260

WtGCBSE Champion Chemistry Class 12

Previous Years' CBSE Board Questions

9 CH,CONH, on reaction with NaOH and Br, in
9.2 Classification alcoholic medium gives
MCQ (a) CHCOONa (b) CHNH2
(c) CH,CH,Br (d) CH,CH,NH,
1. ldentify the primary amine from the given options
(a) (C,Hs)N (b) (C,Hs),NH (2023)R
(c) CzHsNH2 (d) (CH3)3N (2024) 10. Assertion : Ammonolysis of alkyl halides is not a
suitable method for the preparation of pure primary
VSA (1 mark) amines.
2. Choose the primary amine from the following Reason : Ammonolysis of alkyl halides yields mainly
compounds: secondary amines.
(CzHs),CHNH, (CzHs),NH, (CH)3N (a) Both Assertion (A) and Reason (R) are true
(Term I, 2021-22C) O and Reason is the correct explanation of the
assertion.
9.3 Nomenclature (b) Both Assertion (A) and Reason (R) are true, but
VSA (1mark) Reason is not the correct explanation of the
assertion.
3 Write IUPAC name of the following compound: (c) Assertion (A) is true, but Reason (R) is false.
(CH,CH2),NCH3 (Delhi 2017) (U (d) Assertion (A) is false, but Reason (R) is true.
4. Write the structure of 2, 4-dinitrochlorobenzene. (2023)
(Delhi 2017) 11. Which of the following would not be a good choice
5 Write the IUPAC name of thefollowing compound: for reducing nitrobenzene to aniline?
CH;NHCH(CH3)2 (Delhi 2017) (a) LiAlH4 (b) H/Ni
6 Write IUPAC name of the following compound: (c) Fe and HCI (d) Sn and HCI (2023)
(CH3),N CH,CH3 (Delhi 2017) 12. CH,CONH, on reaction with NaOH and Br, in
7. Write the IUPAC name of the given compound : alcoholicmedium gives
NH2 (a) CH,CH,NH, (b) CHCH,Br
Br Br (c) CH3NH2 (d) CH,cOONa
(2020) U)
Br (Delhi 2016) (U) VSA (1 mark)

9.4 Preparation of Amines 13. Ammonolysis of alkyl halides is not a good method
to prepare pure primary amines. Give reason
MCQ
(1/5, 202o) Ap
8. Assertion (A): Aliphatic primary amines can be 14. Write the structures of A and B in the following
prepared by Gabriel phthalimide synthesis
reaction:
Reason (R) : Alkyl halides undergo nucleophilic
substitution with anion formed by phthalimide. CH,COOH ANaOBr>B (1/5, 2020)
A
(a) Both Assertion (A) and Reason (R) are true and 15. Carry out the following conversion:
Reason (R) is the correct explanation of the Benzoic acid to aniline. (1/5, Al 2019)
Assertion (A).
(b) Both Assertion (A) and Reason (R) are true, but 16. Write the chemical equation involved in the
Reason (R) is not the correct explanation of the following reaction:
Assertion(A). Hoffmann bromamide degradation reaction
(c) Assertion (A) is true, but Reason (R) is false. (Al2019, 1/5, 2018, 1/2, A 2016)
(d) Assertion (A) is false, but Reason (R) 17. How do you convert the following:
is true. (2024) (U Ethanenitrile to ethanamine (1/3, Al2015)
Amines 261

SAI (2 marks) lgh 9.6 Chemical Reactions

18. Complete the following: Weilghtage
Toplc (Amines)
CH,Br
KCN
>A LIAIHA B (Term Il, 2021-22C) Basicity of Anines
SA II (3 marks) MCQ
19, (a) Write the IUPAC name for the following organic 27. Assertion (A):p-Nitroaniline is a weaker base than
compound: (CH,CH,),NCH3 p-toluidine.
(b) Write the equations for the following: Reason (R):The electron withdrawing effect of
(0) Gabriel phthalimide synthesis -NO, group in p-nitroaniline makes it a weaker base.
(i) Hoffmann bromamide degradation (a) Both Assertion (A) and Reason (R) are true and
(Term I,2021-22) (R) Reason (R) is the correct explanation of the
Assertion (A).
20. An aromatic compound'A' (C,H,0,) on reaction with
aqueous ammonia and heating forms compound 'B!. (b) Both Assertion (A) and Reason (R) are true, but
'B' on heating with Br, and alcoholic potash forms Reason (R) ís not the correct explanation of the
a compound C of molecular formula CH,N. Write Assertion(A).
the reactions involved and identify 'A,'B,' C: (c) Assertion (A) is true, but Reason (R) is false.
(Term II, 2021-22) (d) Assertion (A) is false, but Reason (R)
21, is true. (2024)
How will youcarry out the following conversions:
(i) Nitrobenzene to aniline 28. Three compounds are given below:
(i) Ethanamide to methanamine
(ii) Ethanenitrile to ethanamine NH2 NH, NH2
(Term I, 2021-22) (Ap
9.5 Physical Properties NO, CH3
VSA (1 mark)

