SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

IIT JEE 2019

EMMET

HYDROCARBON

AMINES

PREPARED BY: ASHISH SIR & NEHA MADAM

 SYNOPSIS

AMINES

EXERCISE - A

One or More Than Correct Type :

1. Correct major product (s) with appropriate condition :-

OH OH NH2 NH2
Br Br

(A) Br2 (B)

Br2

CS2 ,< 5°C CS2 ,< 5°C

Br Br

NH2 NH2 OH OH
O O

COOH
(i) O (i) NaOH

(C) (D) (ii) CO2

(ii) Br2, AcOH

(iii) HCl, EtOH, H2 O reflux (iii) H

Br

2.
(i) HNO3 , H2SO4
[P]
(i) Br2
[Q]
(ii) H2 / Pd - C (ii) NaOH, H2O

(iii) Ac2O (iii) Na NO2,HCl

(iv) H3PO2

Product [Q] will be -

R R OH OH

Br

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

Br Br R

Br

3. The major product [S] of the following reaction sequence is :-

OH

Br2/Fe Sn / HCl excess Br2 1. NaNO2-H2SO4/O°C

P Q R S

H2O 2. CuBr / HBr

Br Br Br
Br

Br Br Br
Br

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

Br Br Br Br Br
Br Br

Br Br Br Br

4. Predict the product for the following reaction :-

HNO3
?

H2SO4
Room temp.

NO2 NO2 NO2 NO2

NO2 NO2

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

5. The product of the following reaction is :-

NaNO2,HCl

0°C
?

N
H

 N

N
Cl

(A) (B)

O N
 O

O2N NO2

(C) (D)

N N

H
N

6. The increasing order of basicity of the following compounds is :-

H Me NH2

NH2

NH H2N NH H2N NH

(I) (II) (III) (IV)

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

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

NH2

(1) NaNO2 / HCl CHCl3

7. (P) (Q)

(2) H2O ,Boil KOH

CH3

Product (Q) is :-

OH
OH OH OH

CHO COOH

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

CHO

CH3 CH3 CHO

CH3 CH3

8. What would be the best series of synthetic reactions to accomplish the following formation ?

NO2 CN

Br

(A) (i) Fe/ HCl (B) (i) Br2 / Fe Br3

(ii) Br2 / Fe Br3 (ii) Fe/ HCl

(iii) NaNO2 / HCl (iii) NaNO2 / HCl

(iv) CuCN / HCN (iv) CuCN / HCN

(C) (i) Fe/ HCl (D) (i) Fe/ HCl

(ii) NaNO2 / HCl (ii) NaNO2 / HCl

(iii) Br2 / Fe Br3 (iii) CuCN

(iv) CuCN / HCN (iv) Br2 / Fe Br3

NH2

9. (1) NaNO2 / HCl

(M) :-
(2) H2O (warm)

NO2

OH NO2 NO2 OH

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

NO2 NO2

10. Choose the best synthesis for toluidine :-

CH3

NH2

(Toluidine)

(1) HNO3,H2SO4 (1) CH3Cl, AlCl3

(A) (B)
(2) Sn / HCl (2) HNO3,H2SO4

(3) CH3cl, Alcl3 (3) Sn / HCl

(1) HNO3,H2SO4
(1) CH3C–Cl, AlCl3

(C) (D) (2) Sn / HCl

(2) Zn (Hg) / HCl

(3) HNO3, H2SO4 (3) CH3–C–Cl, AlCl3

(4) Sn / HCl O
(4) Zn (Hg) / HCl

NH2

1. NaNO2+HCl, 0°–5°C
(M)

11. 2. CH2
:-
OH,
s

mild Basic medium

Product (M) is :-

NH2 OH

(A) (B)

O CH3 H3C N=N

OH CH3

N=N-Ph N=N-Ph

(C) (D)

