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 (2008 E) (LiA/H4) is 1)
N H N H

Powered by myengg.com

2)

NHOH

NH2

3) Ans : 3 Sol:

N

4)
N

NO2 LiA/H2

+8[H]

N

N

2.

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

Ans : 2 Sol: NO2

2

+10[H]

Zn+KOH(alc)

N H

N H

+4H2O

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 Zn + KOH ( alc ) 2C6 H 5 NO2 + 10 ( H ) ⎯⎯⎯⎯⎯ 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 Powered by 1 myengg.com

Powered by myengg.com

Organic Chemistry – II

Sol:

Reaction Zn / HCl C6 H 5 NO2 + 6 ( H ) ⎯⎯⎯→ C6 H 5 NO2 + 2 H 2O 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

5.

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 alcoholic KOH 1) C6 H 5OH + NH 3 2) C6 H 5 NO2 + Zn powder ⎯⎯⎯⎯⎯ → 0 300 C 2000 C HCl 3) C6 H 5Cl + NH 3 ⎯⎯⎯ High pressure 4) C6 H 5 NO2 + Fe + H 2O ⎯⎯→ CHO → ⎯ CH 2O

Ans : 2 Sol: NO2
Zn+KOH

2

+10[H]

N

N

Alconol H H Hydrazobenzene 7.
HNO2 NaNO2 / HCl In the series of reactions C6 H 5 NH 2 ⎯⎯⎯⎯→ X ⎯⎯⎯ Y + N 2 + HCl → Cu2O 0 − 50 C

X and Y are respectivley 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
+ 3) C6 H 5 N 2 + Cl − , C6 H 5 NO2 4) C6 H 5 NO2 , C6 H 6

(2003 M)

Ans : 3 NaNO2 / HCl Sol: C6 H 5 NH 2 ⎯⎯⎯⎯→ O − 50 C
HNO2 C6 H 5 N 2Cl ⎯⎯⎯ C6 H 5 NO2 + N 2 + HCl → Cu2O

(X) 8.

(Y)

Which one of the following is the molecular formula of a tertiary amine ? 1) C2H7N 2) C3H9N 3) CH5N
(2002 E) 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)
Powered by 2 myengg.com

1) C6 H 5 N = NC6 H 5 3) C6 H 5 NH − NHC6 H 5

Powered by myengg.com 2) C6 H 5 NH 2 4) C6 H 5 NHOH

Organic Chemistry – II

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? 2) CH 3 − NH 2 1) C6 H 5 − NH 3 C6 H 5 − N − CH 3 C6 H 5 − N − CH 3 3) | CH 3 4)
| H

(2000 E)

Ans : 4 Sol. Conceptual 11. Which of the following is used to convert nitrobenzene to azobenzene ? (2000 M) 2) Zn / NaOH 3) Zn / NH 4Cl 4) Sn / HCl 1) LiAlH 4 Ans : 1 Sol:
2 +8[H]
LiAlH4

NO2 N N

+4H2O

Azobenzene

Powered by 3 myengg.com

Master your semester with Scribd & The New York Times

Special offer for students: Only $4.99/month.

Master your semester with Scribd & The New York Times

Cancel anytime.