustion if
(3) (4)
the % of carbon is 24 then % hydrogen is-
(1) 76 (2) 8.6
N NO2
(3) 5.6 (4) 50

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2 | Qualitative and Quantitative Analysis
11. Which one of the following set of elements can 16. Which of the following compounds will give
be detected using sodium fusion extract? Prussian blue color when it is converted into
(1) Sulfur, Nitrogen, phosphorous, halogen lassaigne's extract and FeSO4 is added followed
(2) Phosphorous, oxygen, nitrogen, halogen FeCl3 (Fe3+ ion)
(3) Nitrogen, phosphorous, carbon, sulphur NH
(4) Halogen, nitrogen, oxygen, sulfur (I) (II)
S
12. In carius method, halogen containing organic
compound is heated with fuming nitric acid in SO3H
the presence of O

(IV) NH2—NH—C—NH2
(1) HNO3 (2) AgNO3
(III) NH2OH
(3) CuSO4 (4) FeSO4
(1) I and IV (2) IV only
(3) I, III and IV (4) I, II, III and IV
13. Which of the following is a false statement?
(1) Carius tube is used in the estimation of
17. Black precipitate in the detection of sulphur
sulphur in an organic compound
with lead acetate and acetic acid is due to the
(2) Carius method is used for the estimation of
formation of
nitrogen in an organic compound
(1) Pb2S (2) PbS
(3) Phosphoric acid produced on oxidation of
(3) PbS2 (4) PbSO4
phosphorus present in an organic compound is
precipitated as Mg2P2O7 by adding magnesia
18. Which of the following will give positive
mixture
(4) Kjeldahl's method is used for the estimation lassaigne's test for nitrogen
of nitrogen in an organic compound (1) NH2OH
(2) NH2—NH2
14. Match list I with list II (3) KCN
List-I Element List -II Reagent used/ N=N—Cl
detected Product (4)
formed
(A) Nitrogen (i) Na2[Fe(CN)5NO] 19. Which of the following will give blood red
(B) Sulphur (ii) AgNO3 color in lassaigne's test for nitrogen
(C) Phosphorous (iii) Fe4[Fe(CN)6]3 (1) PhNH2 (2) PhNO2
(D) Halogen (iv) (NH4)2MoO4
(3) O2N SO3H (4) PhSO3H
(1) A-(ii), B-(iv), C-(i), D-(iii)
(2) A-(iv), B-(ii), C-(i), D-(iii)
(3) A-(ii), B-(i), C-(iv), D-(iii) 20. The violet color that develops on addition of
(4) A-(iii), B-(i), C-(iv), D-(ii) nitro prusside solution to sodium fusion extract
of a sulphur containing organic compound is
15. The compound formed upon subjecting an due to the formation of
aliphatic amine to lassaigne's test is (1) Na4[Fe(CN)5NOS] (2) Na2[Fe(CN)5NO]
(1) NaNH2 (2) NaNO2 (3) Na3[Fe(SCN)6] (4) Na4[Fe(CN)5S]
(3) NaCN (4) NaN3
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3 | Qualitative and Quantitative Analysis
21. The sodium fusion extract of an organic 26. An organic compound with 51.6% sulphur is
compound on acidification with acetic acid heate in a carius tube. The amount of this
followed by addition of lead acetate solution compound which form 18.74gm of barium
produced a black ppt. So the compound sulphate is-
contains- (1) 15.9 gm (2) 11.8 gm
(1) Nitrogen (2) phosphorous (3) 18.6 gm (4) 4.99 gm
(3) Sulphur (4) Bromine
27. The number of moles of CuO, that will be
22. The sodium fusion extract of an organic utilised in Dumas method for estimation of
nitrogen in a sample of 57.5gm of C7H17N is-
compound is boiled with nitric acid and then
(1) 11.25 (2) 18.6
treated with silver nitrate solution. A white
45
precipitate is formed which dissolves in (3) (4) 30.5
2
aqueous Ammonia solution. The organic
compound contain
28. The kjeldahl method of nitrogen estimation fails
(1) Sulphur (2) Chlorine in which of the following reaction products?
(3) Iodine (4) Bromine NO2

23. Which of the following compound is formed Sn/HCl

(A)
when an organic compound containing both
nitrogen and sulphur is fused with sodium
CN
(avoiding excess)
(1) Sodium sulphide LiAlH4
(2) sodium cyanide (B)
(3) sodium thiocyanate
CH2CN
(4) A mixture of (1) & (2)
(i) SnCl2+HCl
24. An organic compound is fused with sodium (C) (ii) H2O
peroxide and the fused mass is extracted with
NH2
water. The extract is heated with nitric acid and
ammonium molybdate. A yellow precipitate is NaNO2
obtained. The compound contains (D) HCl/0.5
(1) Sulphur (2) Chlorine
(1) (C) and (D) (2) (A) and (D)
(3) nitrogen (4) Phosphorus
(3) (A), (C) and (D) (4) (D) and (C)

