AMINES

AMINES

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 AMINES

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AMINES

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 AMINES

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AMINES

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 AMINES

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AMINES

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 AMINES

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AMINES

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 AMINES

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AMINES

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 Amines

1. Nitrobenzene can be prepared from benzene by using a mixture of concentrated HNO3 and
concentrated H2SO4. In the nitrating mixture, nitric acid acts as a
(a) base
(b) acid
(c) reducing agent
(d) catalyst

2. Amongst the following, the most basic compound is

(a) benzylamine
(b) aniline
(c) acetanilide
(d) p-nitroaniline

3. Which of the following compounds is most basic here

(a) diphenyl ammonia
(b) dimethyl amine
(c) guanidine
(d) tri methyl amine

4. The compound that is most reactive towards electrophilic nitration is

(a) benzene
(b) nitrobenzene
(c) benzoic acid
(d) toluene

5. The melting point is highest for

(a) primary amines
(b) secondary amines
(c) tertiary amines

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(d) quaternary amines

6. Carbylamine test is performed in alcoholic KOH by heating a mixture of

(a) trihalogenated methane and a primary amine
(b) an alkyl halide and a primary amine
(c) an alkyl cyanide and a primary amine
(d) chloroform and silver powder

7. Acetamide is treated separately with the following reagents. Which one of these would give
methylamine?
(a) sodalime
(b) PCl5.
(c) NaOH + Br2
(d) hot conc. H2SO4

8. In the following reaction, X is

(a) Cl
+
(b) N H3Cl-
(c) NH2
(d) SnCl2

9. Which of the following reacts with NaNO2 + HCI at 273 —278 K to give alcohol/phenol?
(a) CH3NH2
(b) C6H5NH2
(c) C6H5CH2NHCH3
(d) (CH3)2NH

10. Hinsberg reagent is

(a) C6H5NO
(b) C6H5N2Cl
(c) C6H5SO2Cl
(d) C6H5SO3H

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11. When acetamide is treated with NaOBr, the product formed is
(a) CH3OH
(b) CH3NH2
(c) CH3CN
(d) CH3COBr

12. The compound which one reaction with aqueous nitrous acid at low temperature produces an
oily nitrosamine is
(a) methylamine
(b) ethylamine
(c) triethylamine
(d) diethylamine

13. Which is formed when (CH3)4NOH is heated?

(a) C2H5NH2
(b) (CH2)3N
(c) CH3NH2
(d) (CH3)3N

14. Among the following compound C3H7NH2, NH3, CH3NH2, C2H5NH2, and C6H5NH2 the least
basic compound is
(a) C6H5NH2
(b) C2H5NH2
(c) CH3NH2
(d) NH3

15. A primary nitroalkane is treated with nitrous acid, which of the following will be the main
product?
(a) Pseudonitrol
(b) Nitrolic acid
(c) A primary amine
(d) Primary alcohol

16. Reaction of aniline with benzaldehyde is a ......... reaction?

(a) addition

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(b) condensation
(c) polymerization
(d) substitution

17. Which amine of the following will not give carbylamine reaction?
(a) ethylamine
(b) dimethylamine
(c) methylamine
(d) phenylamine

18. Which is most basic?

(a) CH3NH2
(b) (CH3)2NH
(c) C2H5NH2
(d) (C6H5)2NH

19. Which of the following reactions does not yield an amine?

(a) R − X+NH 3 →
(b) R − CH = NOH + [H] ⎯⎯⎯⎯
Na,C2 H5OH
→
(c) R − CN + H 2 O ⎯⎯ →
+
H

(d) R − CONH 2 + 4[H ] ⎯⎯⎯

LiAlH 4
→

20. Which of the following reacts with Hinsberg reagent (Benzene sulphonyl chloride) to form a
product, soluble in KOH?
(a) primary amine
(b) secondary amine
(c) tertiary amine
(d) quaternary amine

