1. The document describes the synthesis of various organic compounds including acetic acids, succinic acid, adipic acid, alpha beta unsaturated acids, ketones, and malonic ester from ethyl acetoacetate as the starting material. 2. Reactions include hydrolysis, alkylation, halogenation, dehydration, Knoevenagel condensation, and decarboxylation to obtain the target compounds in high yields. 3. The synthesized compounds include monoalkyl acetic acids, dialkyl acetic acids, succinic acid, glutaric acid, beta keto acids, crotonic acid, and diethyl malonate which are important reagents, intermediates

1. Synthetic Reagent
By
Prof. G. P. Sadawarte
Dept. of Chemistry
B. P. Arts, S.M.A. Sci. and K.K.C. Comm. College
chalisgaon

2. E A A
H3C
O
OC2H5
O
H3C OC2H5
O
+
H3C OC2H5
O
H3C
O
OC2H5
O
C2H5ONa

3. Synthesis of E A A
H3C OC2H5
O
C2H5O-
Na+
H2C OC2H5
O
+ C2 H5 OH
H3C OC2H5
O
H2C OC2H5
O
H3C C
H2
O
OC2H5
O
C2H5O
H3C
O
OC2H5
O
C2H5O
Na +
H3C
O
OC2H5
O
+C2H5O-
Na+

4. Mono Alkyl Acetic acid
H3C C
O
OC2H5
O
H H
C2H5O Na
H3C C
O
OC2H5
O
H
H3C C
O
OC2H5
O
H R
X
H3C C
O
OC2H5
O
H R
+
X
H3C C
O
OC2H5
O
H R
1)H2O / OH
2) H / H2O
C
H2
OH
O
R
C2H5OH
+
H3C OH
O
+

5. Di Alkyl Acetic acid
H3C C
O
OC2H5
O
H H
C2H5O Na
H3C C
O
OC2H5
O
H
H3C C
O
OC2H5
O
H
R
X
H3C C
O
OC2H5
O
H R
+
X
H3C C
O
OC2H5
O
R H
C2H5O Na
H3C C
O
OC2H5
O
R R
X
H3C C
O
OC2H5
O
R R

6. Di Alkyl Acetic acid
H3C C
O
OC2H5
O
R R
H3C OH
O
1)H
2
O
/
O
H
2)
H
/
H
2
O
+ C2H5OH
+
CH OH
O
R
R

7. Succinic acid
H3C C
O
OC2H5
O
H H
C2H5O Na
H3C C
O
OC2H5
O
H
H3C C
O
OC2H5
O
H
H2C OC2H5
O
X
H3C C
O
OC2H5
O
H H2C
O
OC2H5
H3C C
O O
H H2C
O
OC2H5
OC2H5
Conc NaOH
H2O /H
CH3COOH + + 2 C2H5OH
H2C
H2C
C
OH
OH
C
O
O

8. Adipic acid
H3C C
O
OC2H5
O
H H
C2H5O Na
H3C C
O
OC2H5
O
H
H3C C
H
O
OC2H5
O
H3C
H
C OC2H5
O O
H2C
H2C
Br
Br
Conc NaOH
H2O /H
H2C OH
O
H2C OH
O
CH2
CH2
+ 2CH3COOH
+ 2 C2H5OH
H3C CH
O
OC2H5
O
H3C CH OC2H5
O O
CH2
CH2

9. Alpha beta unsaturated acid
H3C C
O
OC2H5
O
H H
C2H5O Na
H3C C
O
OC2H5
O
H
H3C C
H
O
OC2H5
O
R
O
H
+ H
- H2O
H3C C
O
OC2H5
O
C
R
H
Conc NaOH
H / H2O
HC OH
O
HC
R
H3C OH
O
C2H5OH
+
Knoevenagel reaction

10. Alkyl ketone
H3C C
O
OC2H5
O
H H
C2H5O Na
H3C C
O
OC2H5
O
H
H3C C
H
O
OC2H5
O
R
X
H3C C
O
OC2H5
O
H R
i) Dil HCl
ii) Heat
C2H5OH
+
+ CO2
C
H2
O
H3C
R

