Practical Organic

CHAPTER

9 Chemistry

Question Bank

Level 1

1. Sodium nitroprusside Na2[Fe(CN)5NO] is used as reagent for detection of _____ and the
compound formed is ____.
(a) Sulphur, Na4[Fe(CN)5NOS] (b) Nitrogen, Na4[Fe(CN)6]
(c) Sulphur, Na2[Fe(CN)4NOS] (d) Sulphur, Na2[Fe(CN)5NOS]

2. The prussian blue colouration obtained in the test for nitrogen in the organic compound is
(a) K4[Fe(CN)]6 (b) Fe4[Fe(CN)6]3 (c) Fe[Fe(CN)6] (d) Fe3[Fe(CN)6]2

3. If N and S both are present in an organic compound during Lassaigne’s test, both will
change into
(a) Na2S and NaCN (b) NaSCN
(c) Na2SO3 and NaCN (d) Na2S and NaCNO

4. Which of the following will not give test for ‘N’ in sodium extract?
NH2

(a) C6H5NHNH2 (b) NH2CONH2 (c) NH2–NH2 (d)

SO3H
5. Which of the following will be blood red colour with FeCl3 in sodium extract (Lassaigne
extract)?
(a) NH2CONH2 (b) NH2CSNH2 (c) C6H5NHNH2 (d) CH3C≡N
9.2 chapter nine

6. A mixture of acetone and CCl4 can be separated by

(a) Azeotropic distillation (b) Fractional distillation
(c) Steam distillation (d) vacuum distillation

7. Phenol and benzoic acid can be separated by

(a) NaHCO3 (b) NaOH solution
(c) FeCl3 solution (d) All of these

8. Anthracene can be purified by

(a) Distillation (b) Sublimation
(c) Filtration (d) Fractional distillation

9. KOH can be used as a drying agent for

(a) amines (b) phenols (c) acids (d) esters

10. Silver salt method is used to determine molecular weight of

(a) organic acids (b) organic bases
(c) both acids and bases (d) none of these

11. Which of the following observations is correct and is used in the identification of c­ arboxylic
acids?
(a) Carboxylic acids liberate CO2 gas from NaHCO3 solution.
(b) They produce fruity smell of esters when heated with alcohol in presence of Conc.
H2SO4.
(c) Both (a) and (b)
(d) Iodoform test

12. An organic compound is heated with HNO2 at 0ºC and then the resulting solution is added
to a solution of β-naphthol whereby a brilliant red dye is produced. The observations indi-
cate that the compound possesses
(a) –NO2 group (b) –CONH2 group
(c) aromatic NH2 group (d) aliphatic NH2 group

13. An organic compound contains C, H, N, S and Cl. For the detection of chlorine, the sodium
extarct of the compound is first heated with a few drops of concentrated HNO3 and then
AgNO3 is added to get a white ppt. of AgCl. The digestion with HNO3 before the addition
of AgNO3 is
(a) to prevent the formation of NO2
(b) to create a common ion effect
(c) to convert CN– and S2– to volatile HCN and H2S, or else they will interfere with the test
forming AgCN or Ag2S
(d) to prevent the hydrolysis of NaCN and Na2S

14. Rectified spirit contains

(a) 95.6 per cent ethanol and 4.4 per cent methanol
(b) 100 per cent ethanol
(c) 95.6 per cent ethanol and 4.4 per cent water
(d) 95.6 per cent ethanol and 4.4 per cent benzene

15. Aniline can be separated from phenol using

(a) NaHCO3 (b) NaNO2 + HCl at 0ºC
(c) NaCl (d) Acidified KMnO4
 practical organic chemistry 9.3

16. Identify correct statement for A, B and C in the following sequence.

Ether Evaporation
layer A

20%NaOH Diethyl
B Solution
N H 2O Ether
Aqueous 10%HCl
O layer H2O
pH = 2
O C ppt.