21. Towards electrophilic substitution, the most reactive will be

(a) nitrobenzene
(b) aniline
(c) aniline hydrochloric
(d) n-acetylaniline

22. When a mixture of secondary amines is heated with diethyl oxalate, it forms
(a) solid oxamic ester
(b) liquid oxamic ester
(c) form of oxamic ester
(d) gaseous oxamic ester

23. Which of the following compounds cannot by identified by carbylamine test?

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(a) CH3CH2NH2
(b) CH3-CH2-CH2-NH2
(c) C6H5NH2
(d) C2H5-NH-C2H5

24. Which of the following substances on treatment with P2O5 gives ethanenitrile?
(a) Propanamide
(b) Ethanamide
(c) Ethanoic acid
(d) N-Methylethyl amine

25. Arrange the following in increasing basicity order:

I. Cl2CHCH2NH2
II. Cl3CH2NH2

III.
IV.CF3CH2NH2

(a) I < III < II < IV

(b) II < IV < III < I
(c) IV < II < I < III
(d) l < II < IV < III

26. A compound 'A' when treated with HNO3 (in the presence of H2SO4) gives compound 'B',
which is then reduced with Sn and HCl to aniline? The compound 'A' is
(a) acetamide
(b) ethane
(c) benzene
(d) toluene

27. Which of the following is the strongest base?

(a)

(b)

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(c)

(d)

28. What is the end product C in this series? CH 3CN ⎯⎯⎯⎯→

Na/C2 H5 OH
A ⎯⎯⎯
HNO2
→ B ⎯⎯⎯
Cu /573
→C
(a) CH3COOH
(b) CH3CH2NHOH
(c) CH3CONH2
(d) CH3CHO

29. Primary nitro compounds react with nitrous acid to form nitrolic acids which dissolve in
NaOH giving
(a) red solution
(b) blue solution
(c) yellow solution
(d) colourless solution

30. Butanenitrile may be prepared by heating

(a) propyl alcohol with KCN
(b) butyl alcohol with KCN
(c) butyl chloride with KCN
(d) propyl chloride with KCN

31. Methyl cyanide on treatment with methyl .magnesium bromide followed by of subsequent
hydrolysis gives:
(a) Propanone
(b) Ethanone
(c) Ethanal
(d) Propanal

32. The product formed by the treatment of ethanol and ethane nitrile in the presence of
sulphuric acid is:
(a) Ethyl acetate
(b) Diethyl ether

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(c) Ethyl methyl ketone
(d) Butanal

33. Ethyl chloride on heating with AgCN forms a compounds X. the functional isomers of X will
be
(a) C2H5NH2
(b) C2H5NC
(c) C2H5CN
(d) none of these

34. Identify the correct statement among the following.

(a) n,n-dimethylaniline reacts with nitrous acid to give p-nitroso-N,N-dimethyl aniline
(b) bromination of p-toluidine produces 3,5-dibromo, 4-methylaniline .
(c) aliphatic amines are less basic than ammonia
(d) aliphatic primary amines combine with nitrous acid under ice-cold conditions to form stable
diazonium salts

35. which of the following reagents on treatment with benzenamine in basic medium produces
phenyl isocyanide?
(a) CCl4
(b) Trichloromethane
(c) Methylene dichloride
(d) Hexachloroethane

36. Which of the following is not an ambident nucleophile?

(a)

(b)
(c)

(d)

37. (A) is subjected to reduction with Zn-Hg/HCI and the product formed is N-
methylmethanamine. (A) can be:
(a) Ethane nitrile
(b) Nitroethane
(c) Carbylaminoethane

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(d) Carbylaminomethane

38. Compound A on reducing gives B, which on further reaction with CHCl3 and alcoholic KOH
gives compounds C, which on further hydrolysis gives aniline. The compound A is

(a) nitrosobenzene
(b) methylamine
(c) nitromethane
(d) nitrobenzene

39. CH 3CH 2 Cl ⎯⎯⎯

NaCN
→ X ⎯⎯⎯
Ni/H 2
→ Y ⎯⎯⎯⎯⎯
acetic anhydride
→ Z Z in the above reaction sequence is
(a) CH3CH2CH2CONHCONH3
(b) CH3CH2CH2NH2
(c) CH3CH2CH2CONHCH3
(d) CH3CH2CH2NHCOCH3