CH3 OH

12. Which of the following method (s) is / are not used to prepare p-bromo aniline as major product :-

NH2 NH2 NH2 NH2

Br2 (1) CH3COCl

(A) (B) (2) Br2/FeBr3

H2O
(3) NaOH/H2O

Br Br

NH2 NH2 NH2

(1) HNO3/H2SO4 (1) NaNO2/ HCl O°–5°C

(C) (D)
(2) Br2/FeBr3 (2) KCN/CuCN1

(3) LiAlH4
(4) Br2/FeBr3

Br Br

(1) NaNO2/ HCl O°–5°C

13. [M] (2) NaCN H2 N OH :-

(3) LiAlH4(excess)

(4) H3O

NH2 NO2 NO2 NH2

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

O O O O

H MeO MeO

14. The major product formed in the following reaction is :-

CHCl3

N EtONa



Cl OEt

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

N Cl N N N

OEt

15. The final product in the following transformation is :-

(1) Sn / HCl

NO2 (2) NaOH/ H2O

(3) rHCl / H2O

(iv) NaNO2 ae
(v) PhOH, dil OH

tag

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

(C) OH NH2 (D) H2N NH2

16. Identify sandmeyer reaction from the following :-

NH2 NH2 NH2 NH2

Br

(A) (B)

COCH3

NH2 CN NH2

(C) (D)

17. In the following reaction sequence :-

N2.Cl

CuCN H3O Br
(P) (Q) Fe Br
2
(R)

Find the ‘true’ statement :

(A) [R] is more acidic than [Q]

(B) [R] is more reactive towards electrophilic aromatic substitution than [Q]

(C) [Q] is more reactive towards electrophilic substitution than benzene

(D) [R] on reaction with sodalime can form a compound which can undergo phenol formation with aq. NaOH

treatment under normal condition of pressure and temperature.

18. The following reaction :-

Fe, HCl, H O

NO2 neutralize with

2
NaOH

Would yield -

(A) NO2 (B) NH2 (C) N2.Cl (D) Cl

Cl

19. Triethylamine (C2H5)3N, like all amines, has a nitrogen atom with an unshared pair of e . Dichlorocarbene also

has an unshanred pair of e Both can be represented as shown below :-

(C2H5)3N + : CCl2 D
:

D  C2H4

H 2O
F
Emsn.aoqa.my

Product ‘F’ is :-

(A) (C2H5)2 N-CHO (B) C2H5–C–NH–C2H5

O O

to
(C) H–C–N (Et)2
a
(D) C2H5–C–NH2

20. Identify the compound, which is “ LESS” basic than aniline :-

NH2 NH2 CH2NH2 NH2

CH3

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

CH3

CH2

21. An organic base [X], reacts with nitrous acid at O°C to give a clear solution. Heating the Solution with KCN

and cuprous cyanide followed by continued heating with conc. HCl gives a crystalline Solid. Heating this solid

with alkaline KMnO4 gives a compound which dehydrates on heating to a crystalline solid. The [X] is :-

NHCH3 CH2NH2

(A) (B)
CH3 H3C

NH2 NH2

(C) (D)

H 3C CH3

22. Amongst the compounds given, the one that would form a brilliant colored dye on treatment with NaNO2 in dil.

HCl following b addition to an alkaline solution of of -Naphthol:-

y

N (CH3)2 NH CH3

(A) (B)

CH2NH2

NH2

(C) (D)

H3C

23. Which of the following amine (s) will give “ Azo-dye” test .

NH2 NHCH3

CH2NH2 N(CH3)2

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

24. For the identification of -natphthol using dye test, it is necessary to use –

(A) dichloromethane solution of –naphthol (B) acidic solution of -naphthol

(C) neutral solution of -naphtol (D) alkaline solution of -naphthol

25. Complete reduction of benzene diazonium chloride with Zn/HCl gives :-

N N·Cl

Zn / HCl

NH2

NH – NH2

(A) (B)

(C) N=N (D) NH–NH

EXERCISE-B

1. The final product when :-

CH3NH2 
NaNO 2  HCl
?