OH
where
and
NH

Isoquinoline Benzoic acid

(a) A = benzoic acid, B = sodium chloride and C = isoquinoline
(b) A = isoquinoline, B = benzoic acid and C = sodium chloride
(c) A = isoquinoline, B = sodium chloride and C = benzoic acid
(d) A = sodium chloride, B = isoquinoline and C = benzoic acid

17. Dil. H2SO4

O P1 + P2

P1 and P2 products are identify by

(a) Tollen’s reagent (b) Iodoform test
(c) Br2 + H2O test (d) 1 per cent alkaline KMnO4

18. In the following extraction procedure, choose the number where nicotine would be found.
Aqueous Evaporate (iii)
layer
Aqueous Make basic with
layer 20% NaOH
Naphthalene
Diethyl 10% HCl H2O Ether Evaporate (ii)
+ Ether H2O layer

N Ether Evaporate (i)

layer
H
N
Nicotine

(a) i = Nicotine (b) i + iii = Nicotine (c) ii = Nicotine (d) ii + iii = Nicotine

19. Choose the answer that has the following compounds located correctly in the s­ eparation
scheme. Dilute
Dilute HCl
NaOH Precipitate (i)
dilute
4-nitrotoluene H3C NO2 Ether NaOH

Dilute
HCl Evaporate
Ether Precipitate (ii)
p-cresol H3C OH

Dilute NaOH
Dilute HCl Precipitate (iii)
p-toluidine H3C NH2

dissolved in ether
9.4 chapter nine

(a) i = 4-nitrotoluene, ii = p-cresol, iii = p-toluidine

(b) i = 4-nitrotoluene, ii = p-toluidine, iii = p-cresol
(c) i = p-toluidine, ii = 4-nitrotoluene, iii = p-cresol
(d) i = p-cresol, ii = 4-nitrotoluene, iii = p-toluidine

20. Choose the answer that has the following compounds located correctly in the separation
scheme.
Aqueous

CO2H Aqueous HCl

OH
(i) NaHCO3 Ether (X) Aqueous
+ + (ii) Ether Aqueous HCl
pKa = 4.3 pKa = 10 Ether (Y)
Ether NaOH
Ether (Z)
(a) toluene is in (Y); phenylacetic acid is in (Y); phenol is in (Z)
(b) toluene is in (Y); phenylacetic acid is in (X); phenol is in (Z)
(c) toluene is in (Z); phenylacetic acid is in (Y); phenol is in (X)
(d) toluene is in (Z); phenylacetic acid is in (X); phenol is in (Y)

21. Among the following which compound gives precipitate with AgNO3 solution?
Br Br
H2C
(a) (b) (c) (d) None of these
Br

22. Disodium pentacyanonitrosyl ferrate reagent gives purple colour when which of the
­following element is present?
(a) N (b) Cl (c) F (d) S

23. Which of the following compound can liberate CO2 when treated with NaHCO3?
OH
O2N NO2
(a) (b) CH3CO2H

NO2
OH

(c) HCO2H (d)

24. Phenol + Phthalic anhydride Conc


. H2 SO 4
fusion
→ B. B gives which of the following colour in alka-
line medium?
(a) Yellow (b) Colourless (c) Pink (d) Violet

25. Among the following, which will respond to iodoform test?

O O
H3C
(a) (b)
OH H3C CH3
 practical organic chemistry 9.5

OH O O
(c) (d)
H3C CH3 H3C OCH2H5

26. Among the following, which statement is not correct?

O
(a) H3C C OH will not respond to haloform test
(b) Schiff ‘s regent and Schiff ‘s base are different compounds
(c) Fehling’s solution is a good reagent to detect aromatic aldehydes
(d) Both aldehyde and ketone can react with 2, 4-dinitrophenylhydrazise reagent

27. To separate a mixture of amines from each other, one should follow
(a) Beckmann’s method (b) Hinsberg’s method
(c) Zeisel’s method (d) Victor Meyer’s Method