40.
A and B respectively are
(a) RCN, RCH2NH2
(b) RNC, RNHCH3
(c) RCN, RNHCH3
(d) RNC, RCH2NH2
41. Mendius reaction involves the:
(a) Reduction of aldehydes to give alcohols
(b) Reduction of nitrites with sodium and ethanol
(c) Oxidation of nitriles
(d) Hydrolysis of cyanides

42. Identify X and Y in the following sequence.

(a) X = KCN, Y = LiAIH4

(b) X = KCN, Y = H3O+
(c) X = CH3Cl, Y = AICI3/HCI
(d) X = CH3NH2,Y=HNO2

43. Among the amines

I C6H5NH2
II CH3NH2

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III (CH3)2NH
IV (CH3)3N
(a) I< IV < II < III
(b) IV < III < II < I
(c) I < II < III < IV
(d) II< III< IV< I

44. Which of the following statements relating to aniline is not true?

(a) aniline on Schotten-Baumann reaction gives benzanilide
(b) aniline cannot be prepared by the reduction of benzonitrile with LiAIH4
(c) on heating with concentrated H2SO4 at 180°C, aniline gives sulphanilic acid
(d) aniline liberates nitrogen on treatment with ice cold nitrous acid

45. Aniline is less basic than

(a) 4-nitroaniline
(b) 4-aminobenzaldehyde
(c) anilinium hydrochloride
(d) dimethyl amine

46. para chloroaniline and anilinium hydrochloride can be distinguished by

1 Sandmeyer reaction
2 AgNO3
3 Carbylamine reaction
4 NaHCO3
(a) 1, 3,4
(b) 1, 2, 4
(c) 1, 2, 3, 4
(d) 2, 3, 4

47. Identify the final product C in the following sequence of reactions.

(a) C6H5CH2NH2
(b) m-CH3C6H4NH2
(c) C6H5NH2
(d) o-and p-CH3 C6H4NH2

48. Arrange the following:

I CH3NH2
II (CH3)2NH
III C6H5NH2
IV (CH3)3N

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in increasing order of basicity in aqueous medium.
(a) II < I < IV < III
(b) II < III < I < IV
(c) I < II < III < IV
(d) III < IV < I < II

49. The correct order of basicities of the following compounds is

1
2 CH3CH2NH2
3 (CH3)2NH

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

50. The correct order of decreasing base strength among the amines given below is

(a) I > III > IV > II

(b) IV > III > I > II
(c) I > IV > III > II
(d) I > III > IV > II

51. The compound that will react most readily with NaOH to form methanol is
(a) (CH3)4 N+ I–
(b) CH3OCH3

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(c) (CH3)3S+ I–
(d) (CH3)3CCI

52. Ethanamine is treated with nitrous acid at ordinary temperature; the products will be:
(a) Ethanol only
(b) Ethanol, acetic acid, N2, and H2O
(c) Acetic acid, ethane, and H2O
(d) Ethanol, ethene, N2, and H2O

53. Stephen's reduction converts nitriles into:

(a) Aldehydes
(b) Ketones
(c) Amines
(d) Carboxylic acids

54. A positive carbylamine test is given by

(1) N, N-dimethylaniline
(2) 2, 4-dimethylaniline
(3) N-methyl-o-methylaniline
(4) p-methylbenzylamine
(a) 2, 4
(b) 2, 3
(c) 1, 2, 4
(d) 2, 3, 4

55. When propane is subjected to the treatment with fuming nitric acid at 673 K, which of the
following will not be formed?
(a) 1-Nitropropane
(b) 2-Nitropropane
(c) Nitromethane
(d) Nitrohexane

56. Nitrobenzene is subjected to reduction with zinc dust and ammonium chloride. The main
product formed will be:
(a) Benzenamine
(b) Aniline
(c) N-Phenylhydroxylamine
(d) None of these