(A) CH2N2 (B) CH3OH (C) CH3NO2 (D) CH3C  N

2. The major product of the reaction :-

Me Me

Me Me
NaNO2 + HCl
Product is

NH2 OH

Me Me Me

Me Me Me Me Me
(A) (B) Me Me (C) Me (D) Me Me

Me N
O Me H

H OH

NH2

Conc. HNO3 A B C
3. + +

Conc. H2SO4 47% 2% 51%

Product [A] is :-

NH2 NH2 NH2 NO2

NO2

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

NO2 NH2

NO2

OH
1. HNO3, H2SO4

2. EtBr, NaOH

4. [Q]
3. Fe/HCl

4. Followed by NaOH

5. O O

CH3 O CH3

[Q] will be :-

NH2 OCOCH3 NH Me OEt

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

O CH3 NH Me OCH2CH3 O NHCH3

5. Find the correct statement(s)




(A) Ph N 2 undergoes diazotisation with Ph N Me 2 to give Ph–N=N NMe2


(B) Ph N 2 undergoes diazocoupling with phenol to give orange color dye.

(C) Ph N 2 does not undergoes diazocoupling with anisole

(D) Ph N 2 undergoes diazocoupling with -naphthol give blue color dye.

6. Major product of the given reaction is :-

i. Red HOT(Fe), 873 K

H H C H NO
ii. Fuming HNO3, H2SO4, Heat 6 5 3

iii. H2S.NH3

iv. NaNO2, H2SO4

v. Hydrolysis

OH OH OH

OH
NO2

(A)
NO2 (B) (C) (D)

NO2

NO2 NO2

7. Major product of the given reaction is :-

NO2
i. Sn/HCl

ii. CH3COCl

C6H6N2O2
iii. Conc. H2SO4

iv. Conc. HNO3

v. dil. H2SO4, Heat

vi. OH

NO2 NH2 NH CH3

NO2

NH2

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

NH2

NO2 NO2

NO2

Na2S, H2S Na2S

8.
(or)
(P) (Q)

NO2 NH SH
4

P and Q are :-

NO2 NH2 NH2

(A) (B)

NO2 NH2 NH2

(P) (Q) (P) (Q)

NO2 NH2 NH2 NO2

(C) (D)

NaS NO2 NaS NH2 NH2 NH2

(P) (Q) (P) (Q)

NO2

i. KMnO4, OH, Heat

9. C7H6N2O3

ii. H, H2O

CH3 iii. SOCl2

iv. NH3

NO2 NO2 NH2 NO2

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

NH2

O NH2 O Cl O NH2 COONH4

NH2 NO2

(M)

10.
(N)

(A) [M] = Sn/HCl (B) [N] = Sn/HCl

(C) [M] = CF3CO3H (D) [N] = LiAlH4

NH2

11. 
CF3CO3 H
86%
P

2 Mole

NH2

Product [P] is :-

NH2
NO
NO2 NO2

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

NO NO2
NH2 NO2

NH2

K2Cr2O7

12. ?

NH2

O OH O NO

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

O NH
OH NO

13. Find the product?

NH2

i. Ac2O

ii. H2SO4
[R]

iii. HNO3
iv. H3O

Product [R] is :-

NH2 NH2 NH CH3 NH2

NO2

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

NO2

NO2 NO2

14. Final product (Q) in the below reaction sequence –

CH3

(1) NaNO2, HCl

(Q) major
(2) C2H5OH, Heat

NO2

NH2

CH3 CH3 CH3 CH3

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

NO2 NO2 NO2

OH NH-Et NO2

15. Final major product is :-

NH2

(1) NaNO2, HCl

(P)
(2) CuCl, HCl

NO2

Cl Cl Cl Cl

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

NH2
NO2 Cl

NH2

CH3

(1) H2SO4 , 60°C

16.
(2) Cl2/Fe
(Z)

(3) H2SO4 . Steam, 160°C

Product (Z) is :-

CH3 CH3 CH3 CH3

Cl SO3H Cl Cl

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

SO3H Cl Cl

(1) Red HOT (Fe) tube

17. H H (2) HNO , H SO [S]

3 2 4

(3) Sn/HCl

(4) NaOH
(5) Ac2O

(6) H2SO4 conc.