11. Malonic Ester/ diethyl malonate
C2H5O O C2H5
O
O
Malonic Ester
Synthesis of Malonic ester
CN
H2C
COOK
Potassiun Cyno Acetate
+2 HCl + 2 H2O
COOH
H2C
COOH
Malonic Acid
+ KCL +NH4Cl
COOH
H2C
COOH
+ C2H5OH
+ C2H5OH
HCl
COOC2H5
H2C
COOC2H5
Malonic Ester
+ 2 H2O

12. Monoalkyl Acetic Acid
COOC2H5
C
COOC2H5
H
H
C2H5O Na
-C2H5OH
COOC2H5
C
COOC2H5
H
R
X
-X
COOC2H5
C
COOC2H5
R
H
COOC2H5
C
COOC2H5
R
H
H+/H2O
COOH
C
COOH
R
H
Heat
- CO2
R
H2
C
COOH
Alkyl acetic acid
• Propanoic Acid
• Butanoic Acid
• n-Valeric acid/ pentanoic acid

13. Di alkyl Acetic Acid
COOC2H5
C
COOC2H5
H
H
C2H5O Na
-C2H5OH
COOC2H5
C
COOC2H5
H
R
X
-X
COOC2H5
C
COOC2H5
R
H
COOC2H5
C
COOC2H5
R
H
C2H5O Na
-C2H5OH
COOC2H5
C
COOC2H5
R
R
X
-X
COOC2H5
C
COOC2H5
R
R
COOC2H5
C
COOC2H5
R
R
H+/H2O
COOH
C
COOH
R
R
Heat
- CO2 R
CH
COOH
di Alkyl acetic acid
R

14. Succinic Acid
COOC2H5
C
COOC2H5
H
H
C2H5O Na
-C2H5OH
COOC2H5
C
COOC2H5
H
-X
Cl- CH2- COO C2H5
COOC2H5
C
COOC2H5
H2C
H
C2H5OOC
COOC2H5
C
H2C
H
COOC2H5
COOC2H5
H+/H2O
COOH
C
H2C
H
COOH
COOH
Heat
- CO2
H2C
H2C
COOH
COOH
Succinic acid

15. Glutaric Acid
COOC2H5
C
COOC2H5
Malonic Ester
COOC2H5
C
COOC2H5
H
H
C2H5O Na
H
-C2H5OH
C2H5OOC
C
C2H5OOC
H
COOC2H5
C
COOC2H5
H
CH2-I2
-I2
COOC2H5
CH
COOC2H5
C
H2
CH
C2H5OOC
C2H5OOC
COOC2H5
CH
COOC2H5
C
H2
CH
C2H5OOC
C2H5OOC
H+/H2O
COOH
CH
COOH
C
H2
CH
HOOC
HOOC
Heat
- CO2
H2
C
COOH
C
H2
H2
C
HOOC
Glutaric Acid

16. Beta keto Acid
COOC2H5
C
COOC2H5
Malonic Ester
H
H
C2H5O Na
-C2H5OH
COOC2H5
C
COOC2H5
H
C2H5OOC
C
C2H5OOC
H
H3C
C
Cl
O
C2H5OOC
C
C2H5OOC
H
O
CH3
+ Cl
H+/H2O
Hydro
lysis
HOOC
C
HOOC
H
O
CH3
Heat
- CO2
HOOC
H2C
O
CH3

17. Alpha beta unsaturated acid
H3C
H
O
COOC2H5
C
COOC2H5
Malonic Ester
H
H
+
Pyridine
COOC2H5
C
COOC2H5
H
H3C
COOC2H5
C
COOC2H5
H
H3C
H+/H2O
Hydrolysis
COOH
C
COOH
H
H3C
Heat
- CO2
CH
COOH
H
H3C
Crotonic acid

18. Any ?