22. Out of CH,NH, and CH,OH, which has higher The correct decreasing order of their basic strength is
boiling point? (2020) (a) I| >II| >| (b) I|>|| >|
(c) ||> |> || (d) |>I| > || (2023C)
23. Arrange the following compounds in decreasing
order of their boiling points: 29. Among the folowing, which is the strongest base?
SButanol, Butanamine, Butane (1/3, 2020) Ev
24. Propanamine and N,N-dimethylmethanamine contain
(a) (b) HC NH,
the same number of carbon atoms, even though
propanamine has higher boiling point than ()
N,N-dimethylmethanamine. Why? (AI2019)
(2023)
ORie
Give reasons for the following : 30. Which of the following is least basic?
Primary amines have higher boiling point than (a) (CH),NH (b) NH3
tertiary amines. (1/3,Al 2016)
(c) NH, (d) (CH),N (2023)
25. Arrange the following in the increasing order of
their boiling points: 31. Assertion (A):-NH, group is o- and p-directing in
CzHsNH. CzH;OH, (CH),N electrophilic substitution reactions.
(2019, 1/5, Delhi 2015)
Reason (R) :Aniline cannot undergo Friedel-Crafts
SAI (2 marks) reaction.

26. Arrange the following compounds as directed: (a) Both Assertion (A) and Reason (R) are true and
Reason (R) is the correct explanation of the
() In increasing order of solubility in water : Assertion (A).
(CH),NH, CH,NH, C,HNH2 (b) Both Assertion (A) and Reason (R) are true, but
(i) In increasing order of boiling point : Reason (R) 0s not the correct explanation of the
(C,Hs),NH, (CzHs)gN, C,H,NH2 (2/3, 2020) Assertion (A).
 262 wtG) CBSE Champion
39. Give reason:
Chemistry Class 12
(c) Assertion (A) is true, but Reason (R) is false.
(d) Assertion (A) 0s false, but Reason (R) is true. (CHa),NH is more basic than (CH)Nin an
(1/5,aqueous
(2023) solution.

40. Arrange the following in the

2018)
32. Assertion (A): Acetylation of aniline gives a decreasing
monosubstituted product. their basic strength in aqueous solutions: order of
Reason (R) : Activating effect of-NHCOCH, group CH,NH2.(CH),NH, (CHa),N and NHa (1/3,
is more than that of amino group. 41. Arrange the following in increasing order of 2018C)
(a) Both Assertion (A) and Reason (R) are true and strength: basic
Reason (R) is the correct explanation of the Aniline, p-nitroaniline and p-toluidine
Assertion (A).
(b) Both Assertion (A) and Reason (R)are true, but (1/2, Al 2015,Al 2015C)
Reason (R) is not the correct explanation of the 42. Arrange the following in increasing order of
Assertion (A). strength: basic
(c) Assertion (A) is true, but Reason (R) is false. CoHsNH, CoH,NHCHg. CoH,CH,NH,
(d) Assertion (A) is false, but Reason (R) is true. (1/2,Al 2015)
(2023) SAI (2 marks)
33. Assertion (A): (C,H5),NH is more basic than
(C,Hs)N in aqueous solution. 43. Explain briefly
Reason (R) : In (CzHs),NH, there is more steric (a) Carbylamine reaction
hindrance and + effect than (C,Hs)N. (b) Gabriel phthalimide synthesis (2023)
(a) Both Assertion (A) and Reason (R) are true and 44, () Draw the zwitter ion structure for sulphanilic acid
Reason (R) is the correct explanation of the (ii) How can the activating effect of -NH2 group in
Assertion (A). aniline be controlled?
(b) Both Assertion (A) and Reason (R) are true, but (2023)
Reason (R) is not the correct explanation of the 45. Arrange the following compounds as directed:
Assertion (A).
(any two)
() In decreasing order of basic strength in aqueous
(c) Assertion (A) is true, but Reason. (R) is false. solution:
(d) Assertion (A) is false, but Reason (R) is true.
(2023) CzH,NH2 (CgHs),NH, (CzHs),N
(ii) In increasing order of solubility in water:
34. In the reaction
(C,Hs),NH,C,H,NH2, CoH,NH2
CGH,NH, +CHClg + 3KOH -’A+ 3B +3C (iii) In decreasing order of their pk, values :
The product A is CoHsNH2 CzHsNH2 NH3 (Term lI, 2021-22)
(a) CGHsNC (b) CGH,CN Chemical Properties of Amines
(c) CoH5CI (d) CoH,NHCH3 (2023)
35. Out of the following, the strongest base in aqueous MCQ
solution is
46. Assertion (A): Diazonium salts of aromatic amines
(a) methylamine (b) dimethylamine
(2020) An are more stable than those of aliphatic amines.
(c) trimethylamine (d) aniline.
Reason (R) : Diazonium salts of aliphatic amines
VSA (1 mark) show resonance.

