Amines

Single Correct Type Questions OH OH

(a) A = ,B=
1. The conversion of propan-1-ol to n-butylamine involves CHO CO2H
the sequential addition of reagents. The correct sequential
order of reagents is: [24 Jun, 2022 (Shift-II)] OH
(b) A = ,B= COOH
(a) (i) SOCl2 (ii) KCN (iii) H2/Ni,Na(Hg)/C2H5OH NH2
(b) (i) HC1 (ii) H2/Ni, Na(Hg)/C2H5OH
OH OH
(c) (i) SOC12 (ii) KCN (iii) CH3NH2
(c) A = ,B=
(d) (i) HC1 (ii) CH3NH2 NH2 CHO
2. Ammonolysis of Alkyl halides followed by the treatment
with NaOH solution can be used to prepare primary, OH OH
secondary and tertiary amines. The purpose of NaOH in (d) A = ,B=
the reaction is: [16 March, 2021 (Shift-II)] OH CHO
(a) to activate NH3 used in the reaction 5. The most appropriate reagent for conversion of C2H5CN
(b) to remove acidic impurities into CH3CH2CH2NH2 is: [5 Sep, 2020 (Shift-I)]
(c) to increase the reactivity of alkyl halide (a) NaBH4
(d) to remove basic impurities
(b) CaH2
3. Which of the following is not a correct statement for
primary aliphatic amines? [27 Aug, 2021 (Shift-I)] (c) Na(CN)BH3
(d) LiAlH4
(a) The intermolecular association in primary amines is
less than the intermolecular association in secondary 6. The incorrect statement regarding the reaction given below
amines. is [12 Apr, 2023 (Shift-I)]
(b) Primary amines can be prepared by the Gabriel
Me N Me
phthalimide synthesis.
(c) Primary amines on treating with nitrous acid
solution form corresponding alcohols except methyl + NaNO2 + HX 'B'
amine.
'A'
(d) Primary amines are less basic than the secondary
amines. (a) The electrophile involved in the reaction is NO+
4. The major products A and B in the following set of (b) ‘B’ is N-nitroso ammonium compound
reactions are: [31 Aug, 2021 (Shift-I)] (c) The reaction occurs at low temperature
LiAlH 4
OH H3O + (d) The product ‘B’ formed in the above reaction is
A ←   → B
H3O + H 2SO 4 p-nitroso compound at low temperature.
CN

1 JEE PYQs Chemistry

 7. Isomeric amines with molecular formula C8H11N give the 9. The correct order of melting point of dichlorobenzenes is
following tests  [31 Jan, 2023 (Shift-I)]
Isomer (P) ⇒ Can be prepared by Gabriel phthalimide
synthesis (a)
Isomer (Q) ⇒ Reacts with Hinsberg’s reagent to give solid
insoluble in NaOH
Isomer (R) ⇒ Reacts with HONO followed by β-naphthol
in NaOH to give red dye.
Isomers (P), (Q) and (R) respectively are (b)

 [10 Apr, 2023 (Shift-I)]

P     Q      R
NH2 NH2
(a) N H
(c)
CH3
CH3
NH2 N CH3 NH2
(b) CH3
(d)
H
NH2 N
NH2 HCl,D Residue Q
(c) 10. Compound P Filter
Filtrate
(M.F. C14H13ON)
NaOH
M.F = Molecular Formula
NH2 Oily Liquid R.
(d) NHCH3 N H Compound P is neutral. Q gives effervescence with
H3 NaHCO3 while R reacts with Hinsbergs reagent to give
CH3 solid soluble in NaOH. Compound P is [
 6 Apr, 2023 (Shift-I)]
8. Benzyl isocyanide can be obtained by:

(A)
(a)

(B)

(b)
(C)

(D)
(c)

Choose the correct answer from the options given below:

 [30 Jan, 2023 (Shift-I)]
(a) A and D (b) Only B
(d)
(c) A and B (d) B and C

2 JEE PYQs Chemistry

 11. Given below are two statements: 16. The major product of the following reaction is
Statement-I: Pure Aniline and other arylamines are CH 3 O (i) alcoholic NH3
(ii) NaOH, Br 2
usually colourless. CH 3 CH CH 2 CH 2 C Cl Major Product
(iii) NaNO2 , HCl
Statement-II: Arylamines get coloured on storage due to (iv) H 2 O
atmospheric reduction.
 [27 Aug, 2021 (Shift-I)]
In the light of the above statements, choose the most Br
appropriate answer from the options given below:
 [24 Jan, 2023 (Shift-II)] (a) CH 3 CH CH CH 2OH
CH 3
(a) Both Statement-I and Statement-II are incorrect
(b) Both Statement-I and Statement-II are correct (b) CH3 CH CH2 CH2 Cl
CH3
(c) Statement-I is correct but Statement-II is incorrect
(d) Statement-I is incorrect but Statement-II is correct (c) CH 3 CH CH2 CH2OH
HNO2 CH 3
12. o-Phenylenediamine 'X'
Major Product
'X' is [11 Apr, 2023 (Shift-I)] (d) CH3 CH CH 2 CH2 CH2 OH
N CH3
(a) N (b) NH 17. An amine on reaction with benzenesulphonyl chloride
N produces a compound insoluble in alkaline solution. This
amine can be prepared by ammonolysis of ethyl chloride.
H
The correct structure of amine is:[26 Feb, 2021 (Shift-I)]
N N N2 (a) CH3CH2CH2NH–CH3
(c) (d) NH—CH2CH2CH3
N2 NH2 (b)
13. Which statement is NOT correct for p- toluenesulphonyl
chloride?  [26 Jun, 2022 (Shift-II)] (c) CH3CH2NH2
(a) It is known as Hinsberg's reagent
(b) It is used to distinguish primary and secondary amines. (d) CH3CH2CH2NHCH2–CH3
(c) On treatment with secondary amine, it leads to a
product, that is soluble in alkali. 18. In the reaction of hypobromite with amide, the carbonyl
(d) It doesn’t react with tertiary amines. carbon is lost as: [18 March, 2021 (Shift-II)]
2– –
14. The reaction R—C—NH2 with bromine and KOH gives (a) CO3 (b) HCO3
(c) CO (d) CO2
O 19. The increasing order of pKb values of the following
RNH2 as the end product. Which one of the following is
compounds is: [6 Sep, 2020 (Shift-I)]
the intermediate product formed in this reaction?
 [25 Jun, 2022 (Shift-I)] N(CH3)2 N(CH3)2 NHCH3 NHCH3
(a) R—C—N—Br (b) R–NH–Br

O H
(c) R–N=C=O (d) R—C—NBr2 CN OH
OCH3
O I II III IV
15. Reagent, 1-naphthylamine and sulphanilic acid in acetic (a) II < IV < III < I
acid is used for the detection of: [18 March, 2021
(Shift-I)] (b) I < II < IV < III
(a) NO (b) N2O (c) II < I < III < IV
(c) NO2 –
(d) NO3– (d) I < II < III < IV

3 JEE PYQs Chemistry

 20. Consider the following reactions, 23. The increasing order of reactivity of the following
(i) NaNO2/HCl, 0-5°C compounds towards reaction with alkyl halide directly
(ii) -naphthol/NaOH
Colored Solid is: [12 Jan, 2019 (Shift-I)]
[P] O O
Br2/H2O
C7H6NBr3
The compound [P] is: [9 Jan, 2020 (Shift-II)] A.
NH2
B. NH
NH2 NH2

CH3 O
CN
(a) (b) NH2
C. NH2 D.

CH3
NH2 NHCH3
(a) (B) < (A) < (C) < (D)
(b) (A) < (B) < (C) < (D)
(c) (d)
(c) (B) < (A) < (D) < (C)
CH3 CH3
(d) (A) < (C) < (D) < (B)
21. The major product of the following reaction is;
 [10 Apr 2019 (Shift-I)] 24. Identify the product formed (A and E)
OH
|  [25 Jan, 2023 (Shift-I)]
ethylformate(1equiv.)
CH3CHCH 2 CH 2 NH 2 →
triethylamine
OH
|
(a) CH3CHCH 2 CH 2 NHCHO
(b) CH3CH=CH–CH2NH2
O

O H
(a)
(c) CH3CHCH2CH2NH2
OH
|
(d) CH3CH − CH = CH 2
22. The major product of the following reaction is: 
 [9 Jan, 2019 (Shift-II)]
O (b)
C
NH2 (i) Br2/hv
(ii) KOH (dil)
CH2CH3
O
(c)
(a) NH (b) NH

(c) (d) NH
NH (d)
CH3
CH3

4 JEE PYQs Chemistry

25. Consider the following sequence of reactions: 28. The correct stability order of the following diazonium salt
is
 [26 July, 2022 (Shift-I)]
+N Cl – + – + – + –
2 N2 Cl N2 Cl N2 Cl

The product ‘B’ is [15 Apr, 2023 (Shift-I)]

(A) (B) (C) (D)
(a)

OCH 3 NO 2 CN
(b)
(a) (A) > (B) > (C) > (D)
(b) (A) > (C) > (D) > (B)
(c)
(c) (C) > (A) > (D) > (B)
(d) (C) > (D) > (B) > (A)
(d) 29. Benzene diazonium chloride on reaction with aniline in
the presence of dilute hydrochloric acid gives:
 [12 Apr, 2019 (Shift-II)]
26. The product (P) formed from the following multistep
reaction is: [8 Apr, 2023 (Shift-II)] (a) N=N
(i) Br2
NO2
(ii) H2/Pd
(P) H2N
(iii) NaNO2, HCl, 0°C
Product (b)
H 3C
(iv) H3PO2 NH2

OH Br OH (c) N=N NH2

(a) (b)
Br
H 3C H 3C (d) N=N—NH

Br Integer Type Questions

(c) (d) 30. How many of the transformation given below would result
Br in aromatic amines? [31 Jan, 2023 (Shift-I)]
H 3C
H 3C O
27. Choose the correct colour of the product for the following NH2+ Br2 + NaOH
(a)
reaction. [24 Jan, 2023 (Shift-II)]
Cl
O

(b) NK

O
NO2
(c) H2
(a) Yellow Pd/C
(b) White
NH COCH3
(c) Red
(d) Blue (d) dil H2SO4


5 JEE PYQs Chemistry

 ANSWER KEY
1. (a) 2. (b) 3. (a) 4. (b) 5. (d) 6. (b) 7. (a) 8. (c) 9. (d) 10. (b)
11. (c) 12. (a) 13. (c) 14. (c) 15. (c) 16. (c) 17. (d) 18. (a) 19. (b) 20. (c)
21. (a) 22. (c) 23. (a) 24. (b) 25. (b) 26. (d) 27. (c) 28. (b) 29. (c) 30. [3]

EXPLANATIONS
(i) SOCl2 Me Me Me Me
1. (a) CH3–CH2–CH2–OH CH3–CH2–CH2–Cl N N
OCH3
propan-1-ol (ii) KCN
H2/Ni,
CH3CH2CH2CH2–NH2 CH3–CH2–CH2–CN
Na(Hg)/
n-butylamine C2H5OH
NO
2. (b) HCl is formed as by product in ammonolysis after NO
substitution reaction. Thus, treatment of NaOH is P – Nitroso product
carried out to remove acidic impurities. 7. (a) 
(P) Gabriel phthalimide synthesis is used for the
preparation of aliphatic primary amines and this
3. (a)
mthod cannot be used for the preparation of aromatic
primary amines.
(Q) 2°-amines gives solid insoluble in NaOH with
OH OH Hinsberg's reagent.
(1) LiAlH
4. (b) 
+
4→ (R) Aromatic primary amine reacts with HONO at
3 (2) H O CH2NH2
C N low temperature (273 – 298 K) to form diazonium
(A)
salts, which further form red dye with β-Naphthol.
→ Reduction of –CN group, gives –CH2 – NH2
8. (c)
OH
OH
H O + /H SO
3 2 4→

C OH
C N
O
D H⊕/–H2O

O
C OH
  
(B)
4→ LiAIH
5. (d) C2H5CN  C2H5CH2NH2

6. (b) Reaction of tertiary amine with nitrous acid give kOH

p-nitroso product. Only Primary amine can give carbyl amine reaction
NaNO2 + HX → HNO2 + NaX
H+
H O N O NO+ (Nitrosonium ion)
–H2O

6 JEE PYQs Chemistry

 9. (d) Melting point is more for that compounds which are 13. (c) Option (c) is correct.
more symmetrical and has better crystal fitting. Product formed from secondary amine is insoluble
in alkali.

14. (c)
15. (c) For detection of NO2–, the following test is used.
NO2– + CH3COOH → HNO2 + CH3COO–

m.p/K 256 249 323

10. (b)
O NH+3
COOH
NH
+
H3C H3C
NH+3
COOH

H3C
Q Filtrate

NH2
CO2 with NaHCO3

O (Red azodye)
O
NH-S (Red
16. (c) The major product in the reaction azodye)as:
is formed
O
NaOH (i) alcoholic NH3
Soluble CH 3 CH CH 2 CH 2 C Cl
O
11. (c) Statement-I is (True) CH 3
CH 3 CH CH 2 CH 2 C NH 2
Pure aniline is colourless liquid    CH 3
O
Statement-II is (False)
(ii) NaOH+Br2
Aniline undergoes oxidation and become dark brown CH 3 CH CH 2 CH 2 C NH 2
Hoffmann's Bromamide
colour. CH 3 Degradation
12. (a) Reaction of amine with HONO give nitroso product. CH 3
Orthophenyl amine.
CH 3 CH CH 2 CH 2 NH2
NH2 NH2 CH 3
HNO2 (iii) NaNO2 , HCl
CH 3 CH CH 2 CH 2 NH2
NH2 NH N O CH 3 CH CH 2 CH 2 N2 Cl
CH 3
NH2 NH2 Diazonium salt
–H2O
(unstable)
H + (iv) H2 O
+ CH 3 CH CH 2 CH 2 N2 Cl
N N N N OH
CH 3 CH3 CH CH2 CH2 OH
NH
H+ CH3
N
 (Major Product)
 N Hence, (c) is the correct answer.

7 JEE PYQs Chemistry

17. (d) Since, given amine on reaction with PhSO 2Cl 23. (a) Lone pair over nitrogen will act as the reacting centre.
produces a compound insoluble in Alkaline solution, So, more nucleophilic nitrogen will be more reactive
it is a 2º Amine.
Because it is prepared by ammonolysis of C2H5Cl it towards alkyl halide. So, order will be D > C > A > B
must contain an ethyl group 24. (b)
Thus CH3—CH2—CH2—NH—C2H5 is a 2º Amine
as well as it contain ethyl group.

18. (a)

19. (b) pKb a Acidic strength

Electron withdrawing group → increases acidic
strength
Electron releasing group → decreases acidic strength
20. (c)
Sn/HCl → reducing agent
NaNO2/HCl → diazotisation
H3PO3 → convert diazonium salt to Benzene
KMnO4 → convert Methyl to acid
25. (b)

(diazotisation)

OH
ethyl formate (lequiv.)
21. (a) CH3CH—CH2—CH2—NH2 →
triethylamine
OH O
P-dimethylamineazo benzene
CH3CH—CH2—CH2—NH2—C—H
as NH2 is a better nucleophile than OH. 26. (d) The reaction mechanism for the given multi step
22. (c) reaction is shown as,
NO2 NO2 NH2

H2/Pd
+ Br2
Br Br
CH3 CH3 + –
CH3
N2Cl
NaNO2/
HCl
KOH(dil.) H3PO2
H3PO3 + N2 + HCl +
Br Br
CH3 CH3
Step I- Bromination
Step II- Reduction of NO2 to NH2 in presence of H2/Pd.
Step III- Diazotization.
Step IV- Formation of Haloarene.

8 JEE PYQs Chemistry

 27. (c) 30. [3] The following are the products of the reactions given:
O NH2
NH2 N=N–O–C–CH3 NH2
(a) , Hoffmann bromamide degradation
+ + CH3COOH
reaction.
SO3H N (b) It will result in no reaction because in Gabriel
N Cl
phthalimide synthesis, is poor substrate
for SN2
SO3H (Red) NH2
(c)
28. (b) In case of diazoniam salts, electron donating group
increases the stability of diazonium salt, on the other
hand, electron withdrawing group decrease it. NH2
–OCH3(+M), –NO2 & –CN(–M) (d) + CH3COOH

29. (c) Hence, Aromatic amines will produced in the reactions

1, 3, and 4.

9 JEE PYQs Chemistry