Sure Shot Questions

Chapter – 09
Amines
MCQ (1 mark) (a) Sodium amide, NaNH2
(b) Sodium azide, NaN3
1. Which of the following is a 30 amine? (c) Potassium cyanide, KCN
(a) 1-Methylcyclohexylamine (d) Potassium phthalimide, C6 H 4 (CO)2 N  K 
(b) Triethylamine 8. The source of nitrogen in Gabriel synthesis of
(c) Tert-Butylamine amines is
(d) N-Methylaniline (a) Sodium azide, NaN3
2. The correct IUPAC name for (b) Sodium nitrite, NaNO2
CH 2  CHCH 2 NHCH3 is (c) Potassium cyanide, KCN
(a) Allylmethylamine (d) Potassium phthalimide, C6 H 4 (CO)2 N  K  .
(b) 2-amino-4-pentene
(c) 4-aminopent-1-ene 9. Amongst the given set of reactants, the most
(d) N-methylprop-2-en-1-amine. appropriate for preparing 20 amine is _____.
3. Amongst the following, the strongest base in (a) 20 R  Br  NH 3
aqueous medium is ______.
(b) 2 R  Br  NaCN followed by H 2 / Pt
0
(a) CH3NH2 (b) NCCH2NH2
(c) (CH3)2NH (d) C6H5NHCH3 (c) 10 R  NH 2  RCHO followed by H2/Pt
4. Which of the following is the weakest Bronsted
(d) 1 R  Br (2 mol)  potassium phthalimide
0
base?
followed by H 3O  /heat

10. The best reagent for converting 2-

phenylropanamide into 2-phenylpropanamine is
_______.
(a) Excess H2
5. Benzylamine may be alkylated as shown in the (b) Br2 in aqueous NaOH
following equation: (c) Iodine in the presence of red phosphorus
C6 H5CH 2 NH 2  R  X  C6 H5CH 2 NHR (d) LiAlH4 in ether.
Which of the following alkyl halides is best suited
for this reaction through SN1 mechanism? 11. The best reagent for converting, 2-
(a) CH3Br (b) C6H5Br phenylpropanamide into 1-phenylethanamine is
(c) C6H5CH2Br (d) C2H5Br ______.
 (a) Excess H 2 / Pt
(C6 H5 CH 2 ) formed is resonance stabilized.
(b) NaOH / Br2
6. Which of the following reagents would not be a
good choice for reducing an aryl nitro compound (c) NaBH 4 / methanol
to an amine? (d) LiAlH 4 / ether
(a) H 2(excess) / Pt (b) LiAlH 4 in ether
(c) Fe and HCl (d) Sn and HCl 12. Hoffmann bromamide degradation reaction is
shown by __________.
7. In order to prepare a 10 amine from an alkyl halide (a) ArNH 2 (b) ArCONH 2
with simultaneous addition of one CH2 group in the
(c) ArNO2 (d) ArCH 2 NH 2
carbon chain, the reagent used as source of
nitrogen is ______.

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13. The correct increasing order of basic strength for Assertion-Reasoning (1 mark)
the following compounds is _________.
21. Assertion : Ammonolysis of alkyi halides is not a
suitable method for the preparation of pure
primary amines.
Reason : Ammonolysis of alkyI halides yields
mainly secondary amines.
(a) II < III < I (b) III < I < II (a) Both Assertion (A) and Reason (R) are true and
(c) III < II < I (d) II < I < III Reason is the correct explanation of the
14. Methylamine reacts with HNO2 to form assertion.
(a) CH3  O  N  O (b) Both Assertion (A) and Reason (R) are true, but
(b) CH3  O  CH 3 Reason is not the correct explanation of the
assertion.
(c) CH 3OH (c) Assertion (A) is true, but Reason (R) is false.
(d) CH 3CHO (d) Assertion (A) is false, but Reason (R) is true.
[2023]
15. The gas evolved when methylamine reacts with
nitrous acid is _______. 22. Assertion (A): —NH2 group is O- and p-directing in
(a) NH3 (b) N2 electrophilic substitution reactions.
(c) H2 (d) C2H6 Reason (R) : Aniline cannot undergo Friedel-Crafts
16. In the nitration of benzene using a mixture of conc. reaction.
H2SO4 and conc. HNO3, the species which initiates (a) Both Assertion (A) and Reason (R) are true and
the reaction is ________. Reason (R) is the correct explanation of the
Assertion (A).
(a) NO2 (b) NO 
(b) Both Assertion (A) and Reason (R) are true, but