28. Phenol can be distiguished from ethanol by

(a) Tollen’s reagent (b) Benedict’s reagent
(c) FeCl3 (d) Schiff ‘s base

29. p-Cl — C6H4NH2 and PhNH3 +Cl– can be distinguished by

(a) NaOH (b) AgNO2 (c) LiAlH4 (d) Zn
9.6 chapter nine

Level 2

Single and Multiple-choice Type

1. In Lassaigne’s test, the organic compound is first fused with sodium metal. The sodium
metal is used because
(a) The melting point of sodium metal is low.
(b) Sodium metal reacts with elements present in organic compounds to form inorganic
compounds.
(c) All sodium salts are soluble in water.
(d) All sodium salts are not soluble in water.

2. Molecular weight of acids can be detemined by

(a) Silver salt method (b) Volumetric method
(c) Plants chloride method (d) Victor Meyer’s method

3. Ethanol and ethanal are distinguished by

(a) Fehling’s solution test (b) Tollen’s reagent test
(c) Iodoform test (d) Cerric ammonium nitrate

4. Which of the following statements are correct?

(a) An organic compound is pure if mixed melting point is same.
(b) Ethanol and water can be separated by azeotropic distillation because it forms
azeotrope.
(c) Impure aniline is purified by steam distillation as it is steam volatile.
(d) Glycerol is purified by vaccuum distillation because it decomposes at its normal
­boiling point.

5. Which of the following will respond to iodoform test?

O OH
|| |
(a) CH3 – C – COOH (b) CH3 – CH – COOH
OH
|
(c) CH3 – CH – CH3 (d) CH3CH2OH

6. Which of the following will not show iodoform test?

O O O
|| || ||
(a) CH3 – C – CH3 (b) CH3 – C – Cl (c) CH3 – C – NH2 (d) CH3–COOH

7. HCOOH and CH3COOH can be distinguished by

(a) Tollen’s reagent (b) Fehling’s solution
(c) KMnO4 (d) NaHCO3

8. The desiccants used for absorbing water during Liebig’s method for estimation of ­carbon
and hydrogen are
(a) anhydrous CaCl2 (b) anhydrous Na2SO4
(c) Mg(ClO4)2 (d) MgSO4 ⋅ 7H2O
 practical organic chemistry 9.7

CHO

9. An organic compound has the structure . It will give

OH
CH2 – COOH
(a) cerric ammonium nitrate test
(b) brick effervescence with sodium bicarbonate
(c) a characteristic colouration with neutral ferric chloride after decarboxylation and
reduction by Clemenson’s method
(d) Fehling’s test

10. Which of the following organic compounds will give white precipitate with AgNO3?
(a) C6H5NH3+Cl– (b) NaCl
(c) 2,4,6-trinitro chlorobenzene (d) Benzyl chloride

11. Which of the following reactions occur during the detection of nitrogen in organic
­substances by Lassaigne’s test?
(a) Na + C + N ⎯→ NaCN
(b) FeSO4 + 6NaCN ⎯→ Na4[Fe(CN)6] + Na2SO4
(c) 3Na4[Fe(CN)6] + 2Fe2(SO4)3 ⎯→ Fe4[Fe(CN)6]3 + 6Na2SO4
(d) None of these

12. Compound A reacts with CHCl3 and KOH and gives an offensive smelling compound.
A can be
(a) Primary aliphatic amine (b) Primary aromatic amine
(c) Secondary amine (d) Tertiary amine

13. HCOOH and HCHO may be distinguished by

(a) Tollen’s test (b) Sodium bicarbonate test
(c) 2,4-DNP test (d) Benedict’s test
CHO
14. and CH3CHO can be distinguished by

