SND PUBLIC SCHOOL PALWAL

DPP 18
Class 12 - Chemistry

1. Which of the following would not be a good choice for reducing nitrobenzene to aniline? [1]

a) Sn and HCl b) H2/Hi

c) LiA/H4 d) Fe and HCl

2. Best method for preparing primary amines from alkyl halides without changing the number of carbon atoms in [1]
the chain is

a) Hoffmann Bromamide reaction b) Reaction with NH3

c) Gabriel phthalimide synthesis d) Sandmeyer reaction

3. Which of the following reagents would not be a good choice for reducing an aryl nitro compound to an amine? [1]

a) Fe and HCl b) LiAlH4 in ether

c) Sn and HCl d) H2 (excess)/Pt

4. The best reagent for converting 2–phenylpropanamide into 2-phenylpropanamine is ________. [1]

a) excess H2 b) iodine in the presence of red phosphorus

c) Br2 in aqueous NaOH d) LiAlH4 in ether

5. Hoffmann Bromamide Degradation reaction is given by: [1]

a) b)

c) CH3 - C N d)

6. Amide which gives propanamine by Hoffmann bromamide is: [1]

a) Pentanamide b) Hexanamide

c) Butanamine d) Propanamine
7. The Gabriel synthesis of amine undergoes which kind of reaction? [1]

a) Nucleophilic substitution reaction (SN2) b) Elimination reaction

c) Electrophilic substitution reaction d) SN1

8. The best reagent for converting, 2-phenylpropanamide into 1- phenylethanamine is ________. [1]

a) Br2/NaOH b) NaBH4/methanol

c) LiAlH4 d) excess H2/Pt

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 9. The source of nitrogen in Gabriel synthesis of amines is ________. [1]

a) Sodium nitrite, NaNO2 b) Potassium cyanide, KCN

c) Potassium phthalimide, C H (CO) N-K+ d) Sodium azide, NaN3

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10. 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 H2 /Pt d) 2o R-Br + NH3

11. Which gives a primary amine upon reduction? [1]

a) CH3CH2NC b) C6H5N = NC6H5

c) CH3CH2 - O - N = O d) CH3CH2NO2

12. Propanamide on reaction with bromine in aqueous NaOH gives: [1]

a) Ethanamine b) N-Methyl ethanamine

c) Propanamine d) Propanenitrile
13. Gabriel synthesis is used for the preparation of: [1]

a) Quaternary salt b) Primary amines

c) Tertiary amine d) Secondary amine

14. If the starting amide has got four carbon atoms and the amine that is formed has got only 3 carbon atoms, then [1]
the reaction is called______.

a) Gabriel synthesis b) Carbylamines reaction

c) Hoffmann bromamide reaction d) Clemmensen reduction

15. In order to prepare a 1o amine from an alkyl halide with simultaneous addition of one CH2 group in the carbon [1]

chain, the reagent used as source of nitrogen is ________.

a) Sodium amide, NaNH2 b) Sodium azide, NaN3

c) Potassium phthalimide, C H (CO) N-K+ d) Ethanolic NaCN

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

a) N-methylaniline b) Tert-butylamine

c) 1-methylcyclohexylamine d) Triethylamine
17. Which one of the following cannot be obtained by Gabriel phthalimide synthesis? [1]

a) CH3NH2 b) CH4CH3NH5

c) CH3CH2NH2 d) Aromatic primary amines

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

a) Isobutyl amine b) N-methylbenzylamine

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 c) Toluene d) Aniline
19. Which one of the following reagents is most suitable in completing the following synthesis? [1]

a) LiAlH4 b) Br2+ NaOH

c) Sn d) H2 + Ni

20. Which of the following methods of preparation of amines will give same number of carbon atoms in the chain of [1]
amines as in the reactant?

a) Treatment of amide with bromine in an b) Heating alkylhalide with potassium salt of

aqueous solution of sodium hydroxide phthalimide followed by hydrolysis

c) Reaction of nitrite with LiAlH4 d) Reaction of amide with LiAlH4 followed by

treatment with water
21. What is the role of HNO3 in the nitrating mixture used for nitration of benzene? [1]

22. Suggest a route by which the following conversion can be accomplished. [1]

23. What is the Hofmann bromamide reaction? Illustrate with one example. [1]
24. Identify A and B in the following reaction. [1]

25. i. Draw the zwitter ion structure for sulphanilic acid. [1]
ii. How can the activating effect of -NH2 group in aniline be controlled?

