Chemistry

12th

AMINES
Class 12 - Chemistry

1. The order of increasing basicities of CH3NH2 (I), (CH3)2NH (II), (CH3)3N (III) and C6H5NH2 (IV) in aqueous [1]

media is:

a) II < III < I < IV b) II < I < IV < III

c) IV < III < I < II d) I < II < III < IV

2. Hinsberg's reagent is: [1]

a) Benzene sulphonic acid b) Benzene sulphonamide

c) Phenyl isocyanide d) Benzene sulphonyl chloride

3. Amines are soluble in: [1]

a) only slightly soluble in water b) water

c) organic solvents d) only slightly soluble in organic solvents

4. Among the following amines, the strongest Brönsted base is ________. [1]

a) b)

c) d) NH3

5. Which of the following is an example of secondary amine? [1]

a) N,N – dimethylaniline b) 3 – pentanamine

c) methylamine d) N – ethyl – 1 – propanamine

6. Gabriel synthesis is used for the preparation of: [1]

a) Quaternary salt b) Primary amines

c) Tertiary amine d) Secondary amine

7. Which of the following is a 3o amine? [1]

a) N-methylaniline b) Tert-butylamine

c) 1-methylcyclohexylamine d) Triethylamine
8. The below reaction yields [1]

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 Yields the following

The 1, 2, 3 that are involved in completing the above synthesis are

a) HNO4, H3SO4, 353K b) HNO3, H2SO4, 288K

c) HNO3, H2SO4, 473K d) HNO3, H2SO4, 453K

9. Out of the following, the strongest base in aqueous solution is [1]

a) Trimethylamine b) Dimethylamine

c) Methylamine d) Aniline
10. Among the following, which has the highest value of pKb? [1]

a) b)

c) d)

11. Which of the following amines can be prepared by Gabriel synthesis? [1]

a) Isobutyl amine b) N-methylbenzylamine

c) Toluene d) Aniline
12. Benzene diazonium chloride on hydrolysis gives: [1]

a) Chlorobenzene b) Aniline

c) Benzene d) Phenol
13. The gas evolved when methylamine reacts with nitrous acid is ________. [1]

a) H2 b) N2

c) C2H6 d) NH3

14. Among the following, which is the strongest base? [1]

a) b)

c) d)

15. Amongst the given set of reactants, the most appropriate for preparing 2o amine is ________. [1]

a) 1o R-NH2 + RCHO followed by H2 /Pt b) 1o R-Br (2 mol) + potassium phthalimide

followed by H3O+/heat

c) 2o R-Br + NaCN followed by H /Pt d) 2o R-Br + NH

2 3

16. What is the best reagent to convert nitrile to primary amine? [1]

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17. Write an isomer of C3H9N which gives foul smell of isocyanide when treated with chloroform and ethanolic [1]
NaOH.
18. i. Draw the zwitter ion structure for sulphanilic acid. [1]
ii. How can the activating effect of -NH2 group in aniline be controlled?

19. Explain briefly: [1]

a. Carbylamine reaction
b. Gabriel phthalimide synthesis
20. Name the product formed when aniline is first diazotized and then reacted with phenol in the basic medium. [1]
21. Write IUPAC name of the following compound and classify it into primary secondary and tertiary amine. [1]
(CH3)3CNH2
22. Arrange the following in increasing order of base strength in gas phase: [1]
(C2H5)3N, C2H5NH2, (C2H5)2NH

23. Explain why MeNH2 is a stronger base than MeOH? [1]

24. What are the products of exhaustive ammonolysis of an alkyl halide? [1]
25. Out of CH3 - NH2 and (CH3)3N, which one has higher boiling point? [1]
26. Write the IUPAC name of : C 6 H5 − C H2 C H2 N H2 [1]
27. Give the structure of A in the following reaction. [1]

28. Draw the structure of 2-aminotoluene. [1]

29. Mention one commercial use of N, N- Dimethylaniline (DMA). [1]
30. Write the chemical reaction involved in Gabriel phthalimide synthesis. [1]
31. Assertion (A): Hydrolysis of cyanides always gives formic acid as one of the products. [1]
Reason (R): Isocyanides on reduction with SnCl2 / HCl followed by hydrolysis gives aldehydes.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) Both A and R are false.

32. Assertion (A): Aniline does not undergo Friedel-Crafts reaction. [1]
Reason (R): -NH2 group of aniline reacts with AlCl3 (Lewis acid) to give acid-base reaction.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

33. Assertion (A): In Hofmann bromamide reaction, the amine formed has one carbon atom less than the parent 1o [1]

amide.
Reason (R): N-methyl acetamide undergoes Hofmann bromamide reaction.

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 a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

34. Match the items given in column I with that in column II: [2]

Column I Column II

(a) Cyanide. (i) -NH2.

(b) Isocyanide. (ii) -CN.

(c) Nitro. (iii) -NC.

(d) Nitrite. (iv) -NO2.

35. Match the items given in column I with that in column II: [2]

Column I Column II

(a) C6H5NH2 + NaNO2 + HCl →. (i) C2H5OH.