(7) aq. NaOH

(8) Br2/H2O

Product [S] is :-

NH2 NH2 NH2 NH2

Br Br Br Br Br Br

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

SO3H Br Br

OH

Ar·N2·Cl
(P)

(mild H )
18.

Ar·N2·Cl

(Q)
NH2 (mild OH)

OH OH

N = N–Ph

(A) P = (B) P =

N = N–Ph

NH2 NH2

OH NH2

N = N–Ph

(C) Q = (D) Q =

N = N–Ph

NH2 OH

19. Find product of the reaction sequence –

NO2

(1) NH4HS

(2) NaNO2, HCl [R]

(3) H2O (Boil)

NO2

[R] is :-

OH OH OH OH

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

OH NH2 NO2 NO2

OH

Cl
(1) NH3/EtOH, 150°C

(2) CHCl3, KOH

20. major product is :-

NO2

NH2 NC OH OH

CHO CHO

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

NO2 NO2 NO2 NO2

NHCOCH3

i. H, H2O

21. [T]
ii. NaNO2, HCl

iii. HBF4

NO2 iv. NaNO2

[T] is –

NO2 F NO2 NO2

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

NO2
F

NO2 NO2

HCl

22. Ph – NH2 Ph – N N·Cl [M] [N]

50g crushed ice yellow 40 – 45°C

5-10 min 1 hour

ppt

[M] and [N] respectively is :-

(A) NH , NH NH2

(B) N=N NH2 , NH–N = N

(C) NH–N = N , N=N NH2

(D) N=N NH2 , NH–N = N

NO2

(1) Fe/HCl A B C
23. (2) HNO3, H2SO4 51% + 2% + 47%

Identify the correct statement :-

NH2 NH2 NH2 NO2

NO2 NO2

(A) 51% (B) 47% (C) 2% (D) 47%

NH2

NO2

24. In the chemical reactions :-

NH2

NaNO2 HBF4

[A] [B]
HCl, 278K

the compounds (A) and (B) respectively are

(A) Benzene diaznium chloride and fluorobenzene

(B) Nitrobenzene ande chlorobenzene

(C) Nitrobenzene and flurobenzene

(D) Phenols and benzene

25. Reaction of 4-aminophenol with one equivalent of acetylchloride in the presence of pyridine yields :-

O Me OH OH OH O

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

NH2 NH2 Me NH2 NH2

EXERCISE- C

(i) HNO3 / H2SO4

(ii) Sn / HCl
1.

(iii) NaNO2 / HCl

(iv) Cu2(CN)2

+
(v) H3O /

CN NO2

COOH NO2

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

CN
COOH

(1) Br2/hv
O

CH3 (2) – +
N K acetone

2. O

(3) NH2NH2

CH2NH2 CH3 NH–CH3 CH3

NH2

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

NH2

Cl
(i) NaNO2 , HCl,0 C

3.  M  
(ii) CuCl
(iii)1chloro 2 Methyl propane,AlCl3

Identify [M] :

NO2

NH2 Cl

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

OH

(i) HNO3 , H 2SO 4

4. [N] 
(ii)Sn,HCl
(iii) NaOH
(iv) NaNO 2 , HCl, O  C then CuCN NH2

(v) excess LiAlH 4 then aqueous workup

O O O

OH
Br HO

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

5. Which sequence of reactions is useful to prepare 1-propanamine –

(A) CH3CH2CN 

LiAlH 4
 (B) CH3CH2Cl 
AgCN
 
LiAlH 4


(C) CH3Cl 

KCN
 
LiAlH 4
 (D) CH3Cl 
AgCN
 
LiAlH 4


NO2

6. 
Sn, HCl [A] 
NaOH
 [B]

In above reaction [A], is :

NH3.Cl NH3.Cl

NH2
NH3.Cl

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

SO2Cl

7. Identify the compounds give clear solution with Hinsberg reagent (i.e., in KOH)

CH3

NH2
O

(A)
NH2
(B) (C) (D)