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57. In the reaction given below, the product Y is
C6 H 6 ⎯⎯⎯HNO3
H 2SO 4
→ X ⎯⎯⎯
Cl2
FeCl3
→Y
(a) 4-nitrochlorobenzene
(b) 3-nitrochlorobenzene
(c) 1-nitrochlorobenzene
(d) none of the above

58. In the following reaction, X is

(a) benzoic acid

(b) salicylic acid
(c) aniline
(d) phenol +

59. p-nitrotoluene on further nitration gives

(a)

(b)

(c)

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(d)

60. Identify X in the sequence given below

(a)

(b)

(c)

(d)

61. Which of the following is least basic?

(a)

(b)

(c)
(d) all are equally basic

62. The order of basicity among the following compounds is (2017)

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(a) II > I > IV > III
(b) I > IV > III > I
(c) IV > I > II > I
(d) IV > I > II > III

63. In the Hofmann-bromamide degradation reaction, the number of moles of NaOH and Br2
used per mole of amine produced are (2016)
(a) four moles of NaOH and two moles of Br2
(b) two moles of NaOH and two moles of Br2
(c) four moles of NaOH and one mole of Br2
(d) one mole of NaOH and one mole of Br2

64. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb
value? (2014)
(a) (CH3)2NH
(b) CH3NH2
(c) (CH3)3N
(d) C6H5NH2

65. On heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide,
the organic compound formed is (2014)
(a) an alkanol
(b) an alkanediol
(c) an alkyl cyanide
(d) an alkyl isocyanide

66. The gas leaked from a storage tank of the Union Carbide plant in Bhopal gas tragedy was
(2013)
(a) methyl isocyanate
(b) methylamine
(c) ammonia
(d) phosgene

67. The major product of the following reaction is (2011)

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(a)

(b)

(c)

(d)

68. CH3NH2 + CHCl3 +KOH → Nitrogen containing compound + KCl + H2O. Nitrogen
containing compound is (2006)
(a) CH3CN
(b) CH3NHCH3
+
(c) CH3 – N  C
+
(d) CH3 – N  C

69. Benzamide on treatment with POCl3 gives (2004)

(a) aniline
(b) benzonitrile
(c) chlorobenzene
(d) benzyl amine

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70. The correct order of basicities of the following compounds is (2001)

(a) 2 > 1 > 3 > 4

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

71. A positive carbylamine test is given by (1999)

(a) N, N-dimethylaniline
(b) 2, 4-dimethylaniline
(c) N-methyl-o-methylaniline
(d) p-methylbenzylamine

72. p-chloroaniline and anilinium hydrochloride can be distinguished by (1998)

(a) Sandmeyer reaction
(b) NaHCO3
(c) AgNO3
(d) Carbylamine test

73. Carbylamine test is performed in alc. KOH by heating a mixture of (1984)

(a) chloroform and silver powder
(b) trihalogenated methane and a primary amine
(c) an alkyl halide and a primary amine
(d) an alkyl cyanide and a primary amine

74. Acetamide is treated separately with the following reagents. Which of these would give
methylamine? (1983)
(a) PCl5
(b) Sodalime
(c) NaOH + Br2
(d) Hot, conc. H2SO4

75. The compound which on reaction with aqueous nitrous acid at low temperature produces an
oily nitrosamine, is (1981)
(a) methylamine
(b) ethylamine
(c) diethylamine
(d) triethylamine

