IIT-JEE ChEmistry by N.J.

sir ORGANIC chemistry

Date: DPP NO- 33 Time: 15 minutes
PERKIN CONDENSATION:
In Perkin reaction, condensation has been effected between aromatic aldehydes and aliphatic acid
anhydrides in the presence of sodium or potassium salt of the acid corresponding to the anhydride, to
yields - unsaturated aromatic acids.
(i) CH3 COONa,
C6H5 – CHO + CH – C – O – C – CH 
3  C6H5– CH = CH – COOH + CH3COOH
3
||  || (ii) H /H2O,
O O
Mechanism
CH3 C O–
||
O 
CH3– C – O – C – CH3 CH3– C – O – C – CH3
|| || CH3 COOH || ||
O O O O
Ph–C – H
||
O
CH3 C OH
||
O
Ph – CH – CH2 – C – O – C – CH3 Ph – CH – CH2 – C – O – C – CH3
| || || | || ||
OH O O O O O
CH3 C OH
|| H+/ H2O
O


Ph – CH – CH2 – C – OH Ph – CH = CH – COOH
| || H2 O
OH O
- Hydroxy acid

(i)(CH CH CO) O / CH  CH  COONa,

Q.1 H 3C CHO 
3 2 2

3 2
A
(ii) H /H2 O,

OH (i)(CH CO) O / CH COONa, (i)(CH CO) O / CH COONa, 

Q.2 
3 2

3
 B 
C Q.3 
3 2

3
D
(ii) H3 O ,  CHO (ii)H /H2O, 
CHO O
O
||
H2C – C
(i) Sodium Succinate, 
Q.4 C6H5– C – H | O +  
 E
|| (ii)H3 O , 
H2C – C
O ||
O
O
CH– COOH
(i) MeCOONa
C
(ii) H3OO
+,  C
Q.5 O +F O
C
C
O O
Phthalylacetic acid
O
O
CH3 COO O MeCOO 
Q.6 O  G Q.7  H
(MeCO)2 O (MeCO)2 O
O2N
O O
O
|| (i) COONa
O
|| Me– CH – C COONa
Q.8 Ph – C – H+ | O (ii) H O,

I
3
Me– CH – C
||
O

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