36. Arrange the following compounds as directed : (a) Both Assertion (A) and Reason (R) are true and
In decreasing order of basic strength in aqueous Reason (R) is the correct explanation of the
solution:
Assertion (A).
(1/3, 2020)(Cr (b) Both Assertion (A) and Reason (R) are true, but
(CH),N, (CHa),NH,CH,NH, Reason (R) is not the correct explanation of the
37. Arrange the following in decreasing order of basic Assertion(A).
character: (c) Assertion (A) is true, but Reason (R) is false.
CoH,NH2, (CH3)N, C,H,NH, (2019) (d) Assertion (A) is false, but Reason (R)
38. Arrange the following in increasing order of base is true. (2024)
strength in gas phase. 47. Hoffmann bromamide degradation reaction is given
(CzHs)N, CzH,NH2, (CzHs),NH (Delhi 2019)by
Amines 263

NO, 51. Give the structures of A and B in the following

sequence of reactions:
(a) NaNO, +HC,B
CoH,NO, Fe/HC,A 0-5°C
(2/3, 2020)
(c) CHa-C= N 52. Carry out the following conversion:
Bromomethane to ethanol. (1/5, Al 2019) Cr
(d) CH3CH CNH, (2023C) 53. Describe the following by giving the relevant
48. Read the passage given below and answer the chemical equation :
questions (i to iv): Carbylamine reaction (1/3, 2018c) R
Amines can be considered as derivatives of ammonia
and are usually formed from nitriles, nitro, halides, 54. Give a simple chemical test to distinguish between
amides, etc. They show hydrogen bonding which the following pair of compounds :
(CH),NH and (CH),N (1/5, Delhi 2015)
influences their physical properties. In aromatic amines,
electron releasing and withdrawing groups respectively
increase and decrease their basic character.
SA I (2 marks)
Hinsberg test is used for the identification and 55. (a) Write the IUPAC name for the following organic
distinction between primary, secondary and tertiary compounds:
amines. CH3-NCH,CH3
The following questions are multiple choice questions:
() Ethyl amine can be prepared by the action of
LiAlH, on
(a) CHzNO (b) CH,-CN (b) Complete the following:
(c) CH3-NC (d) CH3-CH,-CONH,
(i) Which of the following reagents is used for the
5 Hinsberg test of amines ?
CzH,NO, Brz/H0B
Sn/HCI
>A (2023)
56. How will you distinguish between the following
(a) CeHCOCI (b) CH¡COCI
(c) CoHs SO3H pairs of compounds:
(d) CoHs-SO,CI (i) Aniline and ethanamine
(ii) Out of the following, the strongest base in
(i) Aniline and N-methylaniline (2/3, 2020) (Cr
D2 aqueous solution is
0 (a) (CH3),NH (b) (CH3)N 57. Distinguish between the following:
(c) CHg-NH2 (d) CoHs-NH, (6) CH,CH,NH, and (CH,CH2),NH
(iv) The reaction of ammonia with a large excess of (i) Aniline and CHNH2 (2/5, 2020)
CH-Clwill give mainly 58. Give reasons
(a) CzHo (b) (CH),NH
(c) (CHa),N°CI (d) CH3-NH, ) Although NH, group is o/p directing in
OR electrophilic substitution reactions, yet aniline,
Among the following amines, which one is expected on nitration gives good yield of m-nitroaniline.
to have the lowest boiling point? (i) (CHa),NH is more basic than (CHa),N in an
(a) C,H5-NH, (b) (CH)N S3aqueous solution. (2/5, 2020)
(c) (C,H5),NH (d) CH-NH, (2021 C)
59. Account for the following:
49.CH,-NH, on heating with CHCI, and (a) Gabriel phthalimide synthesis is not preferred
for preparing aromatic primary amines.
alcoholic KOH gives foul smell of
(b) On reaction with benzene sulphonyl chloride,
(a) -CH,OH (b) -CH,NC primary amine yields product soluble in alkali
whereas secondary amine yields product
(c) -CH,CN (d) -CH,CI insoluble in alkali.sbd (2019) 0
(2020) 60. Write structures of compounds A and B in each of
VSA (1 mark)
the following reactions :
NH,
50. Write an isomer of CaH,N which gives foul smell
of isocyanide when treated with chloroform and (a) conc. H,SOAA Heat,453-473K B
ethanolic NaOH. (2020)
 WtG CBSE Champion
264
(i1) Aniline does not give Friedel-
Chemistry Class 12
ÇONH2 (ii) Although -NH2 group is o/p -Crafts reaction.
(b) Br/NaOH,A (CH,CO),O/pyridine, B
(2019 C)
electrophilic substitution reactions,
on nitration gives good yield of
diryetectinanig line
in