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Answer:
1. (a) 2. (a) 3. (c) 4. (d) 5. (a) 6. (a) 7. (c) 8. (b) 9. (a) 10. (c)
11. (b) 12. (d) 13. (d) 14. (a) 15. (b) 16. (b) 17. (b) 18. (b) 19. (c) 20. (a)
21. (b) 22. (b) 23. (d) 24. (b) 25. (c) 26. (c) 27. (b) 28. (d) 29. (a) 30. (d)
31. (a) 32. (a) 33. (c) 34. (a) 35. (b) 36. (b) 37. (d) 38. (d) 39. (d) 40. (b)
41. (b) 42. (a) 43. (a) 44. (d) 45. (d) 46. (b) 47. (a) 48. (d) 49. (b) 50. (d)
51. (c) 52. (d) 53. (a) 54. (a) 55. (d) 56. (c) 57. (b) 58. (c) 59. (b) 60. (a)
61. (a) 62. (d) 63. (c) 64. (a) 65. (d) 66. (a) 67. (a) 68. (d) 69. (b)
70. (b) 71. (d) 72. (c) 73. (b) 74. (c) 75. (c)

Solution:
1. (a)

2. (a)
Electrons not involved in resonance.
3. (c)
Resonance from the 2 nitrogen lone pairs enhances the availability of electrons on the double
bonded Nitrogen. (Check the structure)
4. (d)
Toluene has an electron-donating methyl group and hence reacts fastest while others have either
electron withdrawing groups (-COOH and-NO2 etc.) or no substituent.

5. (a)
Primary amines have highest melting point due to maximum hydrogen bonding.

6. (a)

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7. (c)

8. (b)

9. (a)

10. (c)

11. (b)

12. (d)

13. (d)

14. (a)
Electrons of nitrogen delocalized due to resonance.

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15. (b)

16. (b)

17. (b)
As it is a secondary amine.

18. (b)
As aliphatic amines are more basic than aromatic amines and 2° amines are more basic than 1°
amines

19. (c)
Hydrolysis of CN will produce acid.

20. (a)
With Hinsberg reagent, primary amine forms n-alkyl benzene sulphonamide soluble in alkali.

21. (b)

22. (b)

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23. (d)
Not a primary amine.

24. (b)

25. (c)
As basic nature decreases by the presence of electron attracting groups (-I).

26. (c)

27. (b)

Inductive effect of methyl group increases the electron density on Nitrogen atom.

28. (d)

29. (a)

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30. (d)

31. (a)

32. (a)

33. (c)
C2H5CN + AgCN → C2H5NC + AgCN
The functional isomer of C2H5NC is C2H5CN

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34. (a)
Aromatic tertiary amines react with nitrous acid to give p-nitroso derivative is a correct
statement.

35. (b)

36. (b)

37. (d)

38. (d)

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39. (d)

40. (b)

41. (b)

42. (a)

43. (a)

44. (d)
Aniline gives phenyldiazonium chloride (PhN+  N Cl–) -a salt-on treatment with ice cold nitrous
acid. It liberates nitrogen, only on further treatment with water.

45. (d)
A secondary amine is always more basic than aromatic amine (aniline).

46. (b)

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As both gives carbylamine reaction giving same product so it cannot be distinguished by this
reaction.

47. (a)

48. (d)
The correct order is III < IV < I < II.

49. (b)

50. (d)
The conjugate acid (i) obtained by addition of a proton to I is stabilized by resonance and hence
the compound I is most basic. Thus the order of basic nature is
I > III > II > IV.

51. (c)

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52. (d)

53. (a)

54. (a)
Carbylamine test is given by primary amines only (R-NH2)
55. (d)

56. (c)

57. (b)
(NH4)2Sx reduces one -NO2 to-NH2 group.
58. (c)
NO2 group is meta directing while CH3 group is ortho directing.

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59. (b)

60. (a)

61. (a)
It is due to the electron withdrawing nature of NO2 group.

62. (d)

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63. (c)

64. (a)

65. (d)

NOTE: The mechanism of this reaction included rearrangement of nitrene in which migration of
alkyl group from carbon to nitrogen takes place.

66. (a)
Methyl isocyanate CH3–N = C = 0 (MIC) gas was leaked from the storage tank of the union
carbide plant in Bhopal gas tragedy.
67. (a)

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68. (d)

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69. (b)

70. (b)

71. (d)

72. (c)

73. (b)

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74. (c)

75. (c)
A secondary amine, on treatment with aqueous nitrous acid at low temperature produces oily
nitrosamine.

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