IIT-JEE Chemistry by N.J.

Sir ORGANIC chemistry

Date: DPP NO-03 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 α, β- unsat-
urated aromatic acids.
( i ) CH COONa ,∆
C6H5 – CHO + CH3– C – O – C – CH3   3
 → C6H5– CH = CH – COOH + CH3COOH
|| || ( ii ) H+ / H2O,∆

O O

Mechanism

CH3 C O–
||

IR
O ∆
CH3– C – O – C – CH3 CH3– C – O – C – CH3
|| || CH3 COOH || ||
O O O O
Ph–C – H
||
O
S CH3 C OH
||
O
Ph – CH – CH2 – C – O – C – CH3 Ph – CH – CH2 – C – O – C – CH3
| || || | || ||
J.
OH O O O O O

CH3 C OH
|| H+/ H2O
N.

∆
Ph – CH – CH2 – C – OH Ph – CH = CH – COOH
| || H2O
OH O

β- Hydroxy acid

( i )( CH3CH2CO )2 O / CH3 −CH2 − COONa ,∆

Q.1 H 3C CHO     +     → A
( ii ) H / H2O,∆

OH
( i )( CH3CO )2 O / CH3COONa ,∆
Q.2     ⊕
 → B →
∆
C
( ii ) H3O , ∆
CHO

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IIT-JEE Chemistry by N.J. Sir
A-833, Indra Vihar, near IL back door,
Contact: 9414969800, 9549908816
web : symmetryiitjee.com
 ( i )( CH3CO )2 O / CH3COONa , ∆
Q.3      → D
+
CHO ( ii )H / H2O, ∆
O

O
||
H2C – C
Q.4 C6H5– C – H + | ( i ) Sodium Succinate , ∆
O    → E
|| ( ii )H3O⊕ , ∆
H2C – C
O ||
O

O
(i) MeCOONa CH– COOH
C (ii) H3OO
+, ∆ C
Q.5 O+F O

IR
C C
O O

Phthalylacetic acid

Q.6
O2N
S CH3COOΘ
O  →
(MeCO )2 O
G

O
J.
O MeCOO Θ

Q.7  → H
( MeCO) O 2

O
N.

O
|| (i) COONa
O
|| Me– CH – C COONa
Q.8 Ph – C – H + | O I
(ii) H3O, ∆
Me– CH – C
||
O

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IIT-JEE Chemistry by N.J. Sir
A-833, Indra Vihar, near IL back door,
Contact: 9414969800, 9549908816
web : symmetryiitjee.com