61. Write the

structures of the main
products of the
69. Write equations involved in
m-nitroaniline.,
(Term II, 2021-22) AD
the followingr
following reactions:
NH2
(i) Ethanamine reacts with acetyl chloride
(ii) Aniline reacts with bromine water at
reactions:
(CH,CO),0
Pyridine
temperature. room
(0) (iii) Aniline reacts with chloroform and
(CH),NH (2/5, 2018) An potassium hydroxide. (Term lI, 2021-22) ethanolic
(i1) -SO,CI 70. Account for the following:
chemical test to distinguish (i) pKh of aniline is more than that of
62. (a) Give a simple
between aniline and N,
N-dimethylaniline.
(i) Aniline does not undergo methylreaction.
Friedel-Crafts amine.
in the increasing order of (iii) Primary amines have higher
(b) Arrange the following boiling points than
their pk, values: tertiary amines. (Term II, 2021-22) Ap
2018)
CoHsNH. C,H,NH, CoH,NHCH, (2/5, 71. () Arrange the following compounds in the
63. Give reasons for the following: increasing order of their basic
(i) Aniline does not undergo
Friedel-Crafts reaction. strength in
aqueous solution : CHgNH2 (CHg)aN, (CHa),NH
an
(i) (CH),NH is more basic than (CH)N in (i0) What is Hinsberg's reagent ?
aqueous solution. (2/3, Al2016)
suitable (iii) What is the role of pyridine in the acylation
64. Illustrate the following reactions giving reaction of amines ?(Term II, 2021-22)
example in each case :
() Ammonolysis 72. A compound 'A' on reduction with iron scrap and
(ii) Acetylation of amines (2/5, Foreign 2015) hydrochloric acid gives compound'B' with molecular
formula ChH,N. Compound 'B on reaction with
SA II (3 marks) CHCI, and alcoholic KOH produces an obnoxious
smell of carbylamine due to the formation of
65. A compound 'X with molecular formula CaH,N 'C. ldentify 'A, B' and 'C and write the chemical
reacts with CeHSO,Cl to give a solid, insoluble in
alkali. ldentify 'X and give the IUPAC reactions involved. (Term lI, 2021-22) CBQ
name of the product. Write the 73. Write reasons for the following:
(2024) CBQ
reaction involved. Ethylamine is soluble in water whereas aniline
(i)
66. Answer any three of the following questions: is insoluble.
Give reasons for the following : (i) Amino group is o- and p-directing in aromatic
(a) Reduction with iron scrap and HCl is preferred electrophilic substitution reactions, but aniline
for the preparation of amines from nitro on nitration gives a substantial amount of
compounds. m-nitroaniline.
(b) Lower aliphatic amines are soluble in water.
(ii) Amines behave as nucleophiles.
(c) Pyridine is used in the acylation reaction of (Term lI, 2021-22)
amines.
(d) Although amino group is o- and p-directing in 74. An organic compound (A) with molecular formula
aromatic electrophilic substitution reactions, C3H,NO on heating with Br, and KOH forms a
aniline on nitration gives a substantial amount compound (B). Compound (B) on heating with
of m-nitroaniline. (2023C) CHCl, and alcoholic KOH produces a foul smelling
67. Illustrate the following reactions giving suitable compound (C) and on reacting with CoHsS0,0
example in each case: forms a compound (D) which is soluble in alkai.
() Gabriel phthalimide synthesis. Write the structures of (A), (B), (C) and (D).
(ii) Carbylamine reaction. (Term I, 2021-22)CBQ
(ii) Hoffmann bromamide degradation reaction.
75. Account for the following :
(Term I, 2021-22) (a) Aniline is a weaker base compared to ethanamine.
68. Give reasons: (b) Aniline does not undergo Friedel-Crafts reaction.
(0) Ammonolysis of alkyl halides is not a good (c) Only aliphatic primaryamines can be prepared (2020)
method to prepare pure primary amines. by Gabriel Phthalimide synthesis.
 Amines 265