(c) N O2 (d) NO2 Reason (R) is not the correct explanation of the
Assertion (A).
17. Reduction of aromatic nitro compounds using Fe
(c) Assertion (A) is true, but Reason (R) is false.
and HCl gives ______.
(d) Assertion (A) is false, but Reason (R) is true.
(a) Aromatic oxime
[2023]
(b) Aromatic hydrocarbon
23. Assertion (A) : Acetylation of aniline gives a
(c) Aromatic primary amine
monosubstituted product.
(d) Aromatic amide
Reason (R): Activating effect of—NHCOCH3 group
18. The most reactive amine towards dilute
is more than that of amino group.
hydrochloric acid is __________.
(a) Both Assertion (A) and Reason (R) are true and
Reason (R) is the correct explanation of the
Assertion (A).
(b) Both Assertion (A) and Reason (R) are true, but
Reason (R) is not the correct explanation of the
Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) is false, but Reason (R) is true.
19. Propanamide on reaction with bromine in aqueous [2023]
NaOH gives
(a) propanamine (b) ethanamine 24. Assertion (A): (C2H5)2NH is more basic than
(c) N-methylethanamine (d) propanenitrile. (C2H5)3N in aqueous solution.
Reason (R): In (C2H5)2NH, there is more steric
20. Arrange the following in the increasing order of hindrance and +l effect than (C2 H5 )3 N .
their boiling points: (a) Both Assertion (A) and Reason (R) are true and
A : Butanamine, B : N,N – Dimethylethanamine, Reason (R) is the correct explanation of the
C : N – Ethylethanamine Assertion (A).
(a) C < B < A (b) A < B < C (b) Both Assertion (A) and Reason (R) are true, but
(c) A < C < B (d) B < C < A Reason (R) is not the correct explanation of the
2022 Assertion (A).
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 (c) Assertion (A) is true, but Reason (R) is false. aromatic amine. It undergoes electrophilic substitution
(d) Assertion (A) is false, but Reason (R) is true. reactions in which - NH2 group strongly activates the
[2023] aromatic ring through delocalisation of lone pair of
25. Given below are two statements labelled as electrons of N - atom. Aniline undergoes electrophilic
Assertion (A) and Reason (R). substitution reactions. Ortho and para positions to the
Assertion (A) : Tertiary amines are more basic - NH2 group become centres of high electrons density.
than corresponding secondary and primary Thus, - NH2 group is ortho and para - directing and
amines in gaseous state. powerful activating group.
Reason (R): Tertiary amines have three alkyI
groups which cause +l effect. (a) Cyclohexylamine and aniline can be distinguished
Select the most appropriate answer from the by
options given below: a) Hinsberg test b) Lassaigne test
(a) Both A and R are true and R is the correct c) Azo dye test d) Carbylamine test
explanation of A.
(b) Both A and R are true but R is not the correct (b) Which of the following compounds gives dye test?
explanation of A.
(c) A is true but R is false. a) Methyl amine b) Aniline
(d) A is false but R is true. [2022 – 23] c) Ethyl amine d) Diphenyl amine
(c) Aniline when acetylated, the major product on
26. Assertion (A): N, N - Diethylbenzene sulphonamide nitration followed by alkaline hydrolysis gives
is insoluble in alkali.
Reason (R): Sulphonyl group attached to the a) P - nitroaniline b) O - nitroacetanilide
nitrogen atom is a strong electron - withdrawing c) M - nitroaniline. d) Acetanilide
group.
a) Both A and R are true and R is the correct (d) Oxidation of aniline with manganese dioxide and
explanation of A. sulphuric acid produces
b) Both A and R are true but R is not the correct
explanation of A. a) Phenylhydroxylamine b) Phenol
c) A is true but R is false. c) P - benzoquinone d) Nitrobenzene
d) A is false but R is true.
(e) Aniline when treated with conc. HNO3 and H2SO4
27. Assertion (A):Nitration of aniline can be gives
conveniently done by protecting the amino group a) P - benzoquinone b) Nitrobenzene
by acetylation. c) P - phenylenediamine d) M – nitroaniline
Reason (R):Acetylation increases the electron density
in the benzene ring.
a) Both A and R are true and R is the correct
explanation of A. 29. Read the text carefully and answer the questions:
b) Both A and R are true but R is not the correct A mixture of two aromatic compounds (A) and (B)
explanation of A. was separated by dissolving in chloroform followed
c) A is true but R is false. by extraction with aqueous KOH solution. The
d) A is false but R is true. organic layer containing compound (A), when
heated with alcoholic solution of KOH produce
C7H5N (C) associated with unpleasant odour.
Case study Questions
(a) What is A?
28. Read the text carefully and answer the questions: a) None of these b) C6H5CH3
Amines are alkyl or aryl derivatives of ammonia c) C6H5CHO d) C6H5NH2
formed by replacement of one or more hydrogen
atoms. Alkyl derivatives are called aliphatic amines (b) The reaction of (A) with alcoholic solution of KOH to
and aryl derivatives are known as aromatic amines. produce (C) of unpleasant odour is called
The presence of aromatic amines can be identified
by performing dye test. Aniline is the simplest a) Ullmann reaction
example of b) Sandmeyer reaction
c) Reimer - Tiemann reaction
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d) Carbylamine reaction (e) Direct nitration of an aromatic compound (A) is not
feasible because
(c) The alkaline aqueous layer (B) when heated with i. The reaction cannot be stopped at the mononitration
chloroform and then acidified give a mixture stage
compounds of molecular formula C7H6O2 (B) is ii. A mixture of o, m and p - nitroaniline is always
obtained
a) C6H5CHO b) C6H5OH iii. Nitric acid oxidises most of the aromatic compound
c) C6H5CH3 d) C6H5COOH to give oxidation products along with amount of
nitrated products
(d) In the chemical reaction, CH3CH2NH2 + CHCl3 + iv. All of these
3KOH → (A) + (B) + 3H2O, the compounds (A) and (B)
are respectively a) Option (a) b) Option (c)
c) Option (b) d) Option (d)
a) C2H5CN and KCl b) C2H5NC and K2CO3
c) C2H5NC and KCl d) CH3CH2CONH2 and KCl

