ORGANIC CHEMISTRY –II

5. NITROGEN CONTAINING COMPOUNDS

PREVIOUS EAMCET BITS

1. The structure of the compound formed, when nitrobenzene is reduced by lithium aluminium hydride
(LiA/H4) is (2008 E)

1) 2) NHOH
N N

H H

NH2

3) 4)
N N
Ans : 3
Sol:

.in
NO2

+8[H] LiA/H2
di N N
Ba
Azo benzene
et

2. Nitrobenzene undergoes reduction with Zn/alcoholic KOH to form a compound A. The number of
Sigma and Pi bonds in A, respectively, are (2008 M)
.N

1) 17,6 2) 27,6 3) 27,8 4) 17,8

Ans : 2
w

Sol:
NO2
w
w

Zn+KOH(alc) N
2 +10[H] N +4H2O

H H

3. Nitrobenzene is reduced by Zn and alcoholic potash mixture to get (2007 M)

1) C6 H 5 − NH 2 2) C6 H 5 − NH − NH − C6 H 5
3) C6 H 5 − N − N − C6 H 5 4) C6 H 5 − NH − CO − C6 H 5
Ans : 2
Sol: Reaction
2C6 H 5 NO2 + 10 ( H ) ⎯⎯⎯⎯⎯
Zn + KOH ( alc )
→ C6 H 5 − NH − NH − C6 H 5

4. Which of the following reactions can produce aniline as the main product? (2006 E)
1) C6 H 5 NO2 + Zn / KOH 2) C6 H 5 NO2 + Zn / NH 4Cl
3) C6 H 5 NO2 + LiAlH 4 4) C6 H 5 NO2 + Zn / HCl
Ans : 4

1
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 Organic Chemistry – II
Sol: Reaction
C6 H 5 NO2 + 6 ( H ) ⎯⎯⎯→
Zn / HCl
C6 H 5 NO2 + 2 H 2O

5. Which of the following compounds is soluble in benzene but almost insoluble in water?
(2005 E)
1) C6 H 5OH 2) CH 3CO2 H 3) CH 3CHO 4) C6 H 5 NO2
Ans : 4
Sol: Nitrobenzene is soluble in organic solvents like Benzene but insoluble in water.

6. Aniline is not the major product in one of the following reactions. Identify that reaction
(2003 E)
ZnCl2
1) C6 H 5OH + NH 3 0
2) C6 H 5 NO2 + Zn powder ⎯⎯⎯⎯⎯
alcoholic KOH
→
300 C
3) C6 H 5Cl + NH 3 ⎯⎯⎯
2000 C
CH 2O
→ High pressure 4) C6 H 5 NO2 + Fe + H 2O ⎯⎯ HCl
⎯→ CHO
Ans : 2
Sol:

.in
NO2

2 +10[H]
Zn+KOH
di N N
Ba
Alconol
H H
Hydrazobenzene
et

In the series of reactions C6 H 5 NH 2 ⎯⎯⎯⎯→ X ⎯⎯⎯ → Y + N 2 + HCl

.N

NaNO2 / HCl HNO2

7. 0 − 50 C Cu2O

X and Y are respectivley (2003 M)

w

1) C6 H 5 − H = N − C6 H 5, C6 H 5 N 2 + Cl −
2) C6 H 5 N 2 + Cl − , C6 H 5 − N = N − C6 H 5
w

3) C6 H 5 N 2+ + Cl − , C6 H 5 NO2
w

4) C6 H 5 NO2 , C6 H 6
Ans : 3
Sol: C6 H 5 NH 2 ⎯⎯⎯⎯→
NaNO2 / HCl
O − 50 C

C6 H 5 N 2Cl ⎯⎯⎯
HNO2
Cu2O
→ C6 H 5 NO2 + N 2 + HCl
(X) (Y)

8. Which one of the following is the molecular formula of a tertiary amine ?

(2002 E)
1) C2H7N 2) C3H9N 3) CH5N 4) CH3N
Ans : 2
Sol: In tertiary amine, nitrogen atom is attached to three alkyl groups. The only formula that fits into this
is C3H9N or ( CH 3 )3 N

9. What is the product obtained when nitrobenzene is reacted with HCl in the presence of Sn
(2001 M)

2
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 Organic Chemistry – II
1) C6 H 5 N = NC6 H 5 2) C6 H 5 NH 2
3) C6 H 5 NH − NHC6 H 5 4) C6 H 5 NHOH
Ans : 2
Sol: When reduced in strongly acid medium (Sn + HCl) nitrobenzene gives aniline.
C6 H 5 NO2 + 6 [ H ] → C6 H 5 NH 2 + 2 H 2O

10. Which of the following is a secondary amine? (2000 E)

1) C6 H 5 − NH 3 2) CH 3 − NH 2
C6 H 5 − N − CH 3 C6 H 5 − N − CH 3
3) | 4) |
CH 3 H
Ans : 4
Sol. Conceptual
11. Which of the following is used to convert nitrobenzene to azobenzene ? (2000 M)
1) LiAlH 4 2) Zn / NaOH 3) Zn / NH 4Cl 4) Sn / HCl
Ans : 1
NO2

.in
Sol:
LiAlH4
2 +8[H] di
N N +4H2O
Ba
Azobenzene

DDDD
et
.N
w
w
w

3
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