AMINES
PREVIOUS YEAR QUESTIONS
1. Carry out the following conversions:
(a) Nitrobenzene to aniline
(b) Aniline to phenol
OR
(a) Write a chemical test to distinguish between dimethyl amine and ethanamine.
(b) Write the product formed when benzene diazonium chloride is treated with KI.
2. A compound “X” with molecular formula C3H9N reacts with C6H5SO2Cl to give a solid, insoluble in
alkali. Identify “X” and give the IUPAC name of the product. Write the reaction involved.
3. (I) Give reasons
(a) Aniline on nitration gives good amount of m-nitroaniline, through –NH2 group is o/p directing in
electrophilic substitution reactions.
(b) (CH3)2NH is more basic than (CH3)3N in an aq. Solution.
(c) Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.
(II) Wtite the reaction involved in the following:
(a) Carbylamine test
(b) Gabriel phthalimide synthesis
4. (I) write the structures of A, B and C in the following reactions:
(II) Why aniline does not undergo Friedel-Crafts reaction?
(III) Arrange the following in increasing order of boiling point:
C2H5OH, C2H5NH2, (C2H5)3N
5. Give the structures of A and B in the following sequence of reactions:
6. (a) How will you distinguish between the following pairs of compounds:
(i) Aniline and Ethanamine
(ii) Aniline and N-methylaniline
(b) Arrange the following compounds in decreasing order of their boiling points: Butanol,
Butanamine, Butane
7. Account for the following:
(a) Aniline is a weaker base compared to ethanamine.
(b) Aniline does not undergo Friedel-Crafts reaction.
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(c) Only aliphatic primary amines can be prepared by Gabriel Phthalimide synthesis.
8. (a) Give reasons:
(i) Although – NH2 group is o/p directing in electrophilic substitution reactions, yet aniline, on
nitration gives good yield of m-nitroaniline.
(ii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
(iii) Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.
(b) Distinguish between the following:
(i) CH3CH2NH2 and (CH3CH2)2 NH
(ii) Aniline and CH3NH2
9. Write the structures of A and B in the following reactions:
10. Write an isomer of C3H9N which gives foul smell of isocyanide when treated with chloroform and
ethanolic NaOH.
11. Arrange the following compounds as directed:
(i) In increasing order of solubility in water: (CH3)2NH, CH3NH2, C6H5NH2
(ii) In decreasing order of basic strength in aqueous solution: (CH3)3N, (CH3)2NH, CH3NH2
(iii) In increasing order of boiling point:
(C2H5)2NH, (C2H5)3N, C2H5NH2
12. Out of CH3NH2 and CH3OH, which has higher boiling point?
13. Arrange the following in decreasing order of solubility in water: (CH3)3N, (CH3)2NH, CH3NH2
14. Arrange the following in decreasing order of solubility in water:
(C2H5)2NH, C2H5NH2, C6H5NH2
15. Write structures of compounds A and B in each of the following reactions:
16. Complete the following reactions :
17. 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
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18. Write the structures of the main products of the following reactions:
19. (a) Give a simple chemical test to distinguish between Aniline and N,N-dimethylaniline.
(b) Arrange the following in the increasing order of their pKb values :
C6H5NH2, C2H5NH2, C6H5NHCH3
20. Write the structures of compounds A, B and C in the following reactions :
21. Write the structures of A, B, C, D and E in the following reactions :
22. Write the chemical equations involved in the following reactions:
(i)Hoffmann-bromoamide degradation reaction
(ii) Carbylamines reaction
23. Write the structures of A, B and C in the following:
24. (a) Write the structures of main products when benzene diazonium chloride reacts with the
following reagents: (i) 𝑯𝟑𝑷𝑶𝟐 + 𝑯𝟐𝑶 (ii) CuCN/KCN (iii) 𝑯𝟐𝑶
(b) Arrange the following in the increasing order of their basic character in an aqueous solution:
𝑪𝟐𝑯𝟓𝑵𝑯𝟐, (𝑪𝟐𝑯𝟓)𝟐𝑵𝑯, (𝑪𝟐𝑯𝟓)𝟑𝑵
(c) Give a simple chemical test to distinguish between the following pair of compounds: 𝑪𝟔𝑯𝟓−𝑵𝑯𝟐
and 𝑪𝟔𝑯𝟓−𝑵𝑯–𝑪𝑯3
25. An aromatic compound ‘A’ of molecular formula 𝑪𝟕𝑯𝟕𝑶𝑵 undergoes a series of reactions as shown
below. Write the structures of A, B, C, D and E in the following reactions:
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26. How will you convert the followings:
(I) Nitrobenzene into aniline
(ii) Ethanoic acid into methanamine
(iii) Aniline into N-phenylethanamide (write the chemical equations involved)
27. Complete the following reaction equations:
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