25. The formula of sodium nitro prusside is

29. Distillation under reduced pressure is usefull
(1) Na4[Fe(CN)6]
for?
(2) Na3[Fe(CN)5NO]
(1) Cruide oil (2) Gly cerol
(3) Na2[Fe(CN)5NO]
(3) Benzene (4) Naphthalene
(4) Na4[Fe(CN)5NOS]

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4 | Qualitative and Quantitative Analysis
30. The most suitable method of separation of 1 : 1 33. Match list I with list II
mixture of ortho and para nitrophenols is List-I (Mixture) List -II (Separation
(1) Chromatography (2) Crystallisation Technique)
(3) Steam distillation (4) Sublimation (A) CHCl3+C6H5NH2 (i) Steam distillation
(B) C6H14+C5H12 (ii) Differential
31. The distillation Technique most suited for extraction
separating glycerol from spent lye in the soap (C) C6H5NH2+H2O (iii Distillation
industry is- (Simple)
)
(1) Distillation under reduced pressure (D) Organic (iv) Fractional
(2) Simple distillation compound in distillation
(3) Fractional distillation water
(4) Steam distillation (1) A-(iv), B-(i), C-(iii), D-(ii)
(2) A-(iii), B-(iv), C-(i), D-(ii)
32. Which purification technique is used for high (3) A-(ii), B-(i), C-(iii), D-(iv)
boiling organic compound (decomposes near (4) A-(iii), B-(i), C-(iv), D-(ii)
its boiling point)?
(1) Simple distillation
(2) Steam distillation
(3) Fractional distillation
(4) Reduced pressure distillation

ANSWER KEY [EXERCISE-1]

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 3 4 1 3 2 3 3 2 2 2 1 2 2 4 3
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 2 2 3 3 1 3 2 3 4 3 4 1 1 2 3
Que. 31 32 33
Ans. 1 4 2
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 CHAPTER # 3 : QUALITATIVE AND QUANTITATIVE ANALYSIS
HINT & SOLUTIONS
1. (3) 9. (2)
y
C2 H7 N 
 H2 O
2. (4) 2
y
3. (1) 7= 2
2
Y =7
4. (3)
10. (2)
5. (2) Kjeldahl's method is not applicable in
following comp.
6. (3) (i) Nitro (–NO2) comp.
12 W1 (ii) Azo(–N=N–) group
%C   100
14 W (iii) Nitrogen present in the ring
12 0.220
24   100
44 W ex
1
 W  = =0.25gm N
 4
Because nitrogen of these compound does
Weight of organic comp.
not change to ammonium sulphate under
2 W2
%H   100 these condition
18 W
2 0.126 11. (1)
%H   100
18 0.25
%H = 5.6% 12. (2)

7. (3) 13. (2)

12 W
%C   1 100
44 W 14. (4)
 W 
 Mole  Mw  15. (3)
12 4.4  
60   100  W  mole  Mw 
44 0.01 Mw  W  0.01 Mw  16. (2)
 
  17. (2)
Mw = 200
18. (3)
8. (2) Note:-(i) Lassaigne test of nitrogen is not
(P– P1 ) V1 P2 V2 given if "C" is absent in the compound

T1 T2 NH2OH, NH2–OH etc
Eg.
759  22.78 760  V2
 They don't form cyanide
280 273 (CN )
V2 = 22.18 ml (ii) Diazonium comp.
28  V2 (ml)
%N  100
22400  W 
N2Cl
28  22.18 N gas released
 hence
2
%N  100  'NaCN' will
22400  0.125 R–N2Cl or (N2) not form as a SFE
%N 22%

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QUALITATIVE AND QUANTITATIVE ANALYSIS
19. (3) 28. (1)
NO2 NH2
20. (1)
(A) Sn/HCl
21. (3)