76. (a) Write the chemical reaction of methyl amine (2) Aniline readily reacts with bromine water
with benzoyl chloride and write the IUPAC to give 2, 4, 6-tribromoaniline.
name of the product obtained. (3) Primary amines have higher
(b) Arrange the following in the increasing order of boiling points than tertiary (2024) Ap
their pk, values: amines.
CoH,NH, NH, C,H,NH,. (C,Hs),NH (3/5,2020) 9.9 Chemical Reactions
77. Give reasons:
(0) Aniline does not undergo Friedel-Crafts' (Diazonium salts)
reaction. MCQ
(ii) Aromatic primary amines cannot be prepared 84. The correct name of the given reaction is
by Gabriel's phthalimide synthesis. HBr
(ii) Aliphatic amines are stronger bases than Ar-N;X Cupowder’Ar- Br +N,
ammonia.
(2020) (U (a) Hoffmann bromamide degradation reaction
78. Describe a method for the identification of (b) Gabriel phthalimide synthesis
(c) Carbylamine reaction
CzH,NH, (C,Hs),NH and (C,Hs)3N. Also write the (d) Gatterman reaction. (2024)
chemical equations for the reactions involved.
(2020C) 85. Assertion (A): Benzene diazonium salt is stable and
can be easily stored.
79. (a) Give one chemical test to distinguish between diazonium chloride
Reason (R) : Benzene
the compounds of the following pairs:
decomposes easily.
(6) CH,NH, and (CH),NH (a) Both Assertion (A) and Reason (R) are true and
(ii) Aniline and ethanamine Reason (R) is the correct explanation of the
(b) Why aniline does not undergo Friedel-Crafts Assertion (A).
reaction? (b) Both Assertion (A) and Reason (R) are true, but
(AI 2019) (Cr
80. (a) ldentify Xand Yin the following: Reason (R) is not the correct explanation of the
NH, Assertion (A).
(c) Assertion (A) is true, but Reason (R) is false.
NaNO, + HCl y CucN (d) Assertion (A) is false, but Reason (R) is true.
0-5°C
(2023 C) Ap
(b) Amino group is o, p-directing for aromatic 86. In cold conditions, aniline is diazotized and then
electrophilic substitution reactions. Why does treated with aniline again to give a coloured product.
aniline on nitration give m-nitroaniline? The structure of the coloured product is
(2019C)
81. Give reasons: (a) (CHa)z-N- O-NH-O
(i) Acetylation of aniline.reduces its activation
effect.
(i) CH,NH, is more basic than CoH,NH.
t) HNO-N-N=N
(i) Although -NH, is o/p directing group, yet
aniline on nitration gives a significant amount
of m-nitroaniline. (Delhi 2017) CBQ (d) HO-ON=N-O) (2020C)
82. Write the structures of main products when aniline
reacts with the following reagents: VSA (1 mark)
() Br, water (i) HCI 87. Write the structures of A and B in the following
(ii) (CH,CO),0/pyridine (3/5, Delhi 2015) reactions :
LA (5 marks) CAH,N;CI CuCN AHz01H B (1/5. 2020)(Ev
83. () 1. What is Hinsberg's reagent ? 88. Carry out the following conversion:
2 Arrange the following compounds in the p-nitrotoluene to 2-bromobenzoic acid.
increasing order of their basic strength in (1/5, Al 2019)
gaseous phase: 89. Write the structure of the main product of the
following reaction:
CHsNH2. (CzHs)3N,(C,Hs),NH NGCI CH,CH;OH ,
(ii) Give reasons for the folowing:
(1) Methyl amine is more basic than aniline.
(1/5, 2018) Ap)
266 WtG CBSE
EChampion
90. Complete the following reaction equation:
CGHsN,Cl + H,PO, + H,0’ (Delhi 2015C)
CH3
Br
Chemistry Clas 12
SA I (2 marks)
(b) H,PO, +H,o,
91. (a) Carry out the following conversions: NGCI
() Nitrobenzene to aniline
(ii) Aniline to phenol
OR (c) CH-NH,+
(b) (0) Write a chemical test to distinguish
CHCl,
Ethanolic KOH
between dimethyl amine and ethanamine.
(ii) Write the product formed
when benzene diazonium
99. How do youconvert the following:
(a)
(2019) CBQ
chloride is treated with KI. (2024) (R
(b)
N-phenylethanamide
Benzenediazonium
to p-bromoaniline
tochloride
92. () Complete the reaction with the main product
formed:
N;CI
(c) Benzoic acid to aniline
100.Writethe structures of
nitrobenzene(2019)
compounds A, B
and Cin the
following reactions:
CH,CH;OH
(a) CH3-CoOH NH/A, A Brz/KOHoa), R
(ii) Convert bromoethane to propanamine. (2023) CHCI,+ alc. KOH,c
93. (a) Write the reaction involved in the following :
Diazotisation (b) CGH5N;BF4 NaNO,/Cu’A Fe/HC B
(b) Give reason:
Aromatic diazonium salts are more stable than
aliphatic diazonium salts. (2/5, 2018) (Ap CH,COCVpyridinec
101.Write the structures of A, Band C in the following:
(AI 2017)
94. How do you convert the following:
() CoH,CONH, to CoHsNH, Brp/aq. KOH
(ii) Aniline to phenol (2/3, Al 2015) (Ev (i) CoHs CONH ’A