NH2 N

8. Match the following :

List-I List-II

(P) NH2–NH2 (1) Blue solution with FeSO4 + H2SO4 (in Lasaigne test)

(Q) NH2–C–NH2 (2) Red colour with FeCl3 (In Lassaigne test)

(R) NH2–C–NH2 (3) N2 gas with NaNO2 + HCl

(S) Ph–NH2 (4) Pungent smell with CHCl3 + KOH

P Q R S

(1) 3 2 1 4

(2) 4 3 2 1

(3) 2 1 4 3

(4) 1 2 3 4

9. Column-I Column-II

(Amines) (Distinguished by)

(A) C2H5NH2 and C6H5NH2 (P) Carbylamine test

(B) C2H5NH2 and (C2H5)3N (Q) Azo-dye test

(C) (C2H5)3N and C6H5NH2 (R) Hinsberg test

10. Column-I Column-II

(A) NH2–NH3.Cl (P) Sodium extract of compound gives prussian blue colour with FeSO4

(B) HO
NH3.I
(Q) Neutral FeCl3 test

COOH

(C) HO NH3.Cl (R) White ppt with AgNO3

(D) O2N NH.NH3.Br (S) Reaction with aldehyde to form corresponding hydrazone derivative

NO2

11. White crystalline solid (M) give following chemical test :

(P) It liberates CO2 with NaHCO3

(Q) It forms a coloured dye on diazotising followed by coupling with PhNMe2

(R) With Br2 water, it forms white ppt of 2,4,6-tribromoaniline

[M] can be :

NH2 NH2 NHCOCH3 NH2

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

SO3H COOH

SO3H COOH

O O
NH2

CH3 O CH3

12. O [X] will be :

NH2

O O

NH

NH2

(A) O (B) O

NH

NH

O O

NH NH2

(C) O O (D) O

NH2 NH2

13. When nitrobenzene is treated with Br2 in presence of FeBr3, the major product formed is m-bromonitrobenzene.

Statements which are related to obtain the m-isomer, are

(A) The electron density on meta carbon is more than that on ortho and para-positions

(B) The intermediate carbonium ion formed after initial attack of Br at the meta-position is least destabilised.

(C) Loss of aromaticity when Br attacks at the ortho and para positions and not at meta-position

(D) Easier loss of Hto regain aromaticity from the meta position than from ortho and para-positions

14. p-chloroaniline and anilinium hydrochloride can be distinguished by :

(A) Sandmeyer reaction (B) NaHCO3

(C) AgNO3 (D) Carbylamine test

15. A positive carbylamine test is given by :

(A) N, N – dimethyl aniline (B) 2, 4 – dimethyl aniline

(C) N-methyl-o-methyl aniline (D) p-methyl benzylamine

16. For the following diazonium ions the decreasing order of reactivity of these ions in azo-coupling reactions

(under similar conditions) can be given as :

(I) (II)

(III) Me2N (IV) NC

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

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

17. How many structural isomers of C4H11N can give carbylamine test ?

EXERCISE- D

The following reaction scheme show a possible synthesis of tylenol, a cold medicine, commonly found in

commercial products. From the list of reagents provided in the table below, select the best reagent combinations

(meaning in some steps, you might need more than one reagent) to carry out each of the reaction required to

each numbered step.

(1) (2) (3) (4)

CH3OH H H O O +

HO HO Cl

O O O (5)

O O O
(8) (7)
(6)

NH2 NO2

(9)

O
(10) HO
O O

N N
H H

Tylenol

A NaNO2/H2SO4 BD SOCl2

B PDC/CH2Cl2 BE AlCl3

C NaBH4 CD CH3CO2H / pyridine

D CH3MgBr, then HBr heat CE CH3CH2Li, then H3O+

E K2Cr2O7 / aq. H2SO4 DE Sn/HCl then NaOH

AB Mg/Et2O then CO2, then H+ ABC NaOH/H2O/heat then H3O+

AC (CH3CO)2O/pyridine ABD O3 then H2O

AD HNO3 / H2SO4 ABE CH3I

AE aq. HCl BCD CH3MgBr then H3O+

BC Concentrated HCl BCE CH3CO3H

EXERCISE- E

Subjective :