22. (2) CN CH2–NH2

23. (3) (B) LiAlH4

24. (4)
CH2CN CH2–CHO
25. (3) 'N' absent
(C) (i) SnCl2+HCl
(ii) H2O
26. (4)
32 W1 
%S=  100 NH2 N2Cl
233 W
32 18.74 Diazonium
51.6 =  100 (D) NaNO2/HCl
Compound
233 W (0-5°C)
W = 4.99 gm 
Kjeldahl's
27. (1) method fails
Balance 45 
1C7 H17 N  CuO  
equation 2
29. (2)
17 1 45
7CO2 + H2 O  N2  Cu
2 2 2
30. (3)
45
1 mole C7H17N  mole CuO utilised
2
31. (1)
 57.5 
n   0.5mol 
 115 
32. (4)
45
0.5 mole C7H17N ×0.5 = 11.25 mole
2 33. (2)

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1 | PRACTICAL ORGANIC CHEMISTRY

Exercise - 1 Objective Problems | NEET

1. Number of compound giving (i) red coloration 4. Which one of following is likely to give a
with ceric ammonium nitrate and also (ii) precipitate with AgNO3 solution?
positive iodoform test with NaOH/I2 are- (1) CH2=CH—Cl (2) CCl4
O O (3) CHCl3 (4) (CH3)3CCl

CH3 H 5. Iodoform can be prepared from all except:

, OH , ,
(1) ethyl methyl ketone
(2) Isopropyl alcohol
OH OH (3) 3- methyl -2- butanone
O
, , (4) Isobutyl alcohol
,
6. Aniline dissolved in dilute HCl is reacted with
OH sodium nitrite at 0°C. This solution was added
OH , dropwise to a solution containing phenol in dil
(1) 3 (2) 4 (3) 5 (4) 6 NaOH. The structure of the major product.
(1) N=N—NH
2. Positive Tellen's test is observed in which of the
following comp
(i) CH2=CH—CHO (2) N=N NH2
CHO
(ii)
(3) N=N—O
CH2—OH
O (4) N=N OH
(iii) CH3—CH2
O
7. Benzene diazonium chloride on reaction with
(iv) Ph Ph aniline in the presence of dilute hydrochloric
(1) i, ii, iv (2) i and ii only acid gives
(3) i, ii, and iii (4) i only
(1) N=N—NH
3. The organic compound that gives following
qualitative analysis is-
(A) Dil. HCl ; insoluble (2) N=N NH2
(B) NaOH ; soluble
(C) Br2/water ; decolorisation
N=N
OH NH2 (3)
(1) (2) NH2

NH2 OH (4) NH2

(3) (4)

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2 | PRACTICAL ORGANIC CHEMISTRY
8. Consider the following reaction O
(i) NaNO2/HCl; 0–5°C CHO
Colored solid CH3
(ii) (1) (2)
OH/NaOH
[P]
Br2/ H2O C7H6NBr3 O O
(3) (4) CH3–CHO
Compound [P] is H–C–C–CH2–CH3
NH2
NH2 12. Which of the following statement is incorrect?
(1) Aniline and N, N-dimethyl aniline can be
differentiated by hinsberg reagent
(1) (2) (2) Sucrose and glucose can be differentiated by
CH3 CH3 tollen's reagent
NH2 NH—CH3 (3) Diethylamine and aniline can be
CH3 differentiated by carbylamines test
(4) Glucose and fructose can't be differentiated
(3) (4)
CH3 by Br2/H2O

9. Which of the following will give positive 13. Which of the following amine gives positive
iodoform test and 2,4-DNP test ? isocyanide test
OH NH–CO–CH3 H–N–CH3
O
CH2–C–H
(1) (2) (1) (2)

CH2–NH2
O O
C–CH3 C–CH2–CH3
(3) (4) (CH3)3N

(3) (4)
14. H3O
O P+Q
10. Which of the following does not decolorise
bayer's reagent? In above sequence 'P' and 'Q' Products can be
distinguished by?
(1) CH3–CC–CH3
(1) Tollen's reagent (2) Fehling solution
(2) CH2=CH–CH=CH–CH3
(3) Benedict's solution (4) All of these

(3) OH OH

(4) H2C=C=CH2
COOH COOCH3
15. and
11. The compound which gives iodoform test,
reduces tollen's reagent as well as fehling Can be differentiated by-
solution is (1) NaOH (2) Na metal
(3) NaHCO3 (4) Neutral FeCl3