(b) C6H5NH2 + COCl2 →. (ii) C2H6.

(c) C2H5NH2 + NaNO2 + HCl →. (iii) C6 H5 N

+

2
−
Cl .

(d) (CH3)2NH + C2H5MgBr →. (iv) C6 H5 N = C = O .

36. Match the items given in column I with that in column II: [2]

Column I Column II

(a) R − NC + HgO → . (i) R − NH2 .

+
H2 O/H
(b) R − NC −−−−−→
. (ii) R − N = C = O .

(c) R − NC + Cl2 (g) → . (iii) R − N = C = S .

(d) R − NC + S8 (s) → . (iv) R − N = CCl2 .

37. Match the pKb value given in column I with compound given in column II: [2]

Column I Column II

(a) 4.7. (i) Triethylamine.

(b) 3.27. (ii) Diethylamine.

(c) 3. (iii) Ethylamine.

(d) 3.2. (iv) Ammonia.

38. Match the reaction given in column I with that product given in column II: [2]

Column I Column II
Base

(a) C 2
H5 NH2 + ( CH3 CO) O −−→ . (i) C6H5NC.
2

Base

(b) C 6
H5 NH2 + CH3 COCl −−→ . (ii) C2H5NHCOCH3.
Heat

(c) C 6 H5 NH2 + CH3 CHO → . (iii) C6H5NHCOCH3.

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 Heat

(d) C H5 NH2 + CHCl3 + KOH −−→ . (iv) C

6 H5 N = CHC6 H5 .
6

39. How is aniline obtained from benzene? [2]

40. Arrange the following compounds in an increasing order of basic strength in their aqueous solution. [2]
NH3, CH3NH2, (CH3)NH, (CH3)3N
41. Convert the following: [2]
a. Phenol to N-phenylethanamide.
b. Chloroethane to methanamine.
c. Propanenitrile to ethanal.

42. a. Account for the following: [2]

Alkylamines are stronger bases than arylamines.
b. How would you convert methylamine into ethylamine?
43. Write a chemical reaction in which the iodide ion replaces the diazonium group in a diazonium salt. [2]
44. Give two chemical tests to identify primary, secondary and tertiary amines. [2]
45. How will you convert the following: [2]
i. Aniline to p-bromoaniline
ii. Ethanoic acid to methanamine
iii. Butanenitrile to 1-aminobutane
46. An organic compound 'A' having molecular formula C3H5N, on hydrolysis gave another compound 'B'. The [2]
compound 'B' on treatment with HNO2 gave ethyl alcohol, 'B' on warming with CHCl3 and alcoholic caustic

potash gave an offensive smelling substance 'C'. Identify 'A', 'B', and 'C'.
47. Arrange the following in increasing order of solubility in water: [2]
C6 H5 N H2 , ( C2 H5 )2 N H, C2 H5 N H2

48. Accomplish the following conversion: Aniline to 2, 4, 6 tribromofluorobenzene. [2]

49. How is m-nitroaniline obtained from nitrobenzene. [2]
50. a. Write the IUPAC name for the following organic compound: [2]

b. Complete the following:

Sn/HCl Br 2 /H2 O NaNO2 /HCl HBF 4

C6H5NO2 −−−−→ A −−−−−→ B −−−−−−−→ C −−−→ D

273−278 K Δ

51. A primary amine, RNH2 can be reacted with CH3-X to get secondary amine, R-NHCH3 but the only [2]
disadvantage is that 3° amine and quaternary ammonium salts are also obtained as side products. Can you

suggest a method where RNH2 forms only 2o amine?

52. Why it is difficult to prepare pure amine by ammonolysis of alkyl halides? [2]
53. Accomplish the following conversion: Chlorobenzene to p - chloroaniline. [2]
54. Give reasons: [3]
Methylamine in water reacts with ferric chloride to precipitate ferric hydroxide.
55. Predict, giving reasons the order of basicity of the following compounds: [3]

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 i. gaseous phase
ii. in aqueous solution
(C H3 )3 N , (C H3 )2 N H, C H3 N H3 , N H3

56. An organic compound A (C3H5N ) on hydrolysis in the presence of an alkali as catalyst gives NH3 and an acid B [3]

(C3H6O2).The compound A on reduction gives a compound C(C3H9N) which on further treatment with nitrous

acid gives an alcohol D(C3H8O). Identify compounds A, B, C and D.