NO2

(1) Br2/Fe
NH2 (1) Br2/CH3COOH

(2) NaNO2/H2SO4 (2) Sn/HCl

1. 2. (3) NaNO2/HCl
(3) CuBr
O2N

(4) Sn/HCl (4) H2O/H

(5) NaNO2/HCl
(6) H3PO2

CH3 CH3

(1) HNO3/H2SO4 (1) HNO3/H2SO4

(2) Fe/H (2) Fe/H

3. (3) Ac2O 5. (3) NaNO2 / HBr

(4) Br2 (4) CuBr

(5) H2O/H

(6) NaNO2/HCl

(7) H3PO2

CH3 CH3

(1) HNO3, H2SO4

(1) HNO3/H2SO4

(2) Fe/H (2) Fe/HCl

6. 7.

(3) NaNO2, H2SO4 (3) NaNO2, HCl

(4) H3PO2 (4) CuCN

(5) H2O, H

NH2 NH2

(1) Ac2O
Cl
(2) Br2/CH3COOH (1) NaNO2, H2SO4

8. 9. (2) H3PO2
(3) H2O/H

CH3 Cl

NH2

(1) Red HOT (Fe) tube

10. CH  CH
(2) Fuming HNO3, H2SO4
11.
(CH3CO)2O
?

(3) NH4SH (Py)

(4) NaNO2, H2SO4

(5) H3PO2 (CH3CO)2O

?
AlCl3

OH CH3

(1) K2Cr2O7, H2SO4 (1) NBS, Heat

12. (2) NH3 13. (2) NaCN

(3) H2 / Ni (3) H2/Ni

NO2

(1) NH3, Heat

(1) Fe, 30% HCl, Heat (2) Heat

14. 15. R–COOH

(2) Na2CO3 (3) H2/Ni

COOC2H5 COOC2H5

NH2
H2, Pt Sn/HCl

16. 17.

NO2 NH2 NH–NH2

SnCl2, HCl

NO2 NH2

Zn/HCl

18. 19. CH 3Cl

?
Zn/NH4Cl AlCl3

Zn/NaOH CH3COCl
AlCl 3
?

Li/AlH4

H2/Pt

20. (a) Trimethyl amine + acetic acid 

(b) Benzanilide + boiling aq. NaOH 

(c) Methyl formate + aniline 

(d) m-toluidin + Br2(aq) in excess 

(e) p-toluidine + Br2 (aq) in excess 

(f) p-toluidine + NaNO2 + HCl 

(g) C6H5NHCOCH3 + HNO3 + H2SO4 

(h) p-CH3C6H4NHCOCH3 + HNO3 + H2SO4 

(i) Benzanilide + Br2 + Fe 

H2/Ni (i) LiAlH4

21. R–C N 22. R–C–NH2

Na(Hg)
(Ii) H2O

C2H5OH

(1) KOH/EtOH
23. NH 24. CH3CH2Cl 
(i) Ethanolic NaCN


(2) R–X
(3) NaOH(aq)
(ii) Na (Hg)/Ethanol

NH2

25. C6H5CH2Cl  

(i) Ethanolic NaCN

(ii) H 2 /Pd 26. 

CHCl3 , KOH


+
H or OH
–
– + – + –
H or OH

27. (i) R–C N RCOOH / RCOO 28. (i) R–N C RNH2 r/ HCOOH
H2 O H2O

+
H / H2O
(ii) CH3C N N C +

Heat H
(ii)

C N H2O
+

(iii) H / H2O

Heat

+
H / H2O

(iv) Heat

CN

CH3 NH2

(i) Br2 (i) (CH3CO)2O

29. (ii) Sn/HCl 30. (ii) HNO3, H2SO4, 288K

(iii) NaNO2/HCl, 273K (iii) aq. NaOH

NO2

(iv) H3PO2, H2O

(v) KMnO4/OH

NO2

(i) HNO3, H2SO4

(ii) Sn/HCl

31. (P) 

HBF4
 [Q]
(iii) NaNO2, HCl 0°C Water

insoluble

and stable
at room temp.

