Chapter 25

Amines

Only One Option Correct Type Questions

1. In the following reaction,
O
conc. HNO3
N X
H conc. H2SO4

the structure of the major product ‘X’ is [IIT-JEE-2007 (Paper-1)]

O
(A) NO2 (B) O2N
N O
H N
H
O O
(C) N (D) O2N N
H H
NO2
2. In the reaction,
O
(1) NaOH/Br2
H3C C O
T,
NH2 (2) C
Cl
the structure of the product T is [IIT-JEE-2010 (Paper-2)]
O
(A) H3C C O (B) NH
O C C CH3
O

O
(C) H3C NH (D) H3C C O
C NH C
O

3. The major product of the following reaction is [IIT-JEE-2011 (Paper-1)]

O
C
(i) KOH
NH
C (ii) Br CH2 Cl
O
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O O
C C
(A) N–CH2 Br (B) N CH2Cl
C C
O O
O O
C C
(C) N (D) N

O–CH2– Br O CH2Cl

4. Amongst the compounds given, the one that would form a brilliant colored dye on treatment with NaNO2 in
dil. HCl followed by addition to an alkaline solution of -naphthol is [IIT-JEE-2011 (Paper-2)]
N(CH3)2 NHCH3
(A) (B)

NH2 CH2NH2
(C) (D)
H3C

5. For the identification of -naphthol using dye test, it is necessary to use [JEE (Adv)-2014 (Paper-2)]
(A) Dichloromethane solution of -naphthol (B) Acidic solution of -naphthol
(C) Neutral solution of -naphthol (D) Alkaline solution of -naphthol
6. The order of basicity among the following compounds is [JEE (Adv)-2017 (Paper-2)]

NH
I. II. N NH
H 3C NH2

NH2
III. HN N IV.
H2N NH

(A) IV > I > II > III (B) IV > II > III > I

(C) I > IV > III > II (D) II > I > IV > III

7. The major product of the following reaction is [JEE (Adv)-2017 (Paper-2)]

OH

i) NaNO2, HCl, 0°C

ii) aq.NaOH

NH2
– +
O Na OH

(A) (B)

N2Cl N=N

OH N=N OH

(C) (D)

Cl
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One or More Option(s) Correct Type Questions

8. In the reaction shown below, the major product(s) formed is/are [JEE (Adv)-2014 (Paper-1)]

NH2

acetic anhydride
Product(s)
NH2 CH2Cl2

O
H
N CH3 NH2
O
(A) + CH3COOH (B) H + CH3COOH
NH2 N CH3
O O O
H
N CH3 NH3CH3COO
O
(C) H + H2O (D) H
N CH3 N CH3
O O O O
9. The major product of the reaction is [JEE (Adv)-2015 (Paper-1)]
H3C CO2H NaNO2, aqueous HCl
0ºC
CH3 NH2
H3C NH2 H3C CO2H
(A) (B)
CH3 OH CH3 OH

H3C CO2H H3C NH2

(C) (D)
CH3 OH CH3 OH

10. In the following reactions, the major product W is [JEE (Adv)-2015 (Paper-2)]

OH
NH2 , NaOH
NaNO2, HCl
V W
0°C

OH
(A) (B)
N=N OH N=N

HO
OH
(C) N=N (D)
N=N

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11. In the following reactions, the product S is [JEE (Adv)-2015 (Paper-2)]

H3C
i. O3 NH3
R S
ii. Zn, H2O

H3C H3C N
N
(A) (B)

N
N
(C) (D)
H3C H3C

12. The product(s) of the following reaction sequence is(are) [JEE (Adv)-2016 (Paper-1)]
NH2
(i) Acetic anhydride/pyridine
(ii) KBrO3/HBr
(iii) H3O+, heat
(iv) NaNO2/HCl, 273–278 K
(v) Cu/HBr

Br Br

(A) (B)
Br
Br

Br Br
Br Br Br Br
(C) (D)

Br
13. Aniline reacts with mixed acid (conc. HNO3 and conc. H2SO4) at 288 K to give P (51 %), Q (47%) and R
(2%). The major product(s) of the following reaction sequence is (are) [JEE (Adv)-2018 (Paper-2)]
1) Ac2O, pyridine 1) Sn/HCl
2) Br2, CH3CO2H 2) Br2/H2O (excess)
R +
S Major
3) H3O 3) NaNO2, product(s)
4) NaNO2, HCl/273-278K
HCl/273-278K 4) H3PO2
5) EtOH,

Br Br
Br Br
(A) (B)
Br
Br
Br Br

Br Br

(C) (D)
Br Br
Br Br
Br

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14. Consider the following four compounds I, II, III, and IV.