26. What is the best reagent to convert nitrile to primary amine? [1]
27. Assertion (A): Alkyl isocyanides in acidified water give alkyl formamides. [1]
Reason (R): In isocyanides, carbon first acts as a nucleophile and then as an electrophile.

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.

28. Assertion (A): Nitrating mixture used for carrying out nitration of benzene consists of conc. HNO3 + conc. [1]

H2SO4.

Reason (R): In presence of H2SO4, HNO3 acts as a base and produced ions.

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.

29. Assertion: Aromatic 1o amines can be prepared by Gabriel Phthalimide Synthesis. [1]
Reason: Aryl halides undergo nucleophilic substitution with anion formed by phthalimide.

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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 and R is true.

30. The main product formed by treating an alkyl or benzyl halide with excess ammonia______. [1]

a) Secondary b) Tertiary

c) Mixed d) Primary amine

31. Reduction of aromatic nitro compounds using Fe and HCl gives ________. [1]

a) aromatic amide b) aromatic oxime

c) aromatic hydrocarbon d) aromatic primary amine

32. Hoffmann Bromamide Degradation reaction is shown by ________. [1]

a) ArNH2 b) ArCONH2

c) ArNO2 d) ArCH2NH2

33. Which of the following is least basic? [1]

a) (CH3)3N b) NH3

c) (CH3)2NH d)

34. In the nitration of benzene using a mixture of conc. H2SO4 and conc. HNO3, the species which initiates the [1]

reaction is ________.

a) b) NO+

c) NO+ d)
2

35. Which of the following should be most volatile? [1]

I. CH3CH2CH2NH2
II. (CH3)3N

III.

IV. CH3CH2CH3

a) IV b) II

c) I d) III
36. Which of the following has highest boiling point? [1]

a) HCOOH b) CH3CH3

c) CH3NH2 d) CH3OH

37. Assertion (A): Methyl cyanide has higher boiling point than methyl isocyanide. [1]
Reason (R): Methyl cyanide has higher dipole moment than methyl isocyanide.

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.

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 c) A is true but R is false. d) A is false but R is true.
38. Arrange the following compounds in order of increasing boiling point: CH3NHCH2CH3; CH3OCH2CH3; [1]
(CH3)3N; and CH3CH2CH2OH.

a) Low to high; CH3OCH2CH3.; (CH3)3N; b) Low to high: CH3NHCH2CH3;

CH3NHCH2CH3; CH3CH2CH2OH. CH3CH2CH2OH.; (CH3)3N;

CH3OCH2CH3.

c) Low to high: (CH3)3N ; CH3OCH2CH3; d) Low to high: CH3CH2CH2OH;

CH3NHCH2CH3; CH3CH2CH2OH. CH3NHCH2CH3; (CH3)3N;

CH3OCH2CH3.

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

Column I Column II

(a) CH3CN. (i) Prop-2-ene-nitrile.

(b) C6H5CN. (ii) Ethanenitrile.

(c) CH3NC. (iii) Benzenecarbonitrile.

(d) . (iv) Ethyl isocyanide.

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

Column I Column II

(a) . (i) .

(b) . (ii) .

(c) . (iii) .

(d) . (iv) .

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

Column I Column II

(a) . (i) RCOOR.

(b) . (ii) RCOR.

(c) . (iii) RCHO.

(d) . (iv) RCH2NH2.

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

Column I Column II

(a) . (i) .

(b) . (ii) .

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 (c) . (iii) .

(d) . (iv) .