57. A solution contains 1 g mol. each of p-toluene diazonium chloride and p-nitrophenyl diazonium chloride. To this [3]
1gmol of an alkaline solution of phenol is added. Predict the major product. Explain your answer.
58. a. Aromatic primary amines cannot be prepared by Gabriel Phthalimide synthesis. Why? [3]
b. Aniline is a weaker base than alkyl amines. Why?
c. Arrange the following in increasing order of basic strength in aqueous solution:
(CH3CH2)2NH, (C2H5)3N, C2H5NH2

59. A compound X having a molecular formula, C3H7NO reacts with Br2 in presence of KOH to give another [3]

compound Y. The compound Y reacts with HNO2 to form ethanol and N2 gas. Identify the compounds X and Y
and write the reactions involved.
60. Give reasons: [3]
i. Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.
ii. Aniline does not give Friedel-Crafts reaction.
iii. Although -NH2 group is o/p directing in electrophilic substitution reactions, yet aniline on nitration gives
good yield of m-nitroaniline.
61. A compound (X) having formula C3H7NO reacts with Br in the presence of NaOH to give another compound
2 [3]

(Y). Compound (Y) reacts with HNO2 to form ethanol and N gas. Identify (X) and (Y).Write the reactions
2

involved.
62. Identify the compounds A, B and C in the following equation: [3]
aq. Br2 NaN O2 /H C l H3 P O2

−−−−→ (A) −−−−−−−→ (B) −−−−→ (C )

H NO2 Δ

63. Give one chemical test to distinguish between primary, secondary and tertiary amines. [3]
64. Read the following text carefully and answer the questions that follow: [4]
RCONH2 is converted into RNH2 by means of Hoffmann bromamide degradation. During the reaction amide is
treated with Br2 and alkali to get amine. This reaction is used to descend the series in which carbon atom is
removed as carbonate ion (CO 2−
3
) . Hoffmann bromide degradation reaction can be written as:

i. Hoffmann bromamide degradation is used for the preparation of which amine? (1)
ii. Which is the rate determining step in Hoffmann bromamide degradation which is shown above paragraph?
(1)

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 iii. Identify B in the following reaction. (2)

OR
What are the constituent amines formed when the mixture of (i) and (ii) undergoes Hoffmann bromamide
degradation? (2)

65. Read the following text carefully and answer the questions that follow: [4]
Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms of
ammonia molecule by alkyl/aryl groups. Amines are usually formed from nitro compounds, halides, amides, etc.
They exhibit hydrogen bonding which influences their physical properties. Alkyl amines are found to be
stronger bases than ammonia. In aromatic amines, electron releasing and withdrawing groups, respectively
increase and decrease their basic character. Reactions of amines are governed by availability of the unshared pair
of electrons on nitrogen. Influence of the number of hydrogen atoms at nitrogen atom on the type of reactions
and nature of products is responsible for identification and distinction between primary, secondary and tertiary
amines. Reactivity of aromatic amines can be controlled by acylation process.
i. Why does aniline not give Friedel-Crafts reaction? (1)
ii. Arrange the following in the increasing order of their pKb values: (1)
C6H5NH2, NH3, C2H5NH2, (CH3)3N

iii. How can you distinguish between CH3CH2NH2 and (CH3CH2)2NH by Hinsberg test? (2)
OR
Write the structures of A and B in the following reactions: (2)

I.

Br 2 /alc.KOH CH3 COCl

II. CH 3 CH2 CONH2 −−−−−−−→ A −−−−−→ B

Pyridine

66. Complete the following chemical reactions: [5]

+ − +
H

i. C 6 H5 NCl + C6 H5 NH2 →
2

+ −

ii. C 6 H5 N2 Cl + CH3 CH2 OH →

iii. RNH 2 + CHCl 3 + KOH ⟶

67. Give plausible explanation for each of the following: [5]

i. Why are amines less acidic than alcohols of comparable molecular masses?
ii. Why do primary amines have higher boiling point than tertiary amines?
iii. Why are aliphatic amines stronger bases than aromatic amines?
68. Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. [5]
1. (C H 3 )2 C HN H2

2. C H 3 (C H2 )2 N H 2

3. C H 3 N HC H (C H3 )2

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 4. (C H 3 )3 C N H2

5. C 6 H5 N HC H3

69. Give one chemical test to distinguish between the following pairs of compounds. [5]
i. Methylamine and dimethylamine
ii. Secondary and tertiary amines
iii. Ethylamine and aniline
iv. Aniline and benzylamine
v. Aniline and N-methylaniline.

70. i. Give one chemical test to distinguish between ethylamine and aniline. [5]
ii. Describe a method for the identification of primary, secondary and tertiary amines. Also, write chemical
equations of the reactions involved.
71. Draw structure for the following compounds: [5]
a. p-toluidine
b. N-isopropylaniline
c. t-butylamine
d. p-fluoroaniline
e. P-tert-butylaniline
72. Write the main products of the following reactions: [5]
H NO2

i. CH 3 CH2 NH2 −−−−→

∘
0 C

ii.

iii.

73. i. Write structures of different isomeric amines corresponding to the molecular formula, C4H11N. [5]

ii. Write IUPAC names of all the isomers.

iii. What type of isomerism is exhibited by different pairs of amines?

74. A. Account for the following: [5]

i. Aniline is a weaker base than methylamine.

ii. Aryl cyanides cannot be formed by the reaction of aryl halides and sodium cyanide.
B. How will you convert 4-nitrotoluene to 2-bromobenzoic acid?

75. a. Write the structures of the main products of the following reactions: [5]

i.

ii.

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 iii.

b. Give a simple chemical test to distinguish between aniline and N,N-dimethylaniline.

c. Arrange the following in the increasing order of their pKb, values:
C6H5NH2, C2H5NH2, C6H5NHCH3

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