CHEM ACADEMY 1 Hetrocyclic Compound (Solution)

Hetrocyclic Compound
EXERCISE - I
Single Answer Correct Type

1. N sp2 hybridised (1 lone pair + 2 bond pair)

2.
CHEM ACADEMY
Na / liq. NH
3

N
N H

Na / C H OH
2 5
 
N
H

LiAlH
4

N
H
HI / 
  CH3 (CH 2 )3 CH3  NH 3

3
sp
< R NH 2
3. N 2
(due to more electronegativity of N in pyridine).
sp

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CHEM ACADEMY 2 Hetrocyclic Compound (Solution)
4. thiophene > pyrrole > furan.

NaOH Cl


HCCl3
N N CHO +
5. N
H H Major product
Reimer-Tiemann reaction

O O
C OH  C O
Na OH Soda H O  H
6.     

 H2O Lime
N N N

NO 2
KNO3  H 2SO4

300ºC

7. N N
NO
2

N
CHEM ACADEMY
+ NO
2
N
H
NO 2
N
NO 2

?

CHCl

3 CHO
N  KOH N
8.
H H
:CCl2


Na O H
CCl2  NaOH  H O
2 
+ CCl2  
N N N HCCl2
H

OH
HC H  O H CHO
N N
OH
H

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CHEM ACADEMY 3 Hetrocyclic Compound (Solution)


Na N H 2
 NH2
9. most electrophilic N 

N H N NH2
site due to –I effect
of nitrogen

10. 
 SO3H
O O

N N
+ SO3 SO3 H

O (real attacking O SO 3 SO3H

2 NaNH

100
11.
chichibabin reaction
N N NH2

NaOH

canizaro

12. +
O CHO reaction O CH2OH O COONa

CHEM ACADEMY
Mechanism:

O  O O
Na O H
C H 
 C O H + C H
O O O
H

O O O
H2
IMPTR
C H+ C H 
 C OH + C ONa
O O O O
H

13. E
  electrophilic substitution occurs at 3rd position, 2nd and 4th positions are inactive
N
for electrophilic substitution.

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CHEM ACADEMY 4 Hetrocyclic Compound (Solution)

H H
C
O
H2
C NMe2
14. N Me2NH, H N
(Mannich reaction)
CH 3 CH 3

H H2
C NMe2 H2

:
H 2O:
C NMe2   C NMe2
N N H N
CH 3 CH CH3


O 18 O O
Na O H 18
C 
 C OH + C H
15. O O O
H

O O O OH
18 18 H 
hydrolysis

O
CHEM ACADEMY
C OH +

O
O

OH
C H
H
O
C O +
O
C
H

18
C OH + CH2
O O

N
16. O S
H
I IV III
II
I > III > II > IV

Cl Cl Cl
1eq. MeO

 OMe
N Br N Br N OMe
this step is less
favourable because more stable because
negative charge is –ve charge on nitrogen
not on nitrogen
17.
Cl Cl Cl OMe
OMe OMe OMe
N Br N Br N Br N Br

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CHEM ACADEMY 5 Hetrocyclic Compound (Solution)


CHCl3 / aq.Na O H :CCl 2 

 
insertion in
18. N N  bond.
:CCl2 (intermediate)
H

Cl Cl

N Cl
N

 H2
O MeI Na C N
  CH2   C CN
C N NMe 2 N N
19. N H H NH3
Me2NH (A) (B)
O
P O
2 5

20.
dehydrating O
O
agent

EXERCISE - II

1. CHEM ACADEMY
Pyrrole > Furan > thiophene > benzene.
a & c are correct option.
One or More Than One Correct

N N N
2. CH 3  I CH3I Ag 2O CH3OH
CH2 
 CH2  CH2
CH3 CH3 CH3
After formation of quaternium ammonium hydroxide, -hydrogen elimination takes place.

H 1 H1 N
H2 
Et CH3
N H2
CH 3
CH 2
H3 CH 2 N
 CH 3
Et
Correct answer is b, c, d.

+ CH2 = CH2
N
CH3

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CHEM ACADEMY 6 Hetrocyclic Compound (Solution)

EXERCISE - III
Previous Year Questions
O O
C C
H C O CH
O 4 3 O
Ac 2O HNO  H SO 5 2
 3 2 4
ZnCl2 C CH 3  O2N C CH3
O 0ºC O O1

1. N O2
O
H3C C
(RAE)
Aromatic substitution take place according to activating group hence O activate at 5 & 2 position.

N N
H N H  N sp3
2.
H 


 H H 



most unstable (most acidic) H H H
I

N
CHEM ACADEMY N
H H 
N
H 


 H H 


 sp2
III least unstable IV H

1
pK a   unstability of conjugate acid.
Acidity of compound
III > II > IV > I

3. 
 
 
 

N N N N N N
H H H H

+
N NH
–
H

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CHEM ACADEMY 7 Hetrocyclic Compound (Solution)

O
4. O OH OH
+ H
C H 
 C H C
O O O
H H
less
OH electrophilic
more electrophilic O
||

NH 2  C  NH  NH 2

H
OH OH O
O H
H
NH N C NH2 HN N C NH2

O O
H H
 H

CHEM ACADEMY
N N C NH2   N N C NH2

CH 3 
N aNH
2 3 CH  Br
 
 NH3
5. N CH 2 N

H  NH2
 
N N
Br
CH3 CH3

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CHEM ACADEMY 8 Hetrocyclic Compound (Solution)

N N
N N
6. (conjugate bond) H H H
solution of
H (II)
+ve charge I Aromatic
more solution most stable
less acidic Me Me

N N N N
H H H
H
(IV)
(III)

Acidity  Stability of conjugate base.

CH 2  COONa
| P2S3 Rancy
7.
CHEM ACADEMY
CH 2  COONa

heat
 S 
(X)
Ni
CH3  CH 2  CH 2  CH 3

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