IIT-JEE Chemistry by N.J.

Sir ORGANIC chemistry

Date: DPP NO- 02 Time: 15 minutes

PASSAGE- I:
Claisen Condensation :

Esters undergo SNAE Reaction, when attacked by a NuΘ generated by the interaction of a base
(usually base related to the Alkoxy anion of ester) with one of the molecule of ester and this NuΘ
attacks on another molecule. The reaction over all is considered as condensation of esters known
as claisen ester condensation.

O O O
RONa
→ Me – C – CH2 – C – OR
2 Me –C – OR  

R
A β- keto ester

O O
O

SI RO
−ROH
Θ
CH3 –C – OR  → CH2 – COOR

Nu
Me –C – OR

RDS
Me – C – CH2 – COOR
OR

O
–R – O

Me – C – CH2 – COOR
J.
Some times, when two ester groups are present within the molecule then the condensation occurs
intramolecule then cyclization caused thus is known as Dieckmann cyclization or Dieckmann's
condensation.
Q.1 EtOK
MeCOOEt  → A
N.

Q.2 MeOK
EtCOOMe  → B

MeOK
Q.3 MeCOOEt + EtCOOMe  → C

C2H5ONa
Q.4 C6H5COOC2H5 + CH3COOC2H5   → D + D′
Ethyl benzoate

COOC2H 5
C2H5ONa
Q.5 + C6H5CH2COOC2H5   → E
COOC2H 5

COOPh
Q.6 PhONa
PhOOC  → F

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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
Q.7 Piperidone derivative
CH2CH2COOR
C2H5 – N C H5ONa HO ⊕
2  → G 3 
→ H
CH2CH2COOR ∆

O OEt

OEt NaOEt
Q.8 O Ι
OEt EtOH
O

COOEt
COOEt

R
NaOEt
H3OO
+
Q.9  → J K
∆
COOEt

Q.10 SI
COOC2H5

COOC2H5
+
COOC2H5

COOC2H5
Diethyl-β, β-dimethyl
glutrate
C2H5ONa
 → L
H3OO
∆
+
M
J.
N.

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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