43. Complete the following: [2]

44. a. How will you convert an alkyl halide to a primary amine whose molecule has one more carbon atom than the [2]
alkyl halide molecule?
b. Why are amines more basic than the comparable alcohols?
45. How is m-nitroaniline obtained from nitrobenzene? [2]
46. Accomplish the following conversion: Nitrobenzene to benzoic acid. [2]
47. Accomplish the following conversion: Benzoic acid to aniline. [2]
48. A compound 'X' having molecular formula C3H7NO reacts with Br2 in presence of KOH to give another [2]
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.

49. How is aniline obtained from benzene? [2]
50. How will you convert 4-nitrotoluene to 2-bromobenzoic acid? [2]
51. Write following conversions: [2]
i. nitrobenzene acetanilide
ii. acetanilide p-nitroaniline
52. Complete the following: [2]

53. What is Mendius reduction? Give equation. [2]

54. What happens when: [2]
i. Nitroethane is treated with LiAlH4.

ii. Diazonium chloride reacts with phenol in basic medium.

55. Iodomethane reacts with KCN to form a major product A. Compound A on reduction in presence of LiAlH4 [2]
forms a higher amine B. Compound B on treatment with CuCl2 forms a blue colour complex C. Identify the

compounds A, B and C.
56. An aliphatic compound (A) with molecular formula C2H3Cl on treatment with AgCN gives two isomeric [2]
compounds of unequal amounts with the molecular formula C3H3N. The minor of these two products on
complete reduction with H2 in the presence of Ni gives a compounds 'B' with a molecular formula C3H3N.
Identify the compounds 'A', 'B' and write the reactions involved.
57. How will you carry out the following conversion? [2]

[2]

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58. Arrange the following in decreasing order of pkb giving reason:

a. Aniline, p-nitroaniline and p-toluidine

b. C2H5NH2, (C2H5)2NH, (C2H5)3N in gaseous state

59. Primary amines have higher boiling points than tertiary amines. Why? [2]
60. Write structure and IUPAC names of: [3]
i. The amide which gives propanamide by Hoffmann bromamide reaction.
ii. The amine produced by the Hoffmann degradation of benzamide.
61. Accomplish the following conversion: Benzamide to toluene. [3]
62. Read the text carefully and answer the questions: [4]
Amines have a lone pair of electrons on nitrogen atom due to which they behave as Lewis base. Larger the value
of Kb or smaller the value of pKb stronger is the base. Amines are more basic than alcohols, ethers, esters, etc.
The basic character of aliphatic amines should increase with the increase of alkyl substitution. But it does not
occur in a regular manner as a secondary aliphatic amine is unexpectedly more basic than a tertiary amine in
solutions. Aromatic amines are weaker bases than ammonia and aliphatic amines. Electron-donating groups such
as -CH3, -OCH3, -NH2, etc., increase the basicity while electron-withdrawing substituents such as -NO2, -CN,

halogens. etc. decrease the basicity of amines. The effect of these substituents is more at p- than at m-positions.
(a) Arrange the following in increasing order of their basic strength:
C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2, (C2H5)2NH

(b) Arrange the following compounds in increasing order of their acidic strength:
Methylamine, dimethylamine, aniline, N-methylaniline
(c) Rearrange the following in increasing order of their basic strength:
p-toluidine, N, N-dimethyl-p-toluidine, p-nitroaniline, aniline
(d) Which is more acidic, aniline or ammonia?
63. Write the main products of the following reactions: [5]

i.

ii.

iii.

64. Predict the reagent or the product in the following reaction sequence. [5]

65. A colorless substance ‘A’ (C6H7N) is sparingly soluble in water and gives a water-soluble compound ‘B’ on [5]
treating with a mineral acid. On reacting with CHCl 3 and alcoholic potash ‘A’ produces an obnoxious smell due

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to the formation of compound ‘C’. The reaction of ‘A’ with benzene sulphonyl chloride gives compound ‘D’
which is soluble in alkali. With NaNO2 and HCl, ‘A’ forms compound ‘E’ which reacts with phenol in alkaline
medium to give an orange dye ‘F’. Identify compounds ‘A’ to ‘F’.

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