SA II (3 marks) CKB NaNO, + HCI

0-5°C

95. Write the structures of A, B and C in the following KCN

’A
LiAIH4
reactions: (ii) CHa-Cl ’B
KCN OH C CHCI, +alc. KOH|
(a) CH3-CH,-Br Partial hydrolysis
NaOH +Br2 (Delhi 2016) CBQ

NO2 C 102.Write the structures of A, B and C in the following

reactions:
Fe + HCI
(b)
NaNO, + HCI
A 273 -278KB C,H;OHc (i) CoHsNO,
Sn/HCI
NaNO, +HCc
A
KCN
(2024) CBQ (i) CH,cl ’A LIAlHA B HNO, 273 K
96. (a) Illustrate Sandmeyer's reaction with an
equation. (3/5,Foreign 2015) Ev
(b) Explain why (CH3),NH is more basic than LA (5 marks)
(CHa),N in aqueous solution. (2023) 103.An amide 'A' with molecular formula C,H,On
97. Write the structures of main products when benzene undergoes Hoffmann bromamide degradation
diazonium chloride reacts with the following reagents : reaction to give amine 'B. 'B on treatment with
(i) CuCN (ii) CH,CH,OH
(ii) KI (Delhi 2019) (An nitrous acid at 273-278 Kform'C and on treatment
with chloroform and ethanolic potassium hydroxlae
98. Complete the following reactions : forms 'D. 'C on treatment. with ethanol gives t.
CN
H,/Ni, ldentify 'A, 'B, C;, 'D' and 'E. Write
(2024) CBQ
the sequence of chemical equations.
Amines 267

Case Based Questions Br,/alc. KOH ACH,COCI B

() CH,CH,CONH, Pyridine
104. Amines constitute an important class of organic OR
compounds derived by replacing one or more
hydrogen atoms of ammonia molecule by alkyl/ (b) How will you convert the following
aryl groups. Amines are usually formed from nitro (0) Benzoic acid to aniline
compounds, halides, amides, etc. They exhibit (1) Aniline to p-bromoaniline (Term-lI, 2021-22)
hydrogen bonding which influences their physical 105.An aromatic compound 'A' of molecular formula
properties. Alkyl amines are found to be stronger
C,H,ON undergoes a series of reactions as shown
bases than ammonia. In aromatic amines, electron
releasing and withdrawing groups, respectively below. Write the structures of A, B, C, Dand E in the
increase and decrease their basic character. following reactions :
Reactions of amines are governed by availability of Br, + KOH
the unshared pair of electrons on nitrogen. Influence (C,H,ON) A
of the number of hydrogen atoms at nitrogen atom cHCH,OH B NaNO, + HCI
CzH,NH,
on the type of reactions and nature of products 273 K
CHCl3
is responsible for identification and distinction
between primary, secondary and tertiary amines. JNaOH
Reactivity of aromatic amines can be controlled by E D
acylation process. (Delhi 2015)CBQ
(0) Why does aniline not give Friedel-Crafts
reaction? 106.(i) Write the structures of main products when
(i) Arrange the following in the increasing order of benzenediazonium chloride (C,H,N,*c)
their pK;h values: reacts withthe following reagents:
CoHsNH2 NH3, CgH,NHz, (CHa)aN (a) HBF4/A (b) Cu/HBr
(ii) How can you distinguish between CHCH,NH (ii) Write the structures of A, B and C in the
and (CH,CHNH by Hinsberg test ?
following reactions:
(iv) (a) Write the structures of A and B in the
Sn + NaNO,+ HCI, B H,0
s o e following reactions:
NO2
(a) CoH,NO,+HOSA 273 K A