(a) Tollen’s test (b) Benedict’s test (c) Iodoform test (d) 2,4-DNP test

15. Acetic acid and CH3COCl can be distinguished by

(a) NaHCO3 test (b) Na metal test
(c) Ester formation test (d) Br2(aq.) test

Comprehension Type
Passage 1

Steam distillation is used to purify a compound which is steam volatile and insoluble in water. The
impurities should not be steam volatile. It is based on the principle that liquid will boil when partial
vapour pressure of liquid and partial vapour pressure of steam both become equal to atmospheric
pressure, P = p1 + p2. It reduces the boiling point of a liquid.
Weight of water distilled M. Wt. of water × VP of steam
=
Wt. of substance distilled M. Wt. of substance × VP of aniline
9.8 chapter nine

16. Isolation of essential oils from flowers, etc. is done by

(a) Steam disitllation
(b) Distillation
(c) Fractional distillation
(d) Distillation under reduced pressure

17. Which of the following is steam volatile?

(a) o-nitrophenol (b) p-nitrophenol
(c) p-hydroxy benzaldehyde (d) Ethanol

18. Calculate weight of aniline distilled if weight of water distilled is 100 g when
Porganic compound = 100 mm and PH2 O = 200 mm.
(a) 250 g (b) 258 g (c) 100 g (d) 25.8 g

19. Steam distillation is based on

(a) Dalton’s law of partial pressures
(b) Graham’s law of diffusion
(c) Raoult’s law of non-volatile solute
(d) None of these

20. Which of the following cannot be separated by steam distillation?

(a) Nitrobenzene (b) Essential oil (c) Aniline (d) Glycerol

Passage 2
Test (Q). A compound X was fused with Na metal and the extract gave a white precipitate with
AgNO3. The Lassaigne’s extract gave a red colouration with neutral FeCl3.
Test (R). While compound Y when fused with Na metal and subsequent analysis on its L
­ assaigne’s
extract did not give any characteristic test.
Test (S). While compound Y on fusion with fusion mixture (sodium carbonate + potassium
nitrate) or Na2O2, followed by extraction, followed by addition of Conc. HNO3 and ammonium
molybdate gave a yellow precipitate.

21. Compound X contains

(a) N (b) S (c) N + S (d) P

22. Compound X
(a) will contain halogens (b) may contain halogens
(c) may contain only sulphur (d) will contain only nitrogen

23. Compound Y contain

(a) N (b) S (c) X (d) P

24. The chemical reaction taking place in Y, when it is fused with fusion mixture is
(a) 3Na + P + 4O ⎯→ Na3PO4
(b) 3Na2CO3 + 2P + [O] ⎯→ 2Na3PO4 + 3CO2
(c) 3KNO3 + P + 3O ⎯→ K3PO4 + 3NO2 + O2
(d) None of these

25. The formula of yellow precipitate is

(a) (NH4)3PO4 (b) Mo(PO4)
(c) (NH4)3PO4 ⋅ 12Mo3O3 (d) Mo(PO4)2
 practical organic chemistry 9.9

Passage 3

The 0.2 g of anhydrous organic acid gave on combustion 0.04 g of water and 0.195 g of CO2. The
acid is a dibasic acid and 0.5 g of its silver salt leaves on ignition 0.355 g of silver.

26. The percentage of carbon in the compound is

(a) 50 (b) 52 (c) 26.6 (d) 90

27. The percentage of hydrogen in the compound is

(a) 5.6 (b) 2.22 (c) 4.44 (d) 10

28. The empirical weight of the compound is

(a) 90 (b) 100 (c) 10 (d) 45

29. The molecular weight of the compound is

(a) 90 (b) 100 (c) 10 (d) 45

30. The molecular formula of the compound is

(a) CHO (b) CHO2 (c) C2H2O4 (d) C3H6O2

Passage 4

A student in a lab had a mixture of three compounds, 4-methylbenzoic acid, 4-methylcyclohexy-

lamine and 1,4-dimethylbenzene. In order to separate the three compounds the following extrac-
tion (separation) scheme was followed. At the end of the procedure the student had six separate
flasks containing either an aqueous or an ether solution. Locate each compound by designating
the flask expected to contain each compound. Some relevant pKa data is given.
CO2H NH2 CH3
⊕
CO2H NH3