Questions
30. Write equations involved in the following reactions:
(i) Ethanamine reacts with acetyl chloride.
(ii) Aniline reacts with bromine water at room temperature.
(iii) Aniline reacts with chloroform and ethanolic potassium hydroxide.

31. 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:

32.Write the IUPAC name of the given compound:

33.How will you convert the following :

(i)Nitrobenzene into aniline
(ii) Ethanoic acid into methanamine

34.Propanamine and N, N- dimethylmethanamine contain the same number of carbon

atoms, even though propanamine has higher boiling point than N, N-
dimethylmethanamine, Why?

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35.An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms
compound ‘B’ which on heating with 𝐵𝑟2 and KOH forms a compound ‘C of molecular
formula 𝐶6 𝐻7 𝑁. Write the structures and IUPAC names of compounds A, B and C .

36.Arrange the following compounds in the order of property indicated for each set :
(i) 𝑁𝐻3 , 𝑅𝑁𝐻2 , 𝑅2 𝑁𝐻, 𝑅3 𝑁 (increasing order of their basic strength in aqueous
solutions)
(ii) Ammonia, triethylamine, amiline, ethylamine and dethylamine.

37.Arrange the following compounds in the order of property indicated for each set:
(i) 𝐶𝐻3 𝑁𝐻3 , (𝐶𝐻3 )3 𝑁, (𝐶𝐻3 )2 𝑁𝐻 (increasing oder of their basic strength in aqueous
solution)
(ii) 𝐶6 𝐻5 𝑁𝐻3 , 𝐶6 𝐻5 𝑁𝐻𝐶𝐻3 , 𝐶6 𝐻5 𝑁(𝐶𝐻3 )2 (increasing order of basic strength)

38.Write the reactions involved in the following :

(i) Hoffmann bromamide degradation reaction
(ii) Gabriel phthalimide synthesis
Or
IIIustrate the following reactions giving suitable example in each case:
(i) Hoffmann bromamide degradation reaction
(ii) Gabriel phthalimide synthesis.

39.Give chemical test to distinguish between 𝐶6 𝐻5 𝐶𝐻2 𝑁𝐻2 𝑎𝑛𝑑 𝐶6 𝐻5 𝑁𝐻2 .

40.Arrange the following in increasing order of their basic strength:

(a) 𝐶2 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝐻2 , 𝑁𝐻3 , 𝐶6 𝐻5 𝐶𝐻2 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻
(b) 𝐶2 𝐻5 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻, (𝐶2 𝐻5 )2 𝑁, 𝐶6 𝐻5 𝑁𝐻2
(c) 𝐶𝐻3 𝑁𝐻2 , (𝐶𝐻3 )2 𝑁𝐻, (𝐶𝐻3 )3 𝑁, 𝐶6 𝐻5 𝑁𝐻2 𝑁𝐻2 .

41.In the following cases rearrange the compounds as directed:

(i) In increasing order of basic strength:
(a) Aniline, p-nitroaniline and p-toluidine
(b) 𝐶6 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝐻𝐶𝐻3 , 𝐶6 𝐻5 𝐶𝐻2 𝑁𝐻2
(ii) In increasing order of solubility in water:
𝐶6 𝐻5 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻, 𝐶2 𝐻5 𝑁𝐻2
(iii) In decreasing order of basic strength in gas phase:
𝐶2 𝐻5 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻, (𝐶2 𝐻5 )3 𝑁 𝑎𝑛𝑑 𝑁𝐻3

42.Arrange the following in increasing order of their basic strength:

(i) 𝐶2 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝐻2 , 𝑁𝐻3 , 𝐶6 𝐻5 𝑁𝐻2 𝑎𝑛𝑑 (𝐶2 𝐻5 )2 𝑁𝐻
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 (ii) 𝐶2 𝐻5 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻, (𝐶2 𝐻5 )3 𝑁, 𝐶6 𝐻5 𝑁𝐻2
(iii) 𝐶𝐻3 𝑁𝐻2 , (𝐶𝐻3 )2 𝑁𝐻, 𝐶𝐻3 𝑁, 𝐶6 𝐻5 𝑁𝐻2

43.Arrange the following:

(i) In decreasing order of the p𝐾𝑏 values:
𝐶2 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝐻𝐶𝐻3 , (𝐶2 𝐻5 )2 𝐶6 𝐻5 𝑁𝐻2
(ii) In increasing order of basic strength:
𝐶6 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝐻𝐶𝐻3 , (𝐶2 𝐻5 )2 𝑁𝐻 𝑎𝑛𝑑 𝐶𝐻3 𝑁𝐻2
(iii) in increasing order of boiling point:
𝐶2 𝐻5 𝑂𝐻, (𝐶𝐻3 )2 𝑁𝐻, (𝐶2 𝐻5 )2 𝑁𝐻2

44.Account for the following:

(i) 𝑝𝐾𝑏 of aniline is more than that of methylamine.
(ii) Although trimethylamine and n-propylamine have the same molecular weight, but
the former boils at a lower temperature (276 K) than the latter (322 K). Explain.
(iii) (𝐶𝐻3 )2 𝑁𝐻 is more basic than (𝐶𝐻3 )3 𝑁 in an aqueous solution

45.Account for the following:

(i) 𝑝𝐾𝑏 of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric
oxide.
(iv) Although amino group is o, p- directing in aromatic electrophilic substitution
reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.

46.Write short notes on the following:

(i) Carbylamine reaction
(ii) Hoffmann’s bromamide reaction

47.Write short notes on the following:

(i) Ammonolysis (ii) Acetylation

48.Arrange the following:

(i) In decreasing order of the 𝑝𝐾𝑏 values :
𝐶2 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝑁𝐶𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻 𝑎𝑛𝑑 𝐶6 𝐻5 𝑁𝐻2
(ii) In increasing order of basic strength:
𝐶6 𝐻5 𝑁𝐻2 𝐶6 𝐻5 𝑁(𝐶𝐻3 )2 , (𝐶2 𝐻5 )2 𝑁𝐻 𝑎𝑛𝑑 𝐶𝐻3 𝑁𝐻2
(iii) In increasing order of basic strength:
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 (a) Aniline, p-nitroaniline and p-toluidine
(b) 𝐶6 𝐻5 𝑁𝐻2 , 𝐶6 𝐻5 𝑁𝐻𝐶𝐻3 , 𝐶6 𝐻5 𝐶𝐻2 𝑁𝐻2 .
(iv) In decreasing order of basic strength in gas phase :
𝐶2 𝐻5 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻 (𝐶2 𝐻5 )3 𝑁 𝑎𝑛𝑑 𝑁𝐻3
(v) In increasing order of boiling point :
𝐶2 𝐻5 𝑂𝐻 , (𝐶𝐻3 )2 𝑁𝐻, 𝐶2 𝐻5 𝑁𝐻2
(vi) In increasing order of solubility in water :
𝐶6 𝐻5 𝑁𝐻2 , (𝐶2 𝐻5 )2 𝑁𝐻, 𝐶2 𝐻5 𝑁𝐻2

49. IIIustrate the following reactions giving a chemical equation in each case:
(i) Gabriel phthalimide synthesis
(ii) Hoffmann’s bromamide reaction

50.Write the reactions of the final alkylation product of aniline with excess of methyl Iodide
in the presence of sodium carbonate solution.

51.Convert:
(i) 3-Methylaniline into 3-nitrotoluene
(ii) Aniline into 1, 3, 5, -tribromobenzene.

52.Give one chemical test to distinguish between the following pairs of compounds.
(i) Ethylamine and aniline
(ii) Aniline and benzylamine.

53.Give one chemical test to distinguish between the following pairs of compounds:
(i) Ethylamine and aniline (ii) Aniline and N-methylaniline

54.Account for the following:

(i) Ethylamine is soluble in water, whereas aniline is not.
(ii) Although amino group is o- and p-directing in aromatic electrophilic substitution
reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
(iii) Aniline does not undergo friedel- Crafts reaction.

55. Give reasons:

(i) Ammonolysis of alkyI 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.
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56. Write equations involved in the following reactions:
(i) Ethanamine reacts with acetyl chloride.s
(ii) Aniline reacts with bromine water at room temperature.
(iii) Aniline reacts with chloroform and ethanolic potassium hydroxide.

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