Sn +HCIA Brz water B

(b) CH,CICA
LIAIHAB HNO2C
(Foreign 2015) (U)

CBSE Sample Questions

9.5 Physical Properties 9.6 Chemical Reactions (Amines)
MCQ MCO
1. In which of the following solvents, the CaHgNHX is 3 Which of the following statements is not correct for
soluble? amines?
(a) Most alkyl amines are more basic than ammonia
(a) Ether (b) Acetone
solution.
(c) Water (d) Bromine water
(b) pK; value of ethylamine is lower than benzylamine.
(2023-24) (An (c) CHNH, on reaction with nitrous acid releases
2. Arrange the following in the increasing order of NO, gas.
(d) Hinsberg's reagent reacts with secondary
their boiling points: amines to form sulphonamides. (2022-23)
A: Butanamine, B: N,N-Dimethylethanamine, 4 Given below are two statements labelled as
C:N-Ethylethanamine Assertion (A) and Reason (R).
(a) C<B <A (b) A< B<C
(c) A<C< B (d) B< C<A Assertion (A): Tertiary amines are more basic than
corresponding secondary and primary amines in
(2022-23) Ap gaseous state.
268 WtG CBSE Champion Chemistry Class 1n
Reason (R): Tertiary amines have three alkyl groups (ii) Reduction of nitrobenzene using Fe 2na
which cause + effect. HCl is preferred over Sn and HCI.
Select the most appropriate answer from the options (b) Arrange the following in
given below: (1) decreasing order of pKh values:
(a) Both Aand R are true andR is the correct CaH,NH2, CoHsNHCH3 CoH;CH,NH,
explanation of A. CH,NH2, NH3
(b) Both A andR are true but R is not the correct (i) increasing order of solubility in water :
explanation of A.
(c) A is true but R is false. C,H,CI,C,H,NH, C,H,OH
(d) A is false but R is true. (2022-23) (ii) decreasing boiling point:
SA II (3 marks)
CH,COOH, C,H,OH,CH,NH2, CH,0CH,
5. Account for the following: (2023-24) An
(a) ofAniline cannot be prepared by the anmmonolysis 9.9 Chemical Reactions
chlorobenzene under normal conditions.
(b) N-ethylethanamine boils at 329.3 K and (Diazonium salts)
butanamine boils at 350.8 K, although both are SA II (3 marks)
isomericin nature.
(c) Acylation of aniline is carried out in the 9. Give reasons for any 3of the following observations:
presence of pyridine. (a) Aniline is acetylated before nitration reaction.
OR (b) pkh of aniline is lower than the m-nitroaniline
(c) Primary amine on treatment with
Convert the following :
benzenesulphonyl chloride forms a product
(a) Phenol to N-phenylethanamide
(b) Chloroethane to methanamine which is soluble in NaOH however secondary
amine gives product which is insoluble in NaOH
(c) Propanenitrile to ethanol (Term lI, 2021-22)
H(d) Aniline does not react with methyl chloride
6 What happens when reactions :
(a) N-ethylethanamine reacts with benzenesulphonyl
in the presence of anhydrous AlCl, catalyst.
chloride. (2022-23) Ap
(b) Benzyl chloride is treated with ammonia 10. (a) Write the IUPAC name for the following organic
followed by the reaction with chloromethane. compound:
(c) Aniline reacts with chloroform in the presence
of alcoholic potassium hydroxide. CH3-N-CH,CH3
(Term lI, 202 1-22) (An
LA (5 marks)
(b) Complete the following :
7. The compound CsHs,NHCOCH3 is obtained when
compound A reacts with acetic anhydride in CoH-NO,
Sn/HCI A
Br, /H;0,B NaNO, /HCI
273-278 K HBFA D
presence of pyridine. This compound A does not alaons (Term lI, 2021-22)
undergo Friedel-Crafts reaction.
(a) Write the reaction showing the formation of LA (5 marks)
CoH,NHCOCH3 from compound A. 11. Parul was given two test tubes. One of the test tubes
(b) The pH of the aq. solution of A is less than 7. Is contained ethyl amine and the other contained
this statement true? Give reason. aniline. To distinguish between the two compounds,
(c) State what type of functional group can be she adds a reagent X to both the test tubes. She
introduced into compound A, that will : observes that in only one of the test tubes a yellow
(0) increase the pH of the aqueous solution dye is formed.
(ii) decrease the pH of the aqueous solution (a) ldentify the reagent X.
(b) Describe how this reagent is prepared and
(d) What do you observe when compound A reacts give a reason why it is not readily available in a
with bromine water at room temperature?
laboratory.
(2023-24) APQ Ap (c) Which of the two compounds forms the yellow
8. (a) Account for the following dye?
() N-ethyl benzenesulphonyl amide is soluble (d) Draw the structure of the yellowdye formed.
in alkali: (2023-24)APQ
Amines 269