Cu2Cl2/HCl

32. PhN 2.Cl (or) Sandmeyer reaction + N2

Cu2Br2/HBr (gas)

(or)
CuCN/HCN

Cu / HCl

33. PhN 2.Cl (or) Gattermann reaction + N2

(gas)

Cu/HBr

34. Hg + CH3–N=C=O

Isocyanate

NH2
Br 2

CS2

35.

1. (CH3CO) 2O
2. Br2/CS2

3. H3O

36. Give the structures of A, B and C in the following reactions :

 A 
OH

(i) CH3CH2I 

NaCN
Partial hydrolysis
B 
NaOH  Br2
C

(ii) C6H5N2Cl 

CuCN
 A 
H 2O/H  B 
NH 3
C


 B  C
HNO2
(iii) CH3CH2Br 
KCN
 A 
LiAlH 4

0 C

NaNO2  HCl
 A    B 


(iv) C6H5NO2 

Fe/HCl
273K
H 2O/H

C

(v) CH3COOH 

NH 3

 A 
NaOBr
 B 
NaNO2 /HCl C

 A   B 
HNO3
(vi) C6H5NO2 
Fe/HCl
273K
C6 H5OH
C

NO2

 F   G
(i) HNO2

37. (a) 

HNO3 /H 2SO 4

 E 
( NH 4 ) 2 S
(ii)  , H 2O

CH3

(b) 
HNO3
H 2SO4
 S 
Br2
Fe
 T 
Sn
HCl
U 
NaNO2 /HCl
273 K V 
H 2O
W


CH3

CH3

 Y  Z
(i) CHCl3 /KOH

(c) 
NaNO2 /HCl
273K X 
H 2O
 (ii) H 3O 

NH2

38. Complete the following reactions ;

(i) C6H5NH2 + CHCl3 + alc. KOH 

(ii) C6H5N2Cl + H3PO2 + H2O 

(iii) C6H5NH2 + H2SO4 (conc.) 

(iv) C6H5N2Cl + C2H5OH 

(v) C6H5NH2 + Br2(aq) 

(vi) C6H5NH2 + (CH3CO)2O 

(vii) C6H5N2Cl  

(i) HBF4

(ii) NaNO 2 /Cu, 

ANSWER KEY

EXERCISE-A

1. (A,B,C,D) 2. (A) 3. (B) 4. (A) 5. (C)

6. (C) 7. (B) 8. (A) 9. (A) 10. CBA

(C)

11. (C) 12. (A,C,D) 13. (D) 14. (C) 15. (A)

16. (C) 17. (A) 18. (B) 19. (A,C) 20. (A)

21. (D) 22. (C) 23. (B) 24. ( ) 25. (A)

EXERCISE-B

1. (B) 2. (A) 3. (B,D) 4. (C) 5. (A,B,C)

6. (C) 7. (B) 8. (A) 9. (A) 10. (B,C)

11. (B) 12. (A) 13. (A) 14. (A) 15. (A)

16. (C) 17. (B) 18. (A,D) 19. (C) 20. (B)

21. (C) 22. (C) 23. (C,D) 24. (A) 25. (B)

EXERCISE-C

1. (C) 2. (A) 3. (A) 4. (B) 5. (A)

6. (C) 7. (B,C) 8. (A) 9. (A)Q ; (B)P,R ; (C)P,Q,R

10. (A)R,S ; (B)P,Q ; (C)P,Q,R; (D)P,S 11. (B) 12. (A)

13.

1 ( )3 14. (C) 15. (B,D) 16. (B) 17. (4)

EXERCISE-D

1. B 2. BCD 3. E 4- BD 5- BE

6- BCE 7- AD 8- DE 9- AC 10- ABC