CH3 CH3 CH3

CH3 CH3
(i) Ether
pKa = 4.4 xi (ii) HCl (aqueous)

Ether Aqueous
NaOH NaOH

Aqueous Ether Ether Aqueous

iii iv
HCl HCl

Aqueous Ether Ether Aqueous

i ii v vi
9.10 chapter nine

31. Which flask contains the 4-methylcyclohexylamine?

(a) 1 (b) 2 (c) 3 (d) 4

32. Which flask contains the 4-methylbenzoic acid?

(a) 1 (b) 2 (c) 3 (d) 4

33. Which flask contains the 1,4-dimethylbenzene?

(a) 1 (b) 2 (c) 3 (d) 4

Matrix Type
Match the columns:

34. Column I (pair of compounds) Column II (test to distinguish)

OH OH
(a) and (p) Libermann nitroso test

⊕
OH NH2 N2Cl
(b) (q) (Dye test)
and

NH2 Me
(c) and NH (r) Iodoform
Me
CH2OH

H O H
O
(d) H (s) Lucas
and
OH H
OH HO
H OH
(t) NaHSO3

35. Column I Column II

(pair of compounds) (identification test)

(a) and (p) Tollen’s reagent test

OH OH
(b) and (q) Br2 + H2O test

O O
(c) (r) Lucas test
H – C – OH and CH3 – C – OH

(d) (s) Iodoform test

and
(t) Ammonical Cu2Cl2 test
 practical organic chemistry 9.11

36. Column I (reagents) Column II

(a) Product of reaction of propyne (p) Me–CH=CH–Me
with 1 per cent HgSO4 and Dil. H2SO4
(b) Br2 water test given by (q) Me–C≡C–H

(c) Addition of HBr can be with (r) C ≡ C – CH3

(d) Tollen’s reagent give white ppt. with (s) Me–CH=CH2

O
(t) Me – C – Me

37. Column I (compound) Column II (tests)

O
(a) –C (p) 2,4-DNP test
H
O
(b) (q) Yellow ppt. with NaOH + I2
CH3 – C –

O
(c) CH3 – C – H (r) Red ppt. with Fehling’s solution
O
(d) CH3 (s) Silver mirror with Tollen’s reagent
H3C

38. Column I (reagents) Column II

(a) Tollen’s reagent give white ppt. with (p) Me–CH=CH–Me
(b) Br2 + H2O test given by (q) Me–C≡C–H
⊕
(c) Product of reaction of acetylene with (r) CI NH 3 − NH 2
1 per cent HgSO4 and Dil. H2SO4
O
(d) Pd/H2 reacts with (s) Me – C – H
O
(t) Me – C – Me

39. Column I Column II

(pair of compounds) (test of identification)
O O

(a) Ph – C – H and Me – C – H (p) Tollen’s reagent

O O
(b) Me – C – Me and Me – C – H (q) Fehling’s reagent

OH OH
(c) and (r) Iodoform test

(d) Me – C ≡ C – H and Me – C ≡ C – Me (s) Victor Meyer’s test

(t) Lucas test
9.12 chapter nine

Answer Keys
Level 1
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
a b b c b b a b a a c c c c b
16 17 18 19 20 21 22 23 24 25 26 27 28 29
b ab c d d b d abc c abcd c b c b

Level 2
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
abc ab abd abcd abcd bcd abc ac abc abcd abc ab bc bc ab
16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
a a b a d c b d bc c c b d a c
31 32 33 34(a) 34(b) 34(c) 34(d) 35(a) 35(b) 35(c) 35(d) 36(a) 36(b) 36(c) 36(d)
d b c rs pq p rt q rs p pt t pqrs pqrs q
37(a) 37(b) 37(c) 37(d) 38(a) 38(b) 38(c) 38(d) 39(a) 39(b) 39(c) 39(d)
ps pq pqrs pq qr pq s pqst qr pq rst p