12. An organic compound with molecular formula H,PO,it gets converted to Dwith formula C,H
C,H,NO, exists in three isomeric forms, the isomer which on further reaction with CrO,Ci, followed
'A has the highest melting point of the three. 'A' by hydrolysis forms 'E C,H,0. Write the structure
on reduction gives compound 'B' with molecular of compounds Ato E. Write the chemical equations
formula C,H,N. 'B' on treatment with NaNO,/HCI involved.
at 0-5 °C to form compound'C On treating C with (2023-24)

Detailed sOLUTIONS
Previous Years' CBSE Board Questions NO,
LIAIH
1. (c):(CHa);N and (C,Hs),N are tertiary amines.
Nitrobenzene Azo benzene
(C,Hs),NH is a secondary amine.
c,H,NH, is a primary amine. 12. (c):CH,CONH, +Br, + 4NaOH
CH;NH, + Na,CO, + 2NaBr + 2H,0
2. (C,Hs),CHNH, is a primary amine. 13. The ammonolysis of alkyl halides with ammonia is a
3
H,CH2CN-CHs
H,CH,c
IUPAC name : N-Ethyl-N-methylethanamine
Answer Tips
nucleophilic substitution reaction in which ammonia acts
as a nucleophile by donating the electron pair on nitrogen
atom to form primary amine as the initial product. Now,
the primary amine can act as a nucleophile and combine
with alkyl halide (ifavailable) to give secondaryamineand
3 The largest al kyl group forms a part of the aminoalkane the reaction continues in the same way to form tertiary
while the smaller alkyl groups are considered as
substituents. amine and finally quaternary ammonium salt. Thus, a
mixture of products is formed and it is not possible to
CI separate individual amines from the mixture.

4.
NO, NH2
R-X -HY>RNH, R
-HX RNH -HX
RgN
NO, 14. CH,COOH CH,cONH,- NaOBr ’CH,NH2
2,4-Dinitrochlorobenzene A (B)
5. N-Methylpropan-2-amine (2° amine) Key Points
In Hoffmann degradation, there is one carbon atom
6
HJN-CH,
H,C CHs
N,N-Dimethylethanamine
less in product.
COOH ÇOONH CONH,
7. 2,4, 6-Tribromoaniline
8. (a)
15. NH3, -H,0
Benzoic acid Ammonium Benzamide
9. (b):When amide is treated with NaOH or KOH and benzoate
Br, amine with one less carbon atom is obtained. The
reaction is called as Hoffmann bromamide reaction.
NH2
Br, + KOH
CH,CONH, +4NaOH+Br,CH,NH, +Na,COs
+ 2NaBr + 2H,0 Aniline
10. (c):Alkyl halides when treated with ethanolic Alternative Method (>
solution of NHa give a mixture of primary, secondary and
tertiary amines. C-NH,
COOH COCI NH2
R-X NHa R-NH2
pri-amine
R-XR,NH R R,N
sec-amine tert-amine
SOCh NH3 Brz/KOH
Thus it is not a suitable method.
11. (a):LiAIH, reduces aliphatic nitro compounds to 16. R-CONH, + Br, +4NaOH’R-NH, + NaCO,
amines, but converts aromatic nitro compounds such as Acid amide 1° amine

nitrobenzene to produce azo compounds. + 2NaBr+ 2H,0