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3 | PRACTICAL ORGANIC CHEMISTRY
16. Which of the following is true? 19. Match the following column-I with column-II
(1) Alcohol give red color with ceric and choose the correct option from the code
ammonium nitrate give below
(2) Aldehyde and ketone give orange red color Column-I Column-II
(Distinguish) (By Reagent)
with 2, 4-DNP
(A Methanol and (i) Lucas test
(3) R-COOH give CO2 with NaHCO3
diethyl) ether
(4) All are true
(B) Methanol and (ii) Sodium metal
ethanol
17. An organic compound containing one oxygen (C) Phenol and (iii Iodoform test
give red color with ceric ammonium nitrate cyclo hexanol )
solution, decolourise cold alkaline KMnO4, (D n-propyl (iv) Ferric chloride
respond iodoform test and show geometrical alcohol) and
isomerism it could be tertiary Butyl
(1) Ph–CH=CH–CH2–OH alcohol
OH (1) A-(ii), B-(iv), C-(iii), D-(i)
(2)
Ph–CH=CH–CH–CH3 (2) A-(ii), B-(iii), C-(iv), D-(i)
Ph–CH=CH–C–CH3 (3) A-(ii), B-(iii), C-(i), D-(iv)
(3) (4) A-(iii), B-(ii), C-(i), D-(iv)
O
20. Assertion (A) : when aldehyde is heated with
(4) Ph
OH freshly prepared ammonical silver nitrate
solution, a bright silver mirror is produced
Reason(R) : A bright silver mirror is produced
18. An aromatic compound 'X' (C9H10O) Gives
due to formation of silver metal
chemical test/reaction with followings
(1) (A) and (R) both are correct and, (R) is the
I. gives 2, 4-DNP derivatives
correct explaination of (A)
II. Reduces Tollens reagent
(2) (A) and (R) both are correct and, (R) is not
III. Give cannizaro reaction
the correct explaination of (A)
IV. On strong oxidation, 1-2- benzene di
(3) (A) is correct but (R) is incorrect
carboxylic acid is obtained
(4) (A) and (R) both are incorrect
'X' is-
CHO
21. Assertion (A) : N-ethyl benzene sulphonamide
C2H5 CHO is soluble in basic medium
(1) (2) Reason(R) : The hydrogen attached to the
nitrogen in sulphonamide is strongly acidic due
C2H5 to the strongly electron withdrawing sulphonyl
CHO group
O (1) (A) and (R) both are correct and, (R) is the
CH3 correct explaination of (A)
(3) (4) (2) (A) and (R) both are correct and, (R) is not
CH3 C2H5 the correct explaination of (A)
(3) (A) is correct but (R) is incorrect
(4) (A) and (R) both are incorrect
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4 | PRACTICAL ORGANIC CHEMISTRY
22. Which of the following compound give the 26. The hinsberg test of a compound, C5H14N2
following set of qualitative analysis produces a solid that is insoluble in 10% Aq
(i) Fehling's test : positive NaOH. Which of the following would best
(ii) Na Fusion extract upon treatment with nitro describe these facts?
prusside give a blood red color but not Prussian (1) NH2CH2CH2CH2N(CH3)2
blue (2) (CH3)2NCH2CH2NHCH3
N N (3) NH2CH2C(CH3)2CH2NH2
(1) CHO (2) (4) (CH3)2NCH2N(CH3)2
N S CHO
N N 27. Fructose and glucose can be distinguished by
(3) CHO (4) CHO (1) Fehling's Test (2) Tollens test
S O (3) Bromine water (4) Lucas test

23. During determination of degree of alcohol by 28. Which of the following compound will give
victor mayer test, red color is obtained by instant turbidity with lucas reagent
(1) 3° alcohol (2) 1° alcohol OH
(3) 2° alcohol (4) All of these
CH3
CH2–NH2 (a) (b)
OH
NH2
OH
24. and can be
H3C
(c) (d) OH
differentiated by
(1) Hinsberg's test (2) Isocyanide test
(3) Diazo test (4) All of these (e)
OH
(1) a, b, c (2) a, b, c, d, e
25. Yellow crystal of CHI3 is obtained using
(3) a, b, e (4) a, b, c, e
iodoform test by
(1) CH3–CH2OH
(2) CH3–CH=O
CH3–C–CH2–C–CH3
(3)
O O
(4) All of these

ANSWER KEY [EXERCISE-1]

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 1 3 1 4 4 4 2 2 3 3 4 4 3 4 3
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28
Ans. 4 2 1 2 1 1 2 2 3 4 2 3 4
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 CHAPTER # 3 : PRACTICAL ORGANIC CHEMISTRY
HINT & SOLUTIONS
1. 1 17. 2
OH
18. 1
OH , ,

19. 2
Iodoform positive
OH Red color with 20. 1
"CAN"
21. 1
2. 3
22. 2
3. 1
23. 2
4. 4
24. 3
5. 4
25. 4
6. 4
26. 2
7. 2
27. 3
8. 2
28. 4
9. 3

10. 3

11. 4

12. 4

13. 3

14. 4

15. 3

16. 4

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