Choose the correct statement(s). [JEE (Adv)-2020 (Paper-2)]

(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV.
(D) Steric effect makes compound IV more basic than III.
15. Correct option(s) for the following sequence of reactions is(are) [JEE (Adv)-2021 (Paper-2)]
V
Br2 1. Q CHCl3
PhCH 3 light
P 2.H2,Pd/C
R KOH
S
foul smelling

1. NH3 W
T U
2. heat
(A) Q = KNO2, W = LiAlH4 (B) R = benzenamine, V = KCN
(C) Q = AgNO2, R = phenylmethanamine (D) W = LiAlH4, V = AgCN
16. Considering the reaction sequence given below, the correct statement(s) is(are)
[JEE (Adv)-2022 (Paper-1)]

(A) P can be reduced to a primary alcohol using NaBH4.

(B) Treating P with conc. NH4OH solution followed by acidification gives Q.
(C) Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
(D) P is more acidic than CH3CH2COOH.
17. Considering the following reaction sequence, [JEE (Adv)-2022 (Paper-1)]

the correct option(s) is(are)

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(A) P = H2/Pd, ethanol R = NaNO2/HCl U = 1. H3PO2

2. KMnO4 – KOH, heat

(B) P = Sn/HCl R = HNO2

(C) U = 1. CH3CH2OH

2. KMnO4 – KOH, heat

(D) R = H2/Pd, ethanol

Matrix-Match / Matrix Based Type Questions

18. Match the four starting materials (P, Q, R, S) given in List I with the corresponding reaction schemes
(I, II, III, IV) provided in List II and select the correct answer using the code given below the lists.
[JEE (Adv)-2014 (Paper-2)]
List-I List-II
P. H H 1. Scheme I
(i) KMnO4, HO, heat (ii) H, H2O
(iii) SOCl2 (iv) NH3
? C7H6N2O3
OH

Q. 2. Scheme II
OH (i) Sn/HCl (ii) CH3COCl (iii) conc. H2 SO4
(iv) HNO3 (v) dil. H2SO4 , heat (vi) HO
NO2 ? C6H6N2O2

R. 3. Scheme III
(i) red hot iron, 873 K (ii) fuming HNO3, H2SO4, heat
(iii) H2S.NH3 (iv) NaNO2, H2SO4 (v) hydrolysis
NO2 ? C6H5NO3

S. 4. Scheme IV
(i) conc. H2SO4, 60ºC
CH3 (ii) conc. HNO3, conc. H2SO4 (iii) dil. H 2SO 4, heat
? C6H5NO4
Code :
P Q R S
(A) 1 4 2 3
(B) 3 1 4 2
(C) 3 4 2 1
(D) 4 1 3 2
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Integer / Numerical Value Type Questions

19. In the following reaction sequence, the amount of D (in g) formed from 10 moles of acetophenone
is __________.
(Atomic weights in g mol–1: H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%) corresponding to the
product in each step is given in the parenthesis) [JEE (Adv)-2018 (Paper-2)]
O

NaOBr NH3,  Br2/KOH Br2(3 equiv)

+ A B C D
H3O (60%) (50%) (50%) AcOH (100%)

20. Schemes 1 and 2 describe the conversion of P to Q and R to S, respectively. Scheme 3 describes the
synthesis of T from Q and S. The total number of Br atoms in a molecule of T is __________
[JEE (Adv)-2019 (Paper-1)]
Scheme 1:
NH 2 i) Br 2 (excess), H2 O
ii) NaNO2 , HCl, 273 K
iii) CuCN/KCN
Q
iv) H 3O +,  (major)
v) SOCl2 , pyridine
P
Scheme 2:
i) Oleum
ii) NaOH, 
+
S
iii) H (major)
iv) Br2 , CS2 , 273 K
R
Scheme 3:
i) NaOH
S T
ii) Q (major)

21. Consider the reaction sequence from P to Q shown below. The overall yield of the major product
Q from P is 75%. What is the amount in grams of Q obtained from 9.3 mL of P? (Use density of
P = 1.00 g mL–1; Molar mass of C = 12.0, H = 1.0, O = 16.0 and N = 14.0 g mol–1)
[JEE (Adv)-2020 (Paper-2)]
(i) NaNO2 + HCl/0-5°C
NH2 Q
OH
(ii)
P + NaOH

(iii) CH 3CO 2H/H2 O

Question Stem for Question Nos. 22 and 23

Question Stem
Reaction of x g of Sn with HCl quantitatively produced a salt. Entire amount of the salt reacted with y g of
nitrobenzene in the presence of required amount of HCl to produce 1.29 g of an organic salt (quantitatively).
(Use Molar masses (in g mol–1) of H, C, N, O, Cl and Sn as 1, 12, 14, 16, 35 and 119, respectively).
[JEE (Adv)-2021 (Paper-2)]
22. The value of x is ________.
23. The